Planta Med 2002; 68(1): 55-59
DOI: 10.1055/s-2002-19872
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

Eremophilane Sesquiterpenes from Cacalia ainsliaeflora

Manjun Mao1 , Zhongjian Jia1
  • 1Department of Chemistry, National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, People’s Republic of China
Weitere Informationen

Publikationsverlauf

January 8, 2001

May 13, 2001

Publikationsdatum:
31. Januar 2002 (online)

Abstract

Chemical investigation of Cacalia ainsliaeflora afforded four new eremophilane sesquiterpenes (1 - 3, 5) and a known sesquiterpene (4), which were identified as 3β-angeloyloxy-8α-hydroxy-6β-methoxyeremophil-7(11),9(10)-dien-8,12-olide (1), 3β-angeloyloxy-6β,8α-dihydroxyeremophil-7(11),9(10)-dien-8,12-olide (2), 3β-angeloyloxy-8α-hydroxy-6β-ethoxyeremophil-7(11),9(10)-dien-8,12-olide (3), 3β-angeloyloxy-8-oxo-eremphila-6,9-dien-12-oic acid (4), and 3,8-oxo-eremophila-6,9-dien-12-oic acid (5) respectively. These compounds were assayed against Escherichia coli, Staphylococcus aureus and Bacillus subtilis, and compounds 1, 2, 4 and 5 showed weak antibacterial activity. The structures of the compounds were established by 1D and 2D NMR experiments.

References

  • 1 Masanori K, Hiroshi N, Tadataka N, Akira U, Seigo F. Furanoeremophilane-type sesquiterpenes from Cacalia adenostyloides .  Chemical and Pharmaceutical Bulletin. 1985;  33 4792-7
  • 2 Nasr A E, Tsunematsu T, Genjiro K. New sesquiterpenes from the roots of Cacalia auriculata .  Planta Medica. 1980;  38 161-4
  • 3 Samek Z, Harmatha J, Novotny L, Sorm F. Absolute configuration of adenostylone, neoadenostylone and isoadenostylone from Adenostyles alliariae (Gouan) Kern, and of decompostin from Cacalia decomposita A.Gray.  Collection Czechoslovak Chemical Communication.. 1969;  34 2792-807
  • 4 Zhang S M, Zhao G L, Li R, Lin G Q. Eremophilane sesquiterpenes from Cacalia roborowskii .  Phytochemistry. 1998;  48 519-24
  • 5 Krasovskaya N P, Kulesh N I, Denisenko V A. Natural antioxidants furanoeremophilanes from Cacalia root.  Khim Prirodn Soedin. 1989;  5 643-6
  • 6 Institute of B otany, Chinese Academy of S ciences. Iconographia Cormophytorum Sinicorum. Science Press Beijing; 1983: 554
  • 7 Jiangsu College of New M edicine. A Dictionary of the Traditional Chinese Medicines. Shanghai Science and Technology Press Shanghai; 1997: 22
  • 8 Xu S Y, Bian Q L, Chen X Y. In Pharmacology Experimental Methods. People’s Health Press Beijing; 1982: 1340-7
  • 9 Naya K, Kanazawa R, Sawada M. The photosensitized oxygenation of furanoeremophilanes. I. The isomeric hydroperoxides from petasalbin and their transformations to lactones.  Bulletin of the Chemical Society of Japan. 1975;  48 3220-5
  • 10 Moriyama Y, Takahashi T. New sesquiterpene lactones of eremophilane-type from Ligularia fauriei (Fr.) Koidz.  Bulletin of the Chemical Society of Japan. 1976;  49 3196-9
  • 11 Sugama K, Hayashi K, Mitsuhashi H. Eremophilenolides from Petasites japonicus .  Phytochemistry. 1985;  24 1531-5
  • 12 Zhao Y, Jia Z J, Tan R X, Yang L. Eremophilanolides from the roots of Ligularia veitchiana .  Phytochemistry. 1992;  31 2785-7
  • 13 Zhao Y, Peng H R, Jia Z J. Six new eremophilane derivatives from two Ligularia species.  Journal of Natural Products. 1994;  57 1626-30
  • 14 Zhao Y, Jia Z J, Yang L. Novel sesquiterpenes from Ligularia veitchiana .  Planta Medica. 1994;  60 91-2
  • 15 Lin Y L, Qu J C, Chen C F, Kuo Y H. Eremophilanes from Petasites formosanus Kitamura.  Chemical and Pharmaceutical Bulletin. 1998;  46 1807-9
  • 16 Tobinaga S, Takeuchi N, Kasama T, Yamashita J, Aida Y, Kaneko Y. Anti-histaminic and anti-allergic principles of Petasites japonicus Maxim.  Chemical and Pharmaceutical Bulletin. 1983;  31 745-8
  • 17 Bordoloi M, Shukla V S, Nath S C, Sharma R P. Naturally occurring cadinenes.  Phytochemistry. 1989;  28 2007-37

Prof. Zhong-Jian Jia

Department of Chemistry

Lanzhou University

Lanzhou 730000

P.R. China

eMail: zhengrl@lzu.edu.cn

Fax: +86-0931-8912582