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A Themed Issue in Honor of Professor K.Hüsnü Can Baser—Outstanding Contributions in the Fields of Pharmacognosy, Phytochemistry, Botany and Ethnopharmacology

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

Deadline for manuscript submissions: closed (20 May 2021) | Viewed by 57976

Special Issue Editors

Faculty of Pharmacy, Near East University, Nicosia, N. Cyprus, Turkey
Interests: medicinal plants; isolation and structure elucidation of natural compounds; flavonoids; henylethanoids; isoprenoids; iridoids and secoiridoids; cardiac glycosides; phytosterols; ecdysteroids; triterpene and steroidal saponins; oleanane; ursane; dammarane and cycloartane-type saponins
Department of Pharmacognosy, University of Pécs, Pécs, Hungary
Interests: pharmacognosy; phytotherapy; secondary plant metabolites; essential oil; antibacterial activity; anti-inflammatory effect; biofilm
Special Issues, Collections and Topics in MDPI journals
Department of Pharmacognosy with the Medicinal Plant Garden, Medical University of Lublin, Lublin, Poland
Interests: terpenoids, essential oils and volatile extracts; chromatographic techniques; isolation; bryophytes natural product chemistry; bioactivity-guided isolation of compounds from medicinal; aromatic, and spore-forming plants; chemosystematics of liverworts based on their terpenoid, aromatic, and phenolic constituents
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

This Special Issue will honor Prof. Dr. K. Hüsnü Can Başer for his outstanding contributions in the fields of pharmacognosy, phytochemistry, botany, and ethnopharmacology. His major areas of research include essential oils, alkaloids, and biological, chemical, pharmacological, technological, and biological activity research into natural products. Prof. Başer, a pharmacist, obtained his Ph.D. in pharmacognosy from the University of London (1978). He is the author of 1242 scientific contributions including 850 papers in international peer-reviewed journals, 187 papers in Turkish journals,142 papers in conference proceedings, 61 books and book chapters, as well as 19 project reports. He communicated 1037 papers in 302 symposia and conferences. According to Science Citation Index (SCI) his 607 articles have been cited 11,174 times. His H-index is 49. According to Google Scholar, his articles have been cited 28,115 times and his H-index is 72. His i10 index is 564.

He has taken part and implemented numerous national and international development and research projects.  He served as Dean of the Faculty of Pharmacy at Anadolu University (1993–2001), Vice-Dean of the Faculty of Pharmacy (1982–1993), Head of the Department of Professional Pharmaceutical Sciences (1982–1993), Head of the Pharmacognosy Section (1982–ongoing), Member of the University Board and Senate  (1982–2001; 2007–2010 (Senate)), and Director of the Medicinal and Aromatic Plant and Drug Research Centre (TBAM) (1980–2002) in Anadolu University. Between 1984 and 1994, he was appointed as the National Project Coordinator of Phase I and Phase II of the UNDP/UNIDO projects of the Government of Turkey titled “Production of Pharmaceutical Materials from Medicinal and Aromatic Plants” through which TBAM had been strengthened. Between 1988 and 1997, he organized ten in-plant group training programmes for the benefit of scientists in developing countries. The programme titled “Training in the Utilization of Medicinal and Aromatic Plants in Pharmaceutical and Related Industries (TRUMAP)” was held every September for 25 days for ten selected participants from among those nominated by developing countries. The programme was co-financed by the Government of Turkey and UNIDO (United Nations Industrial Development Organization) and was the only one of its kind in the world. One hundred participants from 40 countries were trained in ten programmes. He also worked as a UNIDO Consultant in Nigeria , Ghana , Sierra Leone , Sudan, and Iran for a total of 6 months to develop projects on the industrial utilization of indigenous medicinal and aromatic plants. Between October 6 and 26, 1997, he worked as a UNIDO consultant on the quality improvement of essential oils in South Africa, Zambia, Malawi, Uganda, Ethiopia, and Ghana, and worked as a short-term consultant on a UNIDO project on essential oils in November–December 2012 in Egypt; at a FAO project on medicinal and aromatic non-wood forest products in February 2013 in Uzbekistan; and at a UNIDO project on fragrances in August 2018 in Oman. He worked as a national point of contact for the Asian-Pacific Information Network of Medicinal and Aromatic Plants (APINMAP) (1992–1997) and Useful Plants of the Mediterranean Network (MEDUSA) in Turkey (1996–2000). He served as Member of the Turkish Pharmacopoeia Commission (1985–2012), Member of the Registration Commission for Plant Drugs at the Ministry of Health (1985–1992), Member of the No. 11 Group of Experts of the European Pharmacopoeia Commission (1995–1999), Member of the 13B Group of Experts of the EP Commission (1999–2012), and as a Member of the TCM Working Party of the EP Commission (2008–2012).

