Emergence of diversity and stereochemical outcomes in the biosynthetic pathways of cyclobutane-centered marine alkaloid dimers

被引:75
作者
Beniddir, Mehdi A. [1 ]
Evanno, Laurent [1 ]
Joseph, Delphine [1 ]
Skiredj, Adam [1 ]
Poupon, Erwan [1 ]
机构
[1] Univ Paris 11, Univ Paris Saclay, CNRS, BioCIS, F-92290 Chatenay Malabry, France
关键词
PYRROLE-IMIDAZOLE ALKALOIDS; VISIBLE-LIGHT PHOTOCATALYSIS; APLYSINOPSIN-TYPE ALKALOIDS; RAY CRYSTAL-STRUCTURE; BROMOPYRROLE ALKALOIDS; NATURAL-PRODUCTS; FAMILY DENDROPHYLLIIDAE; A-D; SECONDARY METABOLITES; ANTINEOPLASTIC AGENTS;
D O I
10.1039/c5np00159e
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Dictazoles and sceptrins are singular metabolites of marine origin. The present dichotomic case study provides a comprehensive perspective on these cyclobutane-centered alkaloids and their respective families. Indeed, their upstream and downstream chemistry are both treated herein. Relevant isolation reports and bio-inspired total syntheses are used to decipher the currently admitted biosynthetic hypotheses as well as the emergence of diversity in the two series. This review proposes a transversal vision of the topic, where most aspects of natural product chemistry have a critical importance.
引用
收藏
页码:820 / 842
页数:23
相关论文
共 143 条
[1]   Novel bioactive bromopyrrole alkaloids from the Mediterranean sponge Axinella verrucosa [J].
Aiello, A ;
D'Esposito, M ;
Fattorusso, E ;
Menna, M ;
Müller, WEG ;
Perovic-Ottstadt, S ;
Schröder, HC .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (01) :17-24
[2]  
Al Mourabit A, 2001, EUR J ORG CHEM, V2001, P237
[3]   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
[4]   STEVENSINE, A NOVEL ALKALOID OF AN UNIDENTIFIED MARINE SPONGE [J].
ALBIZATI, KF ;
FAULKNER, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (21) :4163-4164
[5]   Biosynthetic studies of the alkaloid, stevensine, in a cell culture of the marine sponge Teichaxinella morchella [J].
Andrade, P ;
Willoughby, R ;
Pomponi, SA ;
Kerr, RG .
TETRAHEDRON LETTERS, 1999, 40 (26) :4775-4778
[6]   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
[7]   Benzosceptrins A and B with a Unique Benzocyclobutane Skeleton and Nagelamide S and T from Pacific Sponges [J].
Appenzeller, Jerome ;
Tilvi, Supriya ;
Martin, Marie-Therese ;
Gallard, Jean-Francois ;
El-bitar, Hoda ;
Dau, Elise Tran Huu ;
Debitus, Cecile ;
Laurent, Dominique ;
Moriou, Celine ;
Al-Mourabit, Ali .
ORGANIC LETTERS, 2009, 11 (21) :4874-4877
[8]  
Assmann M, 2002, Z NATURFORSCH C, V57, P153
[9]   New antifeedant bromopyrrole alkaloid from the Caribbean sponge Stylissa caribica [J].
Assmann, M ;
van Soest, RWM ;
Köck, M .
JOURNAL OF NATURAL PRODUCTS, 2001, 64 (10) :1345-1347
[10]   Remodelling of the natural product fumagillol employing a reaction discovery approach [J].
Balthaser, Bradley R. ;
Maloney, Meghan C. ;
Beeler, Aaron B. ;
Porco, John A., Jr. ;
Snyder, John K. .
NATURE CHEMISTRY, 2011, 3 (12) :969-973