Planta Med 2012; 78(10): 1010-1014
DOI: 10.1055/s-0031-1298539
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Sesquiterpenoids from the Rhizomes of Homalomena occulta

Xiao-Yu Xie
1   Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, PR China
2   Graduate University of Chinese Academy of Sciences, Beijing, PR China
,
Rui Wang
1   Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, PR China
,
Yan-Ping Shi
1   Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, PR China
› Author Affiliations
Further Information

Publication History

received 25 February 2012
revised 15 March 2012

accepted 16 April 2012

Publication Date:
09 May 2012 (online)

Abstract

Phytochemical investigation on the rhizomes of Homalomena occulta resulted in the isolation of five new sesquiterpenoids, namely cadinane-4β,5α,10α-triol (1), 5(11)-epoxycadinane-4β,5β,10β,11-tetraol (2), bullatantiol-1β-methyl malate (3), 1β,4β,7α-trihydroxyeudesmane-1β-methyl malate (6), and 1β,4α,7-trihydroxyeudes-mane (7), together with five known sesquiterpenoids, bullatantriol (4), acetylbullatantriol (5), 1β,4β,7α-trihydroxyeudesmane (8), 1β,4β,7β-trihydroxyeude-smane (9), and pterodontriol (10). Their structures were elucidated on the basis of spectroscopic evidences, including various 1D and 2D NMR and HR-ESI-MS. The structure of 1 was further confirmed by single-crystal X-ray diffraction analysis.

Supporting Information

 
  • References

  • 1 Editorial Committee for Flora of the Chinese Academy of Science. Flora of China, Vol. 13. Beijing: Science Press; 1979: 49
  • 2 Chinese Pharmacopoeia Commission. Chinese pharmacopoeia, Vol. 1. Beijing: Chemical Industry Press; 2005: 24
  • 3 Zhou CM, Yao C, Sun HL, Qiu SX, Cui GY. Volatile constituents of the rhizome of Homalomena occulta . Planta Med 1991; 57: 391-392
  • 4 Zeng LB, Zhang ZR, Luo ZH, Zhu JX. Antioxidant activity and chemical constituents of essential oil and extracts of rhizome Homalomenae . Food Chem 2011; 125: 456-463
  • 5 Hu YM, Liu C, Cheng KW, Herman HY, Williams LD, Yang ZL, Ye WC. Sesquiterpenoids from Homalomena occulta affect osteoblast proliferation, differentiation and mineralization in vitro . Phytochemistry 2008; 69: 2367-2373
  • 6 Wang YF, Wang XY, Lai GF, Lu CH, Luo SD. Three new sesquiterpenes from the aerial parts of Homalomena occulta . Chem Biodivers 2007; 4: 925-931
  • 7 Xu LW, Wang GY, Shi YP. Chemical constituents from Tagetes erecta flowers. Chem Nat Compd 2011; 47: 281-283
  • 8 Yuan T, Hua HM, Pei YH. Chemical constituents of Sparganiun stoloniferum (I). Chin Tradit Herb Drug 2005; 11: 1607-1610
  • 9 Kuo YH, Chyu CF, Lin HC. Cadinane-type sesquiterpenes from the roots of Taiwania cryptomerioides Hayata. Chem Pharm Bull 2003; 51: 986-989
  • 10 Valeev FA, Tsypysheva IP, Kunakova AM, Krasnosobodtseva OY, Shitikova OV, Spirikhin LV, Tolstikov GA. Functionalization of the allyl fragment in (+)-δ-cadinol. Russ J Org Chem 2004; 40: 337-345
  • 11 Liu XH, Zhao DB, Yang CR, Wang HQ. New sesquiterpenoids from Hedychium yunnanense gagnep . Chin Chem Lett 2000; 11: 1009-1012
  • 12 Alpegiani M, Hanessian S. A facile access to (R)-malic acid. J Org Chem 1987; 52: 278-279
  • 13 Sung TV, Steffan B, Steglich B, Klebe G, Adam G. Sesquiterpenes from the roots of Homalomena aromatica . Phytochemistry 1992; 31: 3515-3520
  • 14 Zhao Y, Yue JM, Lin ZW, Ding JK, Sun HD. Eudesmane sesquiterpenes from Laggera pterodonta . Phytochemistry 1997; 44: 459-464