He served as Secretary-General of the International Council of Medicinal and Aromatic Plants (ICMAP) between November 1997 and February 2003. In February 2003 in Chiang Mai (Thailand), he was elected as the Vice-President of ICMAP. In November 2008 at Cape Town, South Africa he was elected as the president of ICMAP. In August 2014 in Brisbane, Australia, he was elected as Vice-President responsible for organizing WOCMAP VI in 2019 in Famagusta, North Cyprus. He is currently serving as a member of the ICMAP Bureau. He was appointed as a member of the Executive Committee of the Academy of Pharmacy of the Turkish Pharmacists’ Association in 2006, and as its President in February 2008 and served until 2012. As a result of agreements established between the Institute of the Chemistry of Plant Substances (ICPS) of the Uzbekistan Academy of Sciences and the Medicinal and Aromatic Plant and Drug Research Centre (TBAM) of Anadolu University in 1993, exchanges of many research scientists were established between the two institutions and from 1994 onwards a biennial scientific symposium entitled “International Symposium on the Chemistry of Natural Compounds (SCNC) has been organized alternately in Uzbekistan and Turkey (1st 1994 Tashkent; 2nd 1996 Eskisehir; 3rd 1998 Bukhara; 4th 2001 Isparta; 5th 2003 Tashkent; 6th 2005 Ankara; 7th 2007 Tashkent; 8th 2009 Eskisehir; 9th 2011 Urumqi (China); 10th 2013 Tashkent; 11th 2015 Antalya; 12th 2017 Tashkent; 13th 2019 Shanghai). He is the Founder of the Herbarium of the Faculty of Pharmacy at Anadolu University (Acronym = ESSE), Founding member and President (until 2002) of the Turkish Society of Cosmetic Scientists (TCoS). He was a founding member of the Turkish Phytotherapy Society. He acted as founding member and Vice-President of the Society for Flora Research founded in April 2005 in Istanbul, Turkey. He has organized over 50 national and international scientific meetings since 1987. He is a member of the WHO (World Health Organization) Expert Advisory Panel on Traditional Medicine (2007–2015). His term has been extended recently. He was elected as a member of the Advisory Board of GA (The Society for Medicinal Plant and Natural Product Research) (2009–2014) and organized the 59th International Symposium of GA in September 2011 in Antalya, Turkey.

Since February 1998, he has been a Fellow of the Linnean Society (FLS), the most prestigious society of biological sciences based in London. He is the recipient of many national and international awards: 1995 Recipient of the Distinguished Service Medal of IFEAT (International Federation of Essential Oils and Aroma Trades) based in London , UK, “Memorial Silver Medal” of the Scientific Partnership Foundation of Russia for promoting scientific partnership among young scientists and for his contribution to the development of science (Tashkent, 2003), “Academician Award” (Istanbul, 2004.), “Centennial Success in Career Award” of Rotary Turkey (Hatay, 2005), 1st recipient of the “Science Award” of the Academy of Pharmacy of the Turkish Pharmacists’ Association (Ankara, 2005), “Science Award” (Health Sciences) of the Scientific and Technological Research Council of Turkey (TUBITAK) (Ankara, 2005), “Science Award” of the Society of Contemporary Journalists Eskisehir  (Eskisehir, 2006), Recipient of 2008 “Science Award” (Health Sciences) of Popular Science Magazine (Ankara, 2009), ISHS (International Society for Horticultural Science) Medal, (Brisbane, Australia 2014), votive tablet by the Academy of Pharmacy of the Turkish Pharmacists Association (Ankara, 2017), Publication Award of Near East University in 2017, 2018, 2019; and Publication Honour Award in 2018, the Best Academician Award of Near East University in 2019, Altin Havan (Golden Mortar) Service Award of Eczaci journal (Istanbul, 2019). His name appeared in the 35th rank among the “100 Turks Guiding Science” book published by Sanko Holding in May 2017. He ranked 22nd among the 950 Turkish scientists listed in the “Most Influential Scientists of the World” list in September 2020.

