New alkaloids from Formosan zoanthid Zoanthus kuroshio

被引：19

作者：

Cheng, Yuan-Bin ^{[1
,2
]}

Lo, I-Wen ^{[1
]}

Shyur, Lie-Fen ^{[3
]}

Yang, Chung-Chih ^{[3
]}

Hsu, Yu-Ming ^{[1
]}

Su, Jui-Hsin ^{[4
,5
]}

Lu, Mei-Chin ^{[4
,5
]}

Chiou, Shu-Fen ^{[6
]}

Lan, Chih-Chin ^{[1
]}

Wu, Yang-Chang ^{[1
,7
,8
,9
]}

Chang, Fang-Rong ^{[1
,10
]}

机构：

[1] Kaohsiung Med Univ, Coll Pharm, Grad Inst Nat Prod, Kaohsiung 80708, Taiwan

[2] Kaohsiung Med Univ, Ctr Infect Dis & Canc Res, Kaohsiung 80708, Taiwan

[3] Acad Sinica, Agr Biotechnol Res Ctr, Taipei 11529, Taiwan

[4] Natl Dong Hwa Univ, Grad Inst Marine Biotechnol, Pingtung 94450, Taiwan

[5] Natl Museum Marine Biol & Aquarium, Pingtung 94450, Taiwan

[6] Natl Sun Yat Sen Univ, Dept Marine Biotechnol & Resources, Kaohsiung 80424, Taiwan

[7] China Med Univ, Sch Pharm, Coll Pharm, Taichung 40402, Taiwan

[8] China Med Univ Hosp, Chinese Med Res & Dev Ctr, Taichung 40402, Taiwan

[9] China Med Univ Hosp, Ctr Mol Med, Taichung 40402, Taiwan

[10] Kaohsiung Med Univ Hosp, Ctr Canc, Kaohsiung 80708, Taiwan

来源：

TETRAHEDRON | 2015年 / 71卷 / 45期

关键词：

Zoanthus kuroshio; Zoanthid; Alkaloids; Marine natural products; Melanoma cell line B16; MARINE ZOANTHID; ZOANTHAMINE; NORZOANTHAMINE; STEROL;

D O I：

10.1016/j.tet.2015.09.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Seven new alkaloids, kuroshines C-G (1-5), 3 beta-hydroxyzoanthenamide (6), 7 alpha-hydroxyzoanthenamide (7), along with a known compound, zoanthenamine (8), were isolated from the ethanolic extract of Formosan zoanthid Zoanthus kuroshio. Kuroshines C-G (1-5) are alkaloids possess a densely functionalized ring system on the basis of the zoanthamine framework, and compounds 6 and 7 may be categorized as zoanthenamide derivatives with an additional hydroxyl substitution. The structures of these compounds were determined through the interpretation of mass and spectroscopic methods, especially 2D NMR analyses. The anticancer activities of the isolates against melanoma cell line B16 were evaluated. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：8601 / 8606

页数：6

共 18 条

[1]

Babu UV, 1996, INDIAN J CHEM B, V35, P627

[2] Synthesis of the carbocyclic core of zoanthenol: Implementation of an unusual acid-catalyzed cyclization [J].

Behenna, Douglas C. ;

Stockdill, Jennifer L. ;

Stoltz, Brian M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (22) :4077-4080

[3]

Cen-Pacheco F., 2014, MAR DRUGS

[4] Zoaramine, a Zoanthamine-like Alkaloid with a New Skeleton [J].

Cen-Pacheco, Francisco ;

Norte, Manuel ;

Fernandez, Jose J. ;

Hernandez Daranas, Antonio .

ORGANIC LETTERS, 2014, 16 (11) :2880-2883

[5] Kuroshines A and B, new alkaloids from Zoanthus kuroshio [J].

Cheng, Yuan-Bin ;

Lan, Chih-Chin ;

Liu, Wei-Chun ;

Lai, Wan-Chun ;

Tsai, Yu-Chi ;

Chiang, Michael Y. ;

Wu, Yang-Chang ;

Chang, Fang-Rong .

TETRAHEDRON LETTERS, 2014, 55 (39) :5369-5372

[6] New alkaloids from a marine zoanthid [J].

Daranas, AH ;

Fernández, JJ ;

Gavín, JA ;

Norte, M .

TETRAHEDRON, 1999, 55 (17) :5539-5546

[7] Epioxyzoanthamine, a new zoanthamine-type alkaloid and the unusual deuterium exchange in this series. [J].

Daranas, AH ;

Fernández, JJ ;

Gavín, JA ;

Norte, M .

TETRAHEDRON, 1998, 54 (27) :7891-7896

[8]

Fukuzawa S., 1995, Hetercycl. Commun, V1, P207, DOI [10.1515/HC.1995.1.2-3.207, DOI 10.1515/HC.1995.1.2-3.207]

[9] Stereoselective synthesis of the ABC ring system of norzoanthamine [J].

Ghosh, S ;

Rivas, F ;

Fischer, D ;

González, MA ;

Theodorakis, EA .

ORGANIC LETTERS, 2004, 6 (06) :941-944

[10]

Hirai G, 2004, BIOORG MED CHEM LETT, V14, P2647, DOI 10.1016/S0960-894X(04)00284-7

← 1 2 →