Bruguiesulfurol, a new sulfur compound from Bruguiera gymnorrhiza

被引:28
作者
Homhual, S
Zhang, HJ
Bunyapraphatsara, N [1 ]
Kondratyuk, TP
Santarsiero, BD
Mesecar, AD
Herunsalee, A
Chaukul, W
Pezzuto, JM
Fong, HHS
机构
[1] Mahidol Univ, Fac Pharm, Dept Pharmacognosy, Bangkok 10400, Thailand
[2] Univ Illinois, Coll Pharm, Dept Med Chem & Pharmacognosy, Program Collaborat Res Pharmaceut Sci, Chicago, IL USA
[3] Purdue Univ, Coll Pharm Nursing & Hlth Sci, W Lafayette, IN 47907 USA
[4] Univ Illinois, Coll Pharm, Ctr Pharmaceut Biotechnol, Dept Med Chem & Pharmacognosy, Chicago, IL USA
[5] Minist Publ Hlth, Dept Med Sci, Nonthaburi, Thailand
[6] Mahidol Univ, Fac Pharm, Dept Pharmaceut Bot, Bangkok 10700, Thailand
关键词
Bruguiera gymnorrhiza; Rhizophoraceae; ARE induction; NF-kappa B inhibition; COX-1; COX-2; dithiosulfonate; bruguiesulfurol; X-ray; NMR;
D O I
10.1055/s-2005-873171
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
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 mu M, respectively. Compounds 2 and 3 also inhibited phorbol ester-induced NF-kappa B (nuclear factor-kappa B) luciferase activity with IC50 Values of 85.0 and 14.5 mu M, respectively. In addition, compound 2 inhibited enzyme cyclooxygenase-2 (COX-2) activity with an IC50 value of 6.1 mu M, The structures of these isolates were determined by spectral data, and that of compound 1 was confirmed by X-ray crystallographic analysis.
引用
收藏
页码:255 / 260
页数:6
相关论文
共 33 条
[21]  
MACNAE W, 1981, REVISED HDB FLORA CE, P487
[22]   ORNITHINE DECARBOXYLASE AS AN ENZYME TARGET FOR THERAPY [J].
MCCANN, PP ;
PEGG, AE .
PHARMACOLOGY & THERAPEUTICS, 1992, 54 (02) :195-215
[23]  
OAE S, 1977, TETRAHEDRON LETT, P1195
[24]  
Othman S., 1998, PROSEA, VVolume 5, P122
[25]  
RUDJIMAN, 1992, PROSEA PLANT RESOURC, V3, P53
[26]  
Shaheen F., 2001, MAGN RESON CHEM, V39, P399
[27]   Inhibitory effects of hydroxystilbenes on cyclooxygenase from sheep seminal vesicles [J].
Shin, NH ;
Ryu, SY ;
Lee, H ;
Min, KR ;
Kim, Y .
PLANTA MEDICA, 1998, 64 (03) :283-284
[28]   Gymnorrhizol, an unusual macrocyclic polydisulfide from the Chinese mangrove Bruguiera gymnorrhiza [J].
Sun, YQ ;
Guo, YW .
TETRAHEDRON LETTERS, 2004, 45 (28) :5533-5535
[29]  
Toennies G, 1936, J BIOL CHEM, V113, P571
[30]  
TOSHIHARA M, 1994, KYUSHU KOGYO GIJITSU, V53, P3347