Planta Med 2004; 70(3): 239-243
DOI: 10.1055/s-2004-815541
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

New Eremophilane-Type Sesquiterpenes from Ligularia lapathifolia

Yun-sen Li1 , 2 , Zheng-tao Wang2 , Mian Zhang2 , Hui Zhou1 , Ji-jun Chen3 , Shi-de Luo3
  • 1Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, P. R. China
  • 2Department of Pharmacognosy, China Pharmaceutical University, Nanjing, P. R. China
  • 3Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, P. R. China
This research was financially supported by the Natural Science Foundation (NSFC) for outstanding young scientists for Wang Z. T. (39 825 129)
Further Information

Publication History

Received: July 28, 2003

Accepted: December 12, 2003

Publication Date:
23 March 2004 (online)

Abstract

Seven new eremophilanolides were isolated from the roots and rhizomes of Ligularia lapathifolia. Their structures were established as 3β-angeloyloxy-8βH-eremophil-7(11)-ene-12,8α (14β, 6α)-diolide, 3β-angeloyloxy-8β-hydroxyeremophil-7(11)-ene-12,8α(14β,6α)-diolide,3β-angeloyloxy-8β-methoxyeremophil- 7(11)-ene-12,8α(14β,6α)-diolide,3β-angeloyloxy-8β-ethoxyeremophil-7(11)-ene-12, 8α (14β,6α)-diolide, 3β-angeloyloxy-10β- hydroxyeremophil-8(9),7(11)-diene-12,8(14β,6α)-diolide, 3β-angeloyloxy-8,12-expoy-12α-hydroxy-8β-methoxyeremophil-7(11)-en-14β,6α-olide and 3β-angeloyloxyeremophilan-7,11-dien-14β,6α-olide, by means of spectroscopic analyses. Moreover, application of a photooxygenation reaction on 7 resulted in the generation of 2 with an α,β-unsaturated γ-lactone moiety. This biomimetic transformation supports a biogenetic pathway proposed for 2.

References

  • 1 Yunnan Medicinal Materials Company Ed. Items of Traditional Chinese Medicinal Material Resources in Yunnan Province. Science Press Beijing; 1993: p 577
  • 2 Li Y S, Luo S D, Zhang M, Chen J J, Wang Z T. Constituents of Ligularia vellerea (Franch) Hand-Mazz.  Zhongguo Zhongyao Zazhi. 2001;  26 835-7
  • 3 Li Y S, Wang Z T, Zhang M, Chen J J. Study on identification of terpenes from Ligularia kanaitzensis .  Zhongguo Yaoxue Zazhi. 2002;  37 12-4
  • 4 Saito I, Kuo Y H, Matsuura T. Tetrahedron letters. 1986 27: 2757-60
  • 5 Zhao Y, Jia Z J, Peng H. Eight new eremophilane derivatives from the roots of Ligularia przewalskii .  J Nat Prod. 1995;  58 1358-64
  • 6 Cheng H M, Cai M S, Jia Z J. Sesquiterpenes from the roots of Ligularia intermedia .  Phytochemistry. 1997;  45 1441-4
  • 7 Ishizaki Y, Tanahashi Y, Tsuyuki T, Takeyoshi T, Tori K. Furanoerephilan-14,6α-olide. A new furanosesquiterpene lactone of an eremophilane-type from Ligularia hodgsoni Hook, f.  Bull Chem Soc. 1979;  52 1182-6
  • 8 Schap A p, Zaklika K A, Kaskar B. Mechanisms of photooxygenation. 2. Formation of 1, 2- dioxetanes via 9, 10-dicyanoanthrancene-electron-transfer process.  Journal of the American Chemistry Society. 1980;  102 389-391
  • 9 Foote C S, Wuesthoff M T, Wexler O S. Photosensitized oxygenation of alkyl-substituted furans.  Tetrahedron. 1967;  23 2583
  • 10 Wasserman H H, Ives J L. Syntheses photochimiques de dioxa-1,6-spiro [4,5]decanes pheromones de Pharavespula vulgaris L.  Tetrahedron. 1981;  37 1875-1882

Dr. Yun-sen Li

State Key Laboratory of Drug Research

Shanghai Institute of Materia Medica

Chinese Academy of Sciences

555 Zu Chong Zhi Road

Zhangjiang Hi-Tech Park

Shanghai 201203

People’s Republic of China

Phone: +86-21-50806600 ext 3301

Email: sinodlsia@yahoo.com