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Marine and Terrestrial Sources of Natural Products: Chemical Composition Profiling, Isolation and Characterization

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (31 March 2020) | Viewed by 28259

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Prof. Dr. Artur M. S. Silva

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LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
Interests: organic chemistry; green synthetic organic chemistry; synthesis of heterocyclic compounds; natural products; NMR techniques; synthesis of new compounds with biocidal and antioxidant activities
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Dr. Diana Cláudia Pinto

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LAQV-REQUIMTE, Department of Chemistry, Universidade de Aveiro, 3810-193 Aveiro, Portugal
Interests: organic chemistry; medicinal chemistry; biotransformations; natural products; plant chemical profile; sustainable chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Natural molecules produced by terrestrial sources have important roles in the development of new drugs. Marine and/or halophytes have attracted attention as a result of their unique ability to produce bioactive secondary metabolites. Halophytes, in particular, are considered important sources of secondary metabolites due to their tolerance to saline environments. This Special Issue invites authors to submit original research article contributions related to the isolation, purification, and characterization of new natural bioactive molecules from marine and terrestrial origins, including halophytes. Reviews that make substantial advances within this field are also invited to contribute to this editorial project.

Prof. Dr. Artur M. S. Silva
Prof. Diana Pinto
Guest Editors

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Keywords

marine natural products
halophyte natural products
terrestrial plant natural products
bioactive natural products
novel substances from natural sources
GC-MS profile
UHPLC-MS profile
NMR characterization

Published Papers (7 papers)

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Research

22 pages, 18693 KiB

Open AccessArticle

Julbernardia paniculata and Pterocarpus angolensis: From Ethnobotanical Surveys to Phytochemical Characterization and Bioactivities Evaluation

by Eugénia Solange Santos, Ângelo Luís, Joana Gonçalves, Tiago Rosado, Luísa Pereira, Eugenia Gallardo and Ana Paula Duarte

Molecules 2020, 25(8), 1828; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25081828 - 16 Apr 2020

Cited by 16 | Viewed by 4055

Abstract

Julbernardia paniculata and Pterocarpus angolensis are two plant species with important application in African traditional medicine, particularly in Angola, in the treatment of several diseases. However, scientific studies concerning these species are scarce. The goal of this work was to know better which medicinal approaches are used by the Huíla population in Angola by means of ethnobotanical surveys. Furthermore, extracts of both plants were phytochemically characterized. Antioxidant, anti-inflammatory, wound-healing activities, and potential cytotoxicity were also studied. With this study it was possible to verify that 67% of the individuals that use medicinal plants are women, and their main therapeutic uses are the treatment of problems of the digestive system and skin disorders. Barks of J. paniculata and leaves of P. angolensis are the most often used plant parts. Through high-performance liquid chromatography coupled to diode-array detector (HPLC-DAD) and GC-MS it was possible to characterize the chemical composition of the two species, which are rich in phenolic compounds, terpenes, terpenoids, sesquiterpenoids and fatty acids. Both plants showed to possess antioxidant, anti-inflammatory proprieties, and wound-healing activity. To the best of our knowledge, this is the most comprehensive study of these two species and the first ethnobotanical and ethnopharmacological study of medicinal plants from this region of Angola. Full article

(This article belongs to the Special Issue Marine and Terrestrial Sources of Natural Products: Chemical Composition Profiling, Isolation and Characterization)

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15 pages, 525 KiB

Open AccessArticle

Scrophularia Tenuipes Coss and Durieu: Phytochemical Composition and Biological Activities

by Zeyneb Chaibeddra, Salah Akkal, Houria Ouled-Haddar, Artur M. S. Silva, Ammar Zellagui, Mohamed Sebti and Susana M. Cardoso

Molecules 2020, 25(7), 1647; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25071647 - 03 Apr 2020

