Benzosceptrins A and B with a Unique Benzocyclobutane Skeleton and Nagelamide S and T from Pacific Sponges

被引:44
作者
Appenzeller, Jerome [1 ]
Tilvi, Supriya [1 ]
Martin, Marie-Therese [1 ]
Gallard, Jean-Francois [1 ]
El-bitar, Hoda [1 ]
Dau, Elise Tran Huu [1 ]
Debitus, Cecile [2 ]
Laurent, Dominique [3 ]
Moriou, Celine [1 ]
Al-Mourabit, Ali [1 ]
机构
[1] CNRS, UPR 2301, Inst Chim Subst Nat, Ctr Rech Gif Sur Yvette, Ave Terrasse, F-91198 Gif Sur Yvette, France
[2] Ctr Polynesien Rech Biodiversite Insulaire, IRD UMR 152, Papeete, France
[3] Univ Toulouse 3, UMR IRD 152, F-31062 Toulouse 9, France
关键词
DIMERIC BROMOPYRROLE ALKALOIDS; AGELAS; 2-AMINOIMIDAZOLE; PROLINE; OROIDIN;
D O I
10.1021/ol901946h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Four new dimeric pyrrole-2-aminoimidazole alkaloids have been isolated from the Pacific marine sponges Agelas cf. mauritiana and Phakellia sp. They include the unusual C2 symmetrical benzosceptrins A (4) and B (5), which each possess a unique benzocyclobutane skeleton and nagelamides S (6) and T (7). Their structures and relative configuration were elucidated from spectroscopic data. Plausible biogenetic paths for these compounds are also proposed in this paper.
引用
收藏
页码:4874 / 4877
页数:4
相关论文
共 22 条
[1]   Biogenetically inspired synthesis of marine C6N4 2-aminoimidazole alkaloids:: Ab initio calculations, tautomerism, and reactivity [J].
Abou-Jneid, R ;
Ghoulami, S ;
Martin, MT ;
Dau, ETH ;
Travert, N ;
Al-Mourabit, A .
ORGANIC LETTERS, 2004, 6 (22) :3933-3936
[2]  
Aiello A., 2008, Modern alkaloids structure, isolation, synthesis and biology by, P271, DOI [10.1002/9783527621071.ch10, DOI 10.1002/9783527621071.CH10]
[3]  
Al Mourabit A, 2001, EUR J ORG CHEM, V2001, P237
[4]   Agelasines J, K, and L from the Solomon Islands marine sponge Agelas cf. mauritiana [J].
Appenzeller, Jerome ;
Mihci, Ghezala ;
Martin, Marie-Therese ;
Gallard, Jean-Francois ;
Menou, Jean-Louis ;
Boury-Esnalllt, Nicole ;
Hooper, John ;
Petek, Sylvain ;
Chevalley, Severine ;
Valentin, Alexis ;
Zaparucha, Anne ;
Al-Mourabit, Ali ;
Debitus, Cecile .
JOURNAL OF NATURAL PRODUCTS, 2008, 71 (08) :1451-1454
[5]   Nagelamides K and L, dimeric bromopyrrole alkaloids from sponge Agelas species [J].
Araki, Atsushi ;
Kubota, Takaaki ;
Tsuda, Masashi ;
Mikami, Yuzuru ;
Fromont, Jane ;
Kobayashi, Jun'ichi .
ORGANIC LETTERS, 2008, 10 (11) :2099-2102
[6]   Nagelamide J, a novel dimeric bromopyrrole alkaloid from a sponge Agelas species [J].
Araki, Atsushi ;
Tsuda, Masashi ;
Kubota, Takaaki ;
Mikami, Yuzuru ;
Fromont, Jane ;
Kobayashi, Jun'ichi .
ORGANIC LETTERS, 2007, 9 (12) :2369-2371
[7]   Nagelamides Q and R, Novel Dimeric Bromopyrrole Alkaloids from Sponges Agelas sp. [J].
Araki, Atsushi ;
Kubota, Takaaki ;
Aoyama, Kazuki ;
Mikami, Yuzuru ;
Fromont, Jane ;
Kobayashi, Jun'ichi .
ORGANIC LETTERS, 2009, 11 (08) :1785-1788
[8]   THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].
DEWAR, MJS ;
ZOEBISCH, EG ;
HEALY, EF ;
STEWART, JJP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909
[9]   Nagelamides A-H, new dimeric bromopyrrole alkaloids from marine sponge Agelas species [J].
Endo, T ;
Tsuda, M ;
Okada, T ;
Mitsuhashi, S ;
Shima, H ;
Kikuchi, K ;
Mikami, Y ;
Fromont, J ;
Kobayashi, J .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (08) :1262-1267
[10]   NEW BROMO-PYRROLE DERIVATIVES FROM SPONGE AGELAS-OROIDES [J].
FORENZA, S ;
MINALE, L ;
RICCIO, R .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (18) :1129-&