Bruguiesulfurol, a new sulfur compound from Bruguiera gymnorrhiza.
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 (EC(50)) values of 56.7, 3.7 and 1.8 microM, respectively. Compounds 2 and 3 also inhibited phorbol ester-induced NF-kappaB (nuclear factor-kappaB) luciferase activity with IC (50) values of 85.0 and 14.5 microM, respectively. In addition, compound 2 inhibited enzyme cyclooxygenase-2 (COX-2) activity with an IC(50) value of 6.1 microM. The structures of these isolates were determined by spectral data, and that of compound 1 was confirmed by X-ray crystallographic analysis.
Homhual
Sudarat
S
Department of Pharmacognosy, Faculty of Pharmacy Mahidol University, Bangkok, Thailand.
Zhang
Hong-Jie
HJ
Bunyapraphatsara
Nuntavan
N
Kondratyuk
Tamara P
TP
Santarsiero
Bernard D
BD
Mesecar
Andrew D
AD
Herunsalee
Angkana
A
Chaukul
Wongsatit
W
Pezzuto
John M
JM
Fong
Harry H
HH
D000975:Antioxidants / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D045744:Cell Line, Tumor / Q000187:drug effects; D018360:Crystallography, X-Ray; D016861:Cyclooxygenase Inhibitors / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D035264:Flowers; D006801:Humans; D020128:Inhibitory Concentration 50; D008156:Luciferases / Q000378:metabolism; D016328:NF-kappa B / Q000037:antagonists & inhibitors; D008517:Phytotherapy; D010936:Plant Extracts / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D043982:Rhizophoraceae; D013886:Thiosulfonic Acids / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use
D000975:Antioxidants; D016861:Cyclooxygenase Inhibitors; D016328:NF-kappa B; D010936:Plant Extracts; D013886:Thiosulfonic Acids; C509733:bruguiesulfurol; D008156:Luciferases