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

34 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

User-Defined Keywords

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

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10.1055/s-2005-873171

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@article{5ad9efdab9a14beea086ec7ee2e74ca7,

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.",

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

author = "Sudarat Homhual and Hongjie ZHANG and Nuntavan Bunyapraphatsara and Kondratyuk, \{Tamara P.\} and Santarsiero, \{Bernard D.\} and Mesecar, \{Andrew D.\} and Angkana Herunsalee and Wongsatit Chaukul and Pezzuto, \{John M.\} and Fong, \{Harry H.S.\}",

note = "This study was supported in part by program project P01 CA48112 funded by the National Cancer Institute, NIH, Bethesda, MD, and in part by the Thailand Research Fund through the Royal Golden Jubilee Ph.D. program (Grant No. PHD/0191/2545) awarded to SH and NB. The authors are grateful to the NMR group of the College of Pharmacy, University of Illinois at Chicago for access to NMR instruments required for this study. The authors are also grateful to the Resource Research Center, University of Illinois at Chicago for the acquisition of MS data, and for funding from the National Institutes of Health, NCRR, for purchase of the X-ray diffractometer.",

year = "2006",

month = feb,

doi = "10.1055/s-2005-873171",

language = "English",

volume = "72",

pages = "255--260",

journal = "Planta Medica",

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T1 - Bruguiesulfurol, a new sulfur compound from Bruguiera gymnorrhiza

AU - Homhual, Sudarat

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.

N1 - This study was supported in part by program project P01 CA48112 funded by the National Cancer Institute, NIH, Bethesda, MD, and in part by the Thailand Research Fund through the Royal Golden Jubilee Ph.D. program (Grant No. PHD/0191/2545) awarded to SH and NB. The authors are grateful to the NMR group of the College of Pharmacy, University of Illinois at Chicago for access to NMR instruments required for this study. The authors are also grateful to the Resource Research Center, University of Illinois at Chicago for the acquisition of MS data, and for funding from the National Institutes of Health, NCRR, for purchase of the X-ray diffractometer.

PY - 2006/2

Y1 - 2006/2

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.

KW - ARE induction

KW - Bruguiera gymnorrhiza

KW - Bruguiesulfurol

KW - COX-1

KW - COX-2

KW - Dithiosulfonate

KW - NF-κB inhibition

KW - NMR

KW - Rhizophoraceae

KW - X-ray

UR - https://www.scopus.com/pages/publications/33645008064

U2 - 10.1055/s-2005-873171

DO - 10.1055/s-2005-873171

M3 - Journal article

C2 - 16534731

AN - SCOPUS:33645008064

SN - 0032-0943

VL - 72

SP - 255

EP - 260

JO - Planta Medica

JF - Planta Medica

IS - 3

ER -

Bruguiesulfurol, a new sulfur compound from Bruguiera gymnorrhiza

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