Aplysinopsins - Marine Indole Alkaloids: Chemistry, Bioactivity and Ecological Significance

被引:83
作者
Bialonska, Dobroslawa [1 ,3 ]
Zjawiony, Jordan K. [1 ,2 ]
机构
[1] Univ Mississippi, Dept Pharmacognosy, Sch Pharm, University, MS 38677 USA
[2] Univ Mississippi, Pharmaceut Sci Res Inst, University, MS 38677 USA
[3] Jagiellonian Univ, Inst Environm Sci, PL-30387 Krakow, Poland
关键词
aplysinopsins; natural source; stereochemistry; bioactivity; ecological functions; FAMILY DENDROPHYLLIIDAE; NATURAL-PRODUCTS; SCLERACTINIAN CORALS; SMENOSPONGIA-AUREA; SPONGES; ANALOGS; METABOLITES; ORIGIN; PHOTOISOMERIZATION; DERIVATIVES;
D O I
10.3390/md7020166
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Aplysinopsins are tryptophan-derived marine natural products isolated from numerous genera of sponges and scleractinian corals, as well as from one sea anemone and one nudibranch. Aplysinopsins are widely distributed in the Pacific, Indonesia, Caribbean, and Mediterranean regions. Up to date, around 30 analogues occurring in Nature have been reported. Natural aplysinopsins differ in the bromination pattern of the indole ring, variation in the structure of the C ring, including the number and position of N-methylation, the presence and configuration of the C-8-C-1' double bond, and the oxidation state of the 2-aminoimidazoline fragment. Aplysinopsins can also occur in the form of dimers. This review summarizes 30 years' research on aplysinopsins. The origin, isolation sources, chemistry, bioactivity, and ecological functions of aplysinopsins are comprehensively reviewed.
引用
收藏
页码:166 / 183
页数:18
相关论文
共 38 条
[1]   Novel neuronal nitric oxide synthase (nNOS) selective inhibitor, aplysinopsin-type indole alkaloid, from marine sponge Hyrtios erecta [J].
Aoki, S ;
Ye, Y ;
Higuchi, K ;
Takashima, A ;
Tanaka, Y ;
Kitagawa, I ;
Kobayashi, M .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (10) :1372-1374
[2]   METHYLAPLYSINOPSIN - A NATURAL PRODUCT OF MARINE ORIGIN WITH EFFECTS ON SEROTONERGIC NEUROTRANSMISSION [J].
BAIRDLAMBERT, J ;
DAVIS, PA ;
TAYLOR, KM .
CLINICAL AND EXPERIMENTAL PHARMACOLOGY AND PHYSIOLOGY, 1982, 9 (02) :203-212
[3]  
BAKER JT, 1981, NATURAL PRODUCTS MED, P281
[4]  
Bergquist P.R., 1983, Marine Natural Products, VV, P1, DOI [10.1016/b978-0-12-624005-4.50008-2, DOI 10.1016/B978-0-12-624005-4.50008-2]
[5]  
Delmas G, 1996, HETEROCYCLES, V43, P1229
[6]   SOME METABOLITES OF THE MARINE SPONGES SMENOSPONGIA-AUREA AND SMENOSPONGIA (=POLYFIBROSPONGIA) ECHINA [J].
DJURA, P ;
STIERLE, DB ;
SULLIVAN, B ;
FAULKNER, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (08) :1435-1441
[7]  
DJURA P, 1980, J ORG CHEM, V45, P737
[8]   TRYPTOPHAN DERIVATIVES FROM A MEDITERRANEAN ANTHOZOAN, ASTROIDES-CALYCULARIS [J].
FATTORUSSO, E ;
LANZOTTI, V ;
MAGNO, S ;
NOVELLINO, E .
JOURNAL OF NATURAL PRODUCTS, 1985, 48 (06) :924-927
[9]   BIOACTIVE MARINE METABOLITES .15. ISOLATION OF APLYSINOPSIN FROM THE SCLERACTINIAN CORAL TUBASTREA-AUREA AS AN INHIBITOR OF DEVELOPMENT OF FERTILIZED SEA-URCHIN EGGS [J].
FUSETANI, N ;
ASANO, M ;
MATSUNAGA, S ;
HASHIMOTO, K .
COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY B-BIOCHEMISTRY & MOLECULAR BIOLOGY, 1986, 85 (04) :845-846
[10]   The diversity of naturally occurring organobromine compounds [J].
Gribble, GW .
CHEMICAL SOCIETY REVIEWS, 1999, 28 (05) :335-346