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Review

Structures and Biological Activities of Secondary Metabolites from Xylaria spp.

by
Weikang Chen
1,2,
Miao Yu
1,2,
Shiji Chen
1,2,
Tianmi Gong
1,2,
Linlin Xie
1,2,
Jinqin Liu
1,2,
Chang Bian
1,2,
Guolei Huang
1,2,* and
Caijuan Zheng
1,2,*
1
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, China
2
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, Haikou 571158, China
*
Authors to whom correspondence should be addressed.
J. Fungi 2024, 10(3), 190; https://0-doi-org.brum.beds.ac.uk/10.3390/jof10030190
Submission received: 4 February 2024 / Revised: 25 February 2024 / Accepted: 26 February 2024 / Published: 29 February 2024
(This article belongs to the Section Fungal Cell Biology, Metabolism and Physiology)
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Abstract

:
The fungus genus Xylaria is an important source of drug discoveries in scientific fields and in the pharmaceutical industry due to its potential to produce a variety of structured novel and bioactive secondary metabolites. This review prioritizes the structures of the secondary metabolites of Xylaria spp. from 1994 to January 2024 and their relevant biological activities. A total of 445 new compounds, including terpenoids, nitrogen-containing compounds, polyketides, lactones, and other classes, are presented in this review. Remarkably, among these compounds, 177 compounds show various biological activities, including cytotoxic, antimicrobial, anti-inflammatory, antifungal, immunosuppressive, and enzyme-inhibitory activities. This paper will guide further investigations into the structures of novel and potent active natural products derived from Xylaria and their potential contributions to the future development of new natural drug products in the agricultural and medicinal fields.

1. Introduction

The fungus genus Xylaria, belonging to the family Xylariaceae, is a fungus widely distributed in both marine and terrestrial environments. Most of the genus Xylaria is saprophytic, digesting rotten wood, bark, feces, and other organic matter; similar to most saprophytic fungi, it can produce a variety of species. Xylaria species are famous for producing structured novel and potent bioactive secondary metabolites. The secondary metabolites obtained from the fungus genus Xylaria have high biological activity, including antibacterial, antioxidant, and cytotoxic activities [1,2,3,4]. The fungus genus Xylaria also has the potential to be used as a bioremediation agent and enzymatic degradation agent in industrial and agricultural fields [5,6,7].
The Xylaria fungi are producers of structurally diverse and biologically active compounds. As of 2020, 245 bioactive compounds (118 new compounds), including sesquiterpenoids, terpenoids, cytochalasins, alkaloids, polyketides, and aromatic compounds, have been isolated from the genus Xylaria. These compounds displayed a wide range of biological activities, comprising antibacterial, antifungal, anticancer, antimalarial, anti-inflammatory, and α-glucosidase inhibitory activities. Many of these compounds exhibit a strong potential to be expanded into novel drugs [8,9]. The secondary metabolites with novel structures and diverse bioactivities from Xylaria have continued to attract great attention from chemists, agricultural chemists, and pharmacologists.
The current review summarizes the chemical diversity and bioactivities of 445 new compounds isolated from Xylaria species from 1994 to January 2024. Structurally, they are classified into terpenoids (133 compounds), nitrogen-containing compounds (112 compounds), polyketides (70 compounds), lactones (76 compounds), and other compounds (54 compounds). Among them, 177 compounds display a wide range of biological activities, including cytotoxic, antimicrobial, anti-inflammatory, antifungal, antiplasmodial, immunosuppressive, and enzyme-inhibitory activities. This review summarizes the sources, chemical structures, and biological activities of 445 new compounds reported in the genus Xylaria in the past 30 years (between 1994 and January 2024), in order to provide a reasonable and reliable theoretical basis for the future development of new natural drug products in the agricultural and medicinal fields.

2. Structural and Biological Activity Studies

2.1. Terpenoids

Terpenoids usually comprise isoprene or isopentane unit structures. A total of 133 new terpenoids were discovered from the genus of Xylaria sp., including 84 sesquiterpenes, 43 diterpenes, and six triterpenoids. Remarkably, 38 of them showed cytotoxic activities, antibacterial activities, antifungal activities, α-glucosidase inhibitory activities, and so on.

2.1.1. Sesquiterpenes

One new sesquiterpene, 13,13-dimethoxyintegric acid (1), was isolated from a dead branch-derived fungus Xylaria sp. V-27 (Figure 1). Compound 1 promoted growth-restoring activity against a mutant yeast strain (Saccharomyces cerevisiae zds1Δ erg3Δ pdr1Δ pdr3Δ) and inhibited the degranulation of rat basophilic leukemia RBL-2H3 cells stimulated by Immunoglobulin E+2,4-dinitrophenylated-bovine serum albumin (IgE+DNP-BSA), thapsigargin, and A23187, with half maximal inhibitory concentration (IC50) values of 42.2, 21.2, and 37.5 μM, respectively [10]. Three new compounds, including 10-hydroxythujopsene (2), akotriol (3), and xylaritriol (4), were isolated from the Litsea akoensis-derived fungus [11]. Six new sesquiterpenes, including nigriterpenes A–F (5–10) with eremophilane skeletons, were obtained from the termite nest-derived Xylaria nigripe. Among them, nigriterpene C (7) showed concentration-dependent inhibition of lipopolysaccharide-induced inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2) expression, and nitric oxide (NO) production in murine brain microglial BV-2 cells, with IC50 values of 8.1, 16.6, and 21.7 μM, respectively [12]. Two new sesquiterpenoids, including polymorphines A and B (11 and 12) with drimane skeletons, were separated from the fungus Xylaria polymorpha (Pers.: Fr.) Grer. Compound 12 showed acetylcholinesterase (AChE) inhibitory activity (inhibition rate of 34.3%; final reaction concentration of 50 µg/mL) and also showed weak α-glucosidase inhibitory activity, with an IC50 value of 543.8 µM [13]. Three new compounds, including xylaric acids A–C (13–15), were isolated from the termite nest-derived fungus Xylaria sp. [14]. Two new eremophilane sesquiterpenes, including eremoxylarins A (16) and B (17), were obtained from Xylaria sp. (YUA-026). The fungus YUA-026 was collected from twigs and petioles of Mt. Takadate, Japan. Compounds 16 and 17 displayed activity against S. aureus, with minimum inhibitory concentration (MIC) values of 12.5 and 25 μg/mL, respectively, and against Pseudomonas aeruginosa with MIC values of 6.25 and 12.5 μg/mL, respectively [15]. A new compound, eremoxylarin C (18), was isolated from the wood decay fungus Xylaria allantoidea BCC 23163. Also, 18 showed inhibitory activity against Plasmodium falciparum K1 and human small-cell lung cancer (NCI-H187) cells, with IC50 values of 3.1 and 6.7 μg/mL, respectively [16]. Seven new compounds, including eremoxylarins D–J (19–25) with eremophilane skeletons, were separated from the coculture fermentation of Xylaria hypoxylon and Dendrothyrium variisporum. The fungus X. hypoxylon was derived from the lichen Rhizocarpon geographicum. Compounds 19, 21, 22, and 24 exhibited activity against three Gram-positive bacteria including Staphylococcus aureus, methicillin-resistant S. aureus (MRSA), and S. epidermidis, with MIC values from 0.39 to 12.50 μg/mL. Compound 24 was also active against human coronavirus 229E (HCoV-229E) at a concentration nontoxic to human hepatocellular carcinoma (Huh-7) cells (IC50, 18.1 μM; the median cytotoxic concentration CC50, 46.6 μM) [17]. Ten new compounds, including 10α-hydroxyeremophil-7(11)-en-2,3:12,8-diolide (26), 1β-acetoxy-10α,13-dihydroxyeremophil-7(11)-en-12,8β-olide (27), 1α,10α-epoxy-2α,13-dihydroxyeremophil-7(11)-en-12,8β-olide (28), 1α,10α-epoxy-2β,13-dihydroxyeremophil-7(11)-en-12,8β-olide (29), 1α,10α-epoxy-3α,13-dihydroxyeremophil-7(11)-en-12,8β-olide (30), 1α,10α-epoxy-3β,13-dihydroxyeremophil-7(11)-en-12,8β-olide (31), 1α,10α:2α,3α-diepoxyeremophil-7(11)-en-12,8β-olide (32), 2-oxo-13-hydroxyeremophila-1(10), 7(11)-dien-12,8β-olide(13-hydroxyxylareremophil(33), 7-epi-tessaric acid (34), and 2β-hydroxyeremophila-1(10), 11(13)-dien-12-oic acid (35), were isolated from the mangrove-derived fungus Xylaria sp. BCC 60405. Compound 31 showed cytotoxic activity against Vero cells (IC50, 49.6 μg/mL) [18]. Five new compounds, including xylcarpins A–E (36–40), were obtained from Xylaria carpophila (Pers.) [19]. Four new compounds, including xylarioxides A–D (41–44), were isolated from the Azadirachta indica-derived fungus Xylaria sp. YM 311647. Compound 41 exhibited inhibitory activity against two pathogenic fungi including Curvularia lunata and Botrytis cinerea, with MIC values of 8 and 16 μg/mL, respectively. Compounds 42 and 43 displayed inhibitory activity against two pathogenic fungi including C. lunata and Alternaria alternata, with the same MIC value of 16 μg/mL [20]. One new eremophilane sesquiterpene, xylareremophil (45), was obtained from the leaves of the Sophora tonkinensis-derived Xylaria sp. (GDG-102). Compound 45 displayed weak antibacterial activity against Micrococcus luteus and Proteus vulgaris, with the same MIC value of 25 μg/mL [21]. Three new esquiterpenes, including xylarenones A (46) and B (47) and xylarenic acid (48), were obtained from the Torreya jackii-derived fungus Xylaria sp. (NCY2). Compounds 46, 47, and 48 displayed cytotoxicity against HepG2 cell lines, with IC50 values of 8.7, 23.8, and 2.63 μg/mL, respectively. Also, 46, 47, and 48 showed inhibitory activity against HeLa cells, with IC50 values of 27.8, 21.1, and 19.9 μg/mL, respectively [22]. Five new guaiane sesquiterpenes, including (1S,2S,4S,5S,7R,10R)-guaiane-2,10,11,12-tetraol (49), (1S,2S,4S,5S,7R,10R)-guaiane-2,4,10,11,12-pentaol (50), (1S,4R,5S,7R,10R)-guaiane-4,5,10,11,12-pentaol (51), (1R,4S,5R,7R,10R)-guaiane-1,5,10,11,12-pentaol (52), and (1R,4R,5R,7R,10R)-11-Methoxyguaiane-4,10,12-triol (53), were isolated from the plant Azadirachta indica-derived fungus Xylaria sp. (YM311647). Compounds 49–53 displayed moderate or weak activities against two pathogenic fungi including Pyricularia oryzae and Hormodendrum compactum, with MIC values ranging from 32 to 256 μg/mL. Compound 52 showed potent antifungal activity against P. oryzae with an MIC value of 32 μg/mL. Compounds 51 and 52 exhibited antifungal activity against H. compactum with an MIC value of 32 μg/mL. Compounds 51 and 52 showed antifungal activity against C. albicans with an MIC value of 32 μg/mL. Also, 51 displayed inhibition activity against C. albicans, A. niger, and H. compactum, with the same MIC value of 64 μg/mL [23]. Eight new eremophilane-type sesquiterpenoids, including 1β,7α,10α-trihydroxyeremophil-11(13)-en-12,8β-olide (54), 7α,10α-Dihydroxy-1β-methoxyeremophil-11(13)-en-12,8β-olide) (55), and 1α,10α-epoxy-7α-hydroxyeremophil-11(13)-en-12,8β-olide (56), 1β,10α,13-trihydroxyeremophil-7(11)-en-12,8-olide (57), 10β,13-dihydroxy-1 -methoxyeremophil-7(11)-en-12,8β-olide (58), mairetolide F (59), 1β,10α-epoxy-13-hydroxyeremophil-7(11)-en-12,8β-olide (60), and 1β,10α-epoxy-3-hydroxyeremophil-7(11)-en-12,8β-olide (61), were purified from the palm Licuala spinose-derived fungus Xylaria sp. (BCC 21097). Compounds 54–56, with α-methylene-γ-lactone skeletons, exhibited potent cytotoxicity against human oral epidermal carcinoma KB, human breast cancer MCF-7, NCI-H187, and African green monkey kidney fibroblast Vero cell lines, with IC50 values ranging from 0.066 to 15 μM. Compounds 55 and 56 also exhibited antimalarial activity against P. falciparum K1 with IC50 values of 8.1 and 13 μM, respectively. Also, 56 showed antifungal activity against C. albicans with an IC50 value of 7.8 μM, suggesting that epoxide functionality may play an important role in antifungal activity [24]. Four new 12,8-eudesmanolides, including 3α,4α,7β-trihydroxy-11(13)-eudesmen-12,8-olide (62), 4α,7β-dihydroxy-3α-methoxy-11(13)-eudesmen-12,8-olide (63), 7β-Hydroxy-3,11(13)-eudesmadien-12,8-olide (64), and 13-Hydroxy- 3,7(11)-eudesmadien-12,8-olide (65), were isolated from an unidentified seed-derived fungus Xylaria ianthinovelutina (Mont.). Compounds 62–65 showed cytotoxic activity against NCI-H187, KB, and MCF-7 cell lines, with IC50 values varying range from 0.78 to 19.15 µg/mL. Compound 64 also showed antimalarial activity against the P. falciparumm K-1 strain with an IC50 value of 2.27 μg/mL [25]. Two new presilphiperfolane sesquiterpenes, including 9,15-dihydroxy-presilphiperfolan-4-oic acid (66) and 15-acetoxy-9-hydroxy-presilphiperfolan-4-oic acid (67), were isolated from the leaves of the Piper aduncum-derived fungus Xylaria sp. [26]. Three new eremophilane sesquiterpenes (68–70) were isolated from the mangrove-derived fungus Xylaria sp. BL321 [27]. Five sesquiterpenes, including four oxygenated guaiane-type sesquiterpenes, xylaguaianols A−D (71–74), and an iso-cadinane-type sesquiterpene isocadinanol A (75), were isolated from the moss Hypnum sp.-derived fungus Xylaria sp. NC1214 [28]. Nine new oxygenated guaiane-type sesquiterpenes, including (1S,4S,5R,7R,10R,11R)-guaiane-5,10,11,12-tetraol (76), (1S,4S,5R,7R,10R,11S)-guaiane-1,10,11,12-tetraol (77), (1S,4S,5R,7R,10R,11S)-guaiane-5,10,11,12-tetraol (78), (1S,4S,5S,7R,10R,11R)-guaiane-1,10,11,12-tetraol (79), (1R,3S,4R,5S,7R,10R,11S)-guaiane-3,10,11,12-tetraol (80), (1R,3R,4R,5S,7R,10R,11R)-guaiane-3,10,11,12-tetraol (81), (1R,4S,5S,7S,9R,10S,11R)-guaiane-9,10,11,12-tetraol (82), (1R,4S,5S,7R,10R,11S)-guaiane-10,11,12-triol (83), and (1R,4S,5S,7R,10R,11R)-guaiane-10,11,12-triol (84) were isolated from the Azadirachta indica-derived fungus Xylaria sp. YM 311647. Compounds 76–84 were evaluated for their antifungal activities against Candida albicans, Aspergillus niger, Pyricularia oryzae, Fusarium avenaceum, and Hormodendrum compactum, with MIC values ranging from 32 to 512 μg/mL. Compounds 77 and 82 were the most potent ones against C. albicans with the same MIC value of 32 μg/mL. Compounds 77 and 79, with the same substituted position of hydroxy groups, exhibited the most potent inhibitory activity against A. niger with the same MIC value of 64 μg/mL [29] (Figure 1).

