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Planta Med 2005; 71(1): 72-76
DOI: 10.1055/s-2005-837754
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

Four New 6-Nor-5(6→7)abeo-abietane Type Diterpenes and Antitumoral Cytotoxic Diterpene Constituents from the Bark of Taiwania cryptomerioides

Chi-I Chang1 , Jang-Yang Chang2 , Ching-Chuan Kuo2 , Wen-Yu Pan2 , Yueh-Hsiung Kuo3
  • 1Graduate Institute of Biotechnology, National Pingtung University of Science and Technology, Pingtung, Taiwan
  • 2Division of Cancer Research, National Health Research Institutes, Taipei, Taiwan
  • 3Department of Chemistry, National Taiwan University, Taipei, Taiwan
Further Information

Publication History

Received: March 12, 2004

Accepted: September 6, 2004

Publication Date:
27 January 2005 (online)

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Abstract

Four new 6-nor-5(6→7)abeo-abietane type diterpenes designated as taiwaniaquinone G, taiwaniaquinone H, taiwaniaquinol E and taiwaniaquinol F and eight known diterpenes, taiwaniaquinones A (5), D (6), E, F (8), and taiwaniaquinols A (9), B, C (11), D (12) were isolated from the bark of Taiwania cryptomerioides. Their structures were elucidated on the basis of spectroscopic studies. These twelve diterpenes were evaluated for in vitro antitumoral cytotoxic activity. The result demonstrated that compounds 5, 6, 8, 9, 11, and 12 bearing an aldehyde group possessed potent cytotoxic activity against KB epidermoid carcinoma cancer cell lines with IC50 values of 6.9, 7.2, 4.4, 8.3, 8.1, and 3.5 μM, respectively.

Key words

Taiwania cryptomerioides - Taxodiaceae - diterpenes, 6-nor-5(6→7)abeo-abietane - cytotoxic activity

