Speradine A, a new pentacyclic oxindole alkaloid from a marine-derived fungus Aspergillus tamarii

Tsuda, Masashi; Mugishima, Takao; Komatsu, Keiichi; Sone, Toshio; Tanaka, Michiko; Mikami, Yuzuru; Shiro, Motoo; Hirai, Manabu; Ohizumi, Yasushi; Kobayashi, Jun’ichi

doi:10.1016/s0040-4020(03)00413-7

Cited by 93 publications

(41 citation statements)

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“…1,2) Some strains in the genera Aspergillus and Penicillium have been reported to produce CPA, 3) and the CPA derivatives 2-oxoCPA and speradine A (1-N-methyl-2-oxoCPA) ( Fig. 1(A)) are produced by Aspergillus oryzae NBRC 4177 4) and A. tamarii marine-derived isolate, 5) respectively. The CPA biosynthesis gene cluster (cpa cluster; Fig.…”

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confidence: 99%

Cyclopiazonic acid biosynthesis gene cluster gene cpaM is required for speradine A biosynthesis

Tokuoka

Kikuchi

Shinohara

et al. 2015

Bioscience, Biotechnology, and Biochemistry

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confidence: 99%

Cyclopiazonic acid biosynthesis gene cluster gene cpaM is required for speradine A biosynthesis

Tokuoka

Kikuchi

Shinohara

et al. 2015

Bioscience, Biotechnology, and Biochemistry

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“…Especially, the genus Aspergillus has been known to be a major contributor to the secondary metabolites of marine fungal origin, for example, four sesquiterpenoids with a unique nitrobenzyl ester from Aspergillus versicolor (A. versicolor), two modified cytotoxic tripeptides from Aspergillus sp., novel pentacyclic oxindole alkaloid from Aspergillus tamari [28] , four prenylated indole alkaloids from Aspergillus sp. [29] and two cyclopentapeptides from A. versicolor [30] .…”

Section: Discussionmentioning

confidence: 99%

Analytical characterization and structure elucidation of metabolites from Aspergillus ochraceus MP2 fungi

Meenupriya

Thangaraj

2011

Asian Pacific Journal of Tropical Biomedicine

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“…for C 20 H 21 N 2 O 4 [ M +H] + : 353.1497; found: 353.1501. The relative stereochemistry was deduced from 1 H, 1 H coupling constants, referenced to those of speradine A, which is the 1‐ N ‐methyl analogue of 2‐oxocyclopiazonic acid 30…”

Section: Methodsmentioning

confidence: 99%

Genetic Safeguard against Mycotoxin Cyclopiazonic Acid Production in Aspergillus oryzae

et al. 2011

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Aspergillus oryzae is a fungus widely used in traditional Japanese fermentation industries. Its inability to produce mycotoxins, due to mutation or transcriptional repression of the genes responsible for their biosynthesis, is consistent with the hypothesis that A. oryzae is a domesticated species derived from A. flavus, a wild species that is a well-known producer of aflatoxin. In contrast, the cyclopiazonic acid (CPA) biosynthetic gene (cpa) cluster in A. oryzae contains genes that have been lost in A. flavus. Through targeted gene inactivation, isolation of the corresponding metabolite, and evaluation of biological activity of the metabolite, we demonstrated that an A. oryzae-specific gene-cpaH-mediates the conversion of CPA into the less toxic 2-oxocyclopiazonic acid, a new analogue of CPA. The detoxifying properties of cpaH, which have been lost in the A. flavus pathway, reflect the relationship of the two species.

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Speradine A, a new pentacyclic oxindole alkaloid from a marine-derived fungus Aspergillus tamarii

Cited by 93 publications

References 7 publications

Cyclopiazonic acid biosynthesis gene cluster gene cpaM is required for speradine A biosynthesis

Cyclopiazonic acid biosynthesis gene cluster gene cpaM is required for speradine A biosynthesis

Analytical characterization and structure elucidation of metabolites from Aspergillus ochraceus MP2 fungi

Genetic Safeguard against Mycotoxin Cyclopiazonic Acid Production in Aspergillus oryzae

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