Anti-inflammatory steroids from the octocoral Dendronephthya griffini

被引：24

作者：

Chao, Chih-Hua ^{[1
]}

Wen, Zhi-Hong ^{[1
]}

Chen, I-Ming ^{[1
]}

Su, Jui-Hsin ^{[1
]}

Huang, Ho-Cheng ^{[1
,2
]}

Chiang, Michael Y. ^{[3
]}

Sheu, Jyh-Horng ^{[1
,4
]}

机构：

[1] Natl Sun Yat Sen Univ, Dept Marine Biotechnol & Resources, Kaohsiung 804, Taiwan

[2] Cheng Shiu Univ, Dept Chem & Mat Engn, Kaohsiung 833, Taiwan

[3] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan

[4] Natl Sun Yat Sen Univ, Asia Pacific Ocean Res Ctr, Kaohsiung 804, Taiwan

来源：

TETRAHEDRON | 2008年 / 64卷 / 16期

关键词：

octocoral; steroid; griffinisterones A-E; anti-inflammatory effect;

D O I：

10.1016/j.tet.2008.01.109

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Five new steroids, griffinisterones A-E (1-5), were isolated from the octocoral Dendronephthya griffini. The structures of these compounds were elucidated by extensive spectroscopic analysis. The single-crystal X-ray crystallography on I allowed the determination of the 24R configuration in 1. The absolute stereochemistry of 5 was determined by the application of PGME method. Compounds 3 and 4 were found to significantly inhibit the accumulation of the pro-inflammatory NOS protein of the LPS-stimulated RAW264.7 macrophage cells. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：3554 / 3560

页数：7

共 12 条

[1] Metabolites with cytotoxic activity from the Formosan soft coral Cladiella australis [J].

Ahmed, AF ;

Wu, MH ;

Wu, YC ;

Dai, CF ;

Sheu, JH .

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2006, 53 (02) :489-494

[2] 5 NEW POLAR STEROLS FROM THE BLACK CORAL ANTIPATHES-SUBPINNATA [J].

AIELLO, A ;

FATTORUSSO, E ;

MENNA, M .

STEROIDS, 1991, 56 (10) :513-517

[3] PROTON-TRANSFER STEPS IN STEGLICH ESTERIFICATION - A VERY PRACTICAL NEW METHOD FOR MACROLACTONIZATION [J].

BODEN, EP ;

KECK, GE .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2394-2395

[4] Steroids and sesquiterpenoids from the soft corals Dendronephthya gigantea and Lemnalia cervicorni [J].

Duh, CY ;

El-Gamal, AHA ;

Song, PY ;

Wang, SK ;

Dai, CF .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (10) :1650-1653

[5] The anti-inflammatory carbazole, LCY-2-CHO, inhibits lipopolysaccharide-induced inflammatory mediator expression through inhibition of the p38 mitogen-activated protein kinase signaling pathway in macrophages [J].

Ho, FM ;

Lai, CC ;

Huang, LJ ;

Kuo, TC ;

Chao, CM ;

Lin, WW .

BRITISH JOURNAL OF PHARMACOLOGY, 2004, 141 (06) :1037-1047

[6]

LOWRY OH, 1951, J BIOL CHEM, V193, P265

[7] NEW CHIRAL ANISOTROPIC REAGENTS FOR DETERMINING THE ABSOLUTE-CONFIGURATION OF CARBOXYLIC-ACIDS [J].

NAGAI, Y ;

KUSUMI, T .

TETRAHEDRON LETTERS, 1995, 36 (11) :1853-1856

[8] Inhibitory effect of ginsenoside Rb1 and compound K on NO and prostaglandin E2 biosyntheses of RAW264.7 cells induced by lipopolysaccharide [J].

Park, EK ;

Shin, YW ;

Lee, HU ;

Kim, SS ;

Lee, YC ;

Lee, BY ;

Kim, DH .

BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2005, 28 (04) :652-656

[9] Four new steroids from two octocorals [J].

Tomono, Y ;

Hirota, H ;

Imahara, Y ;

Fusetani, N .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (11) :1538-1541

[10] Isogosterones A-D, antifouling 13,17-Secosteroids from an octocoral Dendronephthya sp. [J].

Tomono, Y ;

Hirota, H ;

Fusetani, N .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2272-2275

← 1 2 →