2.1.2. Diterpenes

Three new isopimarane diterpene derivatives, including xylongoic acids A–C (85–87), were isolated from the Fomitopsis betulina-derived fungus Xylaria longipes HFG1018 (Figure 2) [30]. One new diterpenoid, cubentriol (88), was isolated from the L. akoensis Hayata (Lauraceae)-derived fungus Xylaria cubensis. Two new compounds, including hypoxyterpoids A (89) and B (90), were separated from the mangrove Bruguiera gymnorrhiza-derived fungus Hypoxylon sp. (Hsl2–6). Compound 89 showed moderate α-glucosidase inhibitory activity (IC50, 741.5 ± 2.83 µM) [31]. Compounds xylarianes A (91) and B (92) were obtained from Xylaria sp. 290, collected from Guizhou province, China [32]. Compounds spiropolin A (93) and myrocin E (94), with isopimarane-type skeletons, were isolated from the root of Mt. Gassan Xylaria polymorpha, Yamagata Prefecture, Japan [33]. Eighteen new diterpenes, including xylarinorditerpenes A–R (95–112) with nor-isopimarane skeletons, were isolated from the wood-rotting basidiomycete Fomitopsis betulinus-derived fungus Xylaria longipes HFG1018. Compounds 96–99, 103, and 108 showed immunosuppressive activity, with IC50 values varying from 1.0 to 51.8 μM [34]. Two new bioactive compounds, including acanthoic acid (113) and 3β,7β-dihydroxyacanthoic acid (114), were isolated from the fungus Xylaria sp. (EJCP07). Compound 114 demonstrated activity against Bacillus subtilis, with an MIC of 31.25 µg/mL. Also, 114 showed activity against Escherichia coli, with an MIC of 31.25 µg/mL. Both 113 and 114 exhibited the same MIC value of 62.5 µg/mL against Salmonella typhimurium [35]. Three new diterpene glycosides, including xylarcurcosides A–C (115–117) with isopimarane-type skeletons, were isolated from the Alpinia zerumbet-derived fungus Xylaria curta YSJ-5 [36]. Three new isopimarane diterpene glycosides, including 16-α-D-mannopyranosyloxyisopimar-7-en-19-oic acid (118), 15-hydroxy-16-α-D-mannopyranosyloxyisopimar-7-en-19-oic acid (119), and 16-α-D-glucopyranosyloxyisopimar-7-en-19-oic acid (120), were isolated from the fruit bodies of the fungus Xylaria polymorpha. Compounds 118–120 exhibited cytotoxicity against HL60, K562, HeLa, and lymph node carcinoma of the prostate (LNCaP) cell lines with IC50 values of 71–607 μM, respectively [37]. Two new isopimarane diterpenoids, including xylabisboeins A (121) and B (122), were isolated from the fungus Xylaria sp. SNB-GTC2501 [38]. Three new isopimarane diterpenes, including 14α,16-epoxy-18-norisopimar-7-en-4α-ol (123), 16-O-Sulfo-18-norisopimar-7-en-4α,16-diol (124), and 9-deoxy-hymatoxin A (125), were isolated from the A. indica-derived fungus Xylaria sp. YM 311647. Compound 124 exhibited inhibitory activity against P. oryzae with an MIC value of 32 μg/mL, while 125, with a γ-lactone moiety and a sulfate group, showed the most potent activity against C. albicans and P. oryzae, with an MIC value of 16 μg/mL, and against A. niger, with an MIC value of 32 μg/mL, respectively [29]. Two novel diterpenes, including xylarilongipins A (126) and B (127) with an unusual cage-like bicyclo [2.2.2]octane moiety, were isolated from the medicinal plant Fomitopsis betulinus-derived fungus Xylaria longipes HFG1018. Compound 127 displayed moderate inhibitory activity against the cell proliferation of concanavalin A-induced T lymphocytes and lipopolysaccharide-induced B lymphocytes, with IC50 values of 13.6 and 22.4 μM, respectively [39] (Figure 2).

2.1.3. Triterpenoid

Two new antibacterial terpenoids, including xylarioxides E–F (128–129), were isolated from the Azadirachta indica-derived fungus Xylaria sp. YM 311647 (Figure 3). Compound 128 displayed strongest inhibitory activity against G. saubinetii, C. lunata, and C. gloeosporioides (MIC, 8.0, 8.0, and 16.0 μg/mL). Compound 129 showed antibacterial activity against A. alternata, C. lunata, and Colletotrichum gloeosporioides (MIC, 8.0, 8.0, and 16.0 μg/mL) [20]. Compounds kolokosides A–D (130–133) were isolated from the Hawaiian wood-decay fungus Xylaria sp. Compound 130 exhibited antibacterial activity against B. subtilis and S. aureus at 200 µg/disk (inhibition zones: 16 and 12 mm, after 48 h, respectively) [40] (Figure 3).

2.2. Nitrogen-Containing Compounds

Nitrogen-containing compounds, including cytochalasan alkaloids and other nitrogen-containing metabolites, are notable for their exceptionally diverse class of secondary metabolites and potent bioactivities. A total of 112 new nitrogen-containing compounds were discovered from the genus Xylaria sp., including 67 cytochalasan alkaloids, and 45 other nitrogen-containing metabolites. Among them, 41 compounds showed cytotoxic activities, antibacterial activities, anti-inflammatory activities, enzyme-inhibitory activities, and other activities.

2.2.1. Cytochalasan Alkaloids

Four new cytochalasans, including lagambasines A–D (134–137), were isolated from the Palicourea elata-derived fungus Xylaria sp. WH2D4 (Figure 4) [41]. One new compound karyochalasin A (138) was isolated from the fungus X. karyophthora [42]. Six new cytochalasins, including curtachalasins X1-X6 (139–144), were obtained from the plant Solanum tuberosum-derived fungus Xylaria curta E10. Compounds 139 and 143 showed cytotoxic activity against MCF-7 cell lines with IC50 values of 2.03 and 0.85 µM, respectively [43]. Two new cytochalasins, including 19,20-epoxycytochalasin Q (145) and deacetyl-19,20-epoxycytochalasin Q (146), were isolated from the wood-derived fungus Xylaria obovate. Compounds 145 and 146 displayed toxicity toward brine shrimp with the same LC50 values of 2.5 μg/mL, cytotoxic activity to HL-60 cell lines at the concentration of 1 μg/mL, and cytotoxicity against Vero cells with IC50 values of 0.46 and 1.9 μg/mL, respectively) [44]. Six new eytoehalasins, including 19,20-epoxycytochalasin R (147), 18-deoxy-19,20-epoxycytochalasin R (148), 18-deoxy-19,20-epoxycytochalasin Q (149), 19,20-epoxycytochalasin N (150), 19,20-epoxycytochalasin C (151), 21-acetylengleromycin (152) were isolated from the soil-derived fungus Xylaria hypoxylon [45]. Five new compounds 6,12-epoxycytochalasin D (153), 6-epi-cytochalasin P (154), 7-O-acetylcytochalasin P (155), 7-oxo-cytochalasin C (156), and 12-hydroxylcytochalasin Q (157), were isolated from the fungus Xylaria longipes (Ailao Moutain) [46]. One new cytochalasin, curtachalasin Q (158), was isolated from the fungus Xylaria sp. DO1801 [47]. Nine new epoxycytochalasans, including 19-epi-cytochalasin P1 (159), 6-epi-19,20-epoxycytochalasin P (160), 7-O-acetyl-6-epi-19,20-epoxycytochalasin P (161), 7-O-acetyl-19-epi-cytochalasin P1 (162), 6-O-acetyl-6-epi-19,20-epoxycytochalasin P (163), 7-O-acetyl-19,20-epoxycytochalasin C (164), 7-O-acetyl-19,20-epoxycytochalasin D (165), deacetyl-5,6-dihydro-7-oxo-19,20-epoxycytochalasin C (166), and 18-deoxy-21-oxo-deacetyl-19,20-epoxycytochalasin N (167), were isolated from the Solanum tuberosum-derived fungus Xylaria cf. Curta. Compounds 159, 161, and 165 showed strong cytotoxicity against HL-60 cell lines, with IC50 values of 13.31, 37.16, and 25.83 μM, respectively. Compound 162 showed potent inhibitory effects against MCF-7 cell lines with an IC50 value of 26.64 μM [48]. New compounds, including arbuschalasins A–D (168–171), were isolated from the Bruguiera gymnorrhiza-derived fungus Xylaria arbuscula GZS74 [49]. Two new open-chain cytochalasins, including xylarchalasins A and B (172 and 173), were isolated from the Sophora tonkinensis-derived fungus Xylaria sp. GDGJ-77B. Compound 173 displayed antibacterial activities against B. subtilis and E. coli with MIC values of 25 and 12.5 μg/mL, respectively [50]. Curtachalasins A (174) and B (175) were extracted from the stem of the Solanum tuberosum-derived fungus Xylaria curta (E10). Compounds (174 and 175) showed weak antibacterial activity against M. gypseum (70.3 and 68.4%, respectively, at the concentration of 200 μM) [51]. A new cytochalasin, cytochalasin P1 (176), was isolated from the marine-derived fungus Xylaria sp. SOF11 from the South China Sea. Compound 176 exhibited potent cytotoxicity against central nervous system carcinoma (SF-268) and MCF-7 cell lines with IC50 values of 1.37 and 0.71 μM, respectively [52]. Two new cytochalasins, including 18-deoxycytochalasin Q (177) and 21-O-deacetylcytochalasin Q (178), were isolated from the marine sediment-derived fungus Xylaria sp. SCSIO156. Compound 178 showed weak cytotoxicity against SF-268 and non-small cell lung cancer NCI-H460 cell lines, with MIC values of 44.3 and 96.4 μM, respectively [53]. A new cytochalasan alkaloid, xylastriasan A (179), with a rare 5/6/6/5/6 pentacyclic skeleton, was isolated from the fruiting bodies of the fungus Xylaria striata. Compound 179 showed weak cytotoxic activity against human hepatoma (HepG2), mouse melanoma (B16), and A549 cell lines with IC50 values of 93.61, 85.61, and 91.58 μM, respectively [54]. A new cytochalasin, cytochalasin H2 (180), obtained from the Annona squamosa-derived fungus Xylaria sp. (A23), exhibited weak cytotoxicity against HeLa and human non-hepatic 293T cells with 25.04 and 32.8% inhibition ration at the concentration of 1.0 μg/mL, respectively [55]. A halogenated hexacyclic cytochalasan, xylarichalasin A (181), with unprecedented 6/7/5/6/6/6 fused polycyclic skeletons, was obtained from the Solanum tuberosum-derived fungus Xylaria cf. curta. Compound 181 showed cytotoxicity against five human cancer cell lines including HL-60, A-549, human hepatocellular carcinoma (SMMC-7721), MCF-7, and human colon cancer (SW480) cells, with IC50 values of 17.3, 11.8, 8.6, 6.3, and 13.2 μM, respectively [56]. Two new cytochalasins, including cytochalasins D1 (182) and C1 (183) possessing a unique eleven-membered macrocycle with an oxygen bridge, were isolated from the Solanum tuberosum-derived fungus Xylaria cf. curta. Compounds 182 and 183 showed moderate cytotoxicity against human leukemia cell lines HL-60 with IC50 values of 12.7 and 22.3 μM, respectively [57]. Five new cytochalasans (184–188) were isolated from the fungus Xylaria longipes [46]. Eleven new cytochalasins, including curtachalasins F–P (189–199), were isolated from the Solanum tuberosum-derived fungus Xylaria cf. curta. The immunosuppressive assay against concanavalin A (ConA) induced T lymphocyte cell proliferation and lipopolysaccharide (LPS) induced B lymphocyte cell proliferation showed that 189 had significant selective inhibition on B-cell proliferation (IC50, 2.42 μM) and 198 had selective inhibition on T-cell proliferation (IC50, 12.15 μM). These results provide new clues to fulfill the urgent demand for new immunosuppressive drugs [58]. A new cytochalasin derivative, xylarisin B (200), was isolated from the mangrove-derived fungus Xylaria sp. HNWSW-2 [59] (Figure 4).

