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Artemordins A-S, Cadinane-Type Sesquiterpenoid Dimers from Artemisia ordosica and Their Antihepatoma Activities

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Chinese Journal of Chemistry 2024年第13期42卷 1493-1508页

作者： Yuan Wang Tian-Ze Li Yun-Bao Ma Chang-An Geng Yong-Cui Wang Ji-Jun Chen State key laboratory of phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunmingYunnan 650201China University of Chinese Academy of Sciences Beijing 100049China

Nineteen new cadinane-involving sesquiterpenoid dimers,artemordins A-S(1-—19),together with 13 known SDs(20-32)were isolated from Artemisia *** structures and absolute configurations were established by comprehensive spectral analyses,X-ray single crystal diffraction,theoretical ECD,and NMR ***,artemordins A-F(1—6)were the first examples of two cadinane units constructed by unprecedented C-3−C-15′or C-3−C-13′single bond with an oxido-rearranged 6/5/6/6 fused ring system;artemordins G-K(7-11)were biogenetically connected by[4+2]cycloaddition reaction and artemordins G-J(7-10)possessed a novel 5/6/6/6/6/6/5-heptacyclic fused ring *** L-S(12-19)were formed by esterification,which involved three different types of *** assay suggested that the most active compounds,artemordins B and H(2 and 8),exhibited inhibitory activities on three hepatoma cell lines with IC50 values of 26.9 and 25.1μmol/L(HepG2),29.5 and 18.3μmol/L(Huh7),19.7 and 15.7μmol/L(SK-Hep-1).

关键词： Artemisia ordosica Artemordins A-s Cadinane-type sesquiterpenoid dimers Antihepatoma activities Terpenoids Natural products Cytotoxicity

A New Degraded Sesquiterpene from Marine Actinomycete Streptomyces sp. 0616208

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Chinese Chemical Letters 2006年第11期17卷 1463-1465页

作者： Xiu Chao XIE Wen Li MEI You Xing ZHAO Kui HONG Hao Fu DAI State key laboratory. of Tropical Crops Biotechnology Institute of Tropical Bioscience and Biotechnology Chinese Academy of Tropical Agriculture Sciences Haikou 571101 State key laboratory of phytochemistry and Plant Resources in West China Kunming Institute of Botany Chinese Academy of Sciences Kunming 650204

A new degraded sesquiterpene was isolated from the marine actinomycete Streptomyces sp. 0616208. Its structure was elucidated as （1α; 4aα; 5α, 7β, 8aβ）-5, 8a-dimethyl-decahydrona- phthalene-1, 4a, 7-triol on th... 详细信息

关键词： Marine actinomycete, Streptomyces sp., degraded sesquiterpene, (1α 4aα 5α, 7β, 8aβ)-5, 8a-dimethyl-decahydronaphthalene- 1,4a,7-triol.

Hypermonones A-I,New Polyprenylated Acylphloroglucinols from Hypericum monogynum with Multidrug Resistance Reversal Activity

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Chinese Journal of Chemistry 2021年第9期39卷 2422-2432页

作者： Yan-Rong Zeng Ya-Nan Li Jue Yang Ping Yi Lei Huang Lie-Jun Huang Wei Gu Zhan-Xing Hu Yan-Mei Li Chun-Mao Yuan Xiao-Jiang Hao State key laboratory of Functions and Applications of Medicinal Plants Guizhou Medical UniversityGuiyangGuizhou 550014China The key laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences GuiyangGuizhou 550014China State key laboratory of phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunmingYunnan 650201China

Eleven biogenetically related polyprenylated acylphloroglucinols(PPAPs),including four novel skeletons(1-4)and five new com-pounds(5-9),were isolated from the flowers of Hypericum *** A-D(1-4)represented the first example of a unique dilactone structure containing carbonyl bonded single 5-lactone and tricyclic γ-lactone *** structures were elucidated by NMR analysis,X-ray crystallography,and ECD ***,we revised the structure of hyperibrin B to hy perm on one I(9)via NMR an alysis,a qua ntum computational chemistry method,and hypothetic bios yn thetic con *** compounds(5,6,and 9)with significant MDR reversal activity(RF ranging from 61 to 223)were superior to the positive control verapamil(MCF-7/ADR,RF:53;HepG2/ADRz RF:124).Mechanism study for compound 5 indicated that this compound could inhibit the function of P-gp tran sport rather tha n its expressi on,and the possible recog nition mechanism betwee n compo und 5 and P-gp was predicted by molecular docking.

