Planta Med 2005; 71(12): 1140-1144
DOI: 10.1055/s-2005-873132
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

New Eremophilenolides from Cacalia pilgeriana

Er-Wei Li1 , Jing Pan2 , 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: March 20, 2005

Accepted: May 27, 2005

Publication Date:
14 October 2005 (online)

Abstract

Five new eremophilenolides and a known sesquiterpene were isolated from the methanol extract of the roots of Cacalia pilgeriana. Their structures were identified as 1β-hydroxy-2β-methyl-senecioyloxyeremophil-7(11)-en-8β(12)-olide (1), 1β-hydroxy-2β-methylsenecioyloxy-8α-methoxyeremophil-7(11)-en- 8β(12)-olide (2), 2β-hydroxy-3β-methylsenecioyloxyeremophil-7(11)-en-8α(12)-olide (3), 2β,8β-dihydroxy-3β-methylsenecioyloxyeremophil-7(11)-en-8α(12)-olide (4) and 1β,8β-dihydroxy-2β,3α-diangeloyloxyeremophil-7(11)-en-8α(12)-olide (5) and caryolane-1,9β-diol (6) by spectroscopic methods including 2D-NMR techniques (1H-1H COSY, HMQC, HMBC) and HR-ESI-MS. The structure and relative stereochemistry of compound 1 were unequivocally established by X-ray diffraction analysis. Bioassays showed compounds 3 and 5 to possess strong cytotoxic activity in vitro against human leukemia cells (HL-60) (IC50 < 15 μg mL-1). The structure-activity relationship is discussed.

References

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: +86-0931-891-2582

Email: jiazj@lzu.edu.cn

Email: miaozm@lzu.edu.cn