Structure elucidation and biosynthetic gene cluster analysis of caniferolides A-D, new bioactive 36-membered macrolides from the marine-derived Streptomyces caniferus CA-271066

Organic & Biomolecular Chemistry
Ignacio Pérez-VictoriaFernando Reyes

Abstract

Bioassay-guided isolation based on the antifungal activity of a culture broth of the marine-derived actinomycete Streptomyces caniferus CA-271066 led to the discovery of new 36-membered polyol macrolides, caniferolides A-D (1-4). Their connectivity was determined by spectroscopic methods including ESITOF-MS and 1D/2D NMR. The relative stereochemistry of each stereocluster in these compounds was established using NOE analysis, the universal database method and J-based configuration analysis, further assisted by comparisons with NMR data of structurally related macrolides. Genome sequencing followed by detailed bioinformatics analysis led to the identification of the corresponding biosynthetic gene cluster and allowed the prediction of the stereochemical outcome of their biosynthesis, confirming the relative stereochemistry of each stereocluster already determined by NMR and establishing their stereochemical relationship, ultimately rendering the absolute configuration of all chiral centers. Furthermore, based on our results and already published data, it has been possible to derive the complete absolute configuration of the related macrolides PM100117 and PM100118, astolides A and B, and deplelides A and B. Caniferolides A-D hav...Continue Reading

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Citations

Jul 4, 2020·International Journal of Systematic and Evolutionary Microbiology·Hisayuki Komaki, Tomohiko Tamura
Dec 18, 2019·Pharmaceuticals·Mohammed AldholmiA Ganesan
Jul 22, 2020·Archives of Pharmacal Research·Cong WangShugeng Cao
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Jul 9, 2020·Computational and Structural Biotechnology Journal·Namil LeeByung-Kwan Cho
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Nov 20, 2020·Antibiotics·Chukwuemeka Samson AhamefuleWenxia Fang
Jul 3, 2021·Marine Drugs·Marisa SilvaPaz Otero

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Methods Mentioned

BETA
NMR
glycosylations
gel filtration
glycosylation
sequence-based prediction
sequence-based

Software Mentioned

UPGMA
antiSMASH
PacBio
TMHMM

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