He is co-Editor of the book “Essential Oils: Science, Technology and Applications” together with Prof. Dr. Gerhard Buchbauer of Vienna University, CRC Press (Taylor & Francis), January 2010. A 2nd Edition was published in November 2016 and won the James A. Duke Excellence in Botanical Literature Award of the American Botanical Council in March 2017. The 3rd edition of the book appeared in August 2020. The Natural Product Communications journal dedicated a Special Issue [5(9)2010] in honor of Prof. Başer’s 60th birthday (September 2010). A memorial Issue for his 70th birthday is in preparation. He retired from his Anadolu University job on February 16, 2011 and worked as a visiting Professor at the Botany and Microbiology Department of the College of Science of King Saud University in Riyadh, Saudi Arabia, giving lectures and implementing research projects. He was appointed as an International Board Member of the Organization for the Phyto Taxonomic Investigation of the Mediterranean Area (OPTIMA) (2013–2019). He worked for a short time as Director of the Technology Transfer Office (TTO) at Bahcesehir University in Istanbul, Turkey (November 2013–July 2014). He was elected as Member of the Science Academy of Turkey on November 27, 2016. Prof. Başer is among the group of scientists who named five new plant species and identified two plant species as new record for the flora of Turkey. Three plants have been named after him in recent years: Origanum husnucan-baseri H.Duman, Z.Aytac et A.Duran and Aristolochia baseri Malyer et Erken, Centaurea baseri Kose et Alan. He is the Joint Editor of the 2nd supplement (Vol.11) to the Flora of Turkey and the East Aegean Islands of the late Prof. P.H. Davis (2000). Prof. Başer and Prof. F. Demirci founded a biotechnology company (BadeBIO) at the Eskisehir Technopark (ATAP) (November 2009). Since 2016, he has been working as Head of the Pharmacognosy Department at the Faculty of Pharmacy and Director of the Graduate Institute of Health Sciences at the Near East University in Nicosia (Lefkoşa), Northern Cyprus.

In this Special Issue, we aim to collect original research articles and review articles in the following topics:

  1. Isolation and structure elucidation of bioactive compounds;
  2. Development of new methods for structure elucidation;
  3. Biotransformation of biosynthetically interesting compounds;
  4. Bioactivity studies on natural products;
  5. Natural volatiles and essential oils.

Prof. Dr. İhsan Çalış
Dr. Horváth Györgyi
Dr. Agnieszka Ludwiczuk
Guest Editors

Manuscript Submission Information

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Keywords

  • isolation
  • structure elucidation
  • bioactive compounds
  • natural products
  • Biotransformation
  • essential
  • biological activity

Published Papers (13 papers)

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Editorial

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7 pages, 223 KiB  
Editorial
A Themed Issue in Honor of Professor K. Hüsnü Can Baser—Outstanding Contributions in the Fields of Pharmacognosy, Phytochemistry, Botany and Ethnopharmacology
by İhsan Çalış, Györgyi Horváth and Agnieszka Ludwiczuk
Molecules 2021, 26(18), 5507; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26185507 - 10 Sep 2021
Viewed by 1537
Abstract
Dear Colleagues, [...] Full article

