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Keywords = isopimaranes

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12 pages, 2539 KiB  
Article
Talaroacids A–D and Talaromarane A, Diterpenoids with Anti-Inflammatory Activities from Mangrove Endophytic Fungus Talaromyces sp. JNQQJ-4
by Guisheng Wang, Jianying Wu, Zhaokun Li, Tao Chen, Yufeng Liu, Bo Wang, Yan Chen and Zhigang She
Int. J. Mol. Sci. 2024, 25(12), 6691; https://doi.org/10.3390/ijms25126691 - 18 Jun 2024
Cited by 2 | Viewed by 1167
Abstract
Five new diterpenes including four diterpenes with 1,2,3,4,4a,5,6,8a-octalin skeleton talaroacids A–D (14) and an isopimarane diterpenoid talaromarane A (5) were isolated from the mangrove endophytic fungus Talaromyces sp. JNQQJ-4. Their structures and absolute configurations were determined by [...] Read more.
Five new diterpenes including four diterpenes with 1,2,3,4,4a,5,6,8a-octalin skeleton talaroacids A–D (14) and an isopimarane diterpenoid talaromarane A (5) were isolated from the mangrove endophytic fungus Talaromyces sp. JNQQJ-4. Their structures and absolute configurations were determined by analysis of high-resolution electrospray ionization mass spectroscopy (HRESIMS), 1D/2D Nuclear Magnetic Resonance (NMR) spectra, single-crystal X-ray diffraction, quantum chemical calculation, and electronic circular dichroism (ECD). Talaromarane A (5) contains a rare 2-oxabicyclo [3.2.1] octan moiety in isopimarane diterpenoids. In bioassays, compounds 1, 2, 4, and 5 displayed significant anti-inflammatory activities with the IC50 value from 4.59 to 21.60 μM. Full article
(This article belongs to the Special Issue Nutrients and Active Substances in Natural Products)
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12 pages, 946 KiB  
Article
Untargeted Metabolomics by Using UHPLC–ESI–MS/MS of an Extract Obtained with Ethyl Lactate Green Solvent from Salvia rosmarinus
by Grover Castañeta, Nicolas Cifuentes, Beatriz Sepulveda, Daniela Bárcenas-Pérez, José Cheel and Carlos Areche
Separations 2022, 9(11), 327; https://doi.org/10.3390/separations9110327 - 26 Oct 2022
Cited by 10 | Viewed by 2967
Abstract
Salvia rosmarinus (Lamiaceae), previously known as Rosmarinus officinalis, is a plant cultivated worldwide, native to the Mediterranean region. Its leaves are traditionally used for cooking. This species possesses numerous biological activities, including antioxidant, antimicrobial, anticancer, anti-inflammatory, and hepatoprotective properties. These biological properties [...] Read more.
Salvia rosmarinus (Lamiaceae), previously known as Rosmarinus officinalis, is a plant cultivated worldwide, native to the Mediterranean region. Its leaves are traditionally used for cooking. This species possesses numerous biological activities, including antioxidant, antimicrobial, anticancer, anti-inflammatory, and hepatoprotective properties. These biological properties are due to the presence of phenolic compounds, including rosmarinic acid and phenolic diterpenoids, such as carnosic acid and carnosol. In this study, we investigated the chemical composition of a green extract obtained by maceration with ethyl lactate for the first time. Seventy-five compounds were tentatively identified by UHPLC–ESI–MS/MS, including six organic acids, six cinnamic acid derivatives, five fatty acids, eighteen flavonoids, and thirty-eight terpenoids. Thus, abietane-type diterpenoids from the ethyl lactate extract were the predominant diterpenoids in the Chilean S. rosmarinus species, in contrast to the Chinese species, in which labdane and isopimarane-type diterpenoids were found for the first time. Finally, our study confirms that the extraction of S. rosmarinus with green ethyl lactate as a solvent is efficient and sustainable for the identification of flavonoids, phenols, and terpenoids from leaves. Full article
(This article belongs to the Special Issue Recent Advances in Green Sample Preparation Techniques)
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10 pages, 1608 KiB  
Article
3,4-Seco-Isopimarane Diterpenes from the Twigs and Leaves of Isodon Flavidus
by Wan-Fei Li, Zheng-Ming Liang, Chen-Liang Zhao, Nga Yi Tsang, Ji-Xin Li, Ya-Hua Liu, Kang He, Lu-Tai Pan, Lijun Rong, Juan Zou and Hong-Jie Zhang
Molecules 2022, 27(10), 3098; https://doi.org/10.3390/molecules27103098 - 12 May 2022
Cited by 3 | Viewed by 2239
Abstract
Three isopimarane diterpenes [fladins B (1), C (2), and D (3)] were isolated from the twigs and leaves of Chinese folk medicine, Isodon flavidus. The chemical structures were determined by the analysis of the comprehensive spectroscopic [...] Read more.
