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Planta Med 2004; 70(11): 1095-1097
DOI: 10.1055/s-2004-832656
Letter
© Georg Thieme Verlag KG Stuttgart · New York

A New Cytotoxic Phenylbutenoid Dimer from the Rhizomes of Zingiber cassumunar

Ah-Reum Han1 , Hye-Young Min1 , Tri Windono2 , Gwang-Ho Jeohn2 , Dae Sik Jang3 , Sang Kook Lee1 , Eun-Kyoung Seo1
  • 1College of Pharmacy, Ewha Womans University, Seoul, Korea
  • 2College of Pharmacy, University of Surabaya, Surabaya, Indonesia
  • 3Division of Molecular Life Sciences, Ewha Womans University, Seoul, Korea
Further Information

Publication History

Received: February 20, 2004

Accepted: July 10, 2004

Publication Date:
18 November 2004 (online)

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Abstract

A new phenylbutenoid dimer, (±)-trans-3-(4-hydroxy-3-methoxyphenyl)-4-[(E)-3,4-dimethoxystyryl]cyclohex-1-ene, was isolated from the rhizomes of Zingiber cassumunar along with the three known compounds, (±)-trans-3-(3,4-dimethoxyphenyl)-4-[(E)-3,4-dimethoxystyryl]cyclohex-1-ene, 4-(3,4-dimethoxyphenyl)but-1,3-diene, and 4-(2,4,5-trimethoxyphenyl)but-1,3-diene by bioassay-directed fractionation using the A549 human cancer cell line cytotoxicity assay. Structure of the new compound was elucidated by spectral analysis, including 1D and 2D NMR experiments.

References

  • 1 Mabberley D J. The Plant Book. 1st Edition Cambridge; Cambridge University Press 1995: pp 623-4
    Search in Google Scholar
  • 2 Bruneton J. Pharmacognosy. 2nd Edition New York; Lavoisier Publishing Inc 1999: pp 296-302
    Search in Google Scholar
  • 3 Masuda T, Andoh T, Yonemori S, Takeda Y. Phenylbutenoids from the rhizomes of Alpinia flabellata .  Phytochemistry. 1999;  50 163-6
    CrossrefPubMedSearch in Google Scholar
  • 4 Masuda T, Jitoe A. Phenylbutenoid monomers from the rhizomes of Zingiber cassumunar .  Phytochemistry. 1995;  39 459-61
    CrossrefPubMedSearch in Google Scholar
  • 5 Jitoe A, Masuda T, Nakatani N. Phenylbutenoid dimmers from the rhizomes of Zingiber cassumunar .  Phytochemistry. 1993;  32 357-63
    CrossrefPubMedSearch in Google Scholar
  • 6 Tuntiwachwuttikul P, Pancharoen O, Jaipetch T, Reutrakul V. Phenylbutanoids from Zingiber cassumunar .  Phytochemistry. 1981;  20 1164-5
    CrossrefPubMedSearch in Google Scholar
  • 7 Kuroyanagi M, Fukushima S, Yosihira K, Natori S, Dechatiwongse T, Mihashi K, Nishi M, Hara S. Further characterization of the constituents of a Thai medicinal plants, Zingiber cassumunar Roxb.  Chem Pharm Bull. 1980;  28 2948-59
    PubMedSearch in Google Scholar
  • 8 Masuda T, Jitoe A. Antioxidative and anti-inflammatory compounds from tropical gingers: isolation, structure determination, and activities of cassumunins A, B, and C, new complex curcuminoids from Zingiber cassumunar .  J Agr Food Chem. 1994;  42 1850-6
    CrossrefPubMedSearch in Google Scholar
  • 9 Ozaki Y, Kawahara N, Harada M. Anti-inflammatory effect of Zingiber cassumunar Roxb. and its active principles.  Chem Pharm Bull. 1991;  39 2353-6
    CrossrefPubMedSearch in Google Scholar
  • 10 Nugroho B W, Schwarz B, Wray V, Proksch P. Insecticidal constituents from rhizomes of Zingiber cassumunar and Kaempferia rotunda .  Phytochemistry. 1996;  41 129-32
    CrossrefPubMedSearch in Google Scholar
  • 11 Kanjanapothi D, Soparat P, Panthong A, Tuntiwachwuttikul P, Reutrakul V. A uterine relaxant compound from Zingiber cassumunar .  Planta Medica. 1987;  53 329-32
    PubMedSearch in Google Scholar
  • 12 Vimala S, Norhanom A W, Yadav M. Anti-tumour promoter activity in Malaysian ginger rhizobia used in traditional medicine.  Brit J Cancer. 1999;  80 110-6
    PubMedSearch in Google Scholar
  • 13 Park G, Lee E J, Min H Y, Choi H Y, Han A R, Lee S K, Seo E K. Evaluation of cytotoxic potential of Indonesian medicinal plants in cultured human cancer cells.  Nat Prod Sci. 2002;  8 165-9
    PubMedSearch in Google Scholar
  • 14 Lee S K, Cui B, Mehta R R, Kinghorn A D, Pezzuto J M. Cytostatic mechanism and antitumor potential of novel 1H-cyclopenta[b]benzofuran lignans isolated from Aglaia elliptica .  Chemico-Biol Interact. 1998;  115 215-28
    PubMedSearch in Google Scholar

Prof. Eun-Kyoung Seo, Ph. D.

Natural Products Chemistry Laboratory

College of Pharmacy

Ewha Womans University

Seoul 120-750

Korea

Phone: +82-2-3277-3047

Fax: +82-2-3277-3051

Email: Yuny@ ewha.ac.kr