Discovery and Elucidation of the Biosynthesis of Aspernidgulenes: Novel Polyenes from Aspergillus Nidulans by Using Serial Promoter Replacement

doi:10.1002/cbic.201800486

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Title:	Discovery and Elucidation of the Biosynthesis of Aspernidgulenes: Novel Polyenes from Aspergillus Nidulans by Using Serial Promoter Replacement
Authors:	Lin, Tzu-Shyang Chen, Bethany Chiang, Yi-Ming Wang, Clay C. C.
Contributors:	Univ Southern Calif, Sch Pharm, Dept Pharmacol & Pharmaceut Sci Chia Nan Univ Pharm & Sci, Dept Pharm Univ Southern Calif, Coll Letters Arts & Sci, Dept Chem
Keywords:	aspernidgulenes biosynthesis natural products polyenes polyketides
Date:	2019-02
Issue Date:	2020-07-29 13:48:05 (UTC+8)
Publisher:	WILEY-V C H VERLAG GMBH
Abstract:	Through serial promoter exchanges, we isolated several novel polyenes, the aspernidgulenes, from Aspergillus nidulans and uncovered their succinct biosynthetic pathway involving only four enzymes. An enoyl reductase (ER)-less highly reducing polyketide synthase (HR-PKS) putatively produces a 5,6-dihydro-alpha-pyrone polyene, which undergoes bisepoxidation, epoxide ring opening, cyclization, and hydrolytic cleavage by three tailoring enzymes to generate aspernidgulene A1 and A2. Our findings demonstrate the prowess of fungal-tailoring enzymes to transform a polyketide scaffold concisely and efficiently into complex structures. Moreover, comparison with citreoviridin and aurovertin biosynthesis suggests that methylation of the alpha-pyrone hydroxy group by methyltransferase (CtvB or AurB) is the branching point at which the biosynthesis of these two classes of compounds diverge. Therefore, scanning for the presence or absence of the gatekeeping alpha-pyrone methyltransferase gene in homologous clusters might be a potential way to classify the product bioinformatically as belonging to methylated alpha-pyrone polyenes or polyenes containing rings derived from the cyclization of the unmethylated 5,6-dihydro-alpha-pyrone, such as 2,3-dimethyl-gamma-lactone and oxabicyclo[2.2.1]heptane.
Relation:	Chembiochem, v.20, n.3, pp.329-334
Appears in Collections:	[Dept. of Pharmacy] Periodical Articles

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