Three isopimarane diterpenes [fladins B (1), C (2), and D (3)] were isolated from the twigs and leaves of Chinese folk medicine, Isodon flavidus. The chemical structures were determined by the analysis of the comprehensive spectroscopic data, and the absolute configuration was confirmed by X-ray crystallographic analysis. The structures of 13 were formed from isopimaranes through the rearrangement of ring A by the bond break at C-3 and C-4 to form a new δ-lactone ring system between C-3 and C-9. This structure type represents the first discovery of a natural isopimarane diterpene with an unusual lactone moiety at C-9 and C-10. In the crystal of 1, molecules are linked to each other by intermolecular O-H···O bonds, forming chains along the b axis. Compounds 13 were evaluated for their bioactivities against different diseases. None of these compounds displayed cytotoxic activities against HCT116 and A549 cancer cell lines, antifungal activities against Trichophyton rubrum and T. mentagrophytes, or antiviral activities against HIV entry at 20 µg/mL (62.9–66.7) µM. Compounds 1 and 3 did not show antiviral activities against Ebola entry at 20 µg/mL either; only 2 was found to show an 81% inhibitory effect against Ebola entry activity at 20 µg/mL (66.7 µM). The bioactivity evidence suggested that this type of compound could be a valuable antiviral lead for further structure modification to improve the antiviral potential. Full article
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73 pages, 11699 KiB  
Review
Euphorbia Diterpenes: An Update of Isolation, Structure, Pharmacological Activities and Structure–Activity Relationship
by Douglas Kemboi, Xavier Siwe-Noundou, Rui W. M. Krause, Moses K. Langat and Vuyelwa Jacqueline Tembu
Molecules 2021, 26(16), 5055; https://doi.org/10.3390/molecules26165055 - 20 Aug 2021
Cited by 34 | Viewed by 5605
Abstract
Euphorbia species have a rich history of ethnomedicinal use and ethnopharmacological applications in drug discovery. This is due to the presence of a wide range of diterpenes exhibiting great structural diversity and pharmacological activities. As a result, Euphorbia diterpenes have remained the focus [...] Read more.
Euphorbia species have a rich history of ethnomedicinal use and ethnopharmacological applications in drug discovery. This is due to the presence of a wide range of diterpenes exhibiting great structural diversity and pharmacological activities. As a result, Euphorbia diterpenes have remained the focus of drug discovery investigations from natural products. The current review documents over 350 diterpenes, isolated from Euphorbia species, their structures, classification, biosynthetic pathways, and their structure–activity relationships for the period covering 2013–2020. Among the isolated diterpenes, over 20 skeletal structures were identified. Lathyrane, jatrophane, ingenane, ingenol, and ingol were identified as the major diterpenes in most Euphorbia species. Most of the isolated diterpenes were evaluated for their cytotoxicity activities, multidrug resistance abilities, and inhibitory activities in vitro, and reported good activities with significant half-inhibitory concentration (IC50) values ranging from 10–50 µM. The lathyranes, isopimaranes, and jatrophanes diterpenes were further found to show potent inhibition of P-glycoprotein, which is known to confer drug resistance abilities in cells leading to decreased cytotoxic effects. Structure–activity relationship (SAR) studies revealed the significance of a free hydroxyl group at position C-3 in enhancing the anticancer and anti-inflammatory activities and the negative effect it has in position C-2. Esterification of this functionality, in selected diterpenes, was found to enhance these activities. Thus, Euphorbia diterpenes offer a valuable source of lead compounds that could be investigated further as potential candidates for drug discovery. Full article
(This article belongs to the Section Natural Products Chemistry)
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13 pages, 1697 KiB  
Article
Plant Disease Control Efficacy of Platycladus orientalis and Its Antifungal Compounds
by Sohyun Bae, Jae Woo Han, Quang Le Dang, Hun Kim and Gyung Ja Choi
Plants 2021, 10(8), 1496; https://doi.org/10.3390/plants10081496 - 21 Jul 2021
Cited by 8 | Viewed by 3364
Abstract
Plants contain a number of bioactive compounds that exhibit antimicrobial activity, which can be recognized as an important source of agrochemicals for plant disease control. In searching for natural alternatives to synthetic fungicides, we found that a methanol extract of the plant species [...] Read more.
