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Genomic scanning enabling discovery of a new antibacterial bicyclic carbamate-containing alkaloid

Synthetic and Systems Biotechnology 2021年第1期6卷 12-19页

作者： Qing Fang Linrui Wu Caroline Urwald Morgane Mugat Shan Wang Kwaku Kyeremeh Carol Philips Samantha Law d Yongjun Zhou Hai Deng Marine Biodiscovery Centre Department of ChemistryUniversity of AberdeenMeston WalkAberdeenAB243UEScotlandUK ENSAIA 2 avenue de la forêt de Haye54505 vandoeuvre lès NancyFrance Department of Chemistry University of GhanaP.O.Box LG56Legon-AccraGhana NCIMB Ltd Ferguson BuildingCraibstone EstateBucksburnAberdeenAB219YAScotlandUK Research Centre for Marine Drugs State Key Laboratory of Oncogenes and Related GenesDepartment of PharmacyRen Ji HospitalSchool of MedicineShanghai Jiao Tong UniversityShanghai200127China

Non-ribosomal peptides are a group of structurally diverse natural products with various important therapeutic and agrochemical *** pyrrolizidine alkaloids(PAs),containing a scaffold of two fused five-membered ring system with a nitrogen atom at the bridgehead,have been found to originate from a multidomain non-ribosomal peptide synthetase to generate indolizidine intermediates,followed by multistep oxidation,catalysed by single Bayer-Villiger(BV)enzymes,to yield PA *** bacterial PAs are rare in natural product inventory,bioinformatics analysis suggested that the biosynthetic gene clusters(BGCs)that are likely to be responsible for the production of PA-like metabolites are widely distributed in bacterial ***,most of the strains containing PA-like BGCs are not deposited in the public domain,therefore preventing further assessment of the chemical spaces of this group of bioactive ***,we report a genomic scanning strategy to assess the potential of PA metabolites production in our culture collection without prior knowledge of genome *** the strains tested,we found fifteen contain the key BV enzymes that are likely to be involved in the last step of PA ring *** one-strain-many-compound(OSMAC)method,supported by a combination of HR-MS,NMR,SMART 2.0 technology,and GNPS analysis,allowed identification and characterization of a new[5+7]heterobicyclic carbamate,legoncarbamate,together with five known PAs,bohemamine derivatives,from Streptomyces ***37,a Ghanaian soil *** absolute stereochemistry of legoncarbamate was determined by comparison of measured and calculated ECD *** displays antibacterial activity against *** ATCC 25922 with an MIC value of 3.1μg/***,a biosynthetic model of legoncarbamate and other bohemamines was proposed based on the knowledge we have gained so far.

关键词： Genomic scanning Bayer villiger monooxygenase carbamate alkaloids Pyrrolizidine alkaloids Non-ribosomal peptide synthetases

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