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sesquiterpenoids from the leaves of Sarcandra glabra

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Chinese Journal of Natural Medicines 2022年第3期20卷 215-220页

作者： WANG Yong-Yue LI Qiu-Rong CHI Jun LI Ji-Xin KONG Ling-Yi LUO Jun Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines School of Traditional Chinese PharmacyChina Pharmaceutical UniversityNanjing 210009China

Sarglanoids A-F,six new sesquiterpenoids belonging to eudesmane(1-5)and eremophilane(6)types,were isolated from the leaves of Sarcandra glabra,a famous traditional Chinese medicine(TCM).Their structures including absolute configurations were elucidated through extensive spectroscopic analysis and electronic circular dichroism(ECD)*** 1-2 were rare N-containing eudesmane-type *** 3 exhibited inhibitory activity against nitric oxide(NO)production in lipopolysaccharides(LPS)-induced RAW 264.7 cells with IC_(50) values at 20.00±1.30μmol·L^(-1).These findings provide scientific evidence for sesquiterpenoids as the material foundation of ***.

关键词： Sarcandra glabra sesquiterpenoids N-containing sesquiterpenoids Anti-inflammatory

Natural sesquiterpenoids, Diterpenoids, Sesterterpenoids, and Triterpenoids with Intriguing Structures from 2017 to 2022

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Chinese Journal of Chemistry 2023年第22期41卷 3115-3132页

作者： Xiaotian Zhang Meijia Zheng Aimin Fu Qin Li Chunmei Chen Hucheng Zhu Yonghui Zhang Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation School of PharmacyTongji Medical CollegeHuazhong University of Science and TechnologyWuhanHubei 430030China

This review covers the isolation,structural determination,plausible biosynthetic pathways,and biological activities of 166 natural terpenoids including 57 sesquiterpenoids,65 diterpenoids,15 sesterterpenoids,and 29 tr... 详细信息

关键词： sesquiterpenoids Diterpenoids Sesterterpenoids Triterpenoids Structura scaffolds Biosynthetic pathways Structure elucidation Drug discovery

Seven drimane-type sesquiterpenoids from an earwig-associated Aspergillus sp.

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Chinese Journal of Natural Medicines 2023年第1期21卷 58-64页

作者： SALMAN Khan ZHU Hongjie SUN Ziqian LI Yilin WANG Lan WANG Rong GUO Zhikai JIAO Ruihua State Key Laboratory of Pharmaceutical Biotechnology Institute of Functional BiomoleculesSchool of Life SciencesNanjing UniversityNanjing 210093China Hainan Key Laboratory of Tropical Microbe Resources Institute of Tropical Bioscience and BiotechnologyChinese Academy of Tropical Agricultural SciencesHaikou 571101China Key Laboratory for Biology and Genetic Resources of Tropical Crops of Hainan Province Hainan Institute for Tropical Agricultural ResourcesHaikou 571101China Hainan Academy of Ocean and Fisheries Sciences Hainan Tropical Ocean UniversityHaikou 571126China

Drimane-type sesquiterpenoids are widely distributed in *** the ethyl acetate extract of the earwig-derived Aspergillus ***2396,seven new drimane-type sesquiterpenoids,named drimanenoids A−G(1−7),were *** structures were elucidated by diverse spectroscopic analysis including high-resolution ESI-MS,one-and two-dimensional NMR *** A−F(1−6)are new members of drimane-type sesquiterpenoid esterified with unsaturated fatty acid side chain at *** C(3),D(4)and F(6)showed antibacterial activity against five types of bacteria with different inhibition *** D(4)exhibited moderate cytotoxicity against human myelogenous leukemia cell line K562 with an IC_(50) value of 12.88±0.11μmol·L^(−1).

关键词： Fungus sesquiterpenoids Drimane-type Antibacterial Cytotoxic Aspergillus sp.

Diverse sesquiterpenoids from Litsea lancilimba *** potential neuroprotective effects against H_(2)O_(2)-induced SH-SY5Y cell injury

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Chinese Journal of Natural Medicines 2022年第9期20卷 701-711页

作者： ZHANG Yi-Jie BAI Ming LI Jia-Yi QIN Shu-Yan LIU Yu-Yang HUANG Xiao-Xiao ZHENG Jiang SONG Shao-Jiang Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research&Development Liaoning ProvinceEngineering Research Center of Natural Medicine Active Molecule Research&DevelopmentLiaoning ProvinceKey Laboratory of Natural Bioactive Compounds Discovery&ModificationShenyangSchool of Traditional Chinese Materia MedicaShenyang Pharmaceutical UniversityShenyang 110016China Wuya College of Innovation Shenyang Pharmaceutical UniversityShenyang 110016China State Key Laboratory of Functions and Applications of Medicinal Plants Guizhou Provincial Key Laboratory of PharmaceuticsGuizhou Medical UniversityGuiyang 550004China