Research

Jump to: Editorial, Review

7 pages, 852 KiB  
Article
(E)-2,6,10-Trimethyldodec-8-en-2-ol: An Undescribed Sesquiterpenoid from Copaiba Oil
by Mohammed F. Hawwal, Zulfiqar Ali, Mei Wang, Jianping Zhao, Joseph Lee, Omer I. Fantoukh and Ikhlas A. Khan
Molecules 2021, 26(15), 4456; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26154456 - 23 Jul 2021
Cited by 2 | Viewed by 2058
Abstract
The use of copaiba oil has been reported since the 16th century in Amazon traditional medicine, especially as an anti-inflammatory ingredient and for wound healing. The use of copaiba oil continues today, and it is sold in various parts of the world, including [...] Read more.
The use of copaiba oil has been reported since the 16th century in Amazon traditional medicine, especially as an anti-inflammatory ingredient and for wound healing. The use of copaiba oil continues today, and it is sold in various parts of the world, including the United States. Copaiba oil contains mainly sesquiterpenes, bioactive compounds that are popular for their positive effect on human health. As part of our ongoing research endeavors to identify the chemical constituents of broadly consumed herbal supplements or their adulterants, copaiba oil was investigated. In this regard, copaiba oil was subjected to repeated silica gel column chromatography to purify the compounds. As a result, one new and seven known sesquiterpenes/sesquiterpenoids were isolated and identified from the copaiba oil. The new compound was elucidated as (E)-2,6,10-trimethyldodec-8-en-2-ol. Structure elucidation was achieved by 1D- and 2D NMR and GC/Q-ToF mass spectral data analyses. The isolated chemical constituents in this study could be used as chemical markers to evaluate the safety or quality of copaiba oil. Full article
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18 pages, 3868 KiB  
Article
Dihydroisocoumarins, Naphthalenes, and Further Polyketides from Aloe vera and A. plicatilis: Isolation, Identification and Their 5-LOX/COX-1 Inhibiting Potency
by Hans Wilhelm Rauwald, Ralf Maucher, Gerd Dannhardt and Kenny Kuchta
Molecules 2021, 26(14), 4223; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26144223 - 12 Jul 2021
Cited by 6 | Viewed by 2090
Abstract
The present study aims at the isolation and identification of diverse phenolic polyketides from Aloe vera (L.) Burm.f. and Aloe plicatilis (L.) Miller and includes their 5-LOX/COX-1 inhibiting potency. After initial Sephadex-LH20 gel filtration and combined silica gel 60- and RP18-CC, three dihydroisocoumarins [...] Read more.
The present study aims at the isolation and identification of diverse phenolic polyketides from Aloe vera (L.) Burm.f. and Aloe plicatilis (L.) Miller and includes their 5-LOX/COX-1 inhibiting potency. After initial Sephadex-LH20 gel filtration and combined silica gel 60- and RP18-CC, three dihydroisocoumarins (nonaketides), four 5-methyl-8-C-glucosylchromones (heptaketides) from A. vera, and two hexaketide-naphthalenes from A. plicatilis have been isolated by means of HSCCC. The structures of all polyketides were elucidated by ESI-MS and 2D 1H/13C-NMR (HMQC, HMBC) techniques. The analytical/preparative separation of 3R-feralolide, 3′-O-β-d-glucopyranosyl- and the new 6-O-β-d-glucopyranosyl-3R-feralolide into their respective positional isomers are described here for the first time, including the assignment of the 3R-configuration in all feralolides by comparative CD spectroscopy. The chromones 7-O-methyl-aloesin and 7-O-methyl-aloeresin A were isolated for the first time from A. vera, together with the previously described aloesin (syn. aloeresin B) and aloeresin D. Furthermore, the new 5,6,7,8-tetrahydro-1-O-β-d-glucopyranosyl- 3,6R-dihydroxy-8R-methylnaphtalene was isolated from A. plicatilis, together with the known plicataloside. Subsequently, biological-pharmacological screening was performed to identify Aloe polyketides with anti-inflammatory potential in vitro. In addition to the above constituents, the anthranoids (octaketides) aloe emodin, aloin, 6′-(E)-p-coumaroyl-aloin A and B, and 6′-(E)-p-coumaroyl-7-hydroxy-8-O-methyl-aloin A and B were tested. In the COX-1 examination, only feralolide (10 µM) inhibited the formation of MDA by 24%, whereas the other polyketides did not display any inhibition at all. In the 5-LOX-test, all aloin-type anthranoids (10 µM) inhibited the formation of LTB4 by about 25–41%. Aloesin also displayed 10% inhibition at 10 µM in this in vitro setup, while the other chromones and naphthalenes did not display any activity. The present study, therefore, demonstrates the importance of low molecular phenolic polyketides for the known overall anti-inflammatory activity of Aloe vera preparations. Full article
