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State Key Laboratory of Phytochemistry and Plant Resources in West China
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Elucidating the Biosynthetic Pathway for Vibralactone
source:     author:     2013-03-01

  Vibralactone, a rare fused bicyclic β-lactone from the basidiomycete fungus Boreostereum vibrans, was found to inhibit pancreatic lipases highly relevant to fat absorption. While vibralactone seems structurally simple for its small size, contradicting biosynthetic origins, including sesquiterpenoid and polyketide, of this bicyclic β-lactone have been proposed.

  Zeng Ying’s and Liu Ji-Kai’s groups, from Kunming Institute of Botany, have recently established the biosynthetic origin of vibralactone and obtained evidence for its biosynthetic pathway which includes several very interesting reactions that may involve unusual enzymes. The bicyclic lactone core of vibralactone could be attributed to an intramolecular cyclization of the seven-membered ring intermediate 3, which is likely to arise from an oxidative expansion of the aryl ring moiety that is derived from phenylalanine and shikimate pathways. Vibralactone has a unique chemical structure and potent biological activity, and is isolated from a basidiomycete fungus. All of these attributes make vibralactone a worthy target for biosynthetic investigation. The establishment of its biosynthetic pathway will be valuable for future elucidation of the molecular mechanism for its biosynthesis.

  This research provides the first insight into a novel route for β-lactone formation in mushrooms, which was published on Angewandte Chemie International Edition 2013, 52: 2298-2302 (http://onlinelibrary.wiley.com/doi/10.1002/anie.201208182/abstract). Grants from the National Natural Science Foundation of China and the National Basic Research Program of China, and technical supports provided by the Phytochemistry Analyzing and Testing Center of the Institute were gratefully acknowledged.

   


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