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Planta Med 2006; 72(3): 255-260
DOI: 10.1055/s-2005-873171
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

Bruguiesulfurol, A New Sulfur Compound from Bruguiera gymnorrhiza

Sudarat Homhual1 , Hong-Jie Zhang2 , Nuntavan Bunyapraphatsara1 , Tamara P. Kondratyuk3 , Bernard D. Santarsiero4 , Andrew D. Mesecar4 , Angkana Herunsalee5 , Wongsatit Chaukul6 , John M. Pezzuto3 , Harry H. S. Fong2
  • 1Department of Pharmacognosy, Faculty of Pharmacy Mahidol University, Bangkok, Thailand
  • 2Program for Collaborative Research in the Pharmaceutical Sciences (m/c877), Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy University of Illinois at Chicago, Chicago, USA
  • 3College of Pharmacy, Nursing, and Health Sciences, Purdue University, West Lafayette, Indiana, USA
  • 4The Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy College of Pharmacy University of Illinois at Chicago, Chicago, Illinois, USA
  • 5Department of Medical Sciences, The Ministry of Public Health, Nontaburi, Thailand
  • 6Department of Pharmaceutical Botany, Faculty of Pharmacy Mahidol University, Bangkok, Thailand
Further Information

Publication History

Received: January 25, 2005

Accepted: August 3, 2005

Publication Date:
10 November 2005 (online)

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Abstract

A new cyclic 4-hydroxy-dithiosulfonate, bruguiesulfurol (1), as well as two known 4-hydroxydithiolane 1-oxides, brugierol (2) and isobrugierol (3) were isolated from the flowers of Bruguiera gymnorrhiza. With stably-transfected HepG2 cells, the three isolates activated antioxidant response element (ARE) luciferase activation with (EC50) values of 56.7, 3.7 and 1.8 μM, respectively. Compounds 2 and 3 also inhibited phorbol ester-induced NF-κB (nuclear factor-κB) luciferase activity with IC50 values of 85.0 and 14.5 μM, respectively. In addition, compound 2 inhibited enzyme cyclooxygenase-2 (COX-2) activity with an IC50 value of 6.1 μM. The structures of these isolates were determined by spectral data, and that of compound 1 was confirmed by X-ray crystallographic analysis.

Key words

Bruguiera gymnorrhiza - Rhizophoraceae - ARE induction - NF-κB inhibition - COX-1 - COX-2 - dithiosulfonate - bruguiesulfurol - X-ray - NMR

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Dr. Nuntavan Bunyapraphatsara

Department of Pharmacognosy

Faculty of Pharmacy

Mahidol University

Bangkok 10400

Thailand

Phone: +66-2-644-4566

Fax: +66-2-644-4566

Email: pynby@mahidol.ac.th