2.2.2. Other Nitrogen-Containing Metabolites

One new alkaloid, akodionine (201), was isolated from the L. akoensis Hayata-derived fungus Xylaria cubensis (Figure 5) [11]. A new compound, xylactam B (202), was isolated from young healthy leaves of the Tectaria zeylanica-derived fungus Xylaria sp. [60]. A novel alkaloid, xylarialoid A (203), containing a [5,5,6] fused tricarbocyclic rings and a 13-membered macrocyclic moiety, was isolated from the leaves of the plant Rauvolfia vomitoria-derived fungus Xylaria arbuscula. Compound 203 exhibited potent cytotoxic activity against human A549 and HepG2 cell lines, with IC50 values of 14.6 and 15.3 µM, respectively. Also, 203 showed strong anti-inflammatory activity against LPS-induced nitric oxide (NO) production in RAW 264.7 cells, with an IC50 value of 6.6 µM [61]. One new compound, 2,3-dihydroxy-N-methoxy-6-propylbenzamide (204), was isolated from the Hevea brasiliensis-derived fungus Xylaria sp. PSU-H182 [62]. Xylopyridine A (205), isolated from the mangrove-derived fungus Xylaria sp., showed a strong DNA-binding affinity toward calf thymus (CT) DNA presumably via an intercalation mechanism [63]. A new compound, (Z)-3-{(3-acetyl-2-hydroxyphenyl) diazenyl}-2,4-dihydroxybenzaldehyde (206), was isolated from the lichen host Amandinea medusulina-derived fungus Xylaria psidii. Compound 206 showed moderate cytotoxicity against human lung cancer (NCI-H292) cell lines (IC50, 27.2 µg/mL) [64]. Xylanigripones A–C (207–209) were isolated from Xylaria nigripes (KL.) SACC. Compound 209 showed inhibitory activity against acetylcholinesterase (AChE) up to 38.1% at the concentration of 50 μM (positive control tacrine with 45.4% inhibition rate). Compound 209 exhibited inhibition of Cholesteryl Ester Transfer Protein activity with inhibition rates of 49% [65]. Xylariahgin F (210) was isolated from the Isodon sculponeatus-derived fungus Xylaria sp. [66]. Two new compounds, including (4S)-3,4-dihydro-4-(4-hydroxybenzyl)-3-oxo-1H-pyrrolo [2,1-c][1,4]oxazine-6-carbaldehyde (211) and methyl (2S)-2-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]-3-(4-hydr-oxyphenyl)propanate (212), were isolated from the Wuling Shen-derived fungus Xylaria nigripes [67]. A new cerebroside, allantoside (213), was isolated from Xylaria allantoidea SWUF76, and the fungus was collected from Phukhieo Wildlife Sanctuary [68]. Eight new compounds, including sinuxylamides A–D (214–217), assinuxylamide E (218), 4-(7,8-dihydroxy-4-oxoquinazolin-3(4H)-yl)butanoic acid (219), 4-(8-Hydroxy-4-oxoquinazolin-3(4H)-yl)butanoic acid (220), and 3,4-dihydroisocoumarin derivative 1′-N-Acetyl-5-methylmellein (221), were obtained from the Sinularia densa-derived fungus Xylaria sp. FM1005. Compounds 214 and 215 strongly inhibited the binding of fibrinogen to purified integrin IIIb/IIa in a dose-dependent manner, with IC50 values of 0.89 and 0.61 μM, respectively, and did not show cytotoxicity against human epithelial ovarian cancer A2780 and HEK 293 cells at 40 μM [69]. One new amide derivative, xylariamide (222), was isolated from the Garcinia hombroniana-derived fungus Xylaria plebeja PSU-G30 [70]. Compound xylaramide (223), isolated from the wood-inhabiting ascomycete Xylaria longipes, possessed potent antifungal activity against Nematospora coryli and Saccharomyces cerevisiae, with MIC values of 1.0 and 5.0 µg/mL, respectively [71]. Compound 2,5-diamino-N-(1-amino-1-imino-3-methylbutan-2-yl) pentanamide (224) was isolated from the fungus Xylaria cf. cubensis SWUF08–86 [72]. Compound xylariamino acid A, (225), a new amino acid derivative, was isolated from Xylaria nigripes (Kl.) Sacc. (Xylariaceae). The fungus was collected from Ailao Moutain, China [73]. Two new spirocyclic pyrrole alkaloids, including xylapyrrosides A (226) and B (227), were isolated from the Wuling Powder-derived fungus Xylaria nigripes. Compounds 226 and 227 were successfully synthesized, representing the first total synthesis of such spiroketal alkaloids with a pyranose ring. Compound 226 displayed antibacterial activity against B. anthracis, B. megaterium, B. subtilis, S. aureus, E. coli, S. dysenteriae, and S. paratyphi, with MIC values of 50, 25, 12.5, 25, 12.5, 25, and 25 μg/mL, respectively [74]. Two novel alkaloids, including (±)-xylaridines A (228) and B (229), were isolated from the genus Xylaria longipes Nitschke. Compound 228 possesses a 5/6/6/5/5 fused ring system with a unique 2-azaspiro [4.4]nonane substructure. Compound 228 showed weak antibacterial activity against P. aeruginosa with an MIC value of 128 μg/mL, while 229 displayed activity against S. entericawith with an MIC value of 93 μg/mL [75]. One new compound, (−)-xylariamide A (230), was isolated from the outer bark of the Glochidion ferdinandi-derived fungus Xylaria sp. Compound 230 displayed toxicity against brine shrimp (Artemia salina) with 0% and 71% lethality at the concentrations of 20 and 200 μg/mL, respectively [76].
Cyclotripeptide X-13 (231) and its derivatives xyloallenoide A (232), xyloallenoide A1 (233), and cyclotripeptide X-13a (234), were isolated from the mangrove-derived fungus Xylaria sp. (No. 2508). Compound 232 and its diastereomer 233 were totally synthesized. Compound 231 and its derivatives 232–234 concentration-dependently promoted angiogenesis in zebrafish in vivo and endothelial cell cultures in vitro. Compound 231 dose-dependently induced angiogenesis in zebrafish embryos and human endothelial cells, indicating that 231 possesses potent angiogenic properties that are promising for development as a novel class of pro-angiogenic agents for angiotherapy [77,78]. Xylaroamide A (235), isolated from Xylaria sp. 218–066, exhibited cytotoxic activity against human basal-like breast cancer (BT-549) and human colon cancer (RKO) cell lines with IC50 values of 2.5 and 9.5 μM, respectively. This fungus was isolated from a sample of Usnea sp. collected from Linzhi, Tibet, China [79]. Two new cyclopeptides, including xylarotides A (236) and B (237), were isolated from Xylaria sp. 101. The fungus was collected from the fruiting body of Xylaria sp. collected from Gaoligong Mountain, China [80]. Two new cyclopentapeptides, including xylapeptide A (238) with an uncommon L-pipecolinic acid moiety and xylapeptide B (239), were isolated from the Sophora tonkinensisan-derived fungus Xylaria sp. GDG-102. Compounds 238 and 239 were totally synthesized, and 238 showed moderate activity against B. cereus and B. subtilis, with the same MIC value of 125 µg/mL [81]. Three new proline-containing cyclic nonribosomal peptides, including ellisiiamides A–C (240–242), were isolated from the blueberry Vaccinium angustifolium-derived fungus Xylaria ellisii. Compound 240 showed modest inhibitory activity against E. coli, with an MIC value of 100 μg/mL [82]. Two new cyclic pentapeptides, including cyclo(N-methyl-L-Phe-L-Val-D-Ile-L-Leu-L-Pro) (243) and cyclo(L-Val-D-Ile-L-Leu-L-pro-D-Leu) (244), were isolated from the lichen Leptogium saturninum-derived fungus Xylaria sp. Compound 243 showed synergistic antifungal activity against C, albicans SC5314 with an MIC value of 0.004 μg/mL [83]. A new cyclic pentapeptide, pentaminolarin (245), was isolated from the wood-decaying fungus Xylaria sp. (SWUF08–37). Compound 245 showed weak cytotoxic activity against Vero, HeLa, HT29, HCT116, and MCF-7 cell lines, with IC50 values of 67.89, 44.98, 31.92, 37.98, and 14.62 μg/mL, respectively [84] (Figure 5).

2.3. Polyketides

Polyketides are a class of compounds characterized by their exceptionally diverse structures and bioactivities. Polyketides are generated through a series of Claisen condensation reactions involving acetyl-CoA, malonyl-CoA, and so on. A total of 70 new polyketides were discovered from the genus of Xylaria sp., and 23 of them had cytotoxic activities, antibacterial activities, anti-inflammatory activities, enzyme-inhibitory activities, and so on.
Two new cyclohexenones, including xylariacyclones A (246) and B (247), were isolated from the Garcinia hombroniana-derived fungus Xylaria plebeja PSU-G30 (Figure 6) [74]. A new compound, xylarianin B (248), was isolated from the Panax notoginseng-derived fungus Xylaria sp. SYPF 8246 [85]. One new compound, xylariaone (249), was isolated from the fungal strain Xylaria sp. 12F075 [86]. A pair of new chromone derivatives, including (+)-xylarichromone A (250) and (−)-xylarichromone A (251), were isolated from the fungus Xylaria nigripes (Ailao Moutain, China). The neuroprotective effects of 250 against oxygen and glucose deprivation (OGD)-induced pheochromocytoma-12 cell (PC12) injury were tested, and it was found that 255 significantly enhanced PC12 cell line viability and inhibited apoptosis at the concentrations of 0.1 and 1 µM [87]. Five new 2,5-diarylcyclopentenones, including xylariaones A1-B2 (252–255) and xylaripyone H (256), were isolated from the Cudrania tricuspidata-derived fungus Xylaria sp. [88]. One new azaphilone derivative, xylariphilone (257), was isolated from the seagrass Halophila ovalis-derived fungus Xylaria sp. PSU-ES163 [89]. Three new dimeric chromanones, including xylaromanones A–C (258–260), and one new cyclohexenone, (R)-4-Hydroxy-2-ethyl-2-cyclohexen-1-one (261), were isolated from the lamina of the Hevea. Brasiliensis-derived fungus Xylaria sp. PSU-H182 [62]. A new tetralone derivative, 3,4,5-trihydroxy-1-tetralone (262), was isolated from termite nest-derived fungus Xylaria sp. [14]. One new compound, hemi-cycline A (263), was isolated from the fungus Xylaria cf. cubensis SWUF08-86 (Phu Khieo Wildlife Sanctuary, Thailand) [76]. A new 2H-chromene derivative, hexacycloxylariolone (264), isolated from the plant-associated fungus Xylaria sp., showed inhibitory effects on the growth of THP-1 cells with an IC50 value of 82.3 µg/mL [90]. Two new γ-pyrones, including xylaropyrones B (265) and C (266), were isolated from the Spartina maritima-derived fungus Xylaria sp. SC1440 [91]. Two new benzoquinone metabolites, including 2-chloro-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione (267) and xylariaquinone A (268), were isolated from the Sandoricum koetjape-derived fungus Xylaria sp. Compounds 266 and 267 showed activity against P. falciparum, K1 strain, with IC50 values of 1.84 and 6.68 µM, respectively. Compound 266 also showed cytotoxicity against Vero cells with an IC50 value of 1.35 µM [92]. Ten new compounds, including xylanthraquinone (269), xyloketals A–H (270–277), and xyloketal J (278), were isolated from the mangrove-derived fungus Xylaria sp. (No. 2508). Compounds 270–278 shared identical 5,6-bicyclic acetal moieties fused to a benzene ring in the center. Compounds 270–278 were able to act in a number of different disease models due to the similarity in the underlying pathological mechanisms, including oxidative stress, NO disturbance, intracellular Ca2+ imbalance, and protein aggregation. Compound 271 also showed alleviation of lipid accumulation in a non-alcoholic fatty liver disease model, and treatment with this compound also induces glioblastoma cell death [93,94,95,96,97,98]. Eleven new chromanones, including paecilins F–P (279–289), were isolated from the potato tissue-derived fungus Xylaria curta E10. Compounds 285 and 287 showed antibacterial activity against E. coli with the same MIC value of 16 µg/mL [99]. Three new azaphilone derivatives, including rubiginosins A–C (290–292), were isolated from the Fraxinus excelsior-derived fungus Xylariaceus ascomycete [100]. One new compound, xylaphenoside A (293), was obtained from the Selaginella moellendorffii-derived fungus Xylaria sp. CGMCC No. 5410 and showed antimicrobial activity against S. aureus, with an IC50 value of 6.2 µg/mL [101]. Three cyclohexenoneesordaricin derivatives, including xylarinonericins A–C (294–296), were isolated from the G. hombroniana-derived fungus Xylaria plebeja PSU-G30 [71]. Three new azaphilone derivatives, including rubiginosins A–C (297–299), were isolated from the fruit bodies of Xylariaceus ascomycete [102]. Three new polyketides, including 1,3,8-Trihydroxy-7-methoxy-9-methyldibenzofuran (300) (6S,2′R,6′S)-6-Methyl-2-((6-methyltetrahydro-2H-pyran-2-yl)methyl)-2,3-dihydro-4H-pyran-4-one (301), and (2′R,6′S)-5-((-6-Methyltetrahydro-2H-pyran-2-yl)methyl)benzene-1,3-diol (302), were isolated from the Geophila repens-derived fungus Xylaria feejeensis. Compound 300 showed cytotoxic activity against Vero cells and the HCT116, HT29, MCF-7, and HeLa cell lines with IC50 values of 25.00, 14.36, 8.99, 18.40, and 16.68 µg/mL, respectively. Compound 302 showed cytotoxic activity against HCT116, HT29, MCF-7, and HeLa with IC50 values of 17.50, 19.49, 50.24, and 13.53 µg/mL [103]. Two new compounds, including 6′,7′-didehydrointegric acid (303) and 13-carboxyintegric acid (304), were isolated from the Geophila repens-derived fungus Xylaria feejeensis [104]. One new compound (4S,5S,6S)-5,6-epoxy-4-hydroxy-3-methoxy-5-methyl-cyclohex-2-en-1-one (305), was isolated from the fungus Xylaria carpophila, which was collected from Gaoligong Mountains in Yunnan Province. Compound 305 showed significant specific cytotoxicity against the HL-60, A-549 MCF-7, and SW480 cell lines, with IC50 values of 23.1, 35.7, 28.5, and 29.0 μM, respectively [19]. Two new tetralone derivatives, including xylariol A (306) and B (307), were isolated from the fresh stems of the Ligustrum lucidum-derived fungus Xylaria hypoxylon AT-028. Compounds 306 and 307 showed moderate cytotoxic activities against HepG2 cells, with IC50 values of 22.3 and 21.2 μg/mL, respectively [105]. One new polyketide, 1-(xylarenone A)xylariate A (308), was isolated from the medicinal Torreya jackii-derived fungus Xylaria sp. NCY2 [106]. Two new polyketides, including schweinitzins A (309) and B (310), were isolated from the fungus Xylaria schweinitzii Berk. and M.A. Curtis. Compound 309 exhibited cytotoxicity against KB, Hep-G2, human lung adenocarcinoma (SK-Lu-1), and MCF-7 cell lines with IC50 values of 0.72, 2.13, 2.32, and 4.09 μg/mL, respectively [107]. Two new polyketides, including 6-ethyl-8-hydroxy-4H-chromen-4-one (311) and 6-ethyl-7,8-dihydroxy-4H-chromen-4-one (312), were isolated from the fungus Xylaria sp. SWUF09-62. Compound 312 exhibited anti-inflammatory properties by reducing nitric oxide production in LPS-stimulated RAW264.7 cells, with an IC50 value of 1.57 ± 0.25 μg/mL, and cytotoxicity against HT29 cells, with an IC50 value of 16.46 ± 0.48 μg/mL [108]. A novel polyketide, mellisol (313), was isolated from the fungus Xylaria mellisii (BCC 1005). Compound 313 exhibited antivirus activity against herpes simplex virus type 1, with an IC50 value of 10.50 μg/mL, and also showed cytotoxic activity against Vero cells with an IC50 value of 45.8 μg/mL [109]. A new compound, γ-pyrone-3-acetic acid (314), was obtained from a bark sample of a live oak-derived fungus Xylatia sp. [110]. One new α-pyrone, 9-hydroxyxylarone (315), was isolated from the moss Hypnum sp.-derived fungus Xylaria sp. NC1214 [28] (Figure 6).

