Nagelamides X-Z, Dimeric Bromopyrrole Alkaloids from a Marine Sponge Agelas sp.

被引:41
作者
Tanaka, Naonobu [1 ]
Kusama, Taishi [1 ]
Takahashi-Nakaguchi, Azusa [2 ]
Gonoi, Tohru [2 ]
Fromont, Jane [3 ]
Kobayashi, Jun'ichi [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
[2] Chiba Univ, Mycol Res Ctr, Chiba 2608673, Japan
[3] Western Australian Museum, Welshpool Dc, WA 6986, Australia
关键词
PYRROLE-IMIDAZOLE ALKALOIDS; BENZOSCEPTRIN C; OROIDES;
D O I
10.1021/ol401291n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three new dimeric bromopyrrole alkaloids, nagelamides X-Z (1-3), were isolated from a marine sponge Agelas sp. Nagelamides X (1) and Y (2) possess a novel tricyclic skeleton consisting of spiro-bonded tetrahydrobenzaminoimidazole and aminoimidazolidine moieties. Nagelamide Z (3) is the first dimeric bromopyrrole alkaloid involving the C-8 position in dimerization. The structures of 1-3 were elucidated on the basis of spectroscopic data. Nagelamides X-Z (1-3) exhibited antimicrobial activity.
引用
收藏
页码:3262 / 3265
页数:4
相关论文
共 14 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]   Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids [J].
Al-Mourabit, Ali ;
Zancanella, Manuel A. ;
Tilvi, Supriya ;
Romo, Daniel .
NATURAL PRODUCT REPORTS, 2011, 28 (07) :1229-1260
[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]   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
[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]   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-&
[9]   A Submarine Journey: The Pyrrole-Imidazole Alkaloids [J].
Forte, Barbara ;
Malgesini, Beatrice ;
Piutti, Claudia ;
Quartieri, Francesca ;
Scolaro, Alessandra ;
Papeo, Gianluca .
MARINE DRUGS, 2009, 7 (04) :705-753
[10]   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