Hapalindole-related alkaloids from the cultured cyanobacterium Fischerella ambigua
نویسندگان
چکیده
منابع مشابه
Indole Alkaloids from Fischerella Inhibit Vertebrate Development in the Zebrafish (Danio rerio) Embryo Model
Cyanobacteria are recognized producers of toxic or otherwise bioactive metabolite associated, in particular, with so-called "harmful algal blooms" (HABs) and eutrophication of freshwater systems. In the present study, two apparently teratogenic indole alkaloids from a freshwater strain of the widespread cyanobacterial genus, Fischerella (Stigonemataceae), were isolated by bioassay-guided fracti...
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The formation of C-C bonds in an enantioselective fashion to create complex polycyclic scaffolds in the hapalindole- and fischerindole- type alkaloids from Stigonematales cyanobacteria represents a compelling and urgent challenge in adapting microbial biosynthesis as a catalytic platform in drug development. Here we determine the biochemical basis for tri- and tetracyclic core formation in thes...
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The hapalindole-type alkaloids naturally show striking late stage diversification of what was believed to be a conserved intermediate, cis-indolyl vinyl isonitrile (1a). Here we demonstrate enzymatically, as well as through applying a synthetic biology approach, that the pathway generating 1a (itself, a potent natural broad-spectrum antibiotic) is also dramatically flexible. We harness this to ...
متن کاملمطالعه خواص ضدباکتریایی عصاره های متانولی، اتری و آبی برخی از گونه های سیانوباکتری ها در شرایط آزمایشگاهی
Background and purpose: Cyanobacteria are rich sources of secondary metabolites. Antibiotic resistant pathogens are rising and people are more interested in using natural products these days. Hence, identifying competent cyanobacteria for the extraction of antimicrobial compounds is of great benefit. The main objective of this study was to investigate the in vitro antibacterial activity of ...
متن کاملDivergent enantioselective synthesis of hapalindole-type alkaloids using catalytic asymmetric hydrogenation of a ketone to construct the chiral core structure
A divergent enantioselective approach to hapalindole-type alkaloids is described. The route features a ruthenium-catalyzed asymmetric hydrogenation of a ketone via DKR to construct the chiral trans-1indolyl-2-isopropenylcyclohexane skeleton and a switchable sequence of methylation and acetylation/ aldol reaction to access a chiral quaternary stereocenter. (+)-Hapalindole Q (1, 13 steps, 5.9% ov...
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ژورنال
عنوان ژورنال: Phytochemistry
سال: 2010
ISSN: 0031-9422
DOI: 10.1016/j.phytochem.2010.09.004