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Clerodenoids A-F:C-ring Aromatized and/or Rearranged Abietane diterpenoids from Clerodendrum chinense ***

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Chinese Journal of Chemistry 2021年第7期39卷 1891-1897页

作者： Jingjing Qi Yan Zhang Qunfang Liu Hongchun Liu Yaoyue Fan Jianmin Yue School of Chinese Materia Medica Nanjing University of Chinese Medicine138 Xianlin RoadNanjingJiangsu210023 China State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of Sciences555 Zu Chong Zhi RoadShanghai201203 China

Main observation and conclusion As part of our continuing efforts toward the discovery of the biologically active diterpenoids from medicinal plants,six new C-ring aromatized abietane diterpenoids,clerodenoids A-F(1-6... 详细信息

关键词： Clerodendrum chinense Natural products diterpenoids Structural elucidation Antiproliferative activities

Discovery of Highly Oxidized Abietane diterpenoids from the Roots of Euphorbia fischeriana with Anti-tumor Activities

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Chinese Journal of Chemistry 2021年第11期39卷 2973-2982页

作者： Jiang-Chun Wei Yu-Ning Gao Dong-Dong Wang Xiao-Yu Zhang San-Peng Fan Te-Ri-Gen Bao Xiao-Xu Gao Gao-Sheng Hu An-Hua Wang Jing-Ming Jia School of Traditional Chinese Materia Medica Shenyang Pharmaceutical UniversityShenyangLiaoning110016 China

Four previously undescribed ent-abietane diterpenoids(1—4),along with eleven known analogues(5—15),were isolated from the roots of wild Euphorbia *** gross structures were determined via extensive spectroscopic data,and the absolute configurations were elucidated by means of single-crystal X-ray diffraction analysis,Rh2(OCOCF3)4-induced CD spectrum and ECD *** cervical carcinoma inhibition activities counteract HeLa cells were screened by MTT assay,and the structure-activity relationships were further *** results demonstrated that 2(IC50 value at 3.75μmol/L)was more potent than *** underlying mechanism study revealed that 2 could distinctly induce apoptosis accompanied by increasing reactive oxygen species(ROS)production,Ca^(2+)influx and decreasing mitochondrial membrane ***,signal pathways including MAPKs/AKT might play a significant role in 2-induced cervical cancer cells death.

关键词： Euphorbia fischeriana diterpenoids Structure elucidation Biological activity Anti-tumor

Hawanoids A–E, unprecedented diterpenoids with PAF-induced platelet aggregation inhibitory activities from the deep-sea-derived fungus Paraconiothyrium hawaiiense

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Chinese Chemical Letters 2023年第2期34卷 416-419页

作者： Shushuai Chen Hongxin Liu Saini Li Yuchan Chen Wei Ye Haohua Li Haibo Tan Dongli Li Zhaoming Liu Weimin Zhang State Key Laboratory of Applied Microbiology Southern China Guangdong Provincial Key Laboratory of Microbial Culture Collection and ApplicationInstitute of MicrobiologyGuangdong Academy of SciencesGuangzhou 510070China School of Biotechnology and Health Sciences Wuyi UniversityJiangmen 529020China Program for Natural Product Chemical Biology Key Laboratory Plant Resources Conservation and Sustainable UtilizationSouth China Botanical GardenChinese Academy of SciencesGuangzhou 510650China

Hawanoids A–E(1–5), five highly cyclized diterpenoids were isolated from the deep-sea-derived fungus Paraconiothyrium hawaiiense FS482. Compounds 1 and 2 possessed an unprecedented tetracyclo[6.***.2.0^(2,7).0^(11,15)]cetane carbon skeleton while 3 and 4 possessed an unusual 11,14-macrocyclic ether moiety in phomactin family. Their structures including the stereo-chemistry were determined through spectroscopic analysis, X-ray diffractions and computational calculations. The plausible biosynthetic pathway was proposed based on the predicted biosynthetic gene cluster. All of the isolated compounds exhibited inhibitory activities against PAF-induced platelet aggregation. The molecular docking study was carried out understand the interaction between the PAF receptor and hawanoids with different skeletons.

关键词： diterpenoids Deep-sea-derived fungus Biosynthetic pathway Platelet aggregation inhibition Molecular docking

Cembrane-type diterpenoids from the South China Sea soft coral Sarcophyton mililatensis

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Acta Pharmaceutica Sinica B 2018年第6期8卷 944-955页

作者： Songwei Li Fei Ye Zhengdan Zhu Hui Huang Shuichun Mao Yuewei Guo State Key Laboratory of Drug Research Shanghai Institute of Materia Medica Chinese Academy of Sciences School of Pharmacy Nanchang University Key Laboratory of Marine Bio-resources Sustainable Utilization South China Sea Institute of Oceanology Chinese Academy of Sciences

