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Planta Med 1987; 53(2): 140-143
DOI: 10.1055/s-2006-962656
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© Georg Thieme Verlag Stuttgart · New York

Antitumor Agents: LXXXVII. Cytotoxic Antileukemic Canthin-6-one Alkaloids from Brucea antidysenterica and the Structure Activity Relationships of their Related Derivatives1

Narihiko Fukamiya2 , Masayoshi Okano2 , Takaaki Aratani2 , Kenji Negoro3 , Yuh-Meei Lin4 , Kuo-Hsiung Lee4
  • 2Faculty of Integrated Arts and Sciences, Hiroshima University, Hiroshima 730, Japan.
  • 3Faculty of Engineering, Hiroshima University, Higashihiroshima 724, Japan.
  • 4Natural Products Laboratory, Division of Medicinal Chemistry and Natural Products, School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27514, U.S.A.
1 For paper LXXXVI in this series, see Lee, K. H., Rice, G. K., Hall, I. H., Amarnath, V., J. Med. Chem., in press.
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Publication History

1986

Publication Date:
24 January 2007 (online)

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Abstract

Two cytotoxic antileukemic alkaloids, 11-hydroxy-1-methoxycanthin-6-one (2) and 1-hydroxy-11-methoxycanthin-6-one (3), as well as 1-methoxycanthin-6-one (1) were isolated from Brucea antidysenterica. The methyl ether (7) and a series of esters (8-13) of 11-hydroxycanthin-6-one (5) were prepared for investigating the structure-activity relationships. The results indicated that 1,11-dimethoxycanthin-6-one (4) and 11-hydroxycanthin-6-one (5) showed the most potent cytotoxic activity. Hydroxylation or methoxylation of canthin-6-one alkaloids at C-11 or C-10 are the structural requirement for the potent cytotoxicity in the KB tissue culture cell. Hydroxylation or methoxylation at C-1 of these alkaloids has no significant effect upon cytotoxicity.