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Planta Med 2009; 75(6): 635-640
DOI: 10.1055/s-0029-1185359
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Eremophilane-Type Sesquiterpene Derivatives from Ligularia hodgsonii

Wen-Xian Li1 , Ming Lei2 , Dong-Qing Fei1 , 3 , Kun Gao1
  • 1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, P. R. China
  • 2Shaanxi Key Laboratory of Molecular Biology for Agriculture Biotechnology Center NWAFU, Northwest A & F University, Xian, P. R. China
  • 3School of Pharmacy, Lanzhou University, Lanzhou, P. R. China
Further Information

Publication History

received January 24, 2008 revised Nov. 4, 2008

accepted January 6, 2009

Publication Date:
06 February 2009 (online)

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Abstract

Eight new highly oxygenated eremophilane-type sesquiterpene derivatives (1–8), including two norsesquiterpenes, were isolated from an extract of the roots and the aerial parts of Ligularia hodgsonii Hook. Their structures and relative configurations were elucidated by spectroscopic methods, including IR, UV, HR‐ESI‐MS, and 1D and 2D NMR techniques, as 3β-acetoxy-10β‐hydroxy-6β,8β-dimethoxyeremophil-7(11)-en-8α,12-olide (1), 3β-acetoxy-10β-hydroxy-6β-methoxyeremophil-7(11),8(9)-dien-8,12-olide (2), 3β-acetoxy-10β-hydroxy-6β,8α-dimethoxyeremophil-7(11)-en-8β,12-olide (3), 6β-(2′-methylbutanoyloxy)-3β-acetoxy-10β-hydroxy-8α-methoxyeremophil-7(11)-en-8β,12-olide (4), 6β-(2′-methylbutanoyloxy)-3β-acetoxy-10β-hydroxyeremophil-7(11)-en-8β,12-olide (5), 3β-acetoxy-8-oxoeremophil-6(7),9(10)-dien-12-oic methyl ester (6), 3β-acetoxy-6α,7α-epoxy-9(10)-en-8-oxoeremophil-12-nor-11-one (7), and 2-acetyl-5β-acetoxy-3a,4,5,6,7,7a-hexahydro-7aβ-hydroxy-3aβ,4β-dimethyl-1H-indene (8).

Key words

Ligularia hodgsonii - Compositae - eremophilane‐type sesquiterpene - norsesquiterpene