关键词： Hypericum monogynum phytochemistry Structure elucidation Biological activity Multidrug resistance reversal activity

Two new epimeric pairs of iridoid from mangrove plant Scyphiphora hydrophyllacea

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Chinese Chemical Letters 2007年第12期18卷 1509-1511页

作者： Yan Bo Zeng Wen Li Mei You Xing Zhao Ling Zhuang Kui Hong Hao Fu Dai State key Biotechnology laboratory of Tropical Crops institute of Tropical Bioscience and Biotechnology Chinese Academy of Tropical Agricultural Sciences Haikou 571101 China State key laboratory of phytochemistry and Plant Resources in West China Kunming institute of Botany Chinese Academy of Sciences Kunming 650204 China

Two new epimeric pairs of iridoid scyphiphin A1 （la）, A2 （lb） and scyphiphin B 1 （2a）, B2 （2b） were isolated from Scyphiphora hydrophyllacea Gaertn. F. Their structures were elucidated by spectroscopic methods. The mixture of scyphiphin B 1 and scyphiphin B2 showed moderate cytotoxicity against human hepatoma SMMC-7721 cell line in vitro by MTT method.

关键词： Scyphiphora hydrophyllacea Gaertn. E Iridoid Cytotoxicity SMMC-7721

Artemsieverolactones A—H,Eight Guaiane-Type Sesquiterpenoid Trimers from Artemisia sieversiana

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Chinese Journal of Chemistry 2024年第10期42卷 1084-1092页

作者： Wei Dong Xiao-Yan Huang Tian-Ze Li Yan-Mei Weng Chang-An Geng Ji-Jun Chen State key laboratory of phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunmingYunnan 650201China University of Chinese Academyof Sciences Beijing 100049China

Eight new guaiane-type sesquiterpenoid trimers,artemsieverolactones A—H,possessing unprecedented scaffolds via biocatalyzed[4+2]Diels−Alder cycloaddition reactions were identified from Artemisia *** structures were determined by comprehensive spectroscopic data,single-crystal X-ray diffraction analyses,and ECD *** terms of structure,artemsieverolactones A—H are first examples of sesquiterpenoid trimers from guaiane-type sesquiterpenoid through four different[4+2]Diels−Alder cycloaddition *** fibrosis assay suggested that five compounds exhibited activity against HSC-LX2 with IC_(50)values ranging from 37.8 to 117.1μmol/*** most active artemsieverolactone B(2)displayed significant inhibitory activity against HSC-LX2 with IC_(50)value of 37.8μmol/L,which was 3 times more active than the positive drug silybin(IC_(50),139.7μmol/L).Preliminary mechanism study revealed that artemsieverolactone B could inhibit the deposition of human collagen typeⅠ(ColⅠ),human hyaluronic acid(HA),and human laminin(HL)with IC_(50)values of 40.4μmol/L(Col I),55.1μmol/L(HL),47.3μmol/L(HA),which was 2 to 3-fold more potent than silybin.

关键词： Artemisia sieversiana Artemsieverolactones A-H Guaiane-type sesquiterpenoid trimers Antihepatic fibrosis Extracellular matrix Cancer NMR spectroscopy X-ray diffraction

Lepithiohydimerins A-D:Four Pairs of Neuroprotective Thiohydantoin Dimers Bearing a Disulfide Bond from Maca(Lepidium meyenii Walp.)

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Chinese Journal of Chemistry 2021年第10期39卷 2738-2744页

作者： Xing-Rong Peng Ran-Ran Zhang Jun-Hong Liu Zhong-Rong Li Lin Zhou Ming-Hua Qiu State key laboratory of phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunmingYunnan650201 China University of the Chinese Academy of Sciences Beijing 100049China

Main observation and conclusion An HPLC-UV-guided separation was performed and four pairs of unprecedented macathiohydantoin dimers,lepithiohydimerins A—D(1—4)bearing a rare disulfide bond were isolated from the tubers of *** structures were unambiguously confirmed by NMR spectroscopic,X-ray crystallographic and electronic circular dichroism(ECD)*** the concentration of 20μmol/L,compounds 2-1,2-2,and 4-1 increased the viability of PC12 cells with the cell viability at(72.06±1.14)%,(72.64±1.49)%,and(70.93±1.22)%,***,the serial concentration experiment showed that they can protect PC12 cells in a dose-dependent manner.

