Dataset Information

Discovery and structure elucidation of glycosyl and 5-hydroxy migrastatins from dung beetle gut Kitasatospora sp.

ABSTRACT: Two new macrocyclic secondary metabolites, glycosyl-migrastatin (1) and 5-hydroxy-migrastatin (2), were isolated from a gut bacterium Kitasatospora sp. JL24 in dung beetle Onthophagus lenzii. Based on a comprehensive analysis of the nuclear magnetic resonance (NMR), MS, and UV spectroscopic data, the planar structures of 1 and 2 were successfully identified as new derivatives of migrastatin. Compound 1 was the first glycosylated member of the migrastatin family. The absolute configuration of the sugar moiety was determined to be d-glucose through the analysis of coupling constants and ROESY correlations, followed by chemical derivatization and chromatographic comparison with authentic d- and l-glucose. Compound 2, identified as 5-hydroxy-migrastatin possessing an additional hydroxy group with a previously unreported chiral center, was assigned using Mosher's method through 19F NMR chemical shifts and confirmed with the modified Mosher's method. Genomic analysis of Kitasatospora sp. strain JL24 revealed a putative biosynthetic pathway involving an acyltransferase-less type I polyketide synthase biosynthetic gene cluster.

One-sentence summary

Two secondary metabolites, glycosyl-migrastatin (1) and 5-hydroxy-migrastatin (2), were discovered from the gut bacterium Kitasatospora sp. JL24 in the dung beetle Onthophagus lenzii.

SUBMITTER: Im JH

PROVIDER: S-EPMC10750973 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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Discovery and structure elucidation of glycosyl and 5-hydroxy migrastatins from dung beetle gut Kitasatospora sp.

Im Ji Hyeon JH Oh Seoyoung S Bae Eun Seo ES Um Soohyun S Lee Sang Kook SK Ban Yeon Hee YH Oh Dong-Chan DC

Journal of industrial microbiology & biotechnology 20230201 1

Two new macrocyclic secondary metabolites, glycosyl-migrastatin (1) and 5-hydroxy-migrastatin (2), were isolated from a gut bacterium Kitasatospora sp. JL24 in dung beetle Onthophagus lenzii. Based on a comprehensive analysis of the nuclear magnetic resonance (NMR), MS, and UV spectroscopic data, the planar structures of 1 and 2 were successfully identified as new derivatives of migrastatin. Compound 1 was the first glycosylated member of the migrastatin family. The absolute configuration of the ...[more]

PMID: 38093455

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Project description:Dung beetles are one of the most charismatic animal taxa. Their familiarity as ecosystem service providers is clear, but they also play a range of roles in a variety of different ecosystems worldwide. Here, we give an overview of the current state of dung beetle research and the changes in the prevalence of topics in a collated corpus of 4,145 peer-reviewed articles of dung beetle research, spanning from 1930 until 2024. We used a range of text-analysis tools, including topic modelling, to assess how the peer-reviewed literature on dung beetles has changed over this period. Most of the literature is split into three distinct, but related discourses-the agri/biological topics, the ecological topics, and the taxonomic topics. Publications on the 'effect of veterinary chemicals' and 'nesting behaviour' showed the largest drop over time, whereas articles relating to 'ecosystem function' had a meteoric rise from a low presence before the 2000's to being the most prevelant topic of dung beetle research in the last two decades. Research into dung beetles is global, but is dominated by Europe and North America. However, the research from South America, Africa, and Australia ranges wider in topics. Research in temperate and tropical mixed forests, as well as grasslands, savanna and shrublands dominated the corpus, as would be expected from a group of species directly associated with large mammals. Our assessment of dung beetle research comes when ecosystem service provision is becoming more important and more dominant in the literature globally. This review therefore should be of direct interest to dung beetle researchers, as well as researchers working in agricultural, ecological, and taxonomic arenas globally. Research worldwide and across agri/biological, ecological, and taxonomic discourses is imperative for a continued understanding of how dung beetles and their ecosystem services are modified across rapidly changing natural and agricultural landscapes.

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Dataset Information

Discovery and structure elucidation of glycosyl and 5-hydroxy migrastatins from dung beetle gut Kitasatospora sp.

One-sentence summary

Publications

Discovery and structure elucidation of glycosyl and 5-hydroxy migrastatins from dung beetle gut Kitasatospora sp.

Similar Datasets

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