New Abietane and Kaurane Type Diterpenoids from the Stems of Tripterygium regelii. 2017

Dongsheng Fan, and Shuangyan Zhou, and Zhiyuan Zheng, and Guo-Yuan Zhu, and Xiaojun Yao, and Ming-Rong Yang, and Zhi-Hong Jiang, and Li-Ping Bai
State Key Laboratory of Quality Research in Chinese Medicine, Macau Institute for Applied Research in Medicine and Health, Macau University of Science and Technology, Taipa, Macau 999078, China. fandongsheng1985@sina.com.

Eleven new abietane type (1‒11), and one new kaurane (12), diterpenes, together with eleven known compounds (13-23), were isolated and identified from the stems of Tripterygium regelii, which has been used as a traditional folk Chinese medicine for the treatment of rheumatoid arthritis in China. The structures of new compounds were characterized by means of the interpretation of high-resolution electrospray ionization mass spectrometry (HRESIMS), extensive nuclear magnetic resonance (NMR) spectroscopic data and comparisons of their experimental CD spectra with calculated electronic circular dichroism (ECD) spectra. Compound 1 is the first abietane type diterpene with an 18→1 lactone ring. Compound 19 was isolated from the plants of the Tripterygium genus for the first time, and compounds 14-17 were isolated from T. regelii for the first time. Triregelin I (9) showed significant cytotoxicity against A2780 and HepG2 with IC50 values of 5.88 and 11.74 µM, respectively. It was found that this compound was inactive against MCF-7 cells. The discovery of these twelve new diterpenes not only provided information on chemical substances of T. regelii, but also contributed to the chemical diversity of natural terpenoids.

UI MeSH Term Description Entries
D002942 Circular Dichroism A change from planar to elliptic polarization when an initially plane-polarized light wave traverses an optically active medium. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Circular Dichroism, Vibrational,Dichroism, Circular,Vibrational Circular Dichroism
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D016923 Cell Death The termination of the cell's ability to carry out vital functions such as metabolism, growth, reproduction, responsiveness, and adaptability. Death, Cell
D045744 Cell Line, Tumor A cell line derived from cultured tumor cells. Tumor Cell Line,Cell Lines, Tumor,Line, Tumor Cell,Lines, Tumor Cell,Tumor Cell Lines
D045784 Abietanes A subclass of cyclical DITERPENES that contain the abietane ring structure. Abietane Diterpene,Abietane Diterpenoid,Abietane Diterpenoids,Diterpenes, Abietane,Isopimarane,Isopimaranes,Totarane Diterpene,Totarane Diterpenes,Totaranes,Diterpenes, Pimarane,Pimaranes,Abietane Diterpenes,Diterpene, Abietane,Diterpene, Totarane,Diterpenoid, Abietane,Pimarane Diterpenes
D045786 Diterpenes, Kaurane A group of DITERPENES cyclized into four rings. Ent-Kaurane,Ent-Kaurene,Kaurane,Kaurane Diterpenoid,Kaurane Diterpenoids,Ent-Kauranes,Ent-Kaurenes,Kauranes,Diterpenoid, Kaurane,Diterpenoids, Kaurane,Ent Kaurane,Ent Kaurene,Kaurane Diterpenes
D018547 Plant Stems Parts of plants that usually grow vertically upwards towards the light and support the leaves, buds, and reproductive structures. (From Concise Dictionary of Biology, 1990) Plant Stem,Stem, Plant,Stems, Plant
D029757 Tripterygium A plant genus of the family CELASTRACEAE that is a source of triterpenoids and diterpene epoxides such as triptolide. Tripterygium wilfordii,Leigong Teng,Thundergod Vine,Tripterygium hypoglaucum,Leigong Tengs,Teng, Leigong,Tengs, Leigong,Thundergod Vines,Tripterygium hypoglaucums,Tripterygium wilfordius,Tripterygiums,Vine, Thundergod,Vines, Thundergod,hypoglaucums, Tripterygium,wilfordius, Tripterygium
D066241 Carbon-13 Magnetic Resonance Spectroscopy Magnetic resonance spectroscopy involving detection of changes in the resonance of carbon-13 nuclei in organic molecules. 13C NMR,Carbon 13 Magnetic Resonance Spectroscopy
D066244 Proton Magnetic Resonance Spectroscopy Spectroscopy technique which measures changes in organic compounds by tracking the spectral energy of absorption of HYDROGEN atoms. 1H NMR,1H-MRS,1H-NMR

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