The structures of three new shishididemniols from a tunicate of the family Didemnidae

被引:9
作者
Kobayashi, Hirotsugu [1 ]
Miyata, Yoshinari [1 ]
Okada, Kohtaro [1 ]
Fujita, Tsuyoshi [2 ]
Iwashita, Takashi [2 ]
Nakao, Yoichi [1 ]
Fusetani, Nobuhiro [1 ]
Matsunaga, Shigeki [1 ]
机构
[1] Univ Tokyo, Grad Sch Agr & Life Sci, Lab Aquat Nat Prod Chem, Bunkyo Ku, Tokyo 1138657, Japan
[2] Suntory Inst Bioorgan Res, Osaka 6188503, Japan
基金
日本学术振兴会;
关键词
antibacterial; serinolipid; tunicate; Vibrio anguillarum;
D O I
10.1016/j.tet.2007.04.081
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three new serinolipid derivatives, shishididemniols C (1), D (2), and E (3), were isolated as antibacterial constituents of a tunicate of the family Didemnidae. Their planar structures were elucidated by interpretation of NMR and MS data, whereas the absolute stereochemistry was determined by chemical conversions. Shishididemniols C (3), D (4), and E (5) exhibited antibacterial activity against the fish pathogenic bacterium Vibrio anguillarum. similar to 2007 Published by Elsevier Ltd.
引用
收藏
页码:6748 / 6754
页数:7
相关论文
共 10 条
[1]   Didemniserinolipids A-C, unprecedented serinolipids from the tunicate Didemnum sp. [J].
González, N ;
Rodríguez, J ;
Jiménez, C .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5705-5707
[2]   Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a tunicate Didemnum sp. [J].
Kiyota, H ;
Dixon, DJ ;
Luscombe, CK ;
Hettstedt, S ;
Ley, SV .
ORGANIC LETTERS, 2002, 4 (19) :3223-3226
[3]   Complete structure elucidation of shishididemniols, complex lipids with tyramine-derived tether and two serinol units, from a marine tunicate of the family didemnidae [J].
Kobayashi, Hirotsugu ;
Ohashi, Jun'ichiro ;
Fujita, Tsuyoshi ;
Iwashita, Takashi ;
Nakao, Yoichi ;
Matsunaga, Shigeki ;
Fusetani, Nobuhiro .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1218-1225
[4]   DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF GINNOL, A LONG-CHAIN ALIPHATIC ALCOHOL, BY USE OF A NEW CHIRAL ANISOTROPIC REAGENT [J].
KUSUMI, T ;
TAKAHASHI, H ;
HASHIMOTO, T ;
KAN, Y ;
ASAKAWA, Y .
CHEMISTRY LETTERS, 1994, (06) :1093-1094
[5]   Cyclodidemniserinol trisulfate, a sulfated serinolipid from the Palauan ascidian Didemnum guttatum that inhibits HIV-1 integrase [J].
Mitchell, SS ;
Rhodes, D ;
Bushman, FD ;
Faulkner, DJ .
ORGANIC LETTERS, 2000, 2 (11) :1605-1607
[6]   HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].
OHTANI, I ;
KUSUMI, T ;
KASHMAN, Y ;
KAKISAWA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096
[7]  
Righi G, 2002, EUR J ORG CHEM, V2002, P1573, DOI 10.1002/1099-0690(200205)2002:9<1573::AID-EJOC1573>3.0.CO
[8]  
2-I
[9]   Choosing the right reagent for the determination of the absolute configuration of amines by NMR: MTPA or MPA? [J].
Seco, JM ;
Latypov, SK ;
Quinoa, E ;
Riguera, R .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7569-7574
[10]   HIGHLY REGIOSELECTIVE FORMATION OF BROMOHYDRINS BY REACTION OF EPOXY-AZETIDINONES WITH MGBR2 - AN ALTERNATIVE ROUTE TO 4-BROMOMETHYLCARBONYLMETHYL-2-AZETIDINONE, A KEY CARBAPENEM PRECURSOR [J].
UEDA, Y ;
MAYNARD, SC .
TETRAHEDRON LETTERS, 1988, 29 (41) :5197-5200