Plants contain a number of bioactive compounds that exhibit antimicrobial activity, which can be recognized as an important source of agrochemicals for plant disease control. In searching for natural alternatives to synthetic fungicides, we found that a methanol extract of the plant species Platycladus orientalis suppressed the disease development of rice blast caused by Magnaporthe oryzae. Through a series of chromatography procedures in combination with activity-guided fractionation, we isolated and identified a total of eleven compounds including four labdane-type diterpenes (14), six isopimarane-type diterpenes (510), and one sesquiterpene (11). Of the identified compounds, the MIC values of compounds 1, 2, 5 & 6 mixture, 9, and 11 ranged from 100 to 200 μg/mL against M. oryzae, whereas the other compounds were over 200 μg/mL. When rice plants were treated with the antifungal compounds, compounds 1, 2, and 9 effectively suppressed the development of rice blast at all concentrations tested by over 75% compared to the non-treatment control. In addition, a mixture of compounds 5 & 6 that constituted 66% of the P. orientalis ethyl acetate fraction also exhibited a moderate disease control efficacy. Together, our data suggest that the methanol extract of P. orientalis including terpenoid compounds has potential as a crop protection agent. Full article
(This article belongs to the Section Phytochemistry)
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10 pages, 467 KiB  
Communication
In Vitro Antimicrobial Activity of Isopimarane-Type Diterpenoids
by Vera M. S. Isca, Joana Andrade, Ana Sofia Fernandes, Paulo Paixão, Clara Uriel, Ana María Gómez, Noélia Duarte and Patrícia Rijo
Molecules 2020, 25(18), 4250; https://doi.org/10.3390/molecules25184250 - 16 Sep 2020
Cited by 7 | Viewed by 3098
Abstract
The antimicrobial evaluation of twelve natural and hemisynthetic isopimarane diterpenes are reported. The compounds were evaluated against a panel of Gram-positive bacteria, including two methicillin-resistant Staphylococcus aureus (MRSA) strains and one vancomycin-resistant Enterococcus (VRE) strain. Only natural compounds 7,15-isopimaradien-19-ol (1) and [...] Read more.
The antimicrobial evaluation of twelve natural and hemisynthetic isopimarane diterpenes are reported. The compounds were evaluated against a panel of Gram-positive bacteria, including two methicillin-resistant Staphylococcus aureus (MRSA) strains and one vancomycin-resistant Enterococcus (VRE) strain. Only natural compounds 7,15-isopimaradien-19-ol (1) and 19-acetoxy-7,15-isopimaradien-3β-ol (6) showed promising results. Isopimarane (1) was the most active, showing MIC values between 6.76 µM against S. aureus (ATCC 43866) and 216.62 µM against E. faecalis (FFHB 427483) and E. flavescens (ATCC 49996). Compound (6) showed moderated activity against all tested microorganisms (MIC between value 22.54 and 45.07 µM). These compounds were found to be active against the methicillin-sensitive strains of S. aureus (CIP 106760 and FFHB 29593), showing MIC values of 13.55 (1) and 22.54 (6) µM. Both compounds were also active against vancomycin-resistant E. faecalis (ATCC 51299) (MIC values of 54.14 and 45.07 µM, respectively). In addition, the cytotoxicity of nine compounds 7,15-isopimaradien-3β,19-diol (2); mixture: 15-isopimarene-8β-isobutyryloxy-19-ol and 15-isopimarene-8β-butyryloxy-19-ol (3); 3β-acetoxy-7,15-isopimaradiene-19-ol (5); 19-acetoxy-7,15-isopimaradiene-3β-ol (6); 3β,19-diacetoxy-7,15-isopimaradiene (8); 15-isopimarene-8β,19-diol (9); 19-O-β-d-glucopyranoside-7,15-isopimaradiene (10); lagascatriol-16-O-β-d-glucopyranoside (11) and lagascatriol-16-O-α-d-mannopyranoside (12) was evaluated in the human breast cancer cell line MDA-MB-231. Isopimarane (2) was the only compound showing some cytotoxicity. The IC50 value of compound (2) was 15 µM, suggesting a mild antiproliferative activity against these breast cancer cells. Full article
(This article belongs to the Special Issue Design of Natural Products Lead Molecules Using Organic Synthesis)
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17 pages, 3152 KiB  
Article
Structural Elucidation of Malonylcommunol and 6β-Hydroxy-trans-communic Acid, Two Undescribed Diterpenes from Salvia cinnabarina. First Examples of Labdane Diterpenoids from a Mexican Salvia Species
by Celia Bustos-Brito, Antonio Nieto-Camacho, Simón Hernandez-Ortega, José Rivera-Chávez, Leovigildo Quijano and Baldomero Esquivel
Molecules 2020, 25(8), 1808; https://doi.org/10.3390/molecules25081808 - 15 Apr 2020
Cited by 9 | Viewed by 3661
Abstract
The aerial parts of Salvia cinnabarina afforded two undescribed labdane diterpenoids 1 and 2 (malonylcommunol and 6β-hydroxy-trans-communic acid) along with two known labdane diterpenoids, trans-communic acid (3) and trans-communol (4). Additionally, seven known metabolites were [...] Read more.
