Planta Med 2008; 74(12): 1481-1487
DOI: 10.1055/s-2008-1081348
Natural Products Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Structure-Activity Relationship of Pentacylic Triterpene Esters from Uncaria rhynchophylla as Inhibitors of Phospholipase Cγ1

Ji Suk Lee1 , Hunseung Yoo1 , Young Ger Suh1 , Jae Kyung Jung1 , Jinwoong Kim1
  • 1College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul, Korea
Further Information

Publication History

Received: April 13, 2008 Revised: June 22, 2008

Accepted: June 24, 2008

Publication Date:
24 September 2008 (online)

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Abstract

A systematic structure-activity relationship of 3β-hydroxy-27-p-E-coumaroyloxyurs-12-en-28-oic acid (7), a triterpene ester isolated from Uncaria rhynchophylla as a phospholipase Cγ1 inhibitor, was undertaken with a view toward elucidating its chemical mode of action on PLCγ1. Related derivatives and analogues of 7 were synthesized and their inhibitory activities against PLCγ1 were evaluated in vitro. The results indicate that 3-OH and 27-esterification may be essential, and that 28-COOH and the 2′ double bond appear to be important for activity. Furthermore, the compound possessing a p-coumaroyloxy at position 27 rather than at the 3 and 28 positions shows the greatest inhibitory activity against PLCγ1. Therefore, this inhibitor will be providing a chemical lead for the further development of cancer chemopreventive or cancer chemotherapeutic agents that have lower toxicity against normal tissues.

References

Prof. Ji Suk Lee

College of Pharmacy andResearch Institute ofPharmaceutical Sciences

Department of Pharmacognosy

Seoul National University

599 Kwanangno

Kwanak-gu

Seoul 151–742

Korea

Phone: +82-2-880-7853

Fax: +82-2-887-8509

Email: jslee103@snu.ac.kr