Five undescribed sesquiterpenoids(1–5),and nine known sesquiterpenoids(6–14)were obtained from the fruits of Litsea lancilimba *** LC-MS/MS molecular networking *** A(1)possessed a unique 8-member ring through unexpected cyclization of the methyl group on C-10 of *** structures were elucidated by spectroscopic techniques including IR,UV,NMR,HR-ESI-MS,and their absolute configurations were assigned by ECD *** isolated sesquiterpenoids were analyzed by bioinformatics and evaluated for their neuroprotective effects against H_(2)O_(2)-induced injury in human neuroblastoma SH-SY5Y cells.

关键词： Litsea lancilimba Lauraceae sesquiterpenoids Neuroprotective effect

Artemdubinoids A-N:novel sesquiterpenoids with antihepatoma cytotoxicity from Artemisia dubia

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Chinese Journal of Natural Medicines 2023年第12期21卷 902-915页

作者： GAO Zhen LI Tianze MA Yunbao HUANG Xiaoyan GENG Changan ZHANG Xuemei CHEN Jijun State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201China University of Chinese Academy of Sciences Beijing 100049China

In pursuit of effective agents for hepatocellular carcinoma derived from the Artemisia species,this study built upon initial findings that an ethanol(EtOH)extract and ethyl acetate(EtOAc)fraction of the aerial parts of Artemisia dubia *** *** cytotoxicity against HepG2 cells with inhibitory rates of 57.1%and 84.2%(100μg·mL−1),*** by bioactivity,fourteen previously unidentified sesquiterpenes,artemdubinoids A–N(1–14),were isolated from the EtOAc *** structural elucidation was achieved through comprehensive spectroscopic analyses and corroborated by the comparison between the experimental and calculated ECD *** crystal X-ray diffraction provided definitive structure confirmation for artemdubinoids A,D,F,and *** A and B(1–2)represented unique sesquiterpenes featuring a 6/5-fused bicyclic carbon scaffold,and their putative biosynthetic pathways were discussed;artemdubinoid C(3)was a novel guaianolide derivative that might be formed by the[4+2]Diels–Alder reaction;artemdubinoids D and E(4–5)were rare 1,10-seco-guaianolides;artemdubinoids F–K(6–11)were chlorinecontaining *** compounds exhibited cytotoxicity against three human hepatoma cell lines(HepG2,Huh7,and SKHep-1)with half-maximal inhibitory concentration(IC50)values spanning 7.5−82.5μmol·L^(−1).Artemdubinoid M(13)exhibited the most active cytotoxicity with IC50 values of 14.5,7.5 and 8.9μmol·L^(−1)against the HepG2,Huh7,and SK-Hep-1 cell lines,respectively,which were equivalent to the positive control,sorafenib.

关键词： Artemdubinoids A-N Artemisia dubia sesquiterpenoids Antihepatoma activity

Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China

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Natural Products and Bioprospecting 2022年第1期12卷 12-25页

作者： Lu Zhang Ping Yi Hui Yan Xiao-Nian Li Meng-Yuan Xia Jun Yang Ji-Feng Luo Yue-Qiu He Yue-Hu Wang Key Laboratory of Economic Plants and Biotechnology Yunnan Key Laboratory for Wild Plant Resourcesand State Key Laboratory of Phytochemistry and Plant Resources in West ChinaKunming Institute of BotanyChinese Academy of SciencesKunming 650201People’s Republic of China Key Laboratory of Chemistry for Natural Products of Guizhou Province Chinese Academy of SciencesGuiyang 550014People’s Republic of China Faculty of Plant Protection Yunnan Agricultural UniversityKunming 650201People’s Republic of China

