Cargando…

Marinoterpins A–C: Rare Linear Merosesterterpenoids from Marine-Derived Actinomycete Bacteria of the Family Streptomycetaceae

[Image: see text] 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 Strepto...

Descripción completa

Detalles Bibliográficos
Autores principales: Kim, Min Cheol, Winter, Jaclyn M., Asolkar, Ratnakar N., Boonlarppradab, Chollaratt, Cullum, Reiko, Fenical, William
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8383307/
https://www.ncbi.nlm.nih.gov/pubmed/33844925
http://dx.doi.org/10.1021/acs.joc.1c00262
_version_ 1783741711925641216
author Kim, Min Cheol
Winter, Jaclyn M.
Asolkar, Ratnakar N.
Boonlarppradab, Chollaratt
Cullum, Reiko
Fenical, William
author_facet Kim, Min Cheol
Winter, Jaclyn M.
Asolkar, Ratnakar N.
Boonlarppradab, Chollaratt
Cullum, Reiko
Fenical, William
author_sort Kim, Min Cheol
collection PubMed
description [Image: see text] 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.
format Online
Article
Text
id pubmed-8383307
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-83833072021-08-31 Marinoterpins A–C: Rare Linear Merosesterterpenoids from Marine-Derived Actinomycete Bacteria of the Family Streptomycetaceae Kim, Min Cheol Winter, Jaclyn M. Asolkar, Ratnakar N. Boonlarppradab, Chollaratt Cullum, Reiko Fenical, William J Org Chem [Image: see text] 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. American Chemical Society 2021-04-12 2021-08-20 /pmc/articles/PMC8383307/ /pubmed/33844925 http://dx.doi.org/10.1021/acs.joc.1c00262 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Kim, Min Cheol
Winter, Jaclyn M.
Asolkar, Ratnakar N.
Boonlarppradab, Chollaratt
Cullum, Reiko
Fenical, William
Marinoterpins A–C: Rare Linear Merosesterterpenoids from Marine-Derived Actinomycete Bacteria of the Family Streptomycetaceae
title Marinoterpins A–C: Rare Linear Merosesterterpenoids from Marine-Derived Actinomycete Bacteria of the Family Streptomycetaceae
title_full Marinoterpins A–C: Rare Linear Merosesterterpenoids from Marine-Derived Actinomycete Bacteria of the Family Streptomycetaceae
title_fullStr Marinoterpins A–C: Rare Linear Merosesterterpenoids from Marine-Derived Actinomycete Bacteria of the Family Streptomycetaceae
title_full_unstemmed Marinoterpins A–C: Rare Linear Merosesterterpenoids from Marine-Derived Actinomycete Bacteria of the Family Streptomycetaceae
title_short Marinoterpins A–C: Rare Linear Merosesterterpenoids from Marine-Derived Actinomycete Bacteria of the Family Streptomycetaceae
title_sort marinoterpins a–c: rare linear merosesterterpenoids from marine-derived actinomycete bacteria of the family streptomycetaceae
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8383307/
https://www.ncbi.nlm.nih.gov/pubmed/33844925
http://dx.doi.org/10.1021/acs.joc.1c00262
work_keys_str_mv AT kimmincheol marinoterpinsacrarelinearmerosesterterpenoidsfrommarinederivedactinomycetebacteriaofthefamilystreptomycetaceae
AT winterjaclynm marinoterpinsacrarelinearmerosesterterpenoidsfrommarinederivedactinomycetebacteriaofthefamilystreptomycetaceae
AT asolkarratnakarn marinoterpinsacrarelinearmerosesterterpenoidsfrommarinederivedactinomycetebacteriaofthefamilystreptomycetaceae
AT boonlarppradabchollaratt marinoterpinsacrarelinearmerosesterterpenoidsfrommarinederivedactinomycetebacteriaofthefamilystreptomycetaceae
AT cullumreiko marinoterpinsacrarelinearmerosesterterpenoidsfrommarinederivedactinomycetebacteriaofthefamilystreptomycetaceae
AT fenicalwilliam marinoterpinsacrarelinearmerosesterterpenoidsfrommarinederivedactinomycetebacteriaofthefamilystreptomycetaceae