References

  • 1 Liu S W, Deng D S, Liu J Q. The origin evolution and distribution of Ligularia Cass. (Compositae).  Acta Phytotaxon Sin. 1994;  32 514-524
    PubMedSearch in Google Scholar
  • 2 Hanai R, Gong X, Tori M, Kondo S, Otose K, Okamoto Y, Nishihama T, Murota A, Shen Y, Wu S, Kuroda C. Chemical and genetic study of Ligularia tongolensis, Ligularia cymbulifera and Ligularia atroviolacea in the Hengduan mountains of China.  Bull Chem Soc Jpn. 2005;  78 1302-1308
    CrossrefPubMedSearch in Google Scholar
  • 3 Nagano H, Iwazaki Y, Gong X, Shen Y M, Kuroda C, Hanai R. Chemical and genetic differentiation of Ligularia pleurocaulis in northwestern Yunnan and southwestern Sichuan provinces of China.  Bull Chem Soc Jpn. 2006;  79 300-304
    CrossrefPubMedSearch in Google Scholar
  • 4 Tori M, Honda K, Nakamizo H, Okamato Y, Sakaoku M, Takaoka S, Gong X, Shen Y, Kuroda C, Hanai R. Chemical constituents of Ligularia virgaurea and its diversity in southwestern Sichuan of China.  Tetrahedron. 2006;  62 4988-4995
    CrossrefPubMedSearch in Google Scholar
  • 5 Kuroda C, Kiuchi K, Torihata A, Takeshita K, Gong X, Shen Y M, Hirota H, Onuki H, Hanai R. Chemical and genetic diversity of Ligularia latihastata and Ligularia villosa in Yunnan Province of China.  Chem Biodivers. 2007;  4 2210-2217
    CrossrefPubMedSearch in Google Scholar
  • 6 Torihata A, Hainai R, Gong X, Shen Y M, Kuroda C. Chemical and genetic differentiation of Ligularia tsangchanensis in Yunnan and Sichuan Provinces of China.  Chem Biodivers. 2007;  4 500-507
    CrossrefPubMedSearch in Google Scholar
  • 7 Li P L, Wang C M, Zhang Z X, Jia Z J. Five new eremophilane derivatives from Ligularia sagitta.  Tetrahedron. 2007;  63 12665-12670
    CrossrefPubMedSearch in Google Scholar
  • 8 Chen H M, Jia Z J, Li Y. Sesquiterpenes and a diterpene lactone with an unusual carbon skeleton from Ligularia sagitta.  Phytochemistry. 1992;  31 2146-2147
    CrossrefPubMedSearch in Google Scholar
  • 9 Li X Q, Gao K, Jia Z J. Eremophilenolides and other constituents from the roots of Ligularia sagitta.  Planta Med. 2003;  69 356-360
    Thieme ConnectPubMedSearch in Google Scholar
  • 10 Zhao Yu, Peng H R, Jia Z J. Six new eremophilane derivatives from two Ligularia species.  J Nat Prod. 1994;  57 1626-1630
    CrossrefPubMedSearch in Google Scholar
  • 11 Jiangsu College of New Medicine .A dictionary of the traditional Chinese medicines. Shanghai; Shanghai Science and Technology Press 1977 1557 2348-2350
    Search in Google Scholar
  • 12 Liao J C, Zhu Q X, Yang X P, Jia Z J. Sesquiterpenes from Ligularia hodgsonii.  J Chin Chem Soc. 2002;  49 129-132
    CrossrefPubMedSearch in Google Scholar
  • 13 Xu J Q, Li Y S, Li Y M, Jiang S H, Tan C H, Zhu D Y. New eremophilane-type sesquiterpenes from Ligularia hodgsonii. .  Planta Med. 2006;  72 567-569
    Thieme ConnectPubMedSearch in Google Scholar
  • 14 Ishizaki Y, Tanahaishi Y, Takahashi T, Tori K. Furanoeremophilan-14β,6α-olide, a new furanosesquiterpene lactone from Ligularia hodgsoni. The structure and nuclear Overhauser effects.  J Chem Soc Chem Commun. 1969;  10 551-552
    PubMedSearch in Google Scholar
  • 15 Ishizaki Y, Tanahashi Y, Moriyama Y, Takahashi T. Sesquiterpenes from the roots of Ligularia hodgsonii.  Phytochemistry. 1974;  13 674-675
    CrossrefPubMedSearch in Google Scholar
  • 16 Ishizaki Y, Tanahashi Y, Tsuyuki T, Takahashi T, Tori K. Furanoeremophilan-14β,6α ‐olide. A new furanosesquiterpene lactone of an eremophilane-type from Ligularia hodgsoni Hook, f.  Bull Chem Soc Jpn. 1979;  52 1182-1186
    CrossrefPubMedSearch in Google Scholar
  • 17 Zhang S M, Zhao G L, Li R, Lin G Q. Eremophilane sesquiterpenes from Cacalia roborowskii.  Phytochemistry. 1998;  48 519-524
    CrossrefPubMedSearch in Google Scholar
  • 18 Sugama K, Hayashi K, Mitsuhashi H. Eremophilenolides from Petasites japonicus.  Phytochemistry. 1985;  24 1531-1535
    CrossrefPubMedSearch in Google Scholar
  • 19 Zhao Y, Parsons S, Smart B A, Tan R X, Jia Z J, Sun H D, Rankin D WH. Eremophilane derivatives with a novel carbon skeleton from Ligularia veitchiana.  Tetrahedron. 1997;  53 6195-6208
    CrossrefPubMedSearch in Google Scholar
  • 20 Wang W S, Gao K, Jia Z J. New sesquiterpenes from Ligulariopsis shichuana. .  J Chin Chem Soc. 2004;  51 417-422
    CrossrefPubMedSearch in Google Scholar
  • 21 Naya K, Matsuura T, Makiyama M, Tsumura M. The conversion of furanoeremophilanes to epieremophilenolides.  Heterocycles. 1978;  10 177-184
    CrossrefPubMedSearch in Google Scholar

Prof. Kun Gao

State Key Laboratory of Applied Organic Chemistry
College of Chemistry and Chemical Engineering
Lanzhou University

Lanzhou 730000

People's Republic of China

Phone: + 86 93 18 91 25 92

Fax: + 86 93 18 91 25 82

Email: npchem@lzu.edu.cn