Literature DB >> 1453183

Antitumor agents, 135. Structure and stereochemistry of polacandrin, a new cytotoxic triterpene from Polanisia dodecandra.

Q Shi1, K Chen, T Fujioka, Y Kashiwada, J J Chang, M Kozuka, J R Estes, A T McPhail, D R McPhail, K H Lee.   

Abstract

A new dammarane triterpene, polacandrin [1], has been isolated from Polanisia dodecandra. The structure of 1 was established as 1 beta, 3 alpha, 12 beta, 25-tetrahydroxy-20(S),24(S)-epoxydammarane by chemical and spectroscopic methods, which included the concerted application of a number of 2D nmr techniques that involved 1H-1H COSY, HETCOR, NOESY, and long-range HETCOR. Single-crystal X-ray analysis of polacandrin pentahydrate verified the complete structure and stereochemistry. Polacandrin showed potent cytotoxicities against KB (ED50 = 0.60 microgram/ml), P-388 (ED50 = 0.90 microgram/ml), and RPMI-7951 (ED50 = 0.62 microgram/ml) tumor cells.

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Year:  1992        PMID: 1453183     DOI: 10.1021/np50088a015

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  5 in total

1.  (3R,6R,12R,20S,24S)-3,6,12-Triacetyl-20,24-ep-oxy-dammarane-3,6,12,25-tetra-ol.

Authors:  Huan-Mei Guo; Liang Wang; Nan Wang; Jiang-Feng Zhang; Qing-Guo Meng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-12-11

2.  A review on plant-derived natural products and their analogs with anti-tumor activity.

Authors:  K K Dholwani; A K Saluja; A R Gupta; D R Shah
Journal:  Indian J Pharmacol       Date:  2008-03       Impact factor: 1.200

3.  (3R,6R,12R,20S,24R)-20,24-Ep-oxy-dammarane-3,6,12,25-tetra-ol.

Authors:  Lei Zhang; Huan-Mei Guo; Wen-Juan Li; Yi-Jun Gao; Qing-Guo Meng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-03-12

4.  (3R,6R,12R,20S,24S)-20,24-Ep-oxy-dammarane-3,6,12,25-tetraol dihydrate.

Authors:  Qing-Guo Meng; Lian-Dong Liu; Huan-Mei Guo; Yi Bi; Liang Wang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-17

5.  Protection against diethylnitrosoamine-induced hepatocarcinogenesis by an indigenous medicine comprised of Nigella sativa, Hemidesmus indicus and Smilax glabra: a preliminary study.

Authors:  Samantha S Iddamaldeniya; Nalinie Wickramasinghe; Ira Thabrew; Neelakanthi Ratnatunge; Mayuri G Thammitiyagodage
Journal:  J Carcinog       Date:  2003-10-18
  5 in total

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