2.4. Lactones

Lactones represent a class of compounds that contain lactone rings within their molecular structure. A total of 76 new lactones were discovered from the genus Xylaria sp. Remarkably, 32 compounds had cytotoxic activities, antioxidant activities, antibacterial activities, anti-inflammatory activities, enzyme-inhibitory activities, and so on.
One new compound, xylarolide (316), was isolated from the fungus Xylaria sp. 101, which was isolated from the fruiting body of Xylaria sp. collected from Gaoligong Mountain, China (Figure 7) [80]. One new compound, (3αS,6αR)-4,5-dimethyl-3,3α,6,6β-tetrahydro-2Hcyclopenta [β]furan-2-one (317), isolated from the fungus Xylaria curta 92092022, showed moderate antibacterial activity against S. aureus NBRC 13276 with the inhibition zone of 12 mm at a concentration of 100 μg/disk [111]. A new compound, xylarphthalide A (318), was isolated from the Sophora tonkinensis-derived fungus Xylaria sp. GDG-102. Compound 318 showed antibacterial activities against Bacillus megaterium, B. subtilis, S. aureus, E. coli, and Shigella dysenteriae, with MIC values of 12.5–25 μg/mL [112]. Two new dihydroisocoumarin glycosides, including xylarglycosides A (319) and B (320), were isolated from the Illigera celebica-derived fungus Xylaria sp. KYJ-15 and showed antibacterial activities against S. aureus with MIC values of 4 and 2 μg/mL, respectively. These compounds also exhibited 2,2-diphenyl-1-(2,4,6-trinitrophenyl) hydrazyl stable free radical (DPPH) radical scavenging activity, with IC50 values of 9.2 ± 0.03 and 13.3 ± 0.01 μM, respectively [113]. One new isocoumarin, akolitserin (321), was isolated from the L. akoensis-derived fungus Xylaria cubensis [11]. One new compound, 5-O-α-Dglucopyranosyl-5-hydroxymellein (322), obtained from the Selaginella moellendorffii-derived fungus Xylaria sp. CGMCC No. 5410, showed antimicrobial activity against S. aureus and Micrococcus luteus with IC50 values of 6.2 and 6.2 µg/mL, respectively [101]. Seven new compounds, including xylaripyone A–G (323–329), were isolated from the Cudrania tricuspidata-derived fungus Xylaria sp. Compound 326 showed moderate cytotoxic activity against PC3 cell lines, with an IC50 value of 14.75 μM. Compound 328 displayed weak inhibitory activity against NO production in RAW 264.7 murine macrophages, with IC50 values of 49.76 and 69.68 μM, respectively [98]. Four new isocoumarins, including hypoxymarins A–D (330–333), were obtained from the mangrove Bruguiera gymnorrhiza-derived fungus Hypoxylon sp. (Hsl2-6). Compound 332 showed DPPH radical scavenging activity with an IC50 value of 15.36 ± 0.24 µM, which was better than the positive control ascorbic acid (IC50, 20.49 ± 0.43 µM) [30]. A new lignanoid, xylarianolide (334), was isolated from the fungal strain Xylaria sp. [114]. Six new compounds, including xylariahgins A–F (335–340) and 3-(2,3-dihydroxypropyl)-6,8-dimethoxyiso coumarin (341), were isolated from the Isodon sculponeatus-derived fungus Xylaria sp. hg1009 [66]. Four new α-pyrones, including xylariaopyrones A–D (342–345), were isolated from the fungus Xylariales sp. (HM-1). Compounds 342 and 343 were a pair of epimers with a ketal function group. Compounds 342–345 displayed inhibiting activity against plant-pathogenic Erwinia carotovora, with MIC values ranging from 25.5 to 20.5, 22.6, and 24.7 μg/mL, respectively. Compounds 342–345 also showed brine shrimp inhibiting activity with inhibiting ratios of 42%, 76%, 84%, and 82%, respectively, at a concentration of 50 μg/mL [115]. A new compound, 3S-hydroxy-7melleine (346), was isolated from the mangrove-derived fungus Xylaria sp. (No. 2508) [116]. Two new compounds, including pestalotin 4′-O-methyl-β-mannopyranoside (347) and 3S,4R-(+)-4-hydroxymellein (348), were isolated from the Hintonia latiflora-derived fungus Xylaria feejeensis. Compound 348 inhibited Saccharomyces cerevisiae α-glucosidase (αGHY) with an IC50 value of 441 ± 23 μM, which was better than the positive control acarbose (IC50, 545 ± 19 μM) [117]. Two new compounds, including xylarellein (349) and xylariaindanone (350), were isolated from the Garcinia hombroniana-derived fungus Xylaria sp. PSU-G12 [118]. Six new α-pyrones, including xylapyrones A-F (351–356), were isolated from the Saccharum arundinaceum-derived fungus Xylaria sp. BM9 [119]. One new compound, 6-heptanoyl-4-methoxy-2H-pyran-2-one (357), isolated from the leaf of the Sophora tonkinensis-derived fungus Xylaria sp. GDG-102, showed antimicrobial activity against E. coli and S. aureus, with the same MIC value of 50 μg/mL [120]. Two lactones, including (+)-phomalactone (358) and 6-(1-propenyl)-3,4,5,6-tetrahydro-5-hydroxy-4Hpyran-2-one (359), were isolated from the Siparuna sp.-derived fungus Xylaria sp. Grev. (Xylariaceae). Compound 358 showed weak anti-plasmodial activity against P. falciparum, with an IC50 value of 13 µg/mL [121]. One new compound, xylaolide A (360), was isolated from the mangrove sediment-derived fungus Xylariaceae sp. DPZ-SY43, which was collected in Sanya [122]. Two new lactones, including (S)-8-Hydroxy-6-methoxy-4,5-dimethyl-3-methyleneisochroman-1-one (361) and (R)-7-hydroxy-3-((R)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (362), were isolated from the mangrove-derived fungus Xylaria sp. BL321 [123]. Five new α-pyrones, including xylariaopyrones E–I (363–367), were isolated from the fungus Xylaria sp. (HM-1). Compound 363 is the first example of an α-pyrone derivative with a novel [3, 2, 0] bridge ring system via a ketal function group in the side chain. Compounds 363–365 showed moderate inhibiting activities against E. coli, S. aureus, and P. aeruginosa with MIC values from 25.4 to 64.5 μg/mL, and compound 367 showed significant inhibition of monoamine oxidase B with an IC50 value of 15.6 μM [124]. Two new polyketides, including lasobutones A–B (368–369), were isolated from the Coptis chinensis-derived fungi Xylaria sp. Compound 369 showed inhibitory activity against the NO production in the LPS-induced macrophage RAW264.7, with an IC50 value of 42.5 μM [125]. One new compound, coloratin A (370), isolated from the Xylariaceous mushroom Xylaria intracolorata, showed strong antimicrobial activity against Klebsiella pneumoniae with inhibition zones of 22 mm at a dose of 50 mg per paper disk [126]. Two new compounds, including (3R)-6-methoxy-5-methoxycarbonylmellein (371) and (3S,2′R,6′R)-asperentin-8-O-methylether (372), were obtained from the medicinal plant Geophila repensfungu-derived fungus Xylaria feejeensis. Compound 371 showed cytotoxic activity against HCT116 and HT29 cell lines, with IC50 values of 92.93 and 96.42 µg/mL, respectively. Compound 372 showed cytotoxic activity against HCT116, HT29, and HeLa cell lines with IC50 values of 45.09, 67.60, and 92.93 µg/mL, respectively [93]. A new nonenolide, xyolide (373), was isolated from Xylaria feejeensis (Berk.) Fr. (E6912B), which displayed antifungal activity against the plant pathogen P. ultimum with an MIC value of 425 μM [127]. Two new 10-membered lactones, including multiplolides A (374) and B (375), were isolated from the fungus Xylaria multiplex BCC 1111. Compounds 374 and 375 exhibited antifungal activity against C. albicans with IC50 values of 7 and 2 μg/mL, respectively [128]. Four new latones, including xylariolide A (376), xylariolide B (377), xylariolide C (378), and xylariolide D (379), were isolated from the medicinal plant Torreya jackii-derived fungus Xylaria sp. NCY2 [106]. One new compound, furofurandione (380), was purified from the plant palm Licuala spinose-derived fungus Xylaria sp. (BCC 21097) [24]. One new dihydroisocoumarin, (3R,4R)-3,4-dihydro-4,6-dihydroxy-3-methyl-1-oxo-1H-isochromene-5-carboxylic acid (381), was obtained from the plant Piper aduncum-derived fungus Xylaria sp. Compound 381 exhibited antifungal activity against C. cladosporioides and C. sphaerospermum with detection limits of 10.0 and 25.0 μg, respectively. Compound 381 also exhibited AChE inhibitory activity with a detection limit of 3.0 μg [129]. Two new compounds, including (3S)-3,4-dihydro-8-hydroxy-7-methoxy-3-methylisocoumarin (382) and (3S)-3,4-dihydro-5,7,8-trihydroxy-3-methylisocoumarin (382), were isolated from the fungus Xylaria sp. SWUF09-62. Compound 383 exhibited anti-inflammatory activity by reducing NO production in LPS-stimulated RAW264.7 cells (IC50, 3.02 ± 0.27 μg/mL) and cytotoxicity against HT29 cells (IC50, 97.78 ± 7.14 μg/mL) [108]. Two new compounds, including pestalotin 4’-O-methyl-β-mannopyranoside (384) and 3S,4R-(+)-4-hydroxymellein (385), were isolated from the plant Hintonia latiflora-derived fungus Xylaria feejeensis. Compound 385 showed inhibition activity against Saccharomyces cerevisiae α-glucosidase (αGHY) with an IC50 of 441 ± 23 μM, which was better than the positive control acarbose (IC50, 545 ± 19 μM). Molecular docking predicted that 385 bound to αGHY in a site different from the catalytic domain, which could imply an allosteric type of inhibition [117]. A new phytotoxic bicyclic lactone, (3aS,6aR)-4,5-dimethyl-3,3a,6,6a-tetrahydro-2H-cyclopenta [β]furan-2-one (386), was isolated from the fungus Xylaria curta 92092022. Compound 386 showed moderate antibacterial activity against both Pseudomonas aeruginosa ATCC and S. aureus NBRC, with the same inhibition zone of 13 mm at a concentration of 100 μg/disk [111]. A new ten-membered macrolide (387) and a new α-pyrone derivative (−)-annularin C (388) were isolated from the marine sponge Stylissa massa-derived fungus Xylaria feejeensis. Compound 388 exhibited significant down-regulating activity of osteoclast cell differentiation at concentrations of 0.5 and 1 μM [130]. Two new alpha-pyrone derivatives, including xylarone (389) and 8,9-dehydroxylarone (390), were isolated from the wood-derived fungus Xylaria hypoxylon A27-94. Compound 389 displayed anti-proliferative activity against human colon adenocarcinoma (Colo320) and mouse leukemic (L1210) cell lines, with IC50 values of 40 and 50 μg/mL, respectively. Compound 390 displayed anti-proliferative activity against the Colo-320, L1210, and HL-60 cell lines, with IC50 values of 25, 25, and 50 μg/mL, respectively [131] (Figure 7).

