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Planta Med 1991; 57(4): 380-383
DOI: 10.1055/s-2006-960122
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© Georg Thieme Verlag Stuttgart · New York

Cytotoxic Clerodane Diterpenes from Polyalthia longifolia

Gengxian Zhao1 , Jee H. Jung2 , David L. Smith2 , Karl V. Wood2 , Jerry L. McLaughlin2
  • 1Visiting scholar from Nanjing College of Traditional Chinese Medicine, W.H.O. Nanjing Collaborative Center of Traditional Medicine, Nanjing, 210005, People's Republic of China
  • 2Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907, U.S.A.
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Publication History

1990

Publication Date:
05 January 2007 (online)

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Abstract

Bioassay-directed chemical investigation of the stem bark of Polyalthia longifolia Thw. (Annonaceae) has led to a novel clerodane diterpene, 16-oxo-cleroda-3,13(14)Z-dien-15-oic acid, which was named polyalthialdoic acid (3). The bioassays also led to the previously known related diterpenes, kolavenic acid (2) which has not been reported as a constituent of this plant, and 16α-hydroxy-cleroda-3,13(14)Z-dien-15,16-olide (1) which is previously known to be in this plant. These structures were identified by chemical and spectroscopic methods. All three compounds (1-3) were significantly bioactive in the brine shrimp bioassay; they strongly inhibited the growth of crown gall tumors on potato discs; and they were cytotoxic in three human tumor cell lines. These activities suggest potential antitumor applications. Compound 3 was the most active (ED50 values ca. 6 × 10-1 µg/ml in the human tumor cell culture systems).

Key words

Polyalthia longifolia - clerodane diterpene - polyalthialdoic acid - kolavenic acid - cytotoxic agents