关键词： Lepidium meyenii Walp. Thiohydantoin dimers Natural products Structure elucidation Biological activity

Lycopodine-Type Alkaloids from Lycopodium japonicum

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Natural Products and Bioprospecting 2014年第4期4卷 213-219页

作者： Juan He Xing-De Wu Fei Liu Yu-Cheng Liu Li-Yan Peng Yu Zhao Xiao Cheng Huai-Rong Luo Qin-Shi Zhao State key laboratory of phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201China

Three new lycopodine-type alkaloids,4a-hydroxyanhydrolycodoline(1),4a,6a-dihydroxyanhydrolycodoline(2),and 6-epi-8b-acetoxylycoclavine(3),and an artifact,lycoposerramine G nitrate(4),along with seventeen related known compounds,were isolated from the club moss Lycopodium japonicum *** Murray(Lycopodiaceae).Their structures were elucidated by extensive spectroscopic methods as well as X-ray *** 1–4 were evaluated for their acetylcholine esterase inhibitory activity.

关键词： Lycopodium japonicum Lycopodine-type alkaloids 4a-Hydroxyanhydrolycodoline 4a,6a-Dihydroxyanhydrolycodoline 6-epi-8b-Acetoxylycoclavine Lycoposerramine G nitrate

Guaiane-type Sesquiterpenoid Dimers from Artemisia zhongdianensis and Antihepatoma Carcinoma Activity via the p38MAPK Pathway

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Chinese Journal of Chemistry 2023年第19期41卷 2453-2468页

作者： Wei Dong Wen-Jing Ma Yun-Bao Ma Feng-Jiao Li Tian-Ze Li Yong-Cui Wang Xiao-Feng He Chang-An Geng Xue-Mei Zhang Ji-Jun Chen State key laboratory of phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunmingYunnan650201 China University of Chinese Academy of Sciences Beijing100049 China

17 new guaiane-type sesquiterpenoid dimers(GSDs),artemzhongdianolides B1—B17(1—17),were isolated from Artemisia zhongdianensis under the guidance of bioassay,and elucidated by spectral analyses(HRESIMS,1D and 2D NMR,IR,ECD).The absolute configuration of compounds 1,3,7,9,10,and 13 was determined by single-crystal X-ray diffraction ***,artemzhongdianolides B1(1)and B2(2)were the first example of the GSDs fused via a C-13/C-13'single bond,and artemzhongdianolides B3—B17 were[4+2]Diels–Alder adducts of two monomeric *** of the compounds showed antihepatoma cytotoxicity with IC_(50) values ranging from 9.9 to 170.1μmol/***,artemzhongdianolide B9(9)was the most active one against three hepatoma cell lines with IC_(50) values of 13.1μmol/L(HepG2),19.5μmol/L(Huh7),and 19.5μmol/L(SK-Hep-1),and dose-dependently inhibited cell migration and invasion,induced G1 cell cycle arrest and cell apoptosis in HepG2 *** 9 might suppress HepG2 cells via affecting the p38MAPK signaling pathway suggested by machine learning approach,and significantly upregulated expression of phosphorylated p38 validated by Western blot assay.

关键词： Artemzhongdianolides B1-B17 Artemisia zhongdianensis Guaiane-type sesquiter penoid dimers Antihepatoma activity p38MAPK pathway Cancer NMR spectroscopy X-ray diffraction

Untiring Researches for Alternative Resources of Rhizoma Paridis

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Natural Products and Bioprospecting 2018年第4期8卷 265-278页

作者： Xu-Jie Qin Wei Ni Chang-Xiang Chen Hai-Yang Liu State key laboratory of phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of Sciencesand Yunnan Key Laboratory of Medicinal ChemistryKunming 650201People’s Republic of China

Rhizoma Paridis(RP,M®),a traditional Chinese medicine,is the rhizoma of Paris polyphylla ***(PPY)or *** *** which are widely used as important raw materials for several Chinese patent ***,the wild resources of these herbs have become less and less due to their slow-growing characteristics and previously excessive *** review covers untiring investigations on alternative resources of RP by our research group over the past decades,including non-medicinal parts of PPY as well as other plants of Liliaceae and Liliflorae *** arial parts of PPY and the whole plants of Trillium kamtschaticum might be alternative resources for RP based on the fact that they shared the same or similar saponins and bioactivities.

关键词： Rhizoma Paridis Paris polyphylla Alternative resources Steroidal saponins Bioactivities