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13 pages, 968 KiB  
Article
Isolation of Volatile Compounds with Repellent Properties against Aedes albopictus (Diptera: Culicidae) Using CPC Technology
by Anastasia Liakakou, Apostolis Angelis, Dimitrios P. Papachristos, Nikolas Fokialakis, Antonios Michaelakis and Leandros A. Skaltsounis
Molecules 2021, 26(11), 3072; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26113072 - 21 May 2021
Cited by 7 | Viewed by 1876
Abstract
The present work describes the use of Centrifugal Partition Chromatography (CPC) for the bio-guided isolation of repellent active volatile compounds from essential oils. Five essential oils (EOs) obtained from three Pinus and two Juniperus species were initially analyzed by gas chromatography–mass spectrometry (GC/MS) [...] Read more.
The present work describes the use of Centrifugal Partition Chromatography (CPC) for the bio-guided isolation of repellent active volatile compounds from essential oils. Five essential oils (EOs) obtained from three Pinus and two Juniperus species were initially analyzed by gas chromatography–mass spectrometry (GC/MS) and evaluated for their repellent properties against Aedes albopictus. The essential oil from needles of P. pinea (PPI) presented the higher activity, showing 82.4% repellency at a dose of 0.2 μL/cm2. The above EO, together with the EO from the fruits of J. oxycedrus subsp. deltoides (JOX), were further analyzed by CPC using the biphasic system n-Heptane/ACN/BuOH in ratio 1.6/1.6/0.2 (v/v/v). The analysis of PPI essential oil resulted in the recovery of (−)-limonene, guaiol and simple mixtures of (−)-limonene/β-pheladrene, while the fractionation of JOX EO led to the recovery of β-myrcene, germacrene-D, and mixtures of α-pinene/β-pinene (ratio 70/30) and α-pinene/germacrene D (ratio 65/45). All isolated compounds and recovered mixtures were tested for their repellent activity. From them, (−)-limonene, guaiol, germacrene-D as well the mixtures of (−)-limonene/β-pheladrene presented significant repellent activity (>97% repellency) against Ae. albopictus. The present methodology could be a valuable tool in the effort to develop potent mosquito repellents which are environmentally friendly. Full article
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17 pages, 1519 KiB  
Article
New Cardenolides from Biotransformation of Gitoxigenin by the Endophytic Fungus Alternaria eureka 1E1BL1: Characterization and Cytotoxic Activities
by Erdal Bedir, Çiğdem Karakoyun, Gamze Doğan, Gülten Kuru, Melis Küçüksolak and Hasan Yusufoğlu
Molecules 2021, 26(10), 3030; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26103030 - 19 May 2021
Cited by 8 | Viewed by 2557
Abstract
Microbial biotransformation is an important tool in drug discovery and for metabolism studies. To expand our bioactive natural product library via modification and to identify possible mammalian metabolites, a cytotoxic cardenolide (gitoxigenin) was biotransformed using the endophytic fungus Alternaria eureka 1E1BL1. Initially, oleandrin [...] Read more.
Microbial biotransformation is an important tool in drug discovery and for metabolism studies. To expand our bioactive natural product library via modification and to identify possible mammalian metabolites, a cytotoxic cardenolide (gitoxigenin) was biotransformed using the endophytic fungus Alternaria eureka 1E1BL1. Initially, oleandrin was isolated from the dried leaves of Nerium oleander L. and subjected to an acid-catalysed hydrolysis to obtain the substrate gitoxigenin (yield; ~25%). After 21 days of incubation, five new cardenolides 1, 3, 4, 6, and 8 and three previously- identified compounds 2, 5 and 7 were isolated using chromatographic methods. Structural elucidations were accomplished through 1D/2D NMR, HR-ESI-MS and FT-IR analysis. A. eureka catalyzed oxygenation, oxidation, epimerization and dimethyl acetal formation reactions on the substrate. Cytotoxicity of the metabolites were evaluated using MTT cell viability method, whereas doxorubicin and oleandrin were used as positive controls. Biotransformation products displayed less cytotoxicity than the substrate. The new metabolite 8 exhibited the highest activity with IC50 values of 8.25, 1.95 and 3.4 µM against A549, PANC-1 and MIA PaCa-2 cells, respectively, without causing toxicity on healthy cell lines (MRC-5 and HEK-293) up to concentration of 10 µM. Our results suggest that A. eureka is an effective biocatalyst for modifying cardenolide-type secondary metabolites. Full article
