Bruguiesulfurol, a new sulfur compound from Bruguiera gymnorrhiza

Sudarat Homhual; Hongjie ZHANG; Nuntavan Bunyapraphatsara; Tamara P. Kondratyuk; Bernard D. Santarsiero; Andrew D. Mesecar; Angkana Herunsalee; Wongsatit Chaukul; John M. Pezzuto; Harry H.S. Fong

doi:10.1055/s-2005-873171

Bruguiesulfurol, a new sulfur compound from Bruguiera gymnorrhiza

Sudarat Homhual, Hongjie ZHANG, Nuntavan Bunyapraphatsara^*, Tamara P. Kondratyuk, Bernard D. Santarsiero, Andrew D. Mesecar, Angkana Herunsalee, Wongsatit Chaukul, John M. Pezzuto, Harry H.S. Fong

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › peer-review

32 Citations (Scopus)

Abstract

A new cyclic 4-hydroxy-dithiosulfonato, 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.

Original language	English
Pages (from-to)	255-260
Number of pages	6
Journal	Planta Medica
Volume	72
Issue number	3
DOIs	https://doi.org/10.1055/s-2005-873171
Publication status	Published - Feb 2006

Scopus Subject Areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

User-Defined Keywords

ARE induction
Bruguiera gymnorrhiza
Bruguiesulfurol
COX-1
COX-2
Dithiosulfonate
NF-κB inhibition
NMR
Rhizophoraceae
X-ray

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title = "Bruguiesulfurol, a new sulfur compound from Bruguiera gymnorrhiza",

abstract = "A new cyclic 4-hydroxy-dithiosulfonato, 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.",

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AU - ZHANG, Hongjie

AU - Bunyapraphatsara, Nuntavan

AU - Kondratyuk, Tamara P.

AU - Santarsiero, Bernard D.

AU - Mesecar, Andrew D.

AU - Herunsalee, Angkana

AU - Chaukul, Wongsatit

AU - Pezzuto, John M.

AU - Fong, Harry H.S.

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N2 - A new cyclic 4-hydroxy-dithiosulfonato, 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.

AB - A new cyclic 4-hydroxy-dithiosulfonato, 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.

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Bruguiesulfurol, a new sulfur compound from Bruguiera gymnorrhiza

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