Isolation, Structure Elucidation, and Absolute Configuration of Highly Oxygenated Germacranolides from Carpesium cernuum

J Nat Prod. 2016 Oct 28;79(10):2479-2486. doi: 10.1021/acs.jnatprod.6b00315.

Qing-Xin Liu ¹ ², Yong-Xun Yang ², Jian-Ping Zhang ², Li-Ping Chen ², Yun-Heng Shen ², Hui-Liang Li ², Wei-Dong Zhang ¹ ² ³

Affiliations

1 School of Traditional Chinese Medicine, China Pharmaceutical University , Nanjing 210009, People's Republic of China.
2 Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University , Shanghai 200433, People's Republic of China.
3 Shanghai Institute of Pharmaceutical Industry , Shanghai 200400, People's Republic of China.

PMID: 27668963 DOI: 10.1021/acs.jnatprod.6b00315

Abstract

The new highly oxygenated germacranolides cernuumolides A-J (1-10) and the known compounds 11-20 were isolated from Carpesium cernuum. Among these compounds, 1-4 are 11-methoxymethylgermacranolides and 5-7 as well as 11-17 are 2,9-hemiacetal-linked germacranolides. Their structures were elucidated using NMR and HRESIMS analyses, and X-ray diffraction studies were used to confirm the absolute configurations of 1, 2, 5, 6, 8, and 9. Cernuumolides A-J were evaluated for their in vitro cytotoxicity against the A549, HCT116, MDA-MB-231, and BEL7404 cell lines, and 8 exhibited moderate cytotoxicity with IC₅₀ values in the 0.87-2.02 μM range.

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