Download PDF
Planta Med 2015; 81(07): 600-605
DOI: 10.1055/s-0035-1545882
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Bisbenzylisoquinoline Alkaloids from the Roots of Cyclea tonkinensis

Jian-zhong Wang
West China College of Pharmacy, Sichuan University, Chengdu, P. R. China
,
Jing Liao
West China College of Pharmacy, Sichuan University, Chengdu, P. R. China
,
Wen-long Xu
West China College of Pharmacy, Sichuan University, Chengdu, P. R. China
,
Xiao-bing Chen
West China College of Pharmacy, Sichuan University, Chengdu, P. R. China
› Author Affiliations
Further Information

Publication History

received 09 July 2014
revised 25 February 2015

accepted 26 February 2015

Publication Date:
09 April 2015 (online)

Also available at
    Permissions and Reprints

Abstract

Cissampentine A (1), an enantiomer of cissampentin, three new cycleatjehenine-type bisbenzylisoquinoline alkaloids, cissampentine B–D (2–4), and five known alkaloids were isolated from the roots of Cyclea tonkinensis. Their structures were established by interpretation of NMR, high-resolution ESI-MS data, and CD spectra. In vitro studies indicated that compounds 1 and 4 exhibited cytotoxicity against the HCT-8 tumor cell line (IC50 values of 8.97 and 9.73 µM, respectively), and compound 4 was also active against the Bel-7402 tumor cell line (IC50 value of 5.36 µM).

Key words

Cyclea tonkinensis - Menispermaceae - bisbenzylisoquinoline alkaloid - cissampentine A - cissampentine B - cissampentine C - cissampentine D - cytotoxic activity

Supporting Information

 

  • References

  • 1 Angerhofer CK, Guinaudeau H, Wongpanich V, Pezzuto JM, Cordell GA. Antiplasmodial and cytotoxic activity of natural bisbenzylisoquinoline alkaloids. J Nat Prod 1999; 62: 59-66
    CrossrefPubMedSearch in Google Scholar
  • 2 Hall AM, Chang CJ. Multidrug-resistance modulators from Stephania japonica . J Nat Prod 1997; 60: 1193-1195
    CrossrefPubMedSearch in Google Scholar
  • 3 Schiff jr. PL. Bisbenzylisoquinoline alkaloids. J Nat Prod 1997; 60: 934-953
    CrossrefPubMedSearch in Google Scholar
  • 4 Ndaya TJ, Wright AD, Konig GM. Hplc isolation of the anti-plasmodially active bisbenzylisoquinoline alkaloids present in roots of Cissampelos mucronata . Phytochem Anal 2003; 14: 13-22
    CrossrefPubMedSearch in Google Scholar
  • 5 Luo XR, Zhao SY. Medicinal plant of Menispermaceae in China. Guihaia 1986; 6: 49-61
    PubMedSearch in Google Scholar
  • 6 Wang JZ, Liao J, Lei Y. Study on the chemical constituents of Cycle wattii and structure of curine-type alkaloids. West China J Pharm Sci 2014; 29: 11-13
    PubMedSearch in Google Scholar
  • 7 Wang JZ, Liu XY, Wang FP. Two new curine-type bisbenzylisoquinoline alkaloids from the roots of Cyclea wattii with cytotoxic activities. Chem Pharm Bull 2010; 58: 986-988
    CrossrefPubMedSearch in Google Scholar
  • 8 Tanahashi T, Su Y, Nagakura N, Nayeshiro H. Quaternary isoquinoline alkaloids from Stephania cepharantha . Chem Pharm Bull 2000; 48: 370-373
    CrossrefPubMedSearch in Google Scholar
  • 9 Galinis DL, Wiemer DF, Cazin jr. J. Cissampentin: a new bisbenzylisoquinoline alkaloid from Cissampelos fasiculata . Tetrahedron 1993; 49: 1337-1342
    CrossrefPubMedSearch in Google Scholar
  • 10 Tomita M, Kikuchi T, Fujitani K, Kato A, Furukawa H, Aoyagi Y, Kitano M, Ibuka T. Mass spectrometry of bisbenzylisoquinoline alkaloids. Tetrahedron Lett 1966; 8: 857-864
    PubMedSearch in Google Scholar
  • 11 Koike L, Marsaioli AJ, Reis F. Proton and carbon-13 nuclear magnetic resonance spectroscopy and conformational aspects of the curine class of bisbenzylisoquinoline alkaloids. J Org Chem 1981; 46: 2385-2389
    CrossrefPubMedSearch in Google Scholar
  • 12 Koike L, Marsaioli AJ, Ruveda EA, Reis F. Stereochemical aspects and 13C NMR spectroscopy of the berbamine class of bisbenzylisoquinoline alkaloids. Tetrahedron Lett 1979; 20: 3765-3768
    CrossrefPubMedSearch in Google Scholar
  • 13 Guinaudeau H, Freyer AJ, Shamma M. Spectral characteristics of the bisbenzylisoquinoline alkaloids. Nat Prod Rep 1986; 476-488
    PubMedSearch in Google Scholar