2.5. Other Classes

There were also some other classes of secondary metabolites isolated from Xylaria spp., such as fatty acids, steroids, and benzene derivatives. A total of 54 new compounds were isolated from the genus of Xylaria sp., and 26 of them showed cytotoxic activities, antibacterial activities, anti-inflammatory activities, enzyme-inhibitory activities, and so on.
A new fatty acid, rubiginosic acid (391), was isolated from the fruit bodies of the Corylus avellana-derived fungus Xylariaceus ascomycete (Figure 8) [102]. Three new compounds, including xylarianin A (392), xylarianin C (393), and xylarianin D (394), and three new natural products, including 6-methoxycarbonyl-2′-methyl-3,5,4′,6′-tetramethoxy-diphenyl ether (395), 2-chlor-6-methoxycarbonyl-2′-rnethyl-3,5,4′,6′- tetramethoxy-diphenyl ether (396), and 2-chlor-4′-hydroxy-6-methoxy carbonyl-2′-methyl-3,5,6′-trimethoxy-diphenyl ether (397), were isolated from the Panax notoginseng-derived fungus Xylaria sp. SYPF 8246. Compounds 392 and 395–397 displayed significant inhibitory activities against Human Carboxylesterase 2 (hCE-2), with IC50 values of 10.43, 6.69, 12.36, and 18.25 µM, respectively [85]. Two new steroids, including xylarsteroids A (398) and B (399), the first examples of the C28-steroid with an unusual β- and γ-lactone ring, were isolated from the Illigera celebica-derived fungus Xylaria sp. KYJ-15. Compound 398 exhibited potent AChE inhibitory activity, with an IC50 value of 2.61 ± 0.05 μM. Compounds 398 and 399 exhibited strong antibacterial activity against B. subtilis, with the same MIC value of 2 μg/mL [114]. One aliphatic derivative, akoenic acid (400), was isolated from leaves of the L. akoensis Hayata (Lauraceae)-derived fungus Xylaria cubensis [8]. One new isovaleric acid, phenethylester (401), isolated the fungus Xylaria nigripes (Kl.) Sacc. (Xylariaceae), significantly reduced the percentage of apoptotic cells at a concentration of 1 µM [73]. One new metabolite, 3,7-dimethyl-9-(-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl) nona-1,6-dien-3-ol (402), was isolated from a Taxus mairei-derived strain. Compound 402 exhibited antibacterial activity against B. subtilis ATCC 9372 48.1%, B. pumilus 7061 31.6%, and S. aureus ATCC 25923 47.1%, at a concentration of 10 μg/mL [132]. A new fatty acid, rubiginosic acid (403), was obtained from the Fraxinus excelsior-derived fungus X. ascomycete [100]. Two new glucosides, including xylarosides A (404) and B (405), were isolated from the Garcinia dulcis-derived fungus Xylaria sp. PSU-D14 [133]. One new phenyloxolane compound, 2-methyl-2-(4-hydroxymethylphenyl) oxacyclopentane (406), was isolated from the fungus Xylaria polymorpha (Pers.: Fr.) Grer. Compound 406 showed moderate inhibitory activity against Panagrellus redivivus, with a mortality ratio of 59.6% at 2.5 mg/mL [13]. Four new alkyl aromatics, including penixylarins A–D (407–410), were isolated from a mixed culture of the fungus Penicillium crustosum PRB-2 and the mangrove-derived fungus Xylaria sp. HDN13-249. Compounds 408 and 409 showed inhibitory activity against M. phlei, B. subtilis, and V. parahemolyticus, with MIC values ranging from 6.25 to 100 μM, and compound 409 also possessed potential anti-tuberculosis effects against Mycobacterium phlei, with an MIC value of 6.25 μM [134]. One new phenylacetic acid derivative (411) and one new naphthalenedicarboxylic acid (412) were isolated from the Sinularia densa-derived fungus Xylaria sp. FM1005 [69]. A new polyalcohol xylatriol (413) was isolated from the plant-associated fungus Xylaria sp. [89]. Three new benzofurans, including acumifurans A–C (414–416), were isolated from the nests of the Odontotermes formosanus-derived fungus X. acuminatilongissima YMJ623 [135]. A new fatty acid, (2E,4E,6S)-6-hydroxydeca-2,4-dienoic acid (417), was isolated from the gorgonian-derived fungus Xylaria sp. C-2, which was collected from the South China Sea [136]. Two new steroids, including (24R)-22,23-dihydroxy-ergosta-4,6,8(14)-trien-3-one 23-β-D-glucopyranoside (418) and xylarester (419), were isolated from the fungus Xylaria sp. Compound 418 showed cytotoxicity against MCF-7 cell lines with a ratio of inhibition at 72% for a concentration of 40 μM [137]. One new compound, coloratin B (420), isolated from the Xylariaceous mushroom X. intracolorata, showed strong antimicrobial activity against K. pneumoniae, with inhibition zones of 22 mm at a dose of 50 mg per paper disk [138]. Three new methylsuccinic acid derivatives, including xylaril acids A–C (421–423), and two enoic acid derivatives, including xylaril acids D and E (424 and 425), were isolated from the fungus Xylaria longipes. Compounds 421–425 showed no toxic effects on PC12 cells at a concentration of 10 μM. Compounds 421–425 displayed neuroprotective activities against OGD/R injury in PC12 cells by enhancing cell viability and inhibiting cell apoptosis [99]. A new compound, wheldone (426), was isolated from the coculture of Aspergillus fischeri (NRRL 181) and Xylaria flabelliformis (G536). Compound 426 displayed cytotoxic activity against breast cancer MDA-MB-231, ovarian carcinoma OVCAR-3, and breast carcinoma MDA-MB-435 cell lines, with IC50 values of 7.6, 3.8, and 2.4 μM, respectively [139]. Seven new isoprenyl phenolic ethers, including fimbriethers A–G (427–433), were isolated from termite nest-derived fungus Xylaria fimbriata Lloyd (YMJ491). Compound 433 exhibited the strongest NO inhibition activity with an average maximum inhibition (Emax) of 49.7% at the concentration of 100 μM. Compounds 428 and 431 showed moderate iNOS inhibitory activity with Emax values of 31.3 and 38.9%, respectively. Research on the structure–activity relationship indicated that the methyl benzoate moiety was a possible active site [140]. Two new compounds, including xylarioic acid B (434) and xylariate C (435), were isolated from the medicinal plant Torreya jackii-derived fungus Xylaria sp. NCY2 [106]. A novel 20-norpimarane glucoside, xylopimarane (436), isolated from the fungus Xylaria sp. (BCC 4297), displayed cytotoxic activity against the KB, MCF-7, and NCI-H187 cell lines, with IC50 values of 1.0, 13, and 65 μM, respectively [141]. Two new compounds, including xylarinic acids A (437) and B (438), were isolated from the fruit body of Xylaria polymorpha (Pers.) Grev. Compounds 437 and 438 showed strong antifungal activity against P. ultinum and M. grisea with an inhibition zone of 16–20 mm diameter. They also showed antifungal activity against A. panax, A. niger, and F. oxysporium [142]. Two new succinic acid derivatives, including xylacinic acids A (439) and B (440), were isolated from the mangrove-derived fungus Xylaria cubensis PSU-MA34 [143]. A new cerebroside, allantoside (441), was isolated from the fungus Xylaria allantoidea SWUF76. The fungus was collected from Phukhieo Wildlife Sanctuary, Thailand [68]. A new fluorescent compound, ergosta-4,6,8(14),22-tetraen-3-one (442), was isolated from the fungus Xylaria sp., which was collected in Vietnam. Compound 442 showed inhibitory activity of NO production in RAW 264.7 cells stimulated by lipopolysaccharide, with an IC50 value of 28.96 µM [144]. Two new glucoside derivatives, including xylarosides A (443) and B (444), were isolated from the leaves of the Garcinia dulcis-derived fungus Xylaria sp. PSU-D14 [133]. A new compound, methyl aminobenzoate (445), was isolated from the wood-decayed fungus Xylaria sp. BCC 9653 [145].

3. Comprehensive Overview and Conclusions

In this review, the sources, structural diversity, and biological activity of secondary metabolites from Xylaria fungi are summarized, covering the period from 1994 to January 2024. A total of 445 new compounds were obtained from the genus Xylaria. A sample of 177 notable compounds and their biological activities are summarized in Table 1. The structural diversities and bioactivities of the new secondary metabolites discovered from Xylaria spp. are also shown in Figure 9.
The chemical structures of the 445 new secondary metabolites from Xylaria fungi can mainly be classified into five types, including 133 terpenoids, 112 nitrogen-containing compounds, 70 polyketones, 76 lactones, and 54 other compounds consisting of steroids, fatty acids, and benzene derivatives (Figure 9). However, among these 445 new compounds, terpenoids predominantly accounted for 29.89%, while nitrogen-containing compounds, polyketides, lactones, and other types accounted for 25.18%, 15.73%, 17.07%, and 12.13, respectively.
Moreover, it is worth noting that nearly 39.8% (177 compounds) showed broad-spectrum biological activities, including cytotoxic (52 compounds), antimicrobial (38 compounds), antifungal (30 compounds), anti-inflammatory (18 compounds), enzyme inhibition (12 compounds), immunosuppressive (10 compounds), and other activities (17 compounds). Notably, cytotoxic (29.37%), antibacterial (21.46%), and antifungal (16.95%) activities represent the top three bioactivities (Figure 9). It is important to highlight that many compounds exhibit multiple activities. For example, xyloketal B (271) is able to act in a number of different disease models in the underlying pathological mechanisms, including oxidative stress, NO disturbance, intracellular Ca2+ imbalance, and protein aggregation.
In summary, Xylaria fungi have been proven to be an important source of structured novel and diverse secondary metabolites with a broad range of biological activities, revealing their great untapped potential in medicinal and agrochemical applications. However, for most of these discovered compounds, the lack of deep pharmacological mechanisms and comprehensive pharmacokinetic evaluation limits their applications. Overall, this review shed light on the new secondary metabolites from the Xylaria fungi for their potential contributions to the future development of new natural product drugs in the agricultural and medicinal fields.

Author Contributions

C.Z. and G.H. conceived and revised this article; W.C. prepared and wrote the original draft; L.X., J.L. and C.B. conducted the literature analysis; M.Y., S.C., and T.G. reviewed and edited this article. All authors have read and agreed to the published version of the manuscript.

Funding

This work was supported by the National Natural Science Foundation of China (Nos. 32160108 and 2217702), the Key Research and Development Program of Hainan Province (No. ZDYF2024SHFZ116 and ZDYF2021SHFZ270), the Team Innovation Center for Academicians of Hainan Province, the Specific Research Fund for the Innovation Center of Hainan Province Academicians (No. YSPTZX202309), and the Key Science and Technology Program of Hainan Province (No. ZDKJ202008).

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Not applicable.

Conflicts of Interest

The authors declare no conflicts of interest.

