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

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

• References

• 1 Qin RC, Fu SJ, Wang ZH, Xing GX. Flora of China, Vol. 2. Beijing: Science Press; 1959: 105-113
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 12 Isaev MI, Gorovits MB, Abubakirov NK. Progress in the chemistry of the cycloartanes. Chem Nat Compd 1989; 25: 131-147
• 13 Harrison DM. The biosynthesis of triterpenoids, steroids, and carotenoids. Nat Prod Rep 1990; 7: 459-484
• 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
• 15 Yano K, Akhisa T, Tamura T, Matsumoto T. Four 4α-methylsterols and triterpene alcohols from Neolitsea aciculata . Phytochemistry 1992; 31: 2093-2098
• 16 Kostowa I, Simeonov M, Iossifova T, Tappe R, Pardeshi N. Three 9,19-cyclotetracyclic triterpenes from Skimmia wallichii . Phytochemistry 1996; 43: 643-648
• 17 Repa JJ, Mangelsdorf DJ. The liver X receptor gene team: potential new players in atherosclerosis. Nat Med 2002; 8: 1243-1248
• 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
• 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
• 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