Lentzeacins A-E, New Bacterial-Derived 2,5- and 2,6-Disubstituted Pyrazines from a BGC-Rich Soil Bacterium Lentzea sp. GA3-008

Lentzeacins A-E, New Bacterial-Derived 2,5- and 2,6-Disubstituted Pyrazines from a BGC-Rich Soil Bacterium Lentzea sp. GA3-008

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Pyrazines (1,4-diazirines) are an important group of natural products that have tremendous monetary value in the food and fragrance industries and can exhibit a wide range of biological effects including antineoplastic, antidiabetic and antibiotic activities.As part of a project investigating the secondary metabolites present in understudied and DisplayPort to DVI-I chemically rich Actinomycetes, we isolated a series of six pyrazines from a soil-derived Lentzea sp.GA3-008, four of which are new.Here we describe the structures of lentzeacins A-E (1, 3, 5 and 6) along with two known analogues (2 and 4) and the porphyrin zincphyrin.The structures were determined by NMR spectroscopy and HR-ESI-MS.

The suite of VITAMIN COOLER PEACH MANGO compounds present in Lentzea sp.includes 2,5-disubstituted pyrazines (compounds 2, 4, and 6) together with the new 2,6-disubstituted isomers (compounds 1, 3 and 5), a chemical class that is uncommon.We used long-read Nanopore sequencing to assemble a draft genome sequence of Lentzea sp.which revealed the presence of 40 biosynthetic gene clusters.Analysis of classical di-modular and single module non-ribosomal peptide synthase genes, and cyclic dipeptide synthases narrows down the possibilities for the biosynthesis of the pyrazines present in this strain.