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Jof 10 00190 g001aJof 10 00190 g001bJof 10 00190 g001c
Figure 1. Chemical structures of sesquiterpenes 1–84 from Xylaria spp.
Figure 1. Chemical structures of sesquiterpenes 1–84 from Xylaria spp.
Jof 10 00190 g001aJof 10 00190 g001bJof 10 00190 g001c
Jof 10 00190 g002aJof 10 00190 g002b
Figure 2. Chemical structures of diterpenes 85–127 from Xylaria spp.
Figure 2. Chemical structures of diterpenes 85–127 from Xylaria spp.
Jof 10 00190 g002aJof 10 00190 g002b
Jof 10 00190 g003
Figure 3. Chemical structures of triterpenoids 128–133 from Xylaria spp.
Figure 3. Chemical structures of triterpenoids 128–133 from Xylaria spp.
Jof 10 00190 g003
Jof 10 00190 g004aJof 10 00190 g004bJof 10 00190 g004c
Figure 4. Chemical structures of cytochalasans 134–200 from Xylaria spp.
Figure 4. Chemical structures of cytochalasans 134–200 from Xylaria spp.
Jof 10 00190 g004aJof 10 00190 g004bJof 10 00190 g004c
Jof 10 00190 g005aJof 10 00190 g005bJof 10 00190 g005c
Figure 5. Chemical structures of other nitrogen-containing metabolites 201–245 from Xylaria spp.
Figure 5. Chemical structures of other nitrogen-containing metabolites 201–245 from Xylaria spp.
Jof 10 00190 g005aJof 10 00190 g005bJof 10 00190 g005c
Jof 10 00190 g006aJof 10 00190 g006bJof 10 00190 g006c
Figure 6. Chemical structures of polyketides 246–315 from Xylaria spp.
Figure 6. Chemical structures of polyketides 246–315 from Xylaria spp.
Jof 10 00190 g006aJof 10 00190 g006bJof 10 00190 g006c
Jof 10 00190 g007aJof 10 00190 g007bJof 10 00190 g007c
Figure 7. Chemical structures of lactones 316–390 from Xylaria spp.
Figure 7. Chemical structures of lactones 316–390 from Xylaria spp.
Jof 10 00190 g007aJof 10 00190 g007bJof 10 00190 g007c
Jof 10 00190 g008aJof 10 00190 g008b
Figure 8. Chemical structures of polyketides 391–445 from Xylaria spp.
Figure 8. Chemical structures of polyketides 391–445 from Xylaria spp.
Jof 10 00190 g008aJof 10 00190 g008b
Jof 10 00190 g009
Figure 9. Structural diversity (left) and bioactivities (right) of secondary metabolites in the genus of Xylaria that were discovered from 1994 to January 2023.
Figure 9. Structural diversity (left) and bioactivities (right) of secondary metabolites in the genus of Xylaria that were discovered from 1994 to January 2023.
Jof 10 00190 g009
Table 1. The bioactivities of secondary metabolites 1–445 from Xylaria spp.
Table 1. The bioactivities of secondary metabolites 1–445 from Xylaria spp.
CompoundsProducing StrainsHabitatsBioactivitiesRefs
13,13-dimethoxyintegric acid (1)Xylaria sp. V-27Dead branchCytotoxicity[10]
10-hydroxythujopsene (2)Xylaria cubensis BCRC 09F 0035Litsea akoensis-[11]
Akotriol (3)Xylaria cubensis BCRC 09F 0035Litsea akoensis-[11]
Xylaritriol (4)Xylaria cubensis BCRC 09F 0035Litsea akoensis-[11]
Nigriterpenes A, B (5–6), and D–F (8–10)X. nigripes YMJ653Termite nest-[12]
Nigriterpene C (7)X. nigripes YMJ653Termite nestAnti-inflammatory activity[12]
Polymorphine A (11)Xylaria polymorpha (Pers.: Fr.)Unknown-[13]
Polymorphine B (12)Xylaria polymorpha (Pers.: Fr.)UnknownAChE inhibitory activity[13]
Xylaric acids A–C (13–15)Xylaria sp.Termite nest-[14]
Eremoxylarins A (16) and B (17)Xylaria sp. (YUA-026)Unidentified plantAntibacterial activity[15]
Eremoxylarin C (18)Xylaria allantoidea BCC 23163Decaying woodCytotoxicity[16]
Eremoxylarins D (19), F (20), and G (21)Xylaria allantoidea BCC 23163Rhizocarpon geographicumAntibacterial activity[17]
Eremoxylarin E (22) and H (23)Xylaria allantoidea BCC 23163Rhizocarpon geographicum-[17]
Eremoxylarin I (24)Xylaria allantoidea BCC 23163Rhizocarpon geographicumAntibacterial activity, cytotoxicity[17]
Eremoxylarin J (25)Xylaria allantoidea BCC 23163Rhizocarpon geographicum-[17]
10α-Hydroxyeremophil-7(11)-en-2,3:12,8-diolide (26)Xylaria sp. BCC 60404Mangrove plant-[18]
1β-Acetoxy-10α,13-dihydroxyeremophil-7(11)-en-12,8β-olide (27)Xylaria sp. BCC 60404Mangrove plant-[18]
1α,10α-Epoxy-2α,13-dihydroxyeremophil-7(11)-en-12,8β-olide (28)Xylaria sp. BCC 60404Mangrove plant-[18]
1α,10α-Epoxy-2β,13-dihydroxyeremophil-7(11)-en-12,8β-olide (29)Xylaria sp. BCC 60404Mangrove plant-[18]
1α,10α-Epoxy-3α,13-dihydroxyeremophil-7(11)-en-12,8β-olide (30)Xylaria sp. BCC 60404Mangrove plant-[18]
1α,10α-Epoxy-3β,13-dihydroxyeremophil-7(11)-en-12,8β-olide (31)Xylaria sp. BCC 60404Mangrove plantCytotoxicity[18]
1α,10α,2α,3α-Diepoxyeremophil-7(11)-en-12,8β-olide (32)Xylaria sp. BCC 60404Mangrove plant-[18]
2-Oxo-13-hydroxyeremophila-1(10),7(11)-dien-12,8β-olide (13- hydroxyxylareremophil (33)Xylaria sp. BCC 60404Mangrove plant-[18]
7-Epi-tessaric acid (34)Xylaria sp. BCC 60404Mangrove plant-[18]
2β-Hydroxyeremophila-1(10),11(13)-dien-12-oic acid (35)Xylaria sp. BCC 60404Mangrove plant-[18]
Xylcarpins A–E (36–40)Xylaria carpophila (Pers.)Unknown-[19]
Xylarioxides A–C (41–43)Xylaria sp. YM 311647Azadirachta indicaAntifungal activity[20]
Xylarioxide D (44)Xylaria sp. YM 311648Azadirachta indica-[20]
Xylareremophil (45)Xylaria sp. (GDG-102)Mangrove plantAntibacterial activity[21]
Xylarenones A (46) and B (47)Xylaria sp. (NCY2)UnknownCytotoxicity[22]
Xylarenic acid (48)Xylaria sp. (NCY2)UnknownCytotoxicity[22]
(1S,2S,4S,5S,7R,10R)-Guaiane-2,10,11,12-tetraol (49)Xylaria sp. (YM311647)Azadirachta indicaAntibacterial activity[23]
(1S,2S,4S,5S,7R,10R)-Guaiane-2,4,10,11,12-pentaol (50)Xylaria sp. (YM311647)Azadirachta indicaAntibacterial activity[23]
(1S,4R,5S,7R,10R)-Guaiane-4,5,10,11,12-pentaol (51)Xylaria sp. (YM311647)Azadirachta indicaAntibacterial, antifungal activity[23]
(1R,4S,5R,7R,10R)-Guaiane-1,5,10,11,12-pentaol (52)Xylaria sp. (YM311647)Azadirachta indicaAntibacterial, antifungal activity[23]
(1R,4R,5R,7R,10R)-11-Methoxyguaiane-4,10,12-triol (53)Xylaria sp. (YM311647)Azadirachta indicaAntibacterial activity[23]
1β,7α,10α-Trihydroxyeremophil-11(13)-en-12,8β-olide (54)Xylaria sp. (BCC 21097)Mangrove plantCytotoxicity[24]
7α,10α-Dihydroxy-1β-methoxyeremophil-11(13)-en-12,8β-olide) (55)Xylaria sp. (BCC 21097)Mangrove plantCytotoxicity, antimalarial activity[24]
1α,10α-Epoxy-7α-hydroxyeremophil-11(13)-en-12,8β-olide (56)Xylaria sp. (BCC 21097)Mangrove plantCytotoxicity, antimalarial, antifungal activity[24]
1β,10α,13-Trihydroxyeremophil-7(11)-en-12,8-olide (57)Xylaria sp. (BCC 21097)Mangrove plant-[24]
10β,13-Dihydroxy-1-methoxyeremophil-7(11)-en-12,8β-olide (58)Xylaria sp. (BCC 21097)Mangrove plant-[24]
Mairetolide F (59)Xylaria sp. (BCC 21097)Mangrove plant-[24]
1β,10α-Epoxy-13-hydroxyeremophil-7(11)-en-12,8β-olide (60)Xylaria sp. (BCC 21103)Mangrove plant-[24]
1β,10α-Epoxy-3r-hydroxyeremophil-7(11)-en-12,8β-olide (61)Xylaria sp. (BCC 21104)Mangrove plant-[24]
12,8-Eudesmanolides 3α,4α,7β-trihydroxy-11(13)-eudesmen-12,8-olide (62)Xylaria ianthinovelutinaTorreya jackii Chun-[25]
4α,7β-Dihydroxy-3α-methoxy-11(13)-eudesmen-12,8-olide (63)Xylaria ianthinovelutinaTorreya jackii Chun-[25]
7β-Hydroxy-3,11(13)-eudesmadien-12,8-olide (64)Xylaria ianthinovelutinaTorreya jackii Chun-[25]
13-Hydroxy- 3,7(11)-eudesmadien-12,8-olide (65)Xylaria ianthinovelutinaTorreya jackii Chun-[25]
9,15-Dihydroxy-presilphiperfolan-4-oic acid (66)Xylaria sp. YM 311647Azadirachta indica-[26]
15-Acetoxy-9-hydroxy-presilphiperfolan-4-oic acid (67)Xylaria sp. YM 311647Azadirachta indica-[26]
Eremophilane sesquiterpenes (68–70)Xylaria sp. BL321.Licuala spinosa-[27]
Xylaguaianols A−D (71–74)Xylaria sp. NC1214Unidentified seed-[28]
Isocadinanol A (75)Xylaria sp. NC1214Unidentified seed-[28]
(1S,4S,5R,7R,10R,11R)-Guaiane-5,10,11,12-tetraol (76)Xylaria sp. YM 311647leaves of Piper aduncumAntibacterial activity[29]
(1S,4S,5R,7R,10R,11S)-Fuaiane-1,10,11,12-tetraol (77)Xylaria sp. YM 311647leaves of Piper aduncumAntibacterial activity[29]
(1S,4S,5R,7R,10R,11S)-guaiane-5,10,11,12-tetraol (78)Xylaria sp. YM 311647leaves of Piper aduncumAntibacterial activity[29]
(1S,4S,5S,7R,10R,11R)-guaiane-1,10,11,12-tetraol (79)Xylaria sp. YM 311647leaves of Piper aduncumAntibacterial activity[29]
(1R,3S,4R,5S,7R,10R,11S)-Guaiane-3,10,11,12-tetraol (80)Xylaria sp. YM 311647leaves of Piper aduncumAntibacterial activity[29]
(1R,3R,4R,5S,7R,10R,11R)-Guaiane-3,10,11,12-tetraol (81)Xylaria sp. YM 311647leaves of Piper aduncumAntibacterial activity[29]
(1R,4S,5S,7S,9R,10S,11R)-Guaiane-9,10,11,12-tetraol (82)Xylaria sp. YM 311647leaves of Piper aduncumAntibacterial activity[29]
(1R,4S,5S,7R,10R,11S)-Guaiane-10,11,12-triol (83)Xylaria sp. YM 311647leaves of Piper aduncumAntibacterial activity[29]
(1R,4S,5S,7R,10R,11R)-Guaiane-10,11,12-triol (84)Xylaria sp. YM 311647leaves of Piper aduncumAntibacterial activity[29]
Xylongoic acids A–C (85–87)Xylaria longipes HFG1018Fomitopsis betulina-[30]
Diterpenoid cubentriol (88)Xylaria cubensis BCRC 09F 0035Litsea akoensis-[11]
Hypoxyterpoids A (89)Xylaria cubensisBruguiera gymnorrhiza-[31]
Hypoxyterpoids B (90)Xylaria cubensisBruguiera gymnorrhizaα-glucosidase inhibitory activity[31]
Xylarianes A (91) and B (92)Xylaria sp. 290Unkonwn-[32]
Spiropolin A (93)Xylaria polymorphaWild mushroom-[33]
Myrocin E (94)Xylaria polymorphaWild mushroom-[33]
Xylarinorditerpenes A (95), F–H (100–102), J–M (104–107), and O–R (109–112)Xylaria longipes HFG1018Fomitopsis betulinus-[34]
Xylarinorditerpenes B–E (96–99), I (103), and N (108)Xylaria longipes HFG1018Fomitopsis betulinusImmunosuppressive activity[34]
Acanthoic acid (113)Xylaria sp. (EJCP07)UnkonwnAntibacterial activity[35]
3β,7β-Dihydroxyacanthoic acid (114)Xylaria sp. (EJCP07)UnkonwnAntibacterial activity[35]
