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Bioorg Chem. 2018 Dec;81:396-404. doi: 10.1016/j.bioorg.2018.08.034. Epub 2018 Sep 4.

Cytotoxic withanolides from the aerial parts of Tubocapsicum anomalum.

Author information

1
Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 210009, People's Republic of China.
2
State Key Laboratory of Anti-Infective Drug Development (NO. 2015DQ780357), Sunshine Lake Pharma Co. Ltd, Dongguan 523871, People's Republic of China.
3
Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 210009, People's Republic of China. Electronic address: cpu_lykong@126.com.
4
Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 210009, People's Republic of China. Electronic address: luojg@cpu.edu.cn.

Abstract

Ten new withanolides (1-10) and three artificial withanolides (11-13) were isolated from the aerial parts of Tubocapsicum anomalum, together with five known analogues (14-18). Their structures were determined on the basis of extensive spectroscopic and chemical methods. They include seven acnistin-type (1-4, 11, 14 and 15), three withajardin-type (5-7), and eight normal-type (8-10, 12, 13 and 16-18) withanolides. Of normal-type withanolides, a chemical conversion from the 16α,17α-epoxywithanolide (16) to Δ13,14-16α-hydroxywithanolide (18) was achieved by Wagner-Meerwein rearrangement. All isolates were evaluated for their cytotoxicity against four human tumor cell lines (HCT-116, HepG2, MCF-7 and A375). Among them, compounds 1-3, 6-8, 14, 16-18 showed cytotoxic activity with IC50 values of 0.24-8.71 μM.

KEYWORDS:

Cytotoxicity; Tubocapsicum anomalum; Wagner–Meerwein rearrangement; Withanolides

PMID:
30199842
DOI:
10.1016/j.bioorg.2018.08.034
[Indexed for MEDLINE]

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