Planta Med 2005; 71(6): 543-547
DOI: 10.1055/s-2005-864156
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

New Sesquiterpenes from Sonchus transcaspicus

Yi-Feng Han1 , Qi Zhang2 , Kun Gao1 , Zhong-Jian Jia1
  • 1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, P. R. China
  • 2School of Life Sciences, Lanzhou University, Lanzhou, P. R. China
Further Information

Publication History

Received: August 13, 2004

Accepted: February 13, 2005

Publication Date:
21 June 2005 (online)

Abstract

Four new eudesmanolides were isolated from the whole plant of Sonchus transcaspicus and their structures were elucidated by means of spectroscopic methods, including 2D-NMR (1H-1H COSY, HMQC, HMBC and NOESY) and NOEDS (NOE difference spectra) as 1β-O-β-D-glucopyranosyl-5α,6βH-eudesma-3-en-12,6α-olide (1), 1β-O-β-D-glucopyranosyl-15-O-(p-hydroxyphenylacetyl)-5α,6βH-eudesma-3,11(13)-dien-12,6α-olide (2), 1β-O-β-D-glucopyranosyl-(6′-O-p-hydroxyphenyl acetate)-15-O-(p-hydroxyphenylacetyl)-5α,6βH-eudesma-3,11(13)-dien-12,6α-olide (3) and 1β-hydroxy-15-O-(p-methoxyphenylacetyl)-5α,6βH-eudesma-3,11(13)-dien-12,6α-olide (4). Compounds 1, 2 and 3 showed antibacterial activity against Escherichia coli and Staphylococcus aureus cells. Compounds 2 and 3 were evaluated for their in vitro cytotoxic activity against cultured SMMC-7721 (human hepatoma), HELA (human cervical carcinoma) and B-16 (murine melanoma) cells. The IC50 values for 2 were 108.0, 161.1 and 203.0 μM and those for 3 were 74.1, 117.3 and 135.0 μM, respectively. The structure-activity relationship is discussed.

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Prof. Zhong-Jian Jia

College of Chemistry and Chemical Engineering

State Key Laboratory of Applied Organic Chemistry

Lanzhou University

Lanzhou 730000

People’s Republic of China

Fax: +86-0931-8912582

Email: jiazj@lzu.edu.cn

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