The biosynthesis of bisvertinolone: evidence for oxosorbicillinol as a direct precursor

Abe, Naoki; Arakawa, Tadaharu; Hirota, Akira

doi:10.1039/b109505f

Cited by 22 publications

(22 citation statements)

References 16 publications

(26 reference statements)

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“…have been well confirmed by a biosynthetic method using oxosorbicillinol and sorbicillinol as the direct precursors. 16) The absolute configurations of dihydrobisvertinolone and tetrahydrobisvertinolone were consistent with that of bisvertinolone (5) by comparison of their nuclear Overhauser effect spectroscopy (NOESY) and circular dichroism (CD) spectra. 9) So the absolute configuration of 6 was determined to be the same as 5 on biogenetic ground and by their similar 1 H and 13 C shifts and specific rotations (Ϫ340°for 6, Ϫ495°for 5, lit.…”

mentioning

confidence: 70%

Cytotoxic Sorbicillinoids and Bisorbicillinoids from a Marine-Derived Fungus Trichoderma sp.

Zhu

et al. 2009

Chem. Pharm. Bull.

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mentioning

confidence: 70%

Cytotoxic Sorbicillinoids and Bisorbicillinoids from a Marine-Derived Fungus Trichoderma sp.

Zhu

et al. 2009

Chem. Pharm. Bull.

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“…Based on these results, in silico analyses of the PKS SorA and SorB, and previous data from metabolite identifications and radio-labeled feed experiments, the authors proposed the model described in Figure 1 . An earlier model had claimed that oxosorbicillinol was a key intermediate for sorbicillinol synthesis via a hypothetical compound, and that sorbicillin was derived from sorbicillinol ( Abe et al, 2002 ). Our data support the newer model proposed by Fahad et al (2014) , because we detected the highest amounts of sorbicillin at the earliest time point, and because we observed the accumulation of oxosorbicillinol only after sorbicillinol had been built, timely and hierarchically ( Figures 4 , 6 ).…”

Section: Discussionmentioning

confidence: 99%

In Vivo Study of the Sorbicillinoid Gene Cluster in Trichoderma reesei

Derntl¹,

Guzmán-Chávez

Mello-de-Sousa³

et al. 2017

Front. Microbiol.

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Sorbicillinoids are a diverse group of yellow secondary metabolites that are produced by a range of not closely related ascomycetes, including Penicillium chrysogenum, Acremonium chrysogenum, and Trichoderma reesei. They share a similarity to the name-giving compound sorbicillin, a hexaketide. Previously, a conserved gene cluster containing two polyketide synthases has been identified as the source of sorbicillin, and a model for the biosynthesis of sorbicillin in P. chrysogenum has been proposed. In this study, we deleted the major genes of interest of the cluster in T. reesei, namely sor1, sor3, and sor4. Sor1 is the homolog of P. chrysogenum SorA, which is the first polyketide synthase of the proposed biosynthesis pathway. Sor3 is a flavin adenine dinucleotide (FAD)-dependent monooxygenase, and its homolog in P. chrysogenum, SorC, was shown to oxidize sorbicillin and 2′,3′-dihydrosorbicillin to sorbicillinol and 2′,3′-dihydrosorbicillinol, respectively, in vitro. Sor4 is an FAD/flavin mononucleotide-containing dehydrogenase with an unknown function. We measured the amounts of synthesized sorbicillinoids throughout growth and could verify the roles of Sor1 and Sor3 in vivo in T. reesei. In the absence of Sor4, two compounds annotated to dihydrosorbicillinol accumulate in the supernatant and only small amounts of sorbicillinol are synthesized. Therefore, we suggest extending the current biosynthesis model about Sor4 reducing 2′,3′-dihydrosorbicillin and 2′,3′-dihydrosorbicillinol to sorbicillinol and sorbicillinol, respectively. Sorbicillinol turned out to be the main chemical building block for most sorbicillinoids, including oxosorbicillinol, bisorbicillinol, and bisvertinolon. Further, we detected the sorbicillinol-dependent synthesis of 5-hydroxyvertinolide at early time points, which contradicts previous models for biosynthesis of 5-hydroxyvertinolide. Finally, we investigated whether sorbicillinoids from T. reesei have a growth limiting effect on the fungus itself or on plant pathogenic fungi or on pathogenic bacteria.

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“…22) have been isolated from a marine-derived fungus Penicillium species. Their structures were established on the basis of spectroscopic methods and their cytotoxic effects on P388 and A-549 cell lines were preliminarily examined (Liu et al 2005b) Several studies were performed in order to clarify the biosynthetic origin of this class of compounds (Abe et al 2001(Abe et al , 2002a. In support of the proposed biosynthetic pathways, two research groups independently and concurrently completed the total biomimetic syntheses of bisorbicillinol (138) and trichodimerol (135) (Fig.…”

Section: Bisorbicillinoidsmentioning

confidence: 99%

Secondary metabolites from species of the biocontrol agent Trichoderma

et al. 2007

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Trichoderma species are free-living fungi that are highly interactive in root, soil and foliar environments and have been used successfully in field trials to control many crop pathogens. Structural and biological studies of the metabolites isolated from Trichoderma species are reviewed. This review, encompassing all the literature in this field up to the present and in which 269 references are cited, also includes a detailed study of the biological activity of the metabolites, especially the role of these metabolites in biological control mechanisms. Some aspects of the biosynthesis of these metabolites and related compounds are likewise discussed.

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The biosynthesis of bisvertinolone: evidence for oxosorbicillinol as a direct precursor

Cited by 22 publications

References 16 publications

Cytotoxic Sorbicillinoids and Bisorbicillinoids from a Marine-Derived Fungus Trichoderma sp.

Cytotoxic Sorbicillinoids and Bisorbicillinoids from a Marine-Derived Fungus Trichoderma sp.

In Vivo Study of the Sorbicillinoid Gene Cluster in Trichoderma reesei

Secondary metabolites from species of the biocontrol agent Trichoderma

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