Pachycladins A-E, Prostate Cancer Invasion and Migration Inhibitory Eunicellin-Based Diterpenoids from the Red Sea Soft Coral Cladiella pachyclados

被引:75
作者
Hassan, Hossam M. [2 ,4 ]
Khanfar, Mohammad A. [4 ]
Elnagar, Ahmed Y. [4 ]
Mohammed, Rabab [2 ]
Shaala, Lamiaa A. [1 ]
Youssef, Diaa T. A. [1 ]
Hifnawy, Mohamed S. [3 ]
El Sayed, Khalid A. [4 ]
机构
[1] Suez Canal Univ, Dept Pharmacognosy, Fac Pharm, Ismailia 41522, Egypt
[2] Beni Suief Univ, Dept Pharmacognosy, Coll Pharm, Bani Suwayf, Egypt
[3] Cairo Univ, Dept Pharmacognosy, Coll Pharm, Cairo, Egypt
[4] Univ Louisiana Monroe, Dept Basic Pharmaceut Sci, Coll Pharm, Monroe, LA 71201 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2010年 / 73卷 / 05期
关键词
PACHYCLAVULARIA-VIOLACEA; SCLEROPHYTIN-A; NATURAL-PRODUCTS; KLYXUM-SIMPLEX; AUSTRALIS; OCTOCORALLIA; TERPENOIDS; DRUGS; CELLS;
D O I
10.1021/np900787p
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Alcyonaria species are among the important marine invertebrate classes that produce a wealth of chemically diverse bioactive diterpenes. Examples of these are the potent microtubule disruptor sarcodictyins and eleutherobin. The genus Cladiella has proven to be a rich source of cytotoxic eunicellin-based diterpenoids. Five new eunicellin diterpenes, pachycladins A-E (1-5), were isolated from the Red Sea soft coral Cladiella pachyclados. The known sclerophytin A Cladiellisin, 3-acetylcladiellisin, 3,6-diacetylcladiellisin, (+)-polyanthelin A, klysimplexin G, klysimplexin E, sclerophytin F methyl ether, (6Z)-cladiellin (cladiella-6Z,11(17)-dien-3-ol), sclerophytin 13, and patagonicol were also identified. The structures of the isolated compounds were elucidated by extensive interpretation of their spectroscopic data. These compounds were evaluated for their ability to inhibit growth, proliferation, invasion, and migration of the prostate cancer cells PC-3. Some of the new metabolites exhibited significant anti-invasive activity.
引用
收藏
页码:848 / 853
页数:6
相关论文
共 37 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]   New β-caryophyllene-derived terpenoids from the soft coral Sinularia nanolobata [J].
Ahmed, AF ;
Su, JH ;
Shiue, RT ;
Pan, XJ ;
Dai, CF ;
Kuo, YH ;
Sheu, JH .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (04) :592-597
[3]   Five novel norcembranoids from Sinularia leptoclados and S-parva [J].
Ahmed, AF ;
Shiue, RT ;
Wang, GH ;
Dai, CF ;
Kuo, YH ;
Sheu, JH .
TETRAHEDRON, 2003, 59 (37) :7337-7344
[4]  
BAKER JT, 1981, NATURAL PRODUCTS MED, P281
[5]   Total asymmetric synthesis of the putative structure of the cytotoxic diterpenoid (-)-sclerophytin A and of the authentic natural sclerophytins A and B [J].
Bernardelli, P ;
Moradei, OA ;
Friedrich, D ;
Yang, J ;
Gallou, F ;
Dyck, BP ;
Doskotch, RW ;
Lange, T ;
Paquette, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :9021-9032
[6]  
Bernardelli P, 1998, HETEROCYCLES, V49, P531
[7]  
Borghesani PR, 2002, DEVELOPMENT, V129, P1435
[8]   STUDIES OF AUSTRALIAN SOFT CORALS .46. NEW DITERPENES FROM A BRIAREUM SPECIES (ANTHOZOA, OCTOCORALLIA, GORGONACEA) [J].
BOWDEN, BF ;
COLL, JC ;
VASILESCU, IM .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (10) :1705-1726
[9]   Natural products to drugs: natural product-derived compounds in clinical trials [J].
Butler, Mark S. .
NATURAL PRODUCT REPORTS, 2008, 25 (03) :475-516
[10]   Eunicellin-based diterpenoids from the cultured soft coral Klyxum simplex [J].
Chen, Bo-Wei ;
Wu, Yang-Chang ;
Chiang, Michael Y. ;
Su, Jui-Hsin ;
Wang, Wei-Hsien ;
Fan, Tung-Yung ;
Sheu, Jyh-Horng .
TETRAHEDRON, 2009, 65 (34) :7016-7022