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Planta Med 2004; 70(10): 948-959
DOI: 10.1055/s-2004-832622
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

Nine New Cytotoxic Monotetrahydrofuranic Annonaceous Acetogenins from Annona montana

Chih-Chuang Liaw1 , 2 , Fang-Rong Chang1 , Chin-Chung Wu1 , 2 , Shu-Li Chen1 , Kenneth F. Bastow2 , Ken-ichiro Hayashi3 , Hiroshi Nozaki3 , Kuo-Hsiung Lee2 , Yang-Chang Wu1
  • 1Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan
  • 2Natural Products Laboratory, School of Pharmacy, University of North Carolina, Chapel Hill, NC, USA
  • 3Department of Biochemistry, Faculty of Science, Okayama University of Science, Okayama, Japan
Further Information

Publication History

Received: May 4, 2004

Accepted: July 13, 2004

Publication Date:
18 October 2004 (online)

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Abstract

Nine monotetrahydrofuranic Annonaceous acetogenins, montalicins A - E (1 - 5), cis-annoreticuin (6), montalicins F (7), I (8), and J (9), along with eight known acetogenins 10 - 17, were isolated from the seeds of Annona montana by a high performance liquid chromatographic (HPLC) method. The structures of all new isolates were elucidated and characterized by spectroscopic and chemical methods. These monotetrahydrofuranic Annonaceous acetogenins showed selectively potent cytotoxicity against two human cancer cell lines, 1A9 and Hep G2.

Key words

Annona montana - Annonaceae - montalicin - Annonaceous acetogenins - human hepatoma cell - cytotoxicity