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13 pages, 22584 KiB  
Article
Outlining In Vitro and In Silico Cholinesterase Inhibitory Activity of Twenty-Four Natural Products of Various Chemical Classes: Smilagenin, Kokusaginine, and Methyl Rosmarinate as Emboldening Inhibitors
by F. Sezer Senol Deniz, Gokcen Eren, Ilkay Erdogan Orhan, Bilge Sener, Ufuk Ozgen, Randa Aldaba and Ihsan Calis
Molecules 2021, 26(7), 2024; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26072024 - 01 Apr 2021
Cited by 6 | Viewed by 2169
Abstract
Cholinesterase (ChE) inhibition is an important treatment strategy for Alzheimer’s disease (AD) as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) are involved in the pathology of AD. In the current work, ChE inhibitory potential of twenty-four natural products from different chemical classes (i.e., diosgenin, hecogenin, [...] Read more.
Cholinesterase (ChE) inhibition is an important treatment strategy for Alzheimer’s disease (AD) as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) are involved in the pathology of AD. In the current work, ChE inhibitory potential of twenty-four natural products from different chemical classes (i.e., diosgenin, hecogenin, rockogenin, smilagenin, tigogenin, astrasieversianins II and X, astragalosides I, IV, and VI, cyclocanthosides E and G, macrophyllosaponins A-D, kokusaginin, lamiide, forsythoside B, verbascoside, alyssonoside, ipolamide, methyl rosmarinate, and luteolin-7-O-glucuronide) was examined using ELISA microtiter assay. Among them, only smilagenin and kokusaginine displayed inhibitory action against AChE (IC50 = 43.29 ± 1.38 and 70.24 ± 2.87 µg/mL, respectively). BChE was inhibited by only methyl rosmarinate and kokusaginine (IC50 = 41.46 ± 2.83 and 61.40 ± 3.67 µg/mL, respectively). IC50 values for galantamine as the reference drug were 1.33 ± 0.11 µg/mL for AChE and 52.31 ± 3.04 µg/mL for BChE. Molecular docking experiments showed that the orientation of smilagenin and kokusaginine was mainly driven by the interactions with the peripheral anionic site (PAS) comprising residues of hAChE, while kokusaginine and methyl rosmarinate were able to access deeper into the active gorge in hBChE. Our data indicate that similagenin, kokusaginine, and methyl rosmarinate could be hit compounds for designing novel anti-Alzheimer agents. Full article
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8 pages, 1159 KiB  
Article
Insecticidal Activity and Free Radical Scavenging Properties of Isolated Phytoconstituents from the Saudi Plant Nuxia oppositifolia (Hochst.)
by Shaza M. Al-Massarani, Ali A. El-Gamal, Adnan J. Al-Rehaily, Ebtesam S. Al-Sheddi, Mai M. Al-Oqail, Nida N. Farshori, Alden S. Estep, Nurhayat Tabanca and James J. Becnel
Molecules 2021, 26(4), 914; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26040914 - 09 Feb 2021
Cited by 10 | Viewed by 2579
Abstract
Chromatographic purification of the alcoholic extract from the aerial parts of the Saudi plant Nuxia oppositifolia (Hochst.), Benth., resulted in five isolated phenolic compounds. Two flavones, hispidulin (1) and jaceosidin (2), and the phenylethanoid glycosides, verbascoside (3), [...] Read more.
Chromatographic purification of the alcoholic extract from the aerial parts of the Saudi plant Nuxia oppositifolia (Hochst.), Benth., resulted in five isolated phenolic compounds. Two flavones, hispidulin (1) and jaceosidin (2), and the phenylethanoid glycosides, verbascoside (3), isoverbascoside (4), and conandroside (5), were identified and their chemical structures were determined by spectroscopic analyses. The insecticidal activity of compounds 1 and 2, in addition to 11 compounds isolated in a previous research (616), was evaluated against the Yellow Fever mosquito, Aedes aegypti. Four compounds displayed adulticidal activity with LD50 values of 2–2.3 μg/mosquito. Free radical scavenging properties of the plant extracts and compounds (15) were evaluated by measuring the 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonate radical cation (ABTS•+) scavenging activity. All compounds exhibited notable activity, compared with the positive control, l-Ascorbic acid. This study suggests that N. oppositifolia could be a promising source of secondary metabolites, some with lethal adulticidal effect against Ae. aegypti. Full article
