Download PDF
Planta Med 2012; 78(18): 1971-1975
DOI: 10.1055/s-0032-1327875
Natural Product Chemistry
Letters
Georg Thieme Verlag KG Stuttgart · New York

Unusual 9,19 : 24,32-Dicyclotetracyclic Triterpenoids from Lygodium japonicum

Qing-hua Han
1   School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, China
,
Xin Liu
1   School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, China
,
Wen-qing Yao
2   School of Chemistry and Biological Science, University of Science and Technology, Beijing, China
,
Zhong-bin Cheng
1   School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, China
,
Ting-ting Lin
1   School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, China
,
Ching Song
2   School of Chemistry and Biological Science, University of Science and Technology, Beijing, China
,
Sheng Yin
1   School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, China
› Author Affiliations
Further Information

Publication History

received 10 July 2012
revised 25 September 2012

accepted 01 October 2012

Publication Date:
15 November 2012 (online)

    Permissions and Reprints

Abstract

Lygodipenoids A (1) and B (2), two novel C33 tetracyclic triterpenoids with a new 9,19 : 24,32-dicyclopropane skeleton, were isolated from the whole grass of Lygodium japonicum. Their structures were elucidated by spectroscopic and chemical means. Compounds 1 and 2 were tested in transfected cultured human embryonic kidney 293 HEK293 cells for an agonist assay, and compound 1 was identified as a partial agonist for liver X receptor α.

Key words

>Lygodium japonicum (Thunb.) Sw. - Lygodiaceae - 9,19 : 24,32-dicyclotetracyclic triterpenoid - liver X receptor α

Supporting Information

 

  • References

  • 1 Qin RC, Fu SJ, Wang ZH, Xing GX. Flora of China, Vol. 2. Beijing: Science Press; 1959: 105-113
    Google Scholar
  • 2 Chen LJ, Zhang GG, He J, Guan J, Pan CY, Mi WZ, Wang Q. New naphthoquinone from the root of Lygodium japonicum (Thunb.) Sw. J Nat Med 2010; 64: 114-116
    CrossrefPubMedGoogle Scholar
  • 3 Zhu LX, Zhang GG, Chen LJ, Wang SC, Li P, Li L. A new ecdysteroside from Lygodium japonicum (Thunb.) Sw. J Nat Med 2009; 63: 215-219
    CrossrefPubMedGoogle Scholar
  • 4 Ye WC, Fan CL, Zhang LH, Yin ZQ, Zhao SX. A new phenolic glycoside from the roots of Lygodium japonicum . Fitoterapia 2007; 78: 600-601
    CrossrefPubMedGoogle Scholar
  • 5 Wynne G, Mander LN, Goto N, Yamane H, Omori T. Gibberellin A117 methyl ester, a new antheridiogen from Lygodium circinnatum . Phytochemistry 1998; 49: 1837-1840
    CrossrefPubMedGoogle Scholar
  • 6 Wynne G, Mander LN, Oyama N, Murofuchi N, Yamane H. An antheridiogen, 13-hydroxy-GA73 methyl ester (GA109), from the fern Lygodium circinnatum . Phytochemistry 1998; 47: 1177-1182
    CrossrefPubMedGoogle Scholar
  • 7 Achari B, Chaudhuri C, Saha CR, Pakrashi SC, McPhail DR, McPhail AT. X-ray crystal structure of Lygodinolide: a novel spiro furopyran-perhydrophenanthrene derivative from Lygodium flexuosum . J Org Chem 1990; 55: 4977-4978
    CrossrefPubMedGoogle Scholar
  • 8 Achari B, Basu K, Saha CR, Pakrashi SC. A new triterpene ester, an anthraquinone and other constituents of the fern Lygodium flexuosum . Planta Med 1986; 52: 329-330
    Article in Thieme ConnectPubMedGoogle Scholar
  • 9 Song LR, Hong X, Ding XL, Zang ZY. The dictionary of traditional Chinese medicine. Beijing: Peopleʼs Public Health Publishing House of Beijing; 2001: 1803
    Google Scholar
  • 10 Yoshida K, Hirose Y, Imai Y, Kondo T. Conformational analysis of cycloartenol, 24-methylene cycloartanol and their derivatives. Agric Biol Chem 1989; 53: 1901-1912
    CrossrefPubMedGoogle Scholar
  • 11 Inada A, Ikeda Y, Murata H, Inatomi Y, Nakanishi T, Bhattacharyya K, Kar T, Bocelli G, Cantoni A. Unusual cyclolanostanes from leaves of Pandanus boninensis . Phytochemistry 2005; 66: 2729-2733
    CrossrefPubMedGoogle Scholar
  • 12 Isaev MI, Gorovits MB, Abubakirov NK. Progress in the chemistry of the cycloartanes. Chem Nat Compd 1989; 25: 131-147
    CrossrefPubMedGoogle Scholar
  • 13 Harrison DM. The biosynthesis of triterpenoids, steroids, and carotenoids. Nat Prod Rep 1990; 7: 459-484
    CrossrefPubMedGoogle Scholar
  • 14 Kikuchi T, Akihisa T, Tokuda H, Ukiya M, Watanabe K, Nishino H. Cancer chemopreventive effects of cycloartane-type and related triterpenoids in in vitro and in vivo models. J Nat Prod 2007; 70: 918-922
    CrossrefPubMedGoogle Scholar
  • 15 Yano K, Akhisa T, Tamura T, Matsumoto T. Four 4α-methylsterols and triterpene alcohols from Neolitsea aciculata . Phytochemistry 1992; 31: 2093-2098
    CrossrefPubMedGoogle Scholar
  • 16 Kostowa I, Simeonov M, Iossifova T, Tappe R, Pardeshi N. Three 9,19-cyclotetracyclic triterpenes from Skimmia wallichii . Phytochemistry 1996; 43: 643-648
    CrossrefPubMedGoogle Scholar
  • 17 Repa JJ, Mangelsdorf DJ. The liver X receptor gene team: potential new players in atherosclerosis. Nat Med 2002; 8: 1243-1248
    CrossrefPubMedGoogle Scholar
  • 18 Jayasuriya H, Herath KB, Ondeyka JG, Guan ZQ, Borris RP, Tiwari S, Jong W, Chavez F, Moss J, Stevenson DW, Beck HT, Slattery M, Zamora N, Schulman M, Ali A, Sharma N, MacNaul K, Hayes N, Menke JG, Singh SB. Diterpenoid, steroid, and triterpenoid agonists of liver X receptors from diversified terrestrial plants and marine sources. J Nat Prod 2005; 68: 1247-1252
    CrossrefPubMedGoogle Scholar
  • 19 Ondeyka JG, Jayasuriya H, Herath KB, Guan ZQ, Schulman M, Collado J, Dombrowski AW, Kwon SS, McCallum C, Sharma N, MacNaul K, Hayes N, Menke JG, Singh SB. Steroidal and triterpenoidal fungal metabolites as ligands of liver X receptors. J Antibiot 2005; 58: 559-565
    CrossrefPubMedGoogle Scholar
  • 20 Song C, Hiipakka RA, Liao S. Selective activation of liver X receptor alpha by 6α-hydroxy bile acids and analogs. Steroids 2000; 65: 423-427
    CrossrefPubMedGoogle Scholar