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Isolation, structural elucidation, and chemical transformation of interconvertible 8,12-hemiketal germacranolide sesquiterpenoids from Salvia castanea Diels f. tomentosa Stib. |
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| Authors: | Gang Xu Li-Yan Peng Jing Yang Hong-Xi Xu |
| Affiliation: | a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China b Chinese Medicine Laboratory, Hong Kong Jockey Club Institute of Chinese Medicine, Shatin, Hong Kong, PR China c Department of Pharmacognosy, School of Pharmacy, Fudan University, 138 Yi Xue Yuan Road, Shanghai 200032, PR China d School of Chemistry and Chemical Technology, Shanghai Jiao Tong University, Shanghai 200240, PR China |
| Abstract: | From the aerial parts of Salvia castanea Diels f. tomentosa Stib., four new hemiketal germacranolide sesquiterpenoids, castanins C-F (1-4), were obtained as two pairs of interconvertible forms along with their acetates, 5 and 6. Their structures were elucidated by spectroscopic methods and X-ray analysis of the uninterconvertible isomeric acetates, 5 and 6. The computational study explained that the ratios of 1 and 2, 3 and 4, and their acetates (5 and 6) in the mixtures were 1:1, 1:2, and 1:3, respectively. In addition, the semisynthesis of castanins C (1) and D (2) was conducted by the photooxidation of castanin B (8), the major constituent of this plant. Compounds 5, 6, and 8 were also tested for their inhibitory activity toward MCF-7, HeLa, and HepG2 cell lines. |
| Keywords: | Castanins C-F Salvia castanea Diels f. tomentosa Stib. Structure elucidation Interconvertible hemiketal isomers Chemical transformation |
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