Nagelamides Q and R, Novel Dimeric Bromopyrrole Alkaloids from Sponges Agelas sp.

被引:41
作者
Araki, Atsushi [1 ]
Kubota, Takaaki [1 ]
Aoyama, Kazuki [2 ]
Mikami, Yuzuru [2 ]
Fromont, Jane [3 ]
Kobayashi, Jun'ichi [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
[2] Chiba Univ, Med Mycol Res Ctr, Chiba 2600856, Japan
[3] Western Australian Museum, Welshpool Dc, WA 6986, Australia
关键词
PYRROLE-IMIDAZOLE ALKALOIDS; SCEPTRIN; OROIDIN;
D O I
10.1021/ol900328c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two new dimeric bromopyrrole alkaloids, nagelamides Q (1) and R (2), have been isolated from Okinawan marine sponges of the genus Agelas (SS-1134 and SS-956, respectively), and the structures and stereochemistry were elucidated from spectroscopic data. Nagelamide Q (1) is a rare dimeric bromopyrrole alkaloid possessing a pyrrolidine ring, while nagelamide R (2) is the first bromopyrrole alkaloid having an oxazoline ring. Nagelamides Q (1) and R (2) showed antimicrobial activity.
引用
收藏
页码:1785 / 1788
页数:4
相关论文
共 18 条
[1]  
Aiello A., 2008, Modern alkaloids structure, isolation, synthesis and biology by, P271, DOI [10.1002/9783527621071.ch10, DOI 10.1002/9783527621071.CH10]
[2]  
ALMOURABIT A, 2001, EUR J ORG CHEM, V23, P7
[3]   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
[4]   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
[5]   Sceptrin as a potential biosynthetic precursor to complex pyrrole - Pyrrole-imidazole alkaloids: The total synthesis of ageliferin [J].
Baran, PS ;
O'Malley, DP ;
Zografos, AL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (20) :2674-2677
[6]   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
[7]   Two novel pyrrole-imidazole alkaloids from the Mediterranean sponge Agelas oroides [J].
Fattorusso, E ;
Taglialatela-Scafati, O .
TETRAHEDRON LETTERS, 2000, 41 (50) :9917-9922
[8]  
FORENZA S, 1971, CHEM COMMUN, P11292
[9]   REINVESTIGATION INTO STRUCTURE OF OROIDIN, A BROMOPYRROLE DERIVATIVE FROM MARINE SPONGE [J].
GARCIA, EE ;
BENJAMIN, LE ;
FRYER, RI .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (03) :78-79
[10]   Tauroacidins A and B, new bromopyrrole alkaloids possessing a taurine residue from Hymeniacidon sponge [J].
Kobayashi, J ;
Inaba, K ;
Tsuda, M .
TETRAHEDRON, 1997, 53 (49) :16679-16682