Sesquiterpenes from the Roots of Illicium jiadifengpi

 

 Buy Article Permissions and Reprints

Abstract

Two new sesquiterpenes (1, 2) and two new sesquiterpene glycosides (3, 4) with a seco-prezizaane skeleton, three new allo-cedrane sesquiterpene glycosides (5–7), and a new acorane sesquiterpene (8) as well as 15 known analogues were isolated from the roots of Illicium jiadifengpi used for the treatment of rheumatoid arthritis. The structures of these compounds were elucidated by extensive spectroscopic analysis and chemical methods. The absolute configurations of compounds 5–7 were confirmed by CD experiments. The configuration of compound 8 was assigned by single-crystal X-ray crystallographic analysis and CD experiments. Compounds 4, 6, 7, 14, and 23 showed moderate antiviral activities against Coxsackie virus B3, and all compounds were inactive when evaluated for their cytotoxic activities against five human tumor cell lines and neuroprotection.

• References

• 1 Liu YH, Luo XR, Wu RF. Flora Reipublicae Popularis Sinicae, Vol. 30, Part 1. Beijing: Science Press; 1996: 203-205
  Google Scholar
• 2 Zhang GJ, Li YH, Jiang JD, Yu SS, Qu J, Ma SG, Liu YB, Yu DQ. Anti-Coxsackie virus B diterpenes from the roots of Illicium jiadifengpi . Tetrahedron 2013; 69: 1017-1023
  CrossrefPubMedGoogle Scholar
• 3 Yang CS, Kouno I, Kawano N, Sato S. New anisatin-like sesquiterpene lactones from pericarps of Illicium majus . Tetrahedron Lett 1988; 29: 1165-1168
  CrossrefPubMedGoogle Scholar
• 4 Dong XJ, Zhu XD, Wang YF, Wang Q, Ju P, Luo S. Secoprezizaane sesquiterpene lactones from Illicium micranthrum . Helv Chim Acta 2006; 89: 983-987
  CrossrefPubMedGoogle Scholar
• 5 Kouno I, Baba N, Hashimoto M, Kawano N, Takahashi M, Kaneto H, Yang CS. Sesquiterpene lactones from the pericarps of Illicium majus; 2-oxy derivatives of neomajucin and 3,4-dehydroxyneomajucin. Chem Pharm Bull 1990; 38: 422-425
  CrossrefPubMedGoogle Scholar
• 6 Kouno I, Baba N, Hashimoto M, Kawano N, Yang CS, Sato S. A new sesquiterpene lactone and its glucoside from the pericarps of Illicium majus . Chem Pharm Bull 1989; 37: 2427-2430
  CrossrefPubMedGoogle Scholar
• 7 Powell RG, Weisleder D, Smith CR. Drummondones A and B: unique abscisic acid catabolites incorporating a bicyclo[2.2.2]octane ring system. J Org Chem 1986; 51: 1074-1076
  CrossrefPubMedGoogle Scholar
• 8 Cui B, Nakamura M, Kinjo J, Nohara T. Chemical constituents of Astragali semen. Chem Pharm Bull 1993; 41: 178-182
  CrossrefPubMedGoogle Scholar
• 9 Sung TV, Steffan B, Steglich W, Klebe G, Adam G. Sesquiterpenoids from the roots of Homalomena aromatica . Phytochemistry 1992; 31: 3515-3520
  CrossrefPubMedGoogle Scholar
• 10 Kuo YH, Chyu CF, Lin HC. Cadinane-type sesquiterpenes from the roots of Taiwania cryptomerioides Hayata. Chem Pharm Bull 2003; 51: 986-989
  CrossrefPubMedGoogle Scholar
• 11 Bai J, Chen H, Fang ZF, Yu SS, Wang WJ, Liu Y, Ma SG, Li Y, Qu J, Xu S, Liu JH, Zhao F, Zhao N. Sesquiterpenes from the roots of Illicium dunnianum . Phytochemistry 2012; 80: 137-147
  CrossrefPubMedGoogle Scholar
• 12 Huang JM, Yokoyama R, Yang CS, Fukuyama Y. Structure and neurotrophic activity of seco-prezizaane-type sesquiterpenes from Illicium merrillianum . J Nat Prod 2001; 64: 428-431
  CrossrefPubMedGoogle Scholar
• 13 Schmidt TJ. Novel seco-prezizaane sesquiterpenes from north American Illicium species. J Nat Prod 1999; 62: 684-687
  CrossrefPubMedGoogle Scholar
• 14 Liang D, Hao ZY, Zhang GJ, Zhang QJ, Chen RY, Yu DQ. Cytotoxic triterpenoids saponins from Lysimachia clethroides . J Nat Prod 2011; 74: 2128-2136
  CrossrefPubMedGoogle Scholar
• 15 Nunez YO, Salabarria IS, Collado IG, Hernandez-Galan R. Sesquiterpenes from the wood of Juniperus lucayana . Phytochemistry 2007; 68: 2409-2414
  CrossrefPubMedGoogle Scholar
• 16 Minkin VI, Legrand M, Rougier MJ. Stereochemistry, fundamentals and methods, Volume 2. Stuttgart: Georg Thieme; 1977: 105-107
  Google Scholar
• 17 Song TF, Zhang WD, Xia XH, Shen YH, Liu CM, Lin S, Jin HZ, Li HL. Two new acorane sesquiterpenes from Illicium henryi . Arch Pharm Res 2009; 32: 1233-1236
  CrossrefPubMedGoogle Scholar
• 18 Ni G, Zhang QJ, Zheng ZF, Chen RY, Yu DQ. 2-Arylbenzofuran derivatives from Morus cathayana . J Nat Prod 2009; 72: 966-968
  CrossrefPubMedGoogle Scholar
• 19 Kouno I, Baba N, Hashimoto M, Kawano N, Takahashi M, Kaneto H, Yang CS, Sato S. Isolation of three new sesquiterpene lactones from the pericarps of Illicium majus . Chem Pharm Bull 1989; 37: 2448-2451
  CrossrefPubMedGoogle Scholar
• 20 Kubo M, Okada C, Huang JM, Harada K, Hioki H, Fukuyama Y. Novel pentacyclic seco-prezizaane-type sesquiterpenoids with neurotrophic properties from Illicium jiadifengpi . Org Lett 2009; 11: 5190-5193
  CrossrefPubMedGoogle Scholar
• 21 Li YP, Shan GZ, Peng ZG, Zhu JH, Meng S, Zhang T, Gao LY, Tao RM, Li YH, Jiang JD, Li ZR. Synthesis and biological evaluation of heat-shock protein 90 inhibitors: geldanamycin derivatives with broad antiviral activities. Antiviral Chem Chemother 2010; 20: 259-268
  PubMedGoogle Scholar
• 22 Gan ML, Zhang YL, Lin S, Liu MT, Song WX, Zi JC, Yang YC, Fan XN, Shi JG, Hu JF, Sun JD, Chen NH. Glycosides from the root of Iodes cirrhosa . J Nat Prod 2008; 71: 647-654
  CrossrefPubMedGoogle Scholar

• Supplementary Material