Hirsutalins I-M, eunicellin-based diterpenoids from the soft coral Cladiella hirsuta

被引:18
作者
Chen, Bo-Wei [1 ,7 ]
Wang, Sheng-Yang [2 ]
Huang, Chiung-Yao [1 ]
Chen, Shu-Li [3 ]
Wu, Yang-Chang [3 ,4 ,5 ,6 ]
Sheu, Jyh-Horng [1 ,7 ]
机构
[1] Natl Sun Yat Sen Univ, Dept Marine Biotechnol & Resources, Kaohsiung 804, Taiwan
[2] Natl Chung Hsing Univ, Dept Forestry, Taichung 402, Taiwan
[3] Kaohsiung Med Univ, Grad Inst Nat Prod, Kaohsiung 807, Taiwan
[4] China Med Univ, Coll Chinese Med, Sch Chinese Med, Taichung 404, Taiwan
[5] China Med Univ Hosp, Nat Med Prod Res Ctr, Taichung 404, Taiwan
[6] China Med Univ Hosp, Ctr Mol Med, Taichung 404, Taiwan
[7] Natl Sun Yat Sen Univ, Asia Pacific Ocean Res Ctr, Kaohsiung 804, Taiwan
关键词
Eunicellin-base diterpenoids; Hirsutalins I-M; Cytotoxicity; NO inhibitory activity; ABSOLUTE-CONFIGURATION; NMR APPLICATION; MOSHER METHOD; A-D; AUSTRALIS;
D O I
10.1016/j.tet.2013.01.015
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New eunicellin-base diterpenoids, hirsutalins I-M (1-5), were isolated from the soft coral Cladiella hirsuta. Their structures were elucidated by spectroscopic methods, particularly in 1D and 2D NMR experiments. The absolute configuration of 2 was determined by Mosher's method. These compounds did not exhibit cytotoxicity toward a limited panel of cancer cell lines but showed nitric oxide inhibitory activity in LPS-stimulated RAW264.7 macrophage cells. Among them, compound 3 was found to possess the strongest NO inhibitory activity with an IC50 value of 9.8 mu g/mL. Furthermore, 3 was shown to significantly reduce the expression iNOS protein in the same cells. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2296 / 2301
页数:6
相关论文
共 29 条
[1]   Eunicellin-based diterpenoids, australins A-D, isolated from the soft coral Cladiella australis [J].
Ahmed, AF ;
Wu, MH ;
Wang, GH ;
Wu, YC ;
Sheu, JH .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (07) :1051-1055
[2]   1α,3β,5β-Trihydroxy-24-methylenecholestan-6-one:: a novel steroid from a soft coral Sinularia gibberosa [J].
Ahmed, AF ;
Dai, CF ;
Kuo, YH ;
Sheu, JH .
STEROIDS, 2003, 68 (04) :377-381
[3]  
ALLEY MC, 1988, CANCER RES, V48, P589
[4]   Hirsutosterols A-G, polyoxygenated steroids from a Formosan soft coral Cladiella hirsuta [J].
Chen, Bo-Wei ;
Chang, Shu-Ming ;
Huang, Chiung-Yao ;
Su, Jui-Hsin ;
Wen, Zhi-Hong ;
Wu, Yang-Chang ;
Sheu, Jyh-Horng .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (09) :3272-3278
[5]   Hirsutalins A-H, Eunicellin-Based Diterpenoids from the Soft Coral Cladiella hirsuta [J].
Chen, Bo-Wei ;
Chang, Shu-Ming ;
Huang, Chiung-Yao ;
Chao, Chih-Hua ;
Su, Jui-Hsin ;
Wen, Zhi-Hong ;
Hsu, Chi-Hsin ;
Dai, Chang-Feng ;
Wu, Yang-Chang ;
Sheu, Jyh-Horng .
JOURNAL OF NATURAL PRODUCTS, 2010, 73 (11) :1785-1791
[6]   Cladieunicellins A-E, New Eunicellins from an Indonesian Soft Coral Cladiella sp. [J].
Chen, Yung-Husan ;
Tai, Chia-Ying ;
Kuo, Yueh-Hsiung ;
Kao, Chia-Ying ;
Li, Jan-Jung ;
Hwang, Tsong-Long ;
Fang, Lee-Shing ;
Wang, Wei-Hsien ;
Sheu, Jyh-Horng ;
Sung, Ping-Jyun .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2011, 59 (03) :353-358
[7]   Cladielloides A and B: New Eunicellin-Type Diterpenoids from an Indonesian Octocoral Cladiella sp. [J].
Chen, Yung-Husan ;
Tai, Chia-Ying ;
Hwang, Tsong-Long ;
Weng, Ching-Feng ;
Li, Jan-Jung ;
Fang, Lee-Shing ;
Wang, Wei-Hsien ;
Wu, Yang-Chang ;
Sung, Ping-Jyun .
MARINE DRUGS, 2010, 8 (12) :2936-2945
[8]   Eunicellin diterpenes from two Kenyan soft corals [J].
Chill, L ;
Berrer, N ;
Benayahu, Y ;
Kashman, Y .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (01) :19-25
[9]   Tritoniopsins A-D, Cladiellane-Based Diterpenes from the South China Sea Nudibranch Tritoniopsis elegans and Its Prey Cladiella krempfi [J].
Ciavatta, Maria Letizia ;
Manzo, Emiliano ;
Mollo, Ernesto ;
Mattia, Carlo Andrea ;
Tedesco, Consiglia ;
Irace, Carlo ;
Guo, Yue-Wei ;
Li, Xiu-Bao ;
Cimino, Guido ;
Gavagnin, Margherita .
JOURNAL OF NATURAL PRODUCTS, 2011, 74 (09) :1902-1907
[10]   PYRIDINE-INDUCED SOLVENT SHIFTS IN NUCLEAR MAGNETIC RESONANCE SPECTRA OF HYDROXYLIC COMPOUNDS [J].
DEMARCO, PV ;
FARKAS, E ;
DODDRELL, D ;
MYLARI, BL ;
WENKERT, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5480-&