Cited by 4 | Viewed by 2466

Abstract

Scrophularia tenuipes is an Algerian-Tunisian endemic species, which has not been studied yet. Ethyl acetate (EA) and n-butanol (Bu) fractions obtained from Scrophularia tenuipes were investigated for their health benefit properties, in particular with respect to in vivo/in vitro anti-inflammatory and antioxidant activities, as well as their potential to inhibit key enzymes with impact in diabetes (α-glucosidase and α-amylase). The fractions had a distinct phytochemical composition, of which EA was richer in total phenolic compounds (225 mg GAE/g) and mostly composed of the phenylethanoid acetyl martynoside. Compared to EA, Bu had higher amounts of total flavonoids, and according to the result obtained from UHPLC-DAD-ESI-MSⁿ analysis, harpagoside (iridoid) was its major phytochemical. EA fraction was quite promising with regard to the in vivo (at 200 mg/kg, po) anti-inflammatory effect (62% and 52% for carrageenan-induced rat paw edema and xylene-induced ear edema tests, respectively), while Bu fraction exhibited a stronger antioxidant capacity in all tests (IC₅₀ = 68 µg/mL, IC₅₀ = 18 µg/mL, IC₅₀ = 18 µg/mL and A_0.50 = 43 µg/mL for DPPH^●, ABTS^•+, O₂^•− scavenging assays and cupric-reducing antioxidant capacity method, respectively). Both fractions also showed a strong effect against α-amylase enzyme (IC₅₀ = 8 µg/mL and 10 µg/mL for EA and Bu fraction, respectively). Full article

(This article belongs to the Special Issue Marine and Terrestrial Sources of Natural Products: Chemical Composition Profiling, Isolation and Characterization)

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9 pages, 703 KiB

Open AccessArticle

Brominated Bisindole Alkaloids from the Celtic Sea Sponge Spongosorites calcicola

by Laurence K. Jennings, Neyaz M. D. Khan, Navdeep Kaur, Daniel Rodrigues, Christine Morrow, Aoife Boyd and Olivier P. Thomas

Molecules 2019, 24(21), 3890; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24213890 - 29 Oct 2019

Cited by 17 | Viewed by 4242

Abstract

As part of an ongoing program to identify new bioactive compounds from Irish marine bioresources, we selected the subtidal sponge Spongosorites calcicola for chemical study, as fractions of this species displayed interesting cytotoxic bioactivities and chemical profiles. The first chemical investigation of this marine species led to the discovery of two new bisindole alkaloids of the topsentin family, together with six other known indole alkaloids. Missing the usual central core featured by the representatives of these marine natural products, the new metabolites may represent key biosynthetic intermediates for other known bisindoles. These compounds were found to exhibit weak cytotoxic activity against HeLa tumour cells, suggesting a specificity towards previously screened carcinoma and leukaemia cells. Full article

(This article belongs to the Special Issue Marine and Terrestrial Sources of Natural Products: Chemical Composition Profiling, Isolation and Characterization)

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30 pages, 1506 KiB

Open AccessArticle

Puccinellia maritima, Spartina maritime, and Spartina patens Halophytic Grasses: Characterization of Polyphenolic and Chlorophyll Profiles and Evaluation of Their Biological Activities

by Maria V. Faustino, Maria A. F. Faustino, Helena Silva, Ângela Cunha, Artur M. S. Silva and Diana C. G. A. Pinto

Molecules 2019, 24(20), 3796; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24203796 - 22 Oct 2019

Cited by 17 | Viewed by 4076

Abstract

Halophytic grasses have been recently targeted as possible sources of nutraceutical and medicinal compounds. Nonetheless, few studies have been conducted on the phytochemistry and biological activities of metabolites produced by these plants. Among these, Spartina maritima (Curtis) Fernald, Spartina patens (Aiton.) Muhl., and Puccinellia maritima (Hudson) Parl. are three halophytic grasses whose chemical composition and bioactivities are unknown. The present work broadens the knowledge on the polyphenolic and chlorophyll composition of these species identifying for the first time hydroxycinnamic acids and their derivatives, flavones, flavonols, lignans, as well as chlorophylls and xantophylls. The extracts were particularly rich in caffeic and ferulic acids as well as in trihydroxymethoxyflavone, apigenin and tricin derivatives. Interestingly, several of the identified compounds are relevant from a medicinal and nutraceutical point of view putting in evidence the potential of these species. Thus, the antioxidant, anti-acetylcholinesterase, antibacterial, and antifungal activities of the polyphenolic extracts were assessed as well as the photophysical properties of the chlorophyll-rich extracts. The results, herein presented for the first time, reinforce the nutritional and the medicinal potential of these halophytic grasses. Full article

(This article belongs to the Special Issue Marine and Terrestrial Sources of Natural Products: Chemical Composition Profiling, Isolation and Characterization)

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18 pages, 5697 KiB

Open AccessArticle

Terpenoids of the Swamp Cypress Subfamily (Taxodioideae), Cupressaceae, an Overview by GC-MS

by Bernd R. T. Simoneit, Angelika Otto, Daniel R. Oros and Norihisa Kusumoto

Molecules 2019, 24(17), 3036; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24173036 - 21 Aug 2019

