Planta Med 2006; 72(6): 567-569
DOI: 10.1055/s-2005-916256
Letter
© Georg Thieme Verlag KG Stuttgart · New York

New Eremophilane-Type Sesquiterpenes from Ligularia hodgsonii

Ji-Qing Xu1 , Yun-Sen Li1 , Yi-Ming Li1 , Shan-Hao Jiang1 , Chang-Heng Tan1 , Da-Yuan Zhu1
  • 1State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Science, Chinese Academy of Sciences, Shanghai, P. R. China
Further Information

Publication History

Received: October 13, 2005

Accepted: November 10, 2005

Publication Date:
10 February 2006 (online)

Abstract

Four new eremophilanlides (1 - 4) together with a known sesquiterpene were isolated from the roots and rhizomes of Ligularia hodgsonii. The structures of these new compounds were established as 6β-(2′-methylbutanoyloxy)-10β-acetoxy-3β,8β-dihydroxyeremophil-7(11)-en-8,12-olide (1), 6β,10β-dihydroxyeremophil-7(11)-en-8α,12-olide (2), 3β-acetoxy-6,9-dien-8-oxoeremophil-12-nor-11-ketone (3), and 3β-acetoxy-6α,8α-dihydroxyeremophil-7(11),9-dien-8,12-olide (4) by means of mass, IR and NMR spectroscopy.

References

  • 1 Compiler Group of Yunnan Medicinal Materias C ompany. In: Wu ZY, editor Items of traditional Chinese medicinal materia resources in Yunnan Province. Beijing; Science Press 1993: p 577
  • 2 Ganzer U, Jakupovic J, Bohlmann F, King R M. A highly oxygenated germacrane from Aspilia eenii and constituents from other Aspilia species.  Phytochemistry. 1992;  31 209-12
  • 3 Ishizaki Y, Tanahashi Y, Takahashi T. Furanoeremophilan-14β,6α-olide, a new furanosesquiterpene lactone from Ligularia hodgsonii Hook, f. The structure and nuclear Overhauser effects. J Chem Soc Chem Commun 1969: 551-2
  • 4 Ishizaki Y, Tanahashi Y, Moriyama Y, Takahashi T. Sesquiterpenes from the root of Ligularia hodgsonii .  Phytochemistry. 1974;  13 674-5
  • 5 Ishizaki Y, Tanahashi Y, Tsuyuki T, Takahashi T, Tori K. Furanoeremophilan-14β,6α-olide, a new furanosesquiterpene lactone of an eremophilane-type from Ligularia hodgsonii Hook, f.  Bull Chem Soc Jpn. 1979;  52 1182-6
  • 6 Liao J C, Zhu Q X, Yang X P, Jia Z J. Sesquiterpenes from Ligularia hodgsonii .  J Chin Chem Soc. 2002;  49 129-32
  • 7 Lin G, Rose P, Chatson K B, Hawes E M, Zhao X G, Wang Z T. Characterization of two structural forms of otonecine-type pyrrolizidine alkaloids from Ligularia hodgsonii by NMR spectroscopy.  J Nat Prod. 2000;  63 857-60
  • 8 Li Y S, Wang Z T, Zhang M, Zhou H, Chen J J, Luo S D. New eremophilane-type sesquiterpene from Ligularia lapathifolia .  Planta Med. 2004;  70 239-43
  • 9 Li Y S, Wang Z T, Zhang M, Luo S D, Chen J J. A new pinoresinol-type lignan from Ligularia kanaitizensis .  Nat Prod Res. 2005;  19 125-9
  • 10 Li Y S, Wang Z T, Zhang M, Chen J J, Luo S D. Two new norsesquiterpenes from Ligularia lapathifolia .  Nat Prod Res. 2004;  18 99-104
  • 11 Li Y S, Luo S D, Zhang M, Chen J J, Wang Z T. Constituents of Liguliria vellerea (Franch.) Hand-Mazz.  China J Chin Mater Med. 2001;  26 835-7
  • 12 Zhang S M, Zhao G L, Li R, Lin G Q. Eremophilane sesquiterpenes from Cacalia roborowskii .  Phytochemistry. 1998;  48 519-24
  • 13 Massiot G, Nuzillard J M, Men-Olivier L L, Aclinou P, Benkouider A, Khelifa A. Eremophilenolides from Hertia cheirifolia .  Phytochemistry. 1990;  29 2207-10
  • 14 Moriyama Y, Takahashi T. New sesquiterpene lactones of the eremophilane-type from Ligularia fauriei (Fr.) Koidz.  Bull Chem Soc Jpn. 1976;  49 3196-9
  • 15 Zhao Y, Peng H R, Jia Z J. Six new eremophilane derivatives from two Ligularia species.  J Nat Prod. 1994;  57 1626-30
  • 16 Mao M J, Jia Z J. Eremophilane sesquiterpenes from Cacalia ainsliaeflora .  Planta Med. 2002;  68 55-9

Prof. Da-Yuan Zhu

State Key Laboratory of Drug Research

Shanghai Institute of Materia Medica

Chinese Academy of Sciences

555 ZuChongZhi Road

Shanghai 201203

People’s Republic of China

Fax: +86-21-5080-7088

Email: dyzhu@mail.shcnc.ac.cn

    >