Xylarcurcosides A–C (115–117)Xylaria curta YSJ-5Leaves of Alpinia zerumbet-[36]
16-α-D-mannopyranosyloxyisopimar-7-en-19-oic acid (118)Xylaria polymorphaFruit bodiesCytotoxicity activity[37]
15-Hydroxy-16-α-D-mannopyranosyloxyisopimar-7-en-19-oic acid (119)Xylaria polymorphaFruit bodiesCytotoxicity activity[37]
16-α-D-glucopyranosyloxyisopimar-7-en-19-oic acid (120)Xylaria polymorphaFruit bodiesCytotoxicity activity[37]
Xylabisboeins A (121) and B (122)Xylaria sp. SNB-GTC2501Unknown-[38]
14α,16-epoxy-18-norisopimar-7-en-4α-ol (123)Xylaria sp. YM 311647Licuala spinosa-[27]
16-O-Sulfo-18-norisopimar-7-en-4a,16-diol (124)Xylaria sp. YM 311647Licuala spinosaAntifungal activity[27]
9-Deoxy-hymatoxin A (125)Xylaria sp. YM 311647Licuala spinosaAntibacterial activity[27]
Xylarilongipin A (126)Xylaria longipes HFG1018Leaves of Alpinia zerumbetCytotoxicity[39]
Xylarilongipin B (127)Xylaria longipes HFG1018Leaves of Alpinia zerumbet-[39]
Xylarioxides E–F (128–129)Xylaria sp. YM 311647A. indicaAntibacterial activity[20]
Kolokoside A (130)Xylaria sp.Fruit bodiesAntibacterial activity[40]
Kolokosides B–D (131–133)Xylaria sp.Fruit bodies-[40]
Lagambasines A–D (134–137)Xylaria sp. WH2D4Fruit bodies-[41]
Karyochalasin A (138)X. karyophthoraUnknown-[42]
Curtachalasins X1 (139), X5 (143)Xylaria curta E10Solanum tuberosumCytotoxicity[43]
Curtachalasins X2-X4 (140–142), X6 (144)Xylaria curta E10Solanum tuberosum-[43]
19,20-Epoxycytochalasin Q (145)Xylaria obovateDecaying woodCytotoxicity[44]
Deacetyl-19,20-epoxycytochalasin Q (146)Xylaria obovateDecaying wood-[44]
Eytoehalasins 19,20-epoxycytochalasin R (147)Xylaria hypoxylonUnknown-[45]
18-Deoxy-19,20-epoxycytochalasin R (148)Xylaria hypoxylonUnknown-[45]
18-Deoxy-19,20-epoxycytochalasin Q (149)Xylaria hypoxylonUnknown-[45]
19,20-Epoxycytochalasin N (150)Xylaria hypoxylonUnknown-[45]
19,20-Epoxycytochalasin C (151)Xylaria hypoxylonUnknown-[45]
21-Acetylengleromycin (152)Xylaria hypoxylonUnknown-[45]
6,12-Epoxycytochalasin D (153)Xylaria longipesFruit bodies-[46]
6-Epi-cytochalasin P (154)Xylaria longipesFruit bodies-[46]
7-O-acetylcytochalasin P (155)Xylaria longipesFruit bodies-[46]
7-Oxo-cytochalasin C (156)Xylaria longipesFruit bodies-[46]
12-Hydroxylcytochalasin Q (157)Xylaria longipesFruit bodies-[46]
Curtachalasin Q (158)Xylaria sp. DO1801Solanum tuberosum-[47]
19-Epi-cytochalasin P1 (159)Xylaria cf. CurtaSoilCytotoxicity[48]
6-Epi-19,20-epoxycytochalasin P (160)Xylaria cf. CurtaSoil-[48]
7-O-acetyl-6-epi-19,20-epoxycytochalasin P (161)Xylaria cf. CurtaSoilCytotoxicity[48]
7-O-acetyl-19-epi-cytochalasin P1 (162)Xylaria cf. CurtaSoilCytotoxicity[48]
6-O-acetyl-6-epi-19,20-epoxycytochalasin P (163)Xylaria cf. CurtaSoil-[48]
7-O-acetyl-19,20-epoxycytochalasin C (164)Xylaria cf. CurtaSoil-[48]
7-O-acetyl-19,20-epoxycytochalasin D (165)Xylaria cf. CurtaSoilCytotoxicity[48]
Deacetyl-5,6-dihydro-7-oxo-19,20-epoxycytochalasin C (166)Xylaria cf. CurtaSoil-[48]
18-Deoxy-21-oxo-deacetyl-19,20-Epoxycytochalasin N (167)Xylaria cf. CurtaSoil-[48]
Arbuschalasins A–D (168–171)Xylaria arbuscula GZS74Bruguiera gymnorrhiza-[49]
Xylarchalasin A (172)Xylaria sp. GDGJ-77BSophora tonkinensis-[50]
Xylarchalasin B (173)Xylaria sp. GDGJ-77BSophora tonkinensisAntibacterial activity[50]
Curtachalasins A (174) and B (175)Xylaria curta (E10)Solanum tuberosumAntibacterial activity[51]
Cytochalasin P1(176)Xylaria sp. SOF11Marine sedimentCytotoxicity[52]
18-Deoxycytochalasin Q (177)Xylaria sp. SCSIO156Marine sediment-[53]
21-O-deacetylcytochalasin Q (178)Xylaria sp. SCSIO156Marine sedimentCytotoxicity[53]
Xylastriasan A (179)Xylaria striataUnknownCytotoxicity[54]
Cytochalasin H2 (180)Xylaria sp. (A23)Annona squamosaCytotoxicity[55]
Xylarichalasin A (181)Xylaria cf. curtaSolanum tuberosumCytotoxicity[56]
Cytochalasins D1 (182) and C1 (183)Xylaria cf. curtaUnknownCytotoxicity[57]
Cytochalasans (184–188)Xylaria longipesUnknown-[46]
Curtachalasin F(189)Xylaria cf. curtaUnknownCytotoxicity[58]
Curtachalasins G–N (190–197)Xylaria cf. curtaUnknown-[58]
Curtachalasin O (198)Xylaria cf. curtaUnknownCytotoxicity[58]
Curtachalasin P (199)Xylaria cf. curtaUnknown-[58]
Xylarisin B (200)Xylaria sp. HNWSW-2Xylocarpus granatum-[59]
Akodionine (201)Xylaria cubensisLitsea akoensis-[11]
Xylactam B (202)Xylaria sp.Leaves of Tectaria zeylanica-[60]
Xylarialoid A (203)Xylaria arbusculaLeaves of the plant Rauvolfia vomitoria-[61]
2,3-Dihydroxy-N-methoxy-6-propylbenzamide (204)Xylaria sp. PSU-H182Hevea brasiliensis-[62]
Xylopyridine A (205)Xylaria sp.Unidentified plantCytotoxicity[63]
(Z)-3-{(3-acetyl-2-hydroxyphenyl) diazenyl}-2,4-dihydroxybenzaldehyde (206)Xylaria psidiiAmandinea medusulinaCytotoxicity[64]
Xylanigripones A (207)Xylaria nigripes (KL.)Unidentified plantInhibition of CEPT activity[65]
Xylanigripones B-C (208–209)Xylaria nigripes (KL.)Unidentified plant-[65]
Xylariahgin F (210)Xylaria sp.Isodon sculponeatus-[66]
(4S)-3,4-dihydro-4-(4-hydroxybenzyl)-3-oxo-1H-pyrrolo [2,1-c][1,4]oxazine-6-carbaldehyde (211)Xylaria nigripesTermite nest-[67]
Methyl (2S)-2-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]-3-(4-hydr-oxyphenyl)propanate (212)Xylaria nigripesTermite nest-[67]
Allantoside (213)Xylaria allantoidea SWUF76Unknown-[68]
Sinuxylamides A–B (214–215)Xylaria sp. FM1005Sinularia densaCytotoxicity[69]
Sinuxylamides C–D (216–217)Xylaria sp. FM1005Sinularia densa-[69]
Sssinuxylamide E (218)Xylaria sp. FM1005Sinularia densa-[69]
4-(7,8-Dihydroxy-4-oxoquinazolin-3(4H)-yl)butanoic acid (219)Xylaria sp. FM1005Sinularia densa-[69]
4-(8-Hydroxy-4-oxoquinazolin-3(4H)-yl)butanoic acid (220Xylaria sp. FM1005Sinularia densa-[69]
3,4-Dihydroisocoumarin derivative 1′-N-Acetyl-5-methylmellein (221)Xylaria sp. FM1005Sinularia densa-[69]
Xylariamide (222)Xylaria plebeja PSU-G30Garcinia hombroniana-[70]
Xylaramide (223)Xylaria longipesWoodAntifungal activity[71]
2,5-Diamino-N-(1-amino-1-imino-3-methylbutan-2-yl) pentanamide (224)Xylaria cf. cubensis SWUF08-86Decaying wood-[72]
Xylariamino acid A (225)Xylaria nigripes (Kl.)Unknown-[73]
Xylapyrroside A (226)Xylaria nigripesWuling powderAntibacterial activity[74]
Xylapyrroside B (227)Xylaria nigripesWuling powder-[74]
(±)-Xylaridines A and B (228–229)Xylaria longipesUnknownAntibacterial activity[75]
(−)-Xylariamide A (230)Xylaria sp.Glochidion ferdinandiInsect resistance activity[76]
Cyclotripeptide X-13 (231)Xylaria sp. (No. 2508)MangroveAngiogenic property[77,78]
Xyloallenoide A (232)Xylaria sp. (No. 2508)MangroveAngiogenic property[77,78]
Xyloallenoide A1 (233)Xylaria sp. (No. 2508)MangroveAngiogenic property[77,78]
Cyclotripeptide X-13a (234Xylaria sp. (No. 2508)MangroveAngiogenic property[77,78]
Xylaroamide A (235)Xylaria sp. 218-066MangroveCytotoxicity[79]
Xylarotides A (236) and B (237)Xylaria sp. 101.Gaoligong Mountain-[80]
Xylapeptide A (238)Xylaria sp. GDG-102Sophora tonkinensisanAntibacterial activity[81]
Xylapeptide B (239)Xylaria sp. GDG-102Sophora tonkinensisanAntibacterial activity[81]
Ellisiiamide A 240Xylaria ellisiiBlueberry Vaccinium angustifoliumAntibacterial activity[82]
Ellisiiamides B–C (241–242)Xylaria ellisiiBlueberry Vaccinium angustifolium-[82]
Cyclo(N-methyl-L-Phe-L-Val-D-Ile-L-Leu-L-Pro (243)Xylaria sp.Lichen Leptogium saturninumAntifungal activity[83]
Cyclo(L-Val-D-Ile-L-Leu-L-pro-D-Leu (244)Xylaria sp.Lichen Leptogium saturninumAntifungal activity[83]
Pentaminolarin (245)Xylaria sp. (SWUF08-37)Wood-decayingCytotoxicity[84]
Xylariacyclones A (246) and B (247)Xylaria plebeja PSU-G30Garcinia hombroniana-[74]
Xylarianin B (248)Xylaria sp. SYPF 8246.Panax notoginseng-[85]
Xylariaone (249)Xylaria sp. 12F075Lichen Leptogium saturninum-[86]
(+)-Xylarichromone A (250)Xylaria nigripesDecaying woodCytotoxicity[87]
(-)-Xylarichromone A (251)Xylaria nigripesDecaying wood-[87]
Xylariaones A1-B2 (252–255)Xylaria sp.Cudrania tricuspidata-[88]
Xylaripyone H (256)Xylaria sp.Cudrania tricuspidata-[88]
Xylariphilone (257)Xylaria sp. PSU-ES163Seagrass Halophila ovalis-[89]
Xylaromanones A–C (258–260)Xylaria sp. PSU-H182Hevea brasiliensis-[62]
(R)-4-Hydroxy-2-ethyl-2-cyclohexen-1-one (261)Xylaria sp. PSU-H182Hevea brasiliensis-[63]
3,4,5-Trihydroxy-1-tetralone (262)Xylaria sp.Termite nest-derived-[14]
Hemi-cycline A (263)Xylaria cf. cubensis SWUF08-86Unknown-[76]
Hexacycloxylariolone (264)Xylaria sp.UnknownCytotoxicity[90]
Xylaropyrones B (265) and C (266)Xylaria sp. SC1440Spartina maritima-[91]
2-Chloro-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione (267)Xylaria sp.Sandoricum koetjapeAntifungal activity, cytotoxicity[92]
Xylariaquinone A (268)Xylaria sp.Sandoricum koetjapeAntifungal activity[92]
Xylanthraquinone (269)Xylaria sp. (No. 2508)Mangrove-[93,94,95,96,97,98]
Xyloketal A (270)Xylaria sp. (No. 2508)MangroveAnti-inflammatory[93,94,95,96,97,98]
Xyloketal B(271)Xylaria sp. (No. 2508)MangroveAnti-inflammatory, cytotoxicity, NO disturbance, intracellular Ca2+ imbalance[93,94,95,96,97,98]
Xyloketals C–H (272–277)Xylaria sp. (No. 2508)MangroveAnti-inflammatory[93,94,95,96,97,98]
Xyloketal J (278)Xylaria sp. (No. 2508)MangroveAnti-inflammatory[93,94,95,96,97,98]
Paecilins F–K (279–284, 286)Xylaria curta E10Potato tissues-[99]
Paecilins L and N (285 and 287)Xylaria curta E10Potato tissuesAntibacterial[99]
Paecilins O–P (288–289)Xylaria curta E10Potato tissues-[99]
Rubiginosins A–C (290–292)Xylariaceus ascomyceteFraxinus excelsior-[100]
Xylaphenoside A (293)Xylaria sp. CGMCC No. 5410Selaginella moellendorffiiAntimicrobial[101]
Xylarinonericins A–C (294–296)Xylaria plebeja PSU-G30Wood-[71]
Rubiginosins A–C (297–299)Xylariaceus ascomyceteFruit bodies-[102]