References

  • 1 Alali F Q, Liu X X, McLaughlin J L. Annonaceous acetogenins: recent progress.  J Nat Prod. 1999;  62 504-40
    CrossrefPubMedSearch in Google Scholar
  • 2 Nakanishi Y, Chang F R, Liaw C C, Wu Y C, Bastow K F, Lee K H. Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line.  J Med Chem. 2003;  46 3185-8
    CrossrefPubMedSearch in Google Scholar
  • 3 Wu Y C, Chang K Y, Duh C Y, Wang S K. Cytotoxic alkaloids of Annona montana .  Phytochemistry. 1993;  33 497-500
    CrossrefPubMedSearch in Google Scholar
  • 4 Chang F R, Wu Y C, Duh C Y, Wang S K. Diepoxymontin, a novel acetogenin from Annona montana .  Heterocycles. 1994;  38 1475-8
    CrossrefPubMedSearch in Google Scholar
  • 5 Zafra-Polo M C, Figadère B, Gallardo T, Tormo J R, Cortes D. Natural acetogenins from Annonaceae, synthesis and mechanisms of action.  Phytochemistry. 1998;  48 1087-117
    CrossrefPubMedSearch in Google Scholar
  • 6 Xu L, Chang C J, Yu J G, Cassady J M. Chemistry and selective cytotoxicity of annonacin-10-one, isoannonacin, and isoannonacin-10-one. Novel polyketides from Annona densicoma (Annonaceae).  J Org Chem. 1989;  54 5418-21
    PubMedSearch in Google Scholar
  • 7 Liaw C C, Chang F R, Lin C Y, Chou C J, Chiu H F, Wu M J, Wu Y C. New cytotoxic monotetrahydrofuran Annonaceous acetogenins from Annona muricata .  J Nat Prod. 2002;  65 470-5
    CrossrefPubMedSearch in Google Scholar
  • 8 Fang X P, Anderson J E, Smith D L, McLaughlin J L, Wood K L. Gigantetronenin and gigantrionenin: novel cytotoxic acetogenins from Goniothalamus giganteus .  J Nat Prod. 1992;  55 1655-63
    CrossrefPubMedSearch in Google Scholar
  • 9 McCloud T G, Smith D L, Chang C J, Cassady J M. Annonacin, a novel, biologically active polyketide from Annona densicoma .  Experientia. 1987;  43 947-9
    CrossrefPubMedSearch in Google Scholar
  • 10 Rieser J M, Gu Z M, Fang X P, Zeng L, Wood K V, McLaughlin J L. Five novel mono-tetrahydrofuran ring acetogenins from the seeds of Annona muricata .  J Nat Prod. 1996;  59 100-8
    CrossrefPubMedSearch in Google Scholar
  • 11 Colman-Saizarbitoria T, Zambrano J, Ferrigni N R, Gu Z M, Smith D L, McLaughlin J L. Bioactive annonaceous acetogenins from the bark of Xylopia aromatica .  J Nat Prod. 1994;  57 486-93
    CrossrefPubMedSearch in Google Scholar
  • 12 Wu Y C, Chang F R, Duh C Y, Wang S K. Annoreticuin and isoannoreticuin: two new cytotoxic acetogenins from Annona reticulata .  Heterocycles. 1992;  34 667-74
    CrossrefPubMedSearch in Google Scholar
  • 13 Alkofahi A, Rupprecht J K, Smith D L, Chang C J, McLaughlin J L. Goniothalamicin and annonacin: Bioactive acetogenin from Goniothalamus giganticus (Annonaceae).  Experientia. 1988;  44 83-5
    PubMedSearch in Google Scholar
  • 14 Chang F R, Wu Y C. Novel cytotoxic Annonaceous acetogenins from Annona muricata .  J Nat Prod. 2001;  64 925-31
    CrossrefPubMedSearch in Google Scholar
  • 15 Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren J T, Bokesch H, Kenney S, Boyd M R. New colorimetric cytotoxicity assay for anticancer-drug screening.  J Natl Cancer Inst. 1990;  82 1107-12
    CrossrefPubMedSearch in Google Scholar
  • 16 Rubinstein L V, Shoemaker R H, Paull K D, Simon R M, Tosini S, Skehan P, Scudiero D A, Monks A, Boyd M R. 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.  J Natl Cancer Inst. 1990;  82 1113-8
    CrossrefPubMedSearch in Google Scholar
  • 17 Gawronski J, Wu Y C. A note on the determination of absolute configuration of acetogenins by circular dichroism.  Polish J Chem. 1999;  73 241-3
    PubMedSearch in Google Scholar
  • 18 Cavé A, Figadere B, Laurens A, Cortes D. Acetogenins from Annonaceae.  Fortschr Chem Org Naturst. 1997;  70 81-288
    PubMedSearch in Google Scholar
  • 19 Born L, Lieb F, Lorentzen J P, Moeschler H, Nonfon M, Söllner R, Wendisch D. Die relative Konfiguration der aus Annona squamosa isolierten Acetogenine Annonin I (squamocin) und Annonin VI.  Planta Med. 1990;  56 312-6
    Thieme ConnectPubMedSearch in Google Scholar
  • 20 Fujimoto Y, Murasaki C, Shimada H, Nishioka S, Kakinuma K, Singh S, Singh M, Sahai M, Gupta Y K. Annonaceous acetogenins from the seeds of Annona squamosa. Non-adjacent bis-tetrahydrofuranic acetogenins.  Chem Pharm Bull. 1994;  42 1175-84
    PubMedSearch in Google Scholar
  • 21 Hopp D C. New bioactive Annonaceous acetogenins from the bark of Annona squamosa, and the use of countercurrent chromatography for their isolation. Ph. D. Thesis, Purdue University Indiana; 1997
    Search in Google Scholar
  • 22 Mizutani K, Fukunaga Y, Tanaka O, Takasugi N, Saruwatari Y, Fukunaga Y, Wang J, Jia M R, Li F Y, Ling Y K. Amides from Huajiao, pericarps of Zanthoxylum bungeanum Maxim.  Chem Pharm Bull. 1988;  36 2362-5
    CrossrefPubMedSearch in Google Scholar
  • 23 Dorman D E, Jautelat M, Roberts J D. Carbon-13 nuclear magnetic resonance spectroscopy. Quantitative correlations of the carbon chemical shifts of acyclic alkenes.  J Org Chem. 1971;  36 2757-66
    PubMedSearch in Google Scholar
  • 24 Araya H, Hara N, Fujimoto Y, Srivastava A, Sahai M. Squamosten-A, a novel mono-tetrahydrofuranic acetogenin with a double bond in the hydrocarbon chain, from Annona squamosa L.  Chem Pharm Bull. 1994;  42 388-91
    PubMedSearch in Google Scholar
  • 25 Gu Z M, Fang X P, Zeng L, Song R, Na J H, Wood K W, Smith D L, McLaughlin J L. Gonionenin: a new cytotoxic Annonaceous acetogenin from Goniothalamus giganteus and the conversion of mono-THF acetogenins to bis-THF acetogenins.  J Org Chem. 1994;  59 3472-9
    PubMedSearch in Google Scholar
  • 26 Colman-Saizarbitoria T, Gu Z M, McLaughlin J L. Two new bioactive monotetrahydrofuran Annonaceous acetogenins from the bark of Xylopia aromatica .  J Nat Prod. 1994;  57 1661-9
    CrossrefPubMedSearch in Google Scholar
  • 27 Sahpaz S, González C M, Hocquemiller R, Zafra-Polo M C, Cortes D. Annonsenegalin and annogalene: two cytotoxic mono-tetrahydrofuran acetogenins from Annona senegalensis and Annona cherimolia .  Phytochemistry. 1996;  42 103-7
    CrossrefPubMedSearch in Google Scholar
  • 28 Chih H W, Chiu H F, Tang K S, Chang F R, Wu Y C. Bullatacin, a potent antitumor Annonaceous acetogenin, inhibited proliferation of human hepatocarcinoma cell line 2.2.15 by apoptosis induction.  Life Sci. 2001;  69 1321-31
    CrossrefPubMedSearch in Google Scholar
  • 29 Yuan S SF, Chang H L, Chen H W, Yeh Y T, Kao Y H, Lin K H, Wu Y C, Su J H. Annonacin, a mono-tetrahydrofuran acetogenin, arrests cancer cells at the G1 phase and causes cytotoxicity in a Bax- and caspase-3-related pathway.  Life Sci. 2003;  72 2853-61
    CrossrefPubMedSearch in Google Scholar
  • 30 Jiang S, Song M J, Shin E -C, Lee M -O, Kim S J, Park J H. Apoptosis in human hepatoma cell lines by chemotherapeutic drugs via Fas-dependent and Fas-independent pathways.  Hepatology. 1999;  29 101-10
    CrossrefPubMedSearch in Google Scholar
  • 31 Miyoshi H, Ohshima M, Shimada H, Akagi T, Iwamura H, McLaughlin J L. Essential structural factors of Annonaceous acetogenins as potent inhibitors of mitochondrial complex I.  Biochim Biophys Acta. 1998;  1365 443-52
    PubMedSearch in Google Scholar

Prof. Dr. Yang-Chang Wu

Graduate Institute of Natural Products

Kaohsiung Medical University

Kaohsiung 807

Taiwan

Fax: +886-7-3114773

Email: yachwu@kmu.edu.tw