Five new 2-(2-phenylethyl)chromone derivatives,(5S,6R,7R,8S,7ʹR)-7ʹ-hydroxyagarotetrol(1),(5S,6R,7R,8S,7ʹS)-7ʹ-hydroxyagarotetrol(2),(6S,7S,8R)-2-[2-(4-methoxyphenyl)ethyl]-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone(3),(6S,7S,8R)-2-(2-phenylethyl)-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone(4),(5S,6R,7S,8R)-2-(2-phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-[2-(2-phenylethyl)-7-methoxychromonyl-6-oxy]chromone(5),three new sesquiterpenoids,(4S,5S,7S,8S,10S,13R)-7,8,13-trihydroxyrotunda-1,11-dien-3-one(6),(4S,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one(7),and(4R,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one(8),along with 14 known compounds were isolated from the resinous heartwood of Aquilaria sinensis(Thymelaeaceae).The chemical structures of these new compounds were elucidated by 1D and 2D NMR and MS data,single-crystal X-ray diffraction analysis,and electronic circular dichroism(ECD)*** neuroprotective activities of these isolates were evaluated using an in vitro model of rat adrenal pheochromocytoma(PC12)cell injury induced by *** concentrations from 5 to 40μM,compounds 4 and 6,agarotetrol(9),and 6-hydroxy-2-(2-phenylethyl)chromone(17)showed significant protective activities against corticosterone-induced PC12 cell injury(P<0.001).

关键词： Thymelaeaceae Aquilaria sinensis sesquiterpenoids 2-(2-Phenylethyl)chromones Neuroprotective

sesquiterpenoids from Chloranthus spicatus

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Chinese Journal of Chemistry 2012年第6期30卷 1243-1248页

作者：杨升平陈华东岳建民 State Key Laboratory of Drug Research Shanghai Institute of Materia Medica Shanghai Institutes for Biological Sciences Chinese Academy of Sciences Shanghai 201203 China

Five new sesquiterpenoids （1-5）, namely chlospicates A--E （1-5）, along with ten known sesquiterpenoids and three known sesquiterpenoid dimers, were isolated from the whole plant of Chloranthus spicatus. Their stru... 详细信息

关键词： Chloranthus spicatus sesquiterpenoids sesquiterpenoid dimers chlospicates A--E

sesquiterpenoids from the Whole Plants of Chloranthus holostegius and Their Anti-inflammatory Activities

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Chinese Journal of Chemistry 2021年第5期39卷 1168-1174页

作者： Zhao-Chun Zhan Zhong-Nan Wu Qing Tang Can-Jie Li Wen-Zhi Wang Ji-Hui Zhang Xue-Fang Zhuo Yu-Bo Zhang Guo-Cai Wang Yao-Lan Li Institute of Traditional Chinese Medicine&Natural Products Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs ResearchCollege of PharmacyJinan UniversityGuangzhouGuangdong 510632China The First Affiliated Hospital Jinan UniversityGuangzhouGuangdong 510632China Guangdong Clinical Translational Center for Targeted Drug Deportment of PharmacologySchool of MedicineJinon UniversityGuangzhouGuangdong 510632China

Five new sesquiterpenoids(1-5),chloranholides A-E,along with three known compounds(6-8),were isolated from the whole plants of Chloranthus *** structures were elucidated using the spectroscopic methods(IR,UV,HR-ESI-MS,ID and 2D NMR),and their absolute configurations were determined by the X-ray crystallography and ECD *** 1-8 were evaluated for their anti-inflammatory effects on LPS-induced RAW 264.7 macrophage ***,compound 4 exhibited the most significant anti-inflammatory activity with the secretion levels of TNF-α and IL-6 at 15.52%and 5.98%,respectively,better than that of dexamethasone.

关键词： Chloranthus holostegius sesquiterpenoids NMR spectroscopy X-ray diffraction Inflammation

sesquiterpenoids from the Rhizomes of Homalomena occulta

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Natural Products and Bioprospecting 2016年第4期6卷 211-216页

作者： Jun-Li Yang Ya-Min Zhao Yan-Ping Shi Key Laboratory of Chemistry of Northwestern Plant Resources of CAS and Key Laboratory for Natural Medicine of Gansu Province Lanzhou Institute of Chemical PhysicsChinese Academy of SciencesLanzhou 730000People’s Republic of China State Key Laboratory of Applied Organic Chemistry Lanzhou UniversityLanzhou 730000People’s Republic of China

Naturally occurring oplopanane sesquiterpenoids are rarely reported.A phytochemical investigation on the rhizomes of Homalomena occulta(Lours)has resulted in the discovery of six oplopanane sesquiterpenoids(1–6),including four new(1–4)and one 3,5-seco-oplopanane(6),together with three previously reported sesquiterpenoids(7-9).In addition three new oplopananes(2a–4a)were also obtained by chemical *** structures of these sesquiterpenoids were established based on the comprehensive spectroscopic analyses,including NMR,MS,and IR,and comparing with the literatures.

关键词： Homalomena occulta sesquiterpenoids Oplopananes