The aerial parts of Salvia cinnabarina afforded two undescribed labdane diterpenoids 1 and 2 (malonylcommunol and 6β-hydroxy-trans-communic acid) along with two known labdane diterpenoids, trans-communic acid (3) and trans-communol (4). Additionally, seven known metabolites were also isolated; two isopimarane diterpenoids 5 and 6, two sesquiterpenoids identified as β-eudesmol (7) and cryptomeridiol (8), and three aromatic compounds identified as phthalic acid (9), a mixture of tyrosol fatty acid esters (10) and the flavone salvigenine (11). While compounds compounds 13 showed significant inhibition of yeast α-glucosidase, compounds 2, 3 and 7 had no anti-inflammatory activity in the edema model induced by TPA. This paper is not only the first report on a wild population of Salvia cinnabarina, but also of the presence of labdane-type diterpenoids in a Mexican Salvia sp. Full article
(This article belongs to the Section Natural Products Chemistry)
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33 pages, 11319 KiB  
Review
Recent Advances in Kaempferia Phytochemistry and Biological Activity: A Comprehensive Review
by Abdelsamed I. Elshamy, Tarik A. Mohamed, Ahmed F. Essa, Ahmed M. Abd-El Gawad, Ali S. Alqahtani, Abdelaaty A. Shahat, Tatsuro Yoneyama, Abdel Razik H. Farrag, Masaaki Noji, Hesham R. El-Seedi, Akemi Umeyama, Paul W. Paré and Mohamed-Elamir F. Hegazy
Nutrients 2019, 11(10), 2396; https://doi.org/10.3390/nu11102396 - 7 Oct 2019
Cited by 70 | Viewed by 12181
Abstract
Background: Plants belonging to the genus Kaempferia (family: Zingiberaceae) are distributed in Asia, especially in the southeast region, and Thailand. They have been widely used in traditional medicines to cure metabolic disorders, inflammation, urinary tract infections, fevers, coughs, hypertension, erectile dysfunction, abdominal and [...] Read more.
Background: Plants belonging to the genus Kaempferia (family: Zingiberaceae) are distributed in Asia, especially in the southeast region, and Thailand. They have been widely used in traditional medicines to cure metabolic disorders, inflammation, urinary tract infections, fevers, coughs, hypertension, erectile dysfunction, abdominal and gastrointestinal ailments, asthma, wounds, rheumatism, epilepsy, and skin diseases. Objective: Herein, we reported a comprehensive review, including the traditional applications, biological and pharmacological advances, and phytochemical constituents of Kaempheria species from 1972 up to early 2019. Materials and methods: All the information and reported studies concerning Kaempheria plants were summarized from library and digital databases (e.g., Google Scholar, Sci-finder, PubMed, Springer, Elsevier, MDPI, Web of Science, etc.). The correlation between the Kaempheria species was evaluated via principal component analysis (PCA) and agglomerative hierarchical clustering (AHC), based on the main chemical classes of compounds. Results: Approximately 141 chemical constituents have been isolated and reported from Kaempferia species, such as isopimarane, abietane, labdane and clerodane diterpenoids, flavonoids, phenolic acids, phenyl-heptanoids, curcuminoids, tetrahydropyrano-phenolic, and steroids. A probable biosynthesis pathway for the isopimaradiene skeleton is illustrated. In addition, 15 main documented components of volatile oils of Kaempheria were summarized. Biological activities including anticancer, anti-inflammatory, antimicrobial, anticholinesterase, antioxidant, anti-obesity-induced dermatopathy, wound healing, neuroprotective, anti-allergenic, and anti-nociceptive were demonstrated. Conclusions: Up to date, significant advances in phytochemical and pharmacological studies of different Kaempheria species have been witnessed. So, the traditional uses of these plants have been clarified via modern in vitro and in vivo biological studies. In addition, these traditional uses and reported biological results could be correlated via the chemical characterization of these plants. All these data will support the biologists in the elucidation of the biological mechanisms of these plants. Full article
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10 pages, 1755 KiB  
Article
20-Nor-Isopimarane Epimers Produced by Aspergillus wentii SD-310, a Fungal Strain Obtained from Deep Sea Sediment
by Xiao-Dong Li, Xin Li, Xiao-Ming Li, Gang-Ming Xu, Yang Liu and Bin-Gui Wang
Mar. Drugs 2018, 16(11), 440; https://doi.org/10.3390/md16110440 - 9 Nov 2018
Cited by 25 | Viewed by 4242
Abstract
Four new uncommon 20-nor-isopimarane diterpenoid epimers, aspewentins I−L (14), together with a new methylated derivative of 3, aspewentin M (5), were isolated from the deep sea sediment-derived fungus Aspergillus wentii SD-310. The very similar structures of [...] Read more.
