Marinoterpins A-C: Rare Linear Merosesterterpenoids from Marine-Derived Actinomycete Bacteria of the Family Streptomycetaceae.
Min Cheol KimJaclyn M WinterRatnakar N AsolkarChollaratt BoonlarppradabReiko CullumWilliam FenicalPublished in: The Journal of organic chemistry (2021)
The chemical examination of two undescribed marine actinobacteria has yielded three rare merosesterterpenoids, marinoterpins A-C (1-3, respectively). These compounds were isolated from the culture broth extracts of two marine-derived actinomycetes associated with the family Streptomycetaceae, (our strains were CNQ-253 and AJS-327). The structures of the new compounds were determined by extensive interpretation of 1D and 2D NMR, MS, and combined spectroscopic data. These compounds represent new chemical motifs, combining quinoline-N-oxides with a linear sesterterpenoid side chain. Additionally, consistent in all three metabolites is the rare occurrence of two five-ring ethers, which were derived from an apparent cyclization of methyl group carbons to adjacent hydroxy-bearing methylene groups in the sesterterpenoid side chain. Genome scanning of AJS-327 allowed for the identification of the marinoterpin (mrt) biosynthetic cluster, which consists of 16 open-reading frames that code for a sesterterpene pyrophosphate synthase, prenyltransferase, type II polyketide synthase, anthranilate:CoA-ligase, and several tailoring enzymes apparently responsible for installing the N-oxide and bis-tetrahydrofuran ring motifs.
Keyphrases
- high resolution
- ms ms
- molecular docking
- mass spectrometry
- escherichia coli
- magnetic resonance
- risk assessment
- multiple sclerosis
- minimally invasive
- big data
- working memory
- electronic health record
- fatty acid
- magnetic resonance imaging
- gene expression
- ionic liquid
- computed tomography
- machine learning
- deep learning
- dna methylation
- neural network
- artificial intelligence