Fischerindole L, a new isonitrile from the terrestrial blue-green alga fischerella muscicola

Park, Aeri; Moore, Richard E.; Patterson, Gregory M. L.

doi:10.1016/s0040-4039(00)92061-6

Cited by 110 publications

(89 citation statements)

References 9 publications

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“…Fischerellin A also exhibit fungicidal and herbicidal properties and is a potent photosystem-II inhibitor. Curiously, the chemical study of the terrestrial strains of F. muscicola yielded totally different compounds of indole nature, fischerindoles and welwintindolinones among others (Park et al 1992;Jimenez et al 1999) (Fig. 8), that illustrates the importance of the environment (aquatic, terrestrial) in the development of differentiated chemical interactions with the ecosystem.…”

Section: Other Miscellaneous Compoundsmentioning

confidence: 99%

Allelopathic agents from aquatic ecosystems: potential biopesticides models

et al. 2007

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Allelopathy is usually regarded as a terrestrial science and little attention has been paid to the allelochemicals involved in the interactions between aquatic autotrophs. Also, chemicals involved in the interaction between algae (macro or microscopic) and their environment are not often acknowledged as allelopathic. Allelopathy is a key factor for explaining microalgae assemblages, community structure and the dynamics of the populations within the ecosystem. Herein we present an overview of what is known in this field, describing the chemicals yet identified and which kind of interactions are they involved in.

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Section: Other Miscellaneous Compoundsmentioning

confidence: 99%

Allelopathic agents from aquatic ecosystems: potential biopesticides models

et al. 2007

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“…The isolation of fischerindole L could provide insights into the biosynthesis of these cyanobacterial indole alkaloids. [138] In fact, Moore and coworkers suggest that an isonitrile derived from tryptophan is fused to a geranyl pyrophosphate derivative via a chloronium ioninduced condensation Fig. (18).…”

Section: Indole Alkaloidsmentioning

confidence: 99%

“…Hypothetic biogenesis of hapalindole and fischerindole L from 3-((Z)-2-isocyanovinyl)indole as suggested by Moore and coworkers. [138,139] This biosynthetic proposal is fostered by the isolation of a hapalindole isomer (epi-hapalindole E) by Schwartz and coworkers from Fischerella ATCC 53558. [50] This structure was initially misassigned and later corrected by Moore and coworkers.…”

Section: Indole Alkaloidsmentioning

confidence: 99%

Secondary Metabolites from Cyanobacteria: Complex Structures and Powerful Bioactivities

Gademann¹,

Portmann

2008

COC

237

168

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This review presents natural products from cyanobacteria. Several classes of secondary metabolites are highlighted. Toxic metabolites from these prokaryotic photosynthetic organisms include compounds such as microcystin, anatoxin and saxitoxin, which display hepatotoxicity and neurotoxicity. Their potential as drugs in cancer therapy is discussed based on the cryptophycin class of potent cytotoxic agents. The next part of this review highlights iron chelators from cyanobacteria, including schizokinen, synechobactin and anachelin. The biogenesis of anachelin is investigated as its mechanism of iron acquisition. Several indole alkaloids are then reviewed, from simple carbolines such as bauerines and nostocarboline to complex polycyclic structures such as hapalindole, welwitindolinone and ambiguine. The latter compounds present fascinating structure combined with powerful bioactivities and interesting biogenetic pathways. In the last part, protease inhibitors from cyanobacteria are discussed (cyanopeptolins, micropeptin and oscillapeptin) and their structure/activity relationships and selectivity for trypsin / chymotrypsin are presented. All these examples highlight the large structural variety of cyanobacterial metabolites combined with powerful biological activities. Cyanobacteria can thus be considered a prime source both for novel bioactive compounds and for leads for drugs.

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“…The importance of cyanobacteria as a potential drug resource is evident by the launching of the 'Cyanomyces' project in Europe, anticipated to generate novel therapeutic substances by combining genes from actinomyces and cyanobacteria (http://www.cyanomyces.com). The stigonematalean Fischerella is known to synthesize the tetracyclic indole alkaloid fischerindole L (Park et al, 1992), ambiguine isonitriles A-F, Hapalindole G and H, fungicidal Hapalindole-type alkaloids (Smitka et al, 1992), ambigol A, B and the indole alkaloid tjipanazole D (Falch et al, 1995) and fischerellin A (Hagmann & Jüttner, 1996). In another report, Fischerella ambigua collected from paddy fields excreted parsiguine, a broad-spectrum antibacterial and antifungal substance into the culture medium (Ghasemi et al, 2004).…”

Section: Introductionmentioning

confidence: 99%

Identification of an antimicrobial entity from the cyanobacterium Fischerella sp. isolated from bark of Azadirachta indica (Neem) tree

et al. 2006

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The active principle in a methanolic extract of the laboratory-grown cyanobacterium, Fischerella sp. isolated from Neem (Azadirachta indica) tree bark was active against Mycobacterium tuberculosis, Enterobacter aerogenes, Staphylococcus aureus, Pseudomonas aeruginosa, Salmonella typhi, Escherichia coli as well as three multi-drug resistant E. coli strains in in vitro assays. Based on MS, UV, IR 1 H NMR analyses the active principle is proposed to be Hapalindole T having the empirical formula C 21 H 23 N 2 ClSO and a molecular weight of 386 with the melting point range 179-182 • C. The estimated production of Hapalindole T from the cyanobacterium is 1.25 mg g −1 lyophilized biomass. It is suggested that cyanobacteria colonizing specialized niches such as tree bark could be an antibacterial drug resource.

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Fischerindole L, a new isonitrile from the terrestrial blue-green alga fischerella muscicola

Cited by 110 publications

References 9 publications

Allelopathic agents from aquatic ecosystems: potential biopesticides models

Allelopathic agents from aquatic ecosystems: potential biopesticides models

Secondary Metabolites from Cyanobacteria: Complex Structures and Powerful Bioactivities

Identification of an antimicrobial entity from the cyanobacterium Fischerella sp. isolated from bark of Azadirachta indica (Neem) tree

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