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13 pages, 1861 KiB  
Article
Analyzing the Carotenoid Composition of Melilot (Melilotus officinalis (L.) Pall.) Extracts and the Effects of Isolated (All-E)-lutein-5,6-epoxide on Primary Sensory Neurons and Macrophages
by Györgyi Horváth, Eszter Csikós, Eichertné Violetta Andres, Tímea Bencsik, Anikó Takátsy, Gergely Gulyás-Fekete, Erika Turcsi, József Deli, Éva Szőke, Ágnes Kemény, Maja Payrits, Lajos Szente, Marianna Kocsis, Péter Molnár and Zsuzsanna Helyes
Molecules 2021, 26(2), 503; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26020503 - 19 Jan 2021
Cited by 4 | Viewed by 2692
Abstract
Melilotus officinalis is known to contain several types of secondary metabolites. In contrast, the carotenoid composition of this medicinal plant has not been investigated, although it may also contribute to the biological activities of the drug, such as anti-inflammatory effects. Therefore, this study [...] Read more.
Melilotus officinalis is known to contain several types of secondary metabolites. In contrast, the carotenoid composition of this medicinal plant has not been investigated, although it may also contribute to the biological activities of the drug, such as anti-inflammatory effects. Therefore, this study focuses on the isolation and identification of carotenoids from Meliloti herba and on the effect of isolated (all-E)-lutein 5,6-epoxide on primary sensory neurons and macrophages involved in nociception, as well as neurogenic and non-neurogenic inflammatory processes. The composition of the plant extracts was analyzed by high performance liquid chromatography (HPLC). The main carotenoid was isolated by column liquid chromatography (CLC) and identified by MS and NMR. The effect of water-soluble lutein 5,6-epoxide-RAMEB (randomly methylated-β-cyclodextrin) was investigated on Ca2+-influx in rat primary sensory neurons induced by the activation of the transient receptor potential ankyrin 1 receptor agonist to mustard-oil and on endotoxin-induced IL-1β release from isolated mouse peritoneal macrophages. (all-E)-Lutein 5,6-epoxide significantly decreased the percent of responsive primary sensory neurons compared to the vehicle-treated stimulated control. Furthermore, endotoxin-evoked IL-1β release from macrophages was significantly decreased by 100 µM lutein 5,6-epoxide compared to the vehicle-treated control. The water-soluble form of lutein 5,6-epoxide-RAMEB decreases the activation of primary sensory neurons and macrophages, which opens perspectives for its analgesic and anti-inflammatory applications. Full article
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18 pages, 3074 KiB  
Article
Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro
by Katrin Kuck, Guido Jürgenliemk, Bartosz Lipowicz and Jörg Heilmann
Molecules 2021, 26(1), 42; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26010042 - 23 Dec 2020
Cited by 5 | Viewed by 2627
Abstract
By using various chromatographic steps (silica flash, CPC, preparative HPLC), 16 sesquiterpenes could be isolated from an ethanolic extract of myrrh resin. Their chemical structures were elucidated by 1D and 2D NMR spectroscopy and HRESIMS. Among them, six previously unknown compounds (1–6 [...] Read more.
By using various chromatographic steps (silica flash, CPC, preparative HPLC), 16 sesquiterpenes could be isolated from an ethanolic extract of myrrh resin. Their chemical structures were elucidated by 1D and 2D NMR spectroscopy and HRESIMS. Among them, six previously unknown compounds (1–6) and another four metabolites previously not described for the genus Commiphora (7, 10, 12, 13) could be identified. Sesquiterpenes 1 and 2 are novel 9,10-seco-eudesmanes and exhibited an unprecedented sesquiterpene carbon skeleton, which is described here for the first time. New compound 3 is an 9,10 seco-guaian and the only peroxide isolated from myrrh so far. Compounds 1, 2, 4, 7–9, 11, 13–16 were tested in an ICAM-1 in vitro assay. Compound 7, as well as the reference compound furanoeudesma-1,3-diene, acted as moderate inhibitors of this adhesion molecule ICAM-1 (IC50: 44.8 and 46.3 μM, respectively). These results give new hints on the activity of sesquiterpenes with regard to ICAM-1 inhibition and possible modes of action of myrrh in anti-inflammatory processes. Full article
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Review