Four new uncommon 20-nor-isopimarane diterpenoid epimers, aspewentins I−L (14), together with a new methylated derivative of 3, aspewentin M (5), were isolated from the deep sea sediment-derived fungus Aspergillus wentii SD-310. The very similar structures of these epimers made the separation and purification procedures difficult. The structures of compounds 15 were illustrated based on spectroscopic analysis, and the absolute configurations of compounds 15 were unambiguously determined by the combination of NOESY, time-dependent density functional (TDDFT)-ECD calculations, and X-ray crystallographic analysis. These metabolites represented the rare examples of 20-nor-isopimarane analogues possessing a cyclohexa-2,5-dien-1-one moiety. These compounds were tested for antimicrobial activities against human and aquatic pathogenic bacteria, as well as plant-pathogenic fungi. While compounds 1 and 2 exhibited inhibitory activities against zoonotic pathogenic bacteria such as Escherichia coli, Edwardsiella tarda, Vibrio harveyi, and V. parahaemolyticus, compound 5 showed potent activity against the plant pathogen Fusarium graminearum. Full article
(This article belongs to the Special Issue Marine Antimicrobial Agents)
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9 pages, 423 KiB  
Article
Bioactive Isopimarane Diterpenes from the Fungus, Epicoccum sp. HS-1, Associated with Apostichopus japonicus
by Xuekui Xia, Jun Qi, Yayue Liu, Airong Jia, Yonggang Zhang, Changheng Liu, Cuiling Gao and Zhigang She
Mar. Drugs 2015, 13(3), 1124-1132; https://doi.org/10.3390/md13031124 - 2 Mar 2015
Cited by 24 | Viewed by 7110
Abstract
One new isopimarane diterpene (1), together with two known compounds, 11-deoxydiaporthein A (2) and iso-pimara-8(14),15-diene (3) were isolated from the culture of Epicoccum sp., which was associated with Apostichopus japonicus. Their structures were determined by the analysis [...] Read more.
One new isopimarane diterpene (1), together with two known compounds, 11-deoxydiaporthein A (2) and iso-pimara-8(14),15-diene (3) were isolated from the culture of Epicoccum sp., which was associated with Apostichopus japonicus. Their structures were determined by the analysis of 1D and 2D NMR, as well as mass spectroscopic data. The absolute configuration of Compound 1 was deduced by a single-crystal X-ray diffraction experiment using CuKα radiation. In the bioactivity assay, both Compounds 1 and 2 exhibited α-glucosidase inhibitory activity with IC50 values of 4.6 ± 0.1 and 11.9 ± 0.4 μM, respectively. This was the first report on isopimarane diterpenes with α-glucosidase inhibitory activity. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes)
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15 pages, 501 KiB  
Article
Resin Diterpenes from Austrocedrus chilensis
by Verónica Rachel Olate, Olatz Goikoetxeaundia Usandizaga and Guillermo Schmeda-Hirschmann
Molecules 2011, 16(12), 10653-10667; https://doi.org/10.3390/molecules161210653 - 20 Dec 2011
Cited by 15 | Viewed by 5636
Abstract
Seventeen diterpenes belonging to the labdane, abietane and isopimarane skeleton classes were isolated from the resin of the Chilean gymnosperm Austrocedrus chilensis and identified by spectroscopic and spectrometric methods. The diterpene 12-oxo-labda-8(17),13E-dien-19 oic acid is reported for the first time as [...] Read more.
Seventeen diterpenes belonging to the labdane, abietane and isopimarane skeleton classes were isolated from the resin of the Chilean gymnosperm Austrocedrus chilensis and identified by spectroscopic and spectrometric methods. The diterpene 12-oxo-labda-8(17),13E-dien-19 oic acid is reported for the first time as a natural product and 14 diterpenes are reported for the first time for the species. Full article
(This article belongs to the Section Natural Products Chemistry)
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