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Bioactive Dammarane Triterpenes from the Mangrove Plant Bruguiera gymnorrhiza

Sudarat Homhual,^† Nuntavan Bunyapraphatsara,*^† Tamara Kondratyuk,^‡ Angkana Herunsalee,^§ Wongsatit Chaukul,^# John M. Pezzuto,^‡ Harry H. S. Fong, and Hong-Jie Zhang*

Department of Pharmacognosy, Faculty of Pharmacy, Mahidol University, Bangkok 10400, Thailand, College of Pharmacy, Nursing, and Health Sciences, Purdue University, 575 Stadium Mall Drive, West Lafayette, Indiana 47907-2091, Department of Medical Sciences, The Ministry of Public Health, Nontaburi 11000, Thailand, Department of Pharmaceutical Botany, Faculty of Pharmacy, Mahidol University, Bangkok 10400, Thailand, and Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry and Pharmacognosy (M/C 781), College of Pharmacy, University of Illinois at Chicago, 833 S. Wood Street, Chicago, Illinois 60612

J. Nat. Prod., 2006, 69 (3), pp 421–424

DOI: 10.1021/np058112x

Publication Date (Web): February 25, 2006

Dedicated to Dr. Norman R. Farnsworth of the University of Illinois at Chicago for his pioneering work on bioactive natural products.

†

Department of Pharmacognosy, Mahidol University.

To whom correspondence should be addressed. Tel: 66-2-6444566 (B.N.); 1-312-996-7868 (Z.H.). Fax: 66-2-6444566 (B.N.); 1-312-996-7107 (Z.H.). E-mail: pynby@mahidol.ac.th; zhanghj@uic.edu.

‡

Purdue University.

Ministry of Public Health.

Department of Pharmaceutical Botany, Mahidol University.

University of Illinois at Chicago.

Abstract

Three new dammarane triterpenes, bruguierins A−C (1−3), were isolated from a petroleum ether extract of the flowers of Bruguiera gymnorrhiza. Their structures were determined on the basis of physical and spectroscopic data interpretation. With stably transfected HepG2 cells, the three isolates activated antioxidant response element (ARE luciferase activation) with EC₅₀ values of 7.8, 9.4, and 15.7 μM, respectively. Bruguierin A (1) also inhibited phorbol ester-induced NFκB (nuclear factor-κB) luciferase activation with an IC₅₀ value of 1.4 μM and selectively inhibited cyclooxygenase-2 (COX-2) activity with an IC₅₀ value of 0.37 μM. Compounds 2 and 3 were not active in these bioassays.

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