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59 pages, 3192 KiB  
Review
The Botanical, Chemical and Ethnobotanical Diversity of Southern African Lamiaceae
by Ryan D. Rattray and Ben-Erik Van Wyk
Molecules 2021, 26(12), 3712; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26123712 - 18 Jun 2021
Cited by 12 | Viewed by 8592
Abstract
The Lamiaceae is undoubtedly an important plant family, having a rich history of use that spans the globe with many species being used in folk medicine and modern industries alike. Their ability to produce aromatic volatile oils has made them valuable sources of [...] Read more.
The Lamiaceae is undoubtedly an important plant family, having a rich history of use that spans the globe with many species being used in folk medicine and modern industries alike. Their ability to produce aromatic volatile oils has made them valuable sources of materials in the cosmetic, culinary, and pharmaceutical industries. A thorough account of the taxonomic diversity, chemistry and ethnobotany is lacking for southern African Lamiaceae, which feature some of the region’s most notable medicinal and edible plant species. We provide a comprehensive insight into the Lamiaceae flora of southern Africa, comprising 297 species in 42 genera, 105 of which are endemic to the subcontinent. We further explore the medicinal and traditional uses, where all genera with documented uses are covered for the region. A broad review of the chemistry of southern African Lamiaceae is presented, noting that only 101 species (34%) have been investigated chemically (either their volatile oils or phytochemical characterization of secondary metabolites), thus presenting many and varied opportunities for further studies. The main aim of our study was therefore to present an up-to-date account of the botany, chemistry and traditional uses of the family in southern Africa, and to identify obvious knowledge gaps. Full article
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26 pages, 1671 KiB  
Review
Chemistry and Pharmacology of Cyperaceae Stilbenoids: A Review
by Csilla Zsuzsanna Dávid, Judit Hohmann and Andrea Vasas
Molecules 2021, 26(9), 2794; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26092794 - 10 May 2021
Cited by 15 | Viewed by 3537
Abstract
Cyperaceae is a cosmopolitan plant family with approx. 5000 species distributed worldwide. Several members of this family are used in traditional medicines for the treatment of different diseases. In the last few decades, constituents with great chemical diversity were isolated from sedges, and [...] Read more.
Cyperaceae is a cosmopolitan plant family with approx. 5000 species distributed worldwide. Several members of this family are used in traditional medicines for the treatment of different diseases. In the last few decades, constituents with great chemical diversity were isolated from sedges, and a wide range of biological activities were detected either for crude extracts or for pure compounds. Among the isolated compounds, phenolic derivatives are the most important, especially stilbenoids, and flavonoids. To date, more than 60 stilbenoids were isolated from 28 Cyperaceae species. Pharmacological investigation of Cyperaceae stilbenoids revealed that several compounds possess promising activities; mainly antiproliferative, antibacterial, antioxidant and anthelmintic effects. Isolation, synthesis and pharmacological investigation of stilbenes are increasing constantly. As Cyperaceae species are very good sources of a wide variety of stilbenes, and several of them occur in large amount worldwide, they are worthy for phytochemical and pharmacological investigations. Moreover, stilbenes are important from chemotaxonomical point of view, and they play a key role in plant defense mechanisms as well. This review summarizes the stilbenoids isolated from sedges, and their biological activities. Full article
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29 pages, 3833 KiB  
Review
Cannabinoids, Phenolics, Terpenes and Alkaloids of Cannabis
by Mohamed M. Radwan, Suman Chandra, Shahbaz Gul and Mahmoud A. ElSohly
Molecules 2021, 26(9), 2774; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26092774 - 08 May 2021
Cited by 121 | Viewed by 19979
Abstract
Cannabis sativa is one of the oldest medicinal plants in the world. It was introduced into western medicine during the early 19th century. It contains a complex mixture of secondary metabolites, including cannabinoids and non-cannabinoid-type constituents. More than 500 compounds have been reported [...] Read more.
Cannabis sativa is one of the oldest medicinal plants in the world. It was introduced into western medicine during the early 19th century. It contains a complex mixture of secondary metabolites, including cannabinoids and non-cannabinoid-type constituents. More than 500 compounds have been reported from C. sativa, of which 125 cannabinoids have been isolated and/or identified as cannabinoids. Cannabinoids are C21 terpeno-phenolic compounds specific to Cannabis. The non-cannabinoid constituents include: non-cannabinoid phenols, flavonoids, terpenes, alkaloids and others. This review discusses the chemistry of the cannabinoids and major non-cannabinoid constituents (terpenes, non-cannabinoid phenolics, and alkaloids) with special emphasis on their chemical structures, methods of isolation, and identification. Full article
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21 pages, 4021 KiB  
Review
The Biological Effects of Forsythia Leaves Containing the Cyclic AMP Phosphodiesterase 4 Inhibitor Phillyrin
by Sansei Nishibe, Kumiko Mitsui-Saitoh, Junichi Sakai and Takahiko Fujikawa
Molecules 2021, 26(8), 2362; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26082362 - 19 Apr 2021
Cited by 6 | Viewed by 3785
Abstract
Forsythia fruit (Forsythia suspensa Vahl (Oleaceae)) is a common component of Kampo medicines for treating the common cold, influenza, and allergies. The main polyphenolic compounds in the leaves of F. suspensa are pinoresinol β-d-glucoside, phillyrin and forsythiaside, and their levels [...] Read more.
Forsythia fruit (Forsythia suspensa Vahl (Oleaceae)) is a common component of Kampo medicines for treating the common cold, influenza, and allergies. The main polyphenolic compounds in the leaves of F. suspensa are pinoresinol β-d-glucoside, phillyrin and forsythiaside, and their levels are higher in the leaves of the plant than in the fruit. It is known that polyphenolic compounds stimulate lipid catabolism in the liver and suppress dyslipidemia, thereby attenuating diet-induced obesity and polyphenolic anti-oxidants might attenuate obesity in animals consuming high-fat diets. Recently, phillyrin was reported as a novel cyclic AMP phosphodiesterase 4 (PDE4) inhibitor derived from forsythia fruit. It was expected that the leaves of F. suspensa might display anti-obesity effects and serve as a health food material. In this review, we summarized our studies on the biological effects of forsythia leaves containing phillyrin and other polyphenolic compounds, particularly against obesity, atopic dermatitis, and influenza A virus infection, and its potential as a phytoestrogen. Full article
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