Elucidating the Biosynthetic Pathway for Vibralactone: A Pancreatic Lipase Inhibitor with a Fused Bicyclic β‐Lactone

Zhao, Pengshan; Yang, Yan; Du, Liangchen; Liu, Ji Kai; Zeng, Ying

doi:10.1002/anie.201208182

Cited by 48 publications

(25 citation statements)

References 32 publications

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“…The biogenetic pathway of vibralactone has previously been illustrated . Here, we present a proposed biogenetic pathway of all the compounds by referring to the biosynthetic pathway of vibralactone (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Novel Natural Oximes and Oxime Esters with a Vibralactone Backbone from the Basidiomycete Boreostereum vibrans

Chen

Zhao

et al. 2016

ChemistryOpen

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A variety of novel natural products with significant bioactivities are produced by the basidiomycete Boreostereum vibrans. In the present study, we describe 16 novel natural oximes and oxime esters with a vibralactone backbone, vibralactoximes, which were isolated from the scale‐up fermentation broth of B. vibrans. Their structures were determined through extensive spectroscopic analyses. These compounds represent the first oxime esters from nature. The hypothetical biosynthetic pathway of these compounds was also proposed. Seven compounds exhibited significant pancreatic lipase inhibitory activity, while ten compounds exhibited cytotoxicities against five human cancer cell lines (HL‐60, SMMC‐7721, A‐549, MCF‐7, and SW480), with IC50 values comparable with those of cisplatin.

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Section: Resultsmentioning

confidence: 99%

Novel Natural Oximes and Oxime Esters with a Vibralactone Backbone from the Basidiomycete Boreostereum vibrans

Chen

Zhao

et al. 2016

ChemistryOpen

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“…In recent years, endeavors to explore the potential of producing diverse metabolites of B. vibrans by scale-up fermentation and/or changing culture medium compositions led to the isolation of plenty of bioactive vibralactone congeners and vibralactone biosynthetic-associated compounds [ 3 – 11 ], including vibralactoximes A–P which represented the first class of natural oxime esters [ 3 ]. The biosynthesis of vibralactone and divergent biosynthetic pathway for skeletally distinct vibralactone-associated compounds were illuminated [ 12 , 13 ]. It was proved that all these compounds shared the biosynthetic precursor 3-prenyl-4-hydroxybenzylalcohol.…”

Section: Introductionmentioning

confidence: 99%

Vibralactone Biogenesis-Associated Analogues from Submerged Cultures of the Fungus Boreostereum vibrans

Chen

Jiang

Zhao

et al. 2017

Nat. Prod. Bioprospect.

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A scale-up fermentation of the fungus Boreostereum vibrans facilitated the isolation of six new vibralactone biogenesis-associated analogues, namely vibralactamide A (1), vibralactone T (2), 13-O-lactyl vibralactone (3), 10-O-acetyl vibralactone G (4), (11R,12R)- and (11S,12R)-vibradiol (5, 6). Their structures were established via extensive spectroscopic analyses, specific optical rotation comparison, and Snatzke’s method. The biosynthetic pathway for vibralactamide A was postulated. The absolute configuration of vibralactone B was revised by single crystal X-ray diffraction analysis. This work puts the divergent vibralactone biosynthesis pathway one step further and expands the structural diversity of vibralactone-associated compounds.Graphical Abstract Electronic supplementary materialThe online version of this article (10.1007/s13659-017-0147-5) contains supplementary material, which is available to authorized users.

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“…From culture broths of the basidiomycete fungus Boreostereum vibrans (syn. Stereum vibrans ), vibralactones with distinctly skeletons were identified [5–9] and generated by unusual and divergent biosynthetic pathways that we have recently established by precursor feedings in combination with genome mining [10, 11]. Further analyses of our B. vibrans genome draft assembly revealed several sequences to encode putative sesquiterpene synthases (STS).…”

Section: Introductionmentioning

confidence: 99%

Identification and Characterization of a δ-Cadinol Synthase Potentially Involved in the Formation of Boreovibrins in Boreostereum vibrans of Basidiomycota

Zhou

Yang

Zeng

et al. 2016

Nat. Prod. Bioprospect.

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Sesquiterpenoids are very common among natural products. A large number of sesquiterpene synthase genes have been cloned and functionally characterized. However, until now there is no report about the δ-cadinol synthase predominantly forming δ-cadinol (syn. torreyol) from farnesyl diphosphate. Sesquiterpenoids boreovibrins structurally similar to δ-cadinol were previously isolated from culture broths of the basidiomycete fungus Boreostereum vibrans. This led us to expect a corresponding gene coding for a δ-cadinol synthase that may be involved in the biosynthesis of boreovibrins in B. vibrans. Here we report the cloning and heterologous expression of a new sesquiterpene synthase gene from B. vibrans. The crude and purified recombinant enzymes, when incubating with farnesyl diphosphate as substrate, gave δ-cadinol as its principal product and thereby identified as a δ-cadinol synthase.Graphical AbstractA new sesquiterpene synthase gene was cloned from the basidiomycete fungus Boreostereum vibrans and heterologously expressed in E. coli. The purified recombinant enzyme gave δ-cadinol as its principal product from farnesyl diphosphate and thereby identified as a δ-cadinol synthase (BvCS). Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-016-0096-4) contains supplementary material, which is available to authorized users.

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Elucidating the Biosynthetic Pathway for Vibralactone: A Pancreatic Lipase Inhibitor with a Fused Bicyclic β‐Lactone

Cited by 48 publications

References 32 publications

Novel Natural Oximes and Oxime Esters with a Vibralactone Backbone from the Basidiomycete Boreostereum vibrans

Novel Natural Oximes and Oxime Esters with a Vibralactone Backbone from the Basidiomycete Boreostereum vibrans

Vibralactone Biogenesis-Associated Analogues from Submerged Cultures of the Fungus Boreostereum vibrans

Identification and Characterization of a δ-Cadinol Synthase Potentially Involved in the Formation of Boreovibrins in Boreostereum vibrans of Basidiomycota

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