Cited by 21 | Viewed by 4302

Abstract

The resins bled from stems and in seed cones and leaves of Cryptomeria japonica, Glyptostrobus pensilis, Taxodium distichum, and T. mucronatum were characterized to provide an overview of their major natural product compositions. The total solvent extract solutions were analyzed as the free and derivatized products by gas chromatography-mass spectrometry to identify the compounds, which comprised minor mono- and sesquiterpenoids, and dominant di- and triterpenoids, plus aliphatic lipids (e.g., n-nonacosan-10-ol). Ferruginol, 7α-p-cymenylferruginol, and chamaecydin were the major characteristic markers for the Taxodioideae conifer subfamily. The mass spectrometric data can aid polar compound elucidation in environmental, geological, archeological, forensic and pharmaceutical studies. Full article

(This article belongs to the Special Issue Marine and Terrestrial Sources of Natural Products: Chemical Composition Profiling, Isolation and Characterization)

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20 pages, 2672 KiB

Open AccessArticle

Comprehensive Chemical Profiling in the Ethanol Extract of Pluchea indica Aerial Parts by Liquid Chromatography/Mass Spectrometry Analysis of Its Silica Gel Column Chromatography Fractions

by Jingya Ruan, Jiejing Yan, Dandan Zheng, Fan Sun, Jianli Wang, Lifeng Han, Yi Zhang and Tao Wang

Molecules 2019, 24(15), 2784; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24152784 - 31 Jul 2019

Cited by 42 | Viewed by 4872

Abstract

Pluchea indica Less. is a medicine and food dual-use plant, which belongs to the Pluchea genus, Asteraceae family. Its main constituents are quinic acids, flavonoids, thiophenes, phenolic acids, as well as sesquiterpenes. In order to provide a comprehensive chemical profiling of P. indica, an orthogonal chromatography combining reverse-phase chromatography BEHC18 column with a normal-phase chromatography silica column as the separation system and a ESI-Q-Orbitrap MS as the detector in both positive and negative ion modes were used. According to the retention time (t_R) and the exact mass-to-charge ratio (m/z), 67 compounds were unambiguously identified by comparing to the standard references. Moreover, 47 compounds were tentatively speculated on the basis of the rules of MS/MS fragmentation pattern and chromatographic elution order generalized from the above-mentioned reference standards. Among them, 10 of them were potentially novel. Full article

(This article belongs to the Special Issue Marine and Terrestrial Sources of Natural Products: Chemical Composition Profiling, Isolation and Characterization)

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12 pages, 914 KiB

Open AccessArticle

Mulinum crassifolium Phil; Two New Mulinanes, Gastroprotective Activity and Metabolomic Analysis by UHPLC-Orbitrap Mass Spectrometry

by Carlos Areche, Ronald Fernandez-Burgos, Teresa Cano de Terrones, Mario Simirgiotis, Olimpo García-Beltrán, Jorge Borquez and Beatriz Sepulveda

Molecules 2019, 24(9), 1673; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24091673 - 28 Apr 2019

Cited by 9 | Viewed by 3306

Abstract

Mulinum crassifolium Phil. (Apiaceae) is an endemic shrub from Chile commonly used as infusion in traditional medicine to treat diabetes, bronchial and intestinal disorders and stomach ailments, including ulcers. From the EtOAc extract of this plant, the new mulinane-type diterpenoids 3 and 5 were isolated along with three known diterpenoids. The gastroprotective effect of the infusion of the plant was assayed to support the traditional use and a fast HPLC analysis using high resolution techniques was performed to identify the bioactive constituents. The EtOAc extract and the edible infusion showed gastroprotective effect at 100 mg/kg in the HCl/EtOH induced gastric ulcer model in mice, reducing lesions by 33% and 74%, respectively. Finally, a metabolomic profiling based on UHPLC-ESI-MS/HRMS of the edible infusion was performed and thirty-five compounds were tentatively identified including quercetin, caffeic acid, apigenine glucoside, p-coumaric acid, chlorogenic acids, and caffeoylquinic acids, which have been associated previously with gastroprotective and antiulcer properties. This scientific evidence can support the contribution of polyphenols in the gastroprotective activity of the edible infusion of this plant, and can validate at least in part, its ethnopharmacological use. Full article

(This article belongs to the Special Issue Marine and Terrestrial Sources of Natural Products: Chemical Composition Profiling, Isolation and Characterization)

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