References

  • 1 Cheng Y S, Kuo Y H, Lin Y T. Extractive components from the wood of Taiwania cryptomeriodes Hayata: The structure of T-cadinol and T-muurolol. Journal of Chemical Society Chemical Communications 1967: 565-6
    Search in Google Scholar
  • 2 Lin Y T, Cheng Y S, Kuo Y H. Extractive components from the wood of Taiwania cryptomeriodes Hayata: A new sesquiterpenes keto-alcohols, cadinan-3-ene-9α-ol-2-one. Tetrahedron Letters 1968: 3881-2
    Search in Google Scholar
  • 3 Kuo Y H, Cheng Y S, Lin Y T. Extractive components from the wood of Taiwania cryptomeriodes Hayata: three new sesquiterpenes alcohols, muurolane-3-ene-9α-2-one, muurolane-2α-9β-diol-3-ene and muurolane-2β,9β-diol-3-ene. Tetrahedron Letters 1969: 2375-7
    Search in Google Scholar
  • 4 Kuo Y H, Shih J S, Lin Y T, Lin Y T. 6β-Acetoxy-7α-hydroxyroyleanone.  A new compound from Taiwania cryptomerioides Hayata.  Journal of Chinese Chemical Society. 1979;  26 71-3
    PubMedSearch in Google Scholar
  • 5 Kuo Y H, Lin Y T, Lin Y T. A new lignan from the bark of Taiwania cryptomerioides Hayata.  Journal of Chinese Chemical Society. 1985;  32 381-3
    PubMedSearch in Google Scholar
  • 6 Kuo Y H, Chang C I, Lee C K. Six podocarpane-type trinorditerpenes from the bark of Taiwania cryptomerioides .  Chemical & Pharmaceutical Bulletin. 2000;  48 597-9
    PubMedSearch in Google Scholar
  • 7 Kuo Y H, Chang C I. Podocarpane-type trinorditerpenes from the bark of Taiwania cryptomerioides .  Journal of Natural Products. 2000;  63 650-2
    CrossrefPubMedSearch in Google Scholar
  • 8 Kuo Y H, Chien S C. Quinone-type podocarpanes from the bark of Taiwania cryptomerioides .  Chemical & Pharmaceutical Bulletin. 2001;  49 1033-5
    PubMedSearch in Google Scholar
  • 9 Kuo Y H, Chien S C, Huang S L. Four new podocarpane-type trinorditerpenes from the bark of Taiwania cryptomerioides .  Chemical & Pharmaceutical Bulletin. 2002;  50 544-6
    PubMedSearch in Google Scholar
  • 10 Chang C I, Chien S C, Lee S M, Kuo Y H. Three novel 5(6→7)abeo-abietane-type diterpenes from the bark of Taiwania cryptomerioides .  Chemical & Pharmaceutical Bulletin. 2003;  51 420-2
    PubMedSearch in Google Scholar
  • 11 Lin W H, Fang J M, Cheng Y S. Diterpenoids and steroids from Taiwania cryptomerioides .  Phytochemistry. 1998;  48 1391-7
    CrossrefPubMedSearch in Google Scholar
  • 12 Lin W H, Fang J M, Cheng Y S. Uncommon diterpenes with the skeleton of six-five-six fused-rings from Taiwania cryptomerioides .  Phytochemistry. 1995;  40 871-3
    CrossrefPubMedSearch in Google Scholar
  • 13 Lin W H, Fang J M, Cheng Y S. Diterpenes and related cycloadducts from Taiwania cryptomerioides .  Phytochemistry. 1996;  42 1657-63
    CrossrefPubMedSearch in Google Scholar
  • 14 Lin W H, Fang J M, Cheng Y S. Cycloadducts of terpene quinones from Taiwania cryptomerioides .  Phytochemistry. 1997;  46 169-73
    CrossrefPubMedSearch in Google Scholar
  • 15 He K, Zeng L, Shi G, Zhao G X, Kozlowski J F, McLaughlin J L. Bioactive compounds from Taiwania cryptomerioides .  Journal of Natural Products. 1997;  60 38-40
    CrossrefPubMedSearch in Google Scholar
  • 16 Chang S T, Wang S Y, Wu C L, Shiah S G, Kuo Y H, Chang C J. Cytotoxicity of extractives from Taiwania cryptomerioides heartwood.  Phytochemistry. 2000;  55 227-32
    CrossrefPubMedSearch in Google Scholar
  • 17 Fenlay G J, Baguley B C, Wilson W R. A semiautomated microculture method for investigating exponentially growing carcinoma cells.  Analytic Biochemistry. 1984;  139 272-7
    PubMedSearch in Google Scholar
  • 18 Chang J Y, Chang C Y, Kuo C C, Chen L T, Wein Y S, Kuo Y H. Salvinal, a novel microtubule inhibitor isolated from Salvia miltiorrhiza Bunge (Danshen), with antimitotic activity in multidrug-sensitive and -resistant human tumor cells.  Molecular Pharmacology. 2004;  65 77-84
    CrossrefPubMedSearch in Google Scholar
  • 19 Chang J Y, Liu J F, Juang S H, Liu T W, Chen L T. Novel mutation of topoisomerase I in rendering cells resistant to camptothecin.  Cancer Research. 2002;  62 3716-21
    PubMedSearch in Google Scholar
  • 20 Chai M C, Wang S K, Dai C F, Duh C Y. A Cytotoxic lobdane diterpene from the Formosan soft coral Sinularia inelegans .  Journal of Natural Products. 2000;  63 843-4
    CrossrefPubMedSearch in Google Scholar
  • 21 Kodama K, Higuchi R, Miyamoto T, Van Soest R WM. (-)-Axinyssene: A novel cytotoxic diterpene from a Japanese marine sponge Axinyssa sp.  Organic Letters. 2003;  5 169-71
    CrossrefPubMedSearch in Google Scholar
  • 22 Zhang H, Fan Z, Tan G T, Chai H B, Pezzuto J M, Sun H, Fong H HS. Pseudoirroratin A, a new cytotoxic ent-kaurene diterpene from Isodon pseudo-irrorata .  Journal of Natural Products. 2002;  65 215-7
    CrossrefPubMedSearch in Google Scholar
  • 23 Uddin M J, Kokubo S, Ueda K, Suenaga K, Uemura D. Haterumaimides F - I, four new cytotoxic diterpene alkaloids from an Ascidian Lissoclinum species.  Journal of Natural Products. 2001;  64 1169-73
    CrossrefPubMedSearch in Google Scholar

Professor Yueh-Hsiung Kuo

Department of Chemistry

National Taiwan University

Taipei

Taiwan 106

R.O.C.

Phone: +886-2-2363-8146

Fax: +886-2-2363-6359

Email: yhkuo@ccms.ntu.edu.tw