PDF herunterladen
Planta Med 2003; 69(9): 842-845
DOI: 10.1055/s-2003-43215
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

Cytotoxic Alkaloids from Boehmeria siamensis

Yinggang Luo1 , 2 , Yan Liu3 , Dixiang Luo3 , Xiaoping Gao3 , Bogang Li1 , Guolin Zhang1
  • 1Chengdu Institute of Biology, the Chinese Academy of Sciences, Chengdu, P. R. China
  • 2Chengdu Institute of Organic Chemistry, the Chinese Academy of Sciences, Chengdu, P. R. China
  • 3Pharmaceutical Institute of Di-Ao Pharmaceutical Group, Chengdu, P. R. China
Weitere Informationen

Publikationsverlauf

Received: December 27, 2002

Accepted: March 29, 2003

Publikationsdatum:
04. November 2003 (online)

    Lizenzen und Reprints

Abstract

Two new phenanthroquinolizidine alkaloids, boehmeriasins A and B, were isolated from the aqueous ethanolic extract of Boehmeria siamensis Craib (Urticaceae) by bioassay-guided fractionation. Their structures were elucidated on the basis of spectral evidence. Boehmeriasin A possesses cytotoxic activity against 12 cell lines from 6 panels of cancer including lung cancer, colon cancer, breast cancer, prostate cancer, kidney cancer and leukemia with GI50 between 0.2 and 100 ng/mL, whereas boehmeriasin B showed lower activity.

Key words

Boehmeria siamensis - Urticaceae - boehmeriasin A - boehmeriasin B - cytotoxic activity

References

  • 1 Institute of B otany, the Chinese Academy of S ciences. Iconographia Cormophytorum Sinicorum, Supplementum I. 1995: p. 203
    Google Scholar
  • 2 Working Group of Collects of Chinese Medicines and H erbs. Collects of Chinese Medicines and Herbs, Section B. 1988: p. 781
    Google Scholar
  • 3 Yunnan Medicines and Herbs C ompany. Contents of Chinese Medicines in Yunnan. 1993: p. 82
    Google Scholar
  • 4 Takemoto T, Miyase T, Kusano G. Boehmenan, A new lignan from the roots of Boehmeria tricuspis .  Phytochemistry. 1975;  14 1890-91
    CrossrefPubMedGoogle Scholar
  • 5 Takemoto T, Miyase T, Kusano G. Flavones and other compounds of Boehmeria tricuspis and B. holosericea .  Phytochemistry. 1975;  14 2534
    CrossrefPubMedGoogle Scholar
  • 6 Hart N K, Johns S R, Lamberton J A. 3,4-Dimethoxy-ω-(2′-piperidyl)acetophenone, a new alkaloid from Boehmeria platyphylla Don. (Family Urticaceae).  Australian Journal of Chemistry. 1968;  21 1397-8
    PubMedGoogle Scholar
  • 7 Hart N K, Johns S R, Lamberton J A. Minor alkaloids of Boehmeria platyphylla Don. (Family Urticaceae) II. Isolation of cryptopleurine and a new seco-phenanthroquinolizidine alkaloid.  Australian Journal of Chemistry. 1968;  21 2579-81
    PubMedGoogle Scholar
  • 8 Farnsworth N R, Hart N K, Johns S R, Lamberton J A, Messmer W. Alkaloids of Boehmeria cylindrical (Family Urticaceae): Identification of a cytotoxic agent, highly active against Eagle’s 9KB carcinoma of the nasopharynx in cell culture, as cryptopleurine.  Australian Journal of Chemistry. 1969;  22 1805-7
    PubMedGoogle Scholar
  • 9 Al-Shamma A, Drake S D, Guagliardi L E, Mitscher L A, Swayze J K. Antimicrobial alkaloids from Boehmeria cylindrical .  Phytochemistry. 1982;  21 485-7
    CrossrefPubMedGoogle Scholar
  • 10 Talapatra B, Mallik A K, Talapatra S K. Terpenoid constituents of Boehmeria platyphlla Don.: Sodium borohydride reduction of 5α-stigmastan-3,6-dione.  Journal of Indian Chemical Society. 1981;  58 815-7
    PubMedGoogle Scholar
  • 11 Matsuura S, Lee L T. Studies on the components of Boehmeria sp. II. Studies on the components of the roots of Boehmeria frutescens Thunb. Var. frutescens .  Yakugaku Zasshi. 1974;  94 150-2
    PubMedGoogle Scholar
  • 12 Takemoto T, Miyase T. Studies on the constituents of Boehmeria tricuspis Makino. I.  Yakugaku Zasshi. 1974;  94 1597-602
    PubMedGoogle Scholar
  • 13 Luo Y G, Li B G, Zhang G L. A new quinolizidine alkaloid from Boehmeria siamensis .  Chinese Chemical Letters. 2001;  12 337-8
    PubMedGoogle Scholar
  • 14 Skehan P, Storeng R, Scudiero D, Monk A, McMahon J, Vistica D. et al . New colorimetric cytotoxicity assay for anticancer-drug-screening.  Journal of National Cancer Institute. 1990;  82 1107-12
    CrossrefPubMedGoogle Scholar
  • 15 Rubinstein L V, Shoemaker R H, Paull K D, Simon R M, Tosini S, Skehan P. et al . Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines.  Journal of National Cancer Institute. 1990;  82 1113-8
    CrossrefPubMedGoogle Scholar
  • 16 Li Z G, Jin Z, Huang R Q. Isolation, total synthesis and biological activity of phenanthroindolizidine and phenanthroquinolizidine alkaloids. Synthesis 2001: 2365-78
    Google Scholar
  • 17 Gupta R S, Krepinsky J J, Siminovitch L. Structural determinants responsible for the biological activity of (-)-emetine, (-)-cryptopleurine, and (-)-tylocrebrine: Structure-activity relationship among related compounds.  Molecular Pharmacology. 1980;  18 136-43
    PubMedGoogle Scholar
  • 18 Stærk D, Lykkeberg A K, Christensen J, Budnik B A, Abe F, Jaroszewski J W. In vitro cytotoxic activity of phenanthroindolizidine alkaloids from Cynanchum vincetoxicum and Tylophora tanakae against drug-sensitive and multidrug-resistant cancer cells.  Journal of Natural Products. 2002;  65 1299-302
    CrossrefPubMedGoogle Scholar
  • 19 Abe F, Hirokawa M, Yamauchi T, Honda K, Hayashi N, Ishii M. et al . Further investigation of phenanthroindolizidine alkaloids from Tylophora tanakae .  Chemical and Pharmaceutical Bulletin. 1998;  46 767-9
    PubMedGoogle Scholar
  • 20 Stærk D, Christensen J, Lemmich E, Duus J Ø, Olsen C E, Jaroszewski J W. Cytotoxic activity of some phenanthroindolizidine N-oxide alkaloids from Cynanchum vincetoxicum .  Journal of Natural Products. 2000;  63 1584-6
    CrossrefPubMedGoogle Scholar

Prof. Dr. Guolin Zhang

Chengdu Institute of Biology

The Chinese Academy of Sciences

P. O. 416

Chengdu 610041

P. R. China

Telefon: /Fax: +86-28-85225401

eMail: Zhanggl@cib.ac.cn

      >