1,3,8-Trihydroxy-7-methoxy-9-methyldibenzofuran (300)Xylaria feejeensisGeophila repensCytotoxicity[103]
(6S,2′R,6′S)-6-Methyl-2-((6-methyltetrahydro-2H-pyran-2-yl)methyl)-2,3-dihydro-4H-pyran-4-one (301)Xylaria feejeensisGeophila repens-[103]
(2′R,6′S)-5-((-6-Methyltetrahydro-2H-pyran-2-yl)methyl)benzene-1,3-diol (302)Xylaria feejeensisGeophila repensCytotoxicity[103]
6′,7′-Didehydrointegric acid (303)Xylaria feejeensisGeophila repens-[104]
13-Carboxyintegric acid (304)Xylaria feejeensisGeophila repens-[104]
(4S,5S,6S)-5,6-epoxy-4-hydroxy-3-methoxy-5-methyl-cyclohex-2-en-1-one (305)Xylaria carpophilaLigustrum lucidumCytotoxicity[19]
Xylariols A (306) and B (307)Xylaria hypoxylon AT-028Ligustrum lucidumCytotoxicity[105]
1-(Xylarenone A)xylariate A (308)Xylaria sp. NCY2Torreya jacki [106]
Schweinitzin A (309)Xylaria schweinitzii Berk. and M.AGeophila repensCytotoxicity[107]
Schweinitzin B (310)Xylaria schweinitzii Berk. and M.AGeophila repens-[107]
6-Ethyl-8-hydroxy-4H-chromen-4-one (311)Xylaria sp. SWUF09-62Ligustrum lucidum-[108]
6-Ethyl-7,8-dihydroxy-4H-chromen-4-one (312)Xylaria sp. SWUF09-62Ligustrum lucidumAnti-inflammatory activity[108]
Mellisol (313)Xylaria mellisii (BCC 1005).Torreya jackiAntivirus activity[109]
γ-pyrone-3-acetic acid (314)XylatiaUnknown-[110]
α-pyrone 9-hydroxyxylarone (315)Xylaria sp. NC1214Moss-[28]
Xylarolide (316)Xylaria sp. 101Mushroom-[80]
(3αS,6αR)-4,5-Dimethyl-3,3α,6,6v-Tetrahydro-2Hcyclopenta [β]furan-2-one (317)Xylaria curta 92092022UnknownAntibacterial activity[111]
Xylarphthalide A (318)Xylaria sp. GDG-102Sophora tonkinensisAntibacterial activity[112]
Xylarglycosides A (319) and B (320)Xylaria sp. KYJ-15Illigera celebicaAntibacterial, antioxidant activity[113]
Akolitserin (321)Xylaria cubensisLitsea akoensis-[11]
5-O-α-Dglucopyranosyl-5-Hydroxymellein (322)Xylaria sp. CGMCC No.5410Selaginella moellendorffiiAntimicrobial activity[101]
Xylaripyones A-C(323), E (327), G (329)Xylaria sp.Cudrania tricuspidata-[98]
Xylaripyone D (326)Xylaria sp.Cudrania tricuspidataCytotoxicity[98]
Xylaripyone F (328)Xylaria sp.Cudrania tricuspidataAnti-inflammatory activity[98]
Hypoxymarins A, B, and D (330–331 and 333)Hypoxylon sp. (Hsl2-6)Bruguiera gymnorrhiza-[114]
Hypoxymarin C (332)Hypoxylon sp. (Hsl2-6)Bruguiera gymnorrhizaAntioxidant activity[114]
Xylariahgins A–E (335–340)Xylaria sp. hg1009Isodon sculponeatus [66]
3-(2,3-Dihydroxypropyl)-6,8-dimethoxyiso coumarin (341)Xylaria sp. hg1009Isodon sculponeatus-[66]
Xylariaopyrones A–D (342–345)Xylariales sp. (HM-1)Sophora tonkinensisAntibacterial activity[115]
3S-Hydroxy-7melleine (346)Xylaria sp. (No. 2508)Mangrove-[116]
4′-O-Methyl-β-mannopyranoside (347)Xylaria feejeensisHintonia latiflora-[117]
3S,4R-(+)-4-Hydroxymellein (348)Xylaria feejeensisHintonia latifloraα-glucosidase enzyme inhibitory activity[117]
Xylarellein (349)Xylaria sp. PSU-G12Garcinia hombroniana-[118]
Xylariaindanone (350)Xylaria sp. PSU-G12Garcinia hombroniana-[118]
Xylapyrones A–F (351–356)Xylaria sp. BM9Saccharum arundinaceum-[119]
6-Heptanoyl-4-methoxy-2H-pyran-2-one (357)Xylaria sp. GDG-102Sophora tonkinensisAntimicrobial activity[120]
(+)-Phomalactone (358)Xylaria sp. Grev. (Xylariaceae)Siparuna sp.Anti-plasmodial activity[121]
6-(1-Propenyl)-3,4,5,6-tetrahydro-5-hydroxy-4Hpyran-2-one (359)Xylaria sp. Grev. (Xylariaceae)Siparuna sp.-[121]
Xylaolide A (360)Xylariaceae sp. DPZ-SY43Mangrove sediment-[122]
(S)-8-Hydroxy-6-methoxy-4,5-dimethyl-3-methyleneisochroman-1-one (361)Xylaria sp. BL321Mangrove-derived-[123]
(R)-7-hydroxy-3-((R)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (362)Xylaria sp. BL321Mangrove-[123]
Xylariaopyrone E-G (363–365)Xylaria sp. (HM-1)Siparuna sp.Antimicrobial[124]
Xylariaopyrone H (366)Xylaria sp. (HM-1)Siparuna sp.-[124]
Xylariaopyrone I (367)Xylaria sp. (HM-1)Siparuna sp.Enzyme inhibitory activity[124]
Lasobutone A (368)Xylaria sp.Coptis chinensis-[125]
Lasobutone B (369)Xylaria sp.Coptis chinensisAnti-inflammatory activity[125]
Coloratin A (370)Xylaria intracolorataMangrove-derivedAntimicrobial activity[126]
(3R)-6-Methoxy-5-methoxycarbonylmellein (371)Xylaria feejeensisGeophila repensfunguCytotoxicity[93]
(3S,2′R,6′R)-Asperentin-8-O-methylether (372)Xylaria feejeensisGeophila repensfunguCytotoxicity[93]
Xyolide (373)Xylaria feejeensis (Berk.) Fr. (E6912B)Coptis chinensisAntifungal activity[127]
Multiplolides A (374) and B (375)Xylaria multiplex BCC 1111UnknownAntifungal activity[128]
Xylariolides A–D (376–379)Xylaria sp. NCY2Torreya jacki-[106]
Furofurandione (380)Xylaria sp. (BCC 21097)Licuala spinose-[24]
3R,4R)-3,4-Dihydro-4,6-dihydroxy-3-methyl-1-oxo-1H-isochromene-5-carboxylic acid (381)Xylaria sp.MushroomAntifungal activity[129]
(3S)-3,4-Dihydro-8-hydroxy-7-methoxy-3-methylisocoumarin (382)Xylaria sp. SWUF09-62Ligustrum lucidum-[108]
(3S)-3,4-Dihydro-5,7,8-trihydroxy-3-methylisocoumarin (383)Xylaria sp. SWUF09-62Ligustrum lucidumAnti-inflammatory activity, cytotoxicity[108]
4’-O-methyl-β-mannopyranoside (384)Xylaria feejeensisHintonia latiflora [117]
3S,4R-(+)-4-Hydroxymellein (385)Xylaria feejeensisHintonia latifloraEnzyme inhibitory activity[117]
(3aS,6aR)-4,5-Dimethyl-3,3a,6,6a-tetrahydro-2H-cyclopenta [β]furan-2-one (386)Xylaria curta 92092022UnknownAntibacterial activity[111]
Macrolide (387)Xylaria feejeensisPiper aduncumAnti-osteoporosis activity[130]
(−)-Annularin C (388)Xylaria feejeensisPiper aduncum-[130]
Xylarone (389)Xylaria hypoxylon A27-94UnknownAnti-proliferative[131]
8,9-Dehydroxylarone (390)Xylaria hypoxylon A27-94Unknown-[131]
Rubiginosic acid (391)Xylariaceus ascomyceteCorylus avellana-[102]
Xylarianins A, C and D (392–394)Xylaria sp. SYPF 8246Panax notoginseng-[85]
6-Methoxycarbonyl-2′-methyl-3,5,4′,6′-tetramethoxy-diphenyl ether (395)Xylaria sp. SYPF 8246Panax notoginseng-[85]
2-Chlor-6-methoxycarbonyl-2′-rnethyl-3,5,4′,6′- tetramethoxy-diphenyl ether (396)Xylaria sp. SYPF 8246Panax notoginseng-[85]
2-Chlor-4′-hydroxy-6-methoxy carbonyl-2′-methyl-3,5,6′-trimethoxy-diphenyl ether (397)Xylaria sp. SYPF 8246Panax notoginseng-[85]
Akoenic acid (400)Xylaria cubensisLeaves of L. akoensis Hayata (Lauraceae)-[11]
Phenethylester (401)Xylaria nigripes (Kl.) SaccGarcinia hombronianaCytotoxicity[73]
3,7-Dimethyl-9-(-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl) nona-1,6-dien-3-ol (402)Xylaria sp.Taxus maireiAntibacterial activity[132]
Rubiginosic acid (403)Xylaria ascomyceteFraxinus excelsior-[100]
Xylarosides A (404) and B (405)Xylaria sp. PSU-D14Garcinia dulcis-[133]
2-Methyl-2-(4-hydroxymethylphenyl) oxacyclopentane (406)Xylaria polymorpha (Pers.: Fr.)Dead branchAntifungal activity[13]
Penixylarins A and D (407 and 410)Penicillium crustosum PRB-2 and Xylaria sp. HDN13-249Antarctic deep sea-[134]
Penixylarins B and C (408 and 409)Penicillium crustosum PRB-2 and Xylaria sp. HDN13-249Antarctic deep seaAntibacterial activity[134]
Phenylacetic acid derivative (411)Xylaria sp. FM1005Sinularia densa-[69]
Naphthalenedicarboxylic acid (412)Xylaria sp. FM1005Sinularia densa-[69]
Xylatriol (413)Xylaria sp.--[89]
Acumifurans A–C (414–416)X. acuminatilongissima YMJ623Odontotermes formosanus-[135]
(2E,4E,6S)-6-Hydroxydeca-2,4-dienoic acid (417)Xylaria sp. C-2Gorgonian-[136]
(24R)-22,23-Dihydroxy-ergosta-4,6,8(14)-trien-3-one 23-β-D-glucopyranoside (418)Xylaria sp.MangroveCytotoxicity[137]
Xylarester (419)Xylaria sp.Mangrove-[137]
Coloratin B (420)Xylaria intracolorataMushroom-[119]
Xylaril acids A–C (421–423)Xylaria longipesTermite nestNeuroprotective activity[138]
Xylaril acids D and E (424 and 425)Xylaria longipesTermite nestNeuroprotective activity[138]
Wheldone (426)Aspergillus fischeri (NRRL 181) and Xylaria flabelliformis (G536)Termite nestCytotoxicity[139]
Fimbriether A, C, D, and F (427, 429, 430, and 432)Xylaria fimbriata Lloyd (YMJ491)Termite nest-[140]
Fimbriethers B and E (428 and 431)Xylaria fimbriata Lloyd (YMJ491)Termite nestAnti-inflammatory activity[140]
Xylarioic acid B (434)Xylaria sp. NCY2Torreya jacki-[106]
Xylariate C (435)Xylaria sp. NCY2Torreya jacki-[106]
Xylopimarane (436)Xylaria sp. (BCC 4297)MushroomCytotoxicity[141]
Xylarinic acids A (437) and B (438)Xylaria polymorpha (Pers.) GrevFruit bodyAntifungal activity[142]
Xylacinic acids A (439) and B (440)Xylaria cubensis PSU-MA34Termite nest-[143]
Allantoside (441)Xylaria allantoidea SWUF76.Unknown-[68]
Ergosta-4,6,8(14),22-tetraen-3-one (442)Xylaria sp.UnknownAnti-inflammatory activity[144]
Xylarosides A (443) and B (444)Xylaria sp. PSU-D14Leaves of Garcinia dulcis-[133]
Aminobenzoate (445)Xylaria sp. BCC 9653Wood-decayed-[145]
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MDPI and ACS Style

Chen, W.; Yu, M.; Chen, S.; Gong, T.; Xie, L.; Liu, J.; Bian, C.; Huang, G.; Zheng, C. Structures and Biological Activities of Secondary Metabolites from Xylaria spp. J. Fungi 2024, 10, 190. https://0-doi-org.brum.beds.ac.uk/10.3390/jof10030190

AMA Style

Chen W, Yu M, Chen S, Gong T, Xie L, Liu J, Bian C, Huang G, Zheng C. Structures and Biological Activities of Secondary Metabolites from Xylaria spp. Journal of Fungi. 2024; 10(3):190. https://0-doi-org.brum.beds.ac.uk/10.3390/jof10030190

Chicago/Turabian Style

Chen, Weikang, Miao Yu, Shiji Chen, Tianmi Gong, Linlin Xie, Jinqin Liu, Chang Bian, Guolei Huang, and Caijuan Zheng. 2024. "Structures and Biological Activities of Secondary Metabolites from Xylaria spp." Journal of Fungi 10, no. 3: 190. https://0-doi-org.brum.beds.ac.uk/10.3390/jof10030190

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