Eight cembrane-type diterpenoids, namely,(t)-(6 R)-6-hydroxyisosarcophytoxide(1),(t)-(6 R)-6-acetoxyisosarcophytoxide(2),(t)-17-hydroxyisosarcophytoxide(3), sarcomililatins A–D(4–7), and sarcomililatol(8), were isolated from the soft coral Sarcophyton mililatensis collected from Weizhou Island, Guangxi Autonomous Region, together with 2 known related analogues,(t)-isosarcophytoxide(9) and(t)-isosarcophine(10). The structures of these compounds were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported *** absolute configuration of compound 1 was established by the modified Mosher's method, while the absolute configurations of compounds 4 and 5 were assigned by electronic circular dichroism(ECD)spectroscopy and that of compound 8 was established by time-dependent density functional theory electronic circular dichroism(TD-DFT ECD) calculation. In in vitro bioassays, compound 9 displayed significant cytotoxicity against the human cancer cell lines human promyelocytic leukemia cells(HL-60)and human lung adenocarcinoma cells(A-549) with IC_(50) values of 0.7870.21 and 1.2670.80 μmol/L,respectively. Compounds 4 and 9 also showed moderate inhibitory effects on the TNFα-induced Nuclear factor kappa B(NF-κB, a therapeutical target in cancer) activation, showing IC_(50) values of 35.23712.42 and 22.5274.44 μmol/L, respectively.

关键词： Soft coral Sarcophyton Sarcophyton mililatensis Cembrane-type diterpenoids Modified Mosher’s method ECD calculation Cytotoxicity NF-κB inhibitory activity

Tagetones A and B, new cytotoxic monocyclic diterpenoids from flowers of Tagetes minuta

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Chinese Journal of Natural Medicines 2017年第7期15卷 546-549页

作者： Sabrin Ragab Mohamed Ibrahim Gamal Abd Allah Mohamed Department of Pharmacognosy and Pharmaceutical Chemistry College of Pharmacy Taibah University Al-Madinah Al-Munawarah 30078 Saudi Arabia Department of Natural Products and Alternative Medicine Faculty of Pharmacy King Abdulaziz University Jeddah 21589 Saudi Arabia

Tagetones A(1) and B(2), two new monocyclic diterpenoids were isolated from the n-hexane fraction of fresh flowers of Tagetes minuta L.(Asteraceae). Their structures were established by multiple spectroscopic methods(IR, HR-ESI-MS, and 1D-, and 2D-NMR), in addition to comparison with literature data. Compound 1 showed cytotoxic activity towards MCF7 and A549 cancer cells with IC_(50) values being 4.68 and 4.24 μmol·L^(-1), respectively, compared to doxorubicin(IC_(50) 0.13 and 1.12 μmol·L^(-1), respectively). Compound 2 also exhibited significant activity against HCT116 cancer cells(IC_(50), 6.30 μmol·L^(-1)).

关键词： Tagetes minuta Asteraceae Monocyclic diterpenoids Tagetones Cytotoxic

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

Two new myrinsol diterpenoids from Euphorbia dracunculoides Lam.

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Chinese Chemical Letters 2015年第1期26卷 121-123页

作者： Li Wang Zhen Zang Yu-Fei Wang Sheng-Xiong Huang Pei Cao Yong Zhao College of Chemistry and Chemical Engineering Yunnan Normal University State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of Sciences

Two new myrinsol diterpenoids, euphordracunculins A（1） and B（2）, together with three known analogues, euphorprolitherin B（3）, proliferins A（4） and B（5）,were isolated from the petroleum ether extract of the aerial parts of Euphorbia dracunculoides Lam. Their structures were elucidated by means of extensive spectroscopic analysis（NMR and ESI-MS） and comparison with data reported in the literature.

关键词： Spurge Euphorbia dracunculoides Myrinsol diterpenoids

New diterpenoids from Coleus forskohlii

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Chinese Chemical Letters 2002年第8期13卷 740-743页

作者： Yun Heng SHEN Chun Suo YAO Yun Long XU State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming 650204

Two new diterpenoids, forskolin G and H were isolated from the chloroform extract of the roots of Coleus forskohlii, and based on spectroscopic data, their structures were identified as 1a-hydroxy-6b,7b-diacetoxy-8,13... 详细信息

关键词： Coleus forskohlii diterpenoids forskolin G and H.

diterpenoids and Limonoids from the Leaves and Twigs of Swietenia mahagoni

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Natural Products and Bioprospecting 2014年第1期4卷 53-57页

作者： Wei-Ming Zhang Jie-Qing Liu Yuan-Yuan Deng Jian-Jun Xia Zhi-Run Zhang Zhong-Rong Li Ming-Hua Qiu 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

Three new compounds,including two diterpenoids,nemoralisins H and I(1 and 2),and a limonoid,2-methoxy khayseneganin E(3),along with four known constituents(4-7),were isolated from the leaves and twigs of Swietenia *** chemical structures were elucidated by means of spectroscopic *** cytotoxities of these isolated constituents were assayed.

关键词： Meliaceae Swietenia mahagoni diterpenoids Limonoids