Cargando…

Naphthoquinone-Based Meroterpenoids from Marine-Derived Streptomyces sp. B9173

Naphthoquinone-based meroterpenoids are hybrid polyketide-terpenoid natural products with chemical diversity and a broad range of biological activities. Here, we report the isolation of a group of naphthoquinone-containing compounds from Streptomyces sp. B9173, and their structures were elucidated b...

Descripción completa

Detalles Bibliográficos
Autores principales: Shen, Xinqian, Wang, Xiaozheng, Huang, Tingting, Deng, Zixin, Lin, Shuangjun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7463872/
https://www.ncbi.nlm.nih.gov/pubmed/32824158
http://dx.doi.org/10.3390/biom10081187
_version_ 1783577233828347904
author Shen, Xinqian
Wang, Xiaozheng
Huang, Tingting
Deng, Zixin
Lin, Shuangjun
author_facet Shen, Xinqian
Wang, Xiaozheng
Huang, Tingting
Deng, Zixin
Lin, Shuangjun
author_sort Shen, Xinqian
collection PubMed
description Naphthoquinone-based meroterpenoids are hybrid polyketide-terpenoid natural products with chemical diversity and a broad range of biological activities. Here, we report the isolation of a group of naphthoquinone-containing compounds from Streptomyces sp. B9173, and their structures were elucidated by using a combination of spectroscopic techniques, including 1D, 2D NMR, and high-resolution mass (HRMS) analysis. Seven flaviogeranin congeners or intermediates, three of which were new, have been derived from common naphthoquinone backbone and subsequent oxidation, methylation, prenylation, and amino group incorporation. Both flaviogeranin B1 (1) and B (2) contain an amino group which was incorporated into the C8 of 1,3,6,8-terhydroxynaphthalene (THN). Flaviogeranin D (3) contains an intact C-geranylgeranyl residue attached to the C2 of THN, while the O-geranylgeranyl group of 2 links with the hydroxyl on the C2 site of THN. Four compounds were selected and tested for antibacterial activity and cytotoxicity, with 3 and flaviogeranin C2 (5) displaying potent activity against selected bacteria and cancer cell lines. In light of the structure features of isolated compounds and the biosynthetic genes, a biosynthetic pathway of naphthoquinone-based flaviogeranins has been proposed. These isolated compounds not only extend the structural diversity but also represent new insights into the biosynthesis of naphthoquinone-based meroterpenoids.
format Online
Article
Text
id pubmed-7463872
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-74638722020-09-04 Naphthoquinone-Based Meroterpenoids from Marine-Derived Streptomyces sp. B9173 Shen, Xinqian Wang, Xiaozheng Huang, Tingting Deng, Zixin Lin, Shuangjun Biomolecules Article Naphthoquinone-based meroterpenoids are hybrid polyketide-terpenoid natural products with chemical diversity and a broad range of biological activities. Here, we report the isolation of a group of naphthoquinone-containing compounds from Streptomyces sp. B9173, and their structures were elucidated by using a combination of spectroscopic techniques, including 1D, 2D NMR, and high-resolution mass (HRMS) analysis. Seven flaviogeranin congeners or intermediates, three of which were new, have been derived from common naphthoquinone backbone and subsequent oxidation, methylation, prenylation, and amino group incorporation. Both flaviogeranin B1 (1) and B (2) contain an amino group which was incorporated into the C8 of 1,3,6,8-terhydroxynaphthalene (THN). Flaviogeranin D (3) contains an intact C-geranylgeranyl residue attached to the C2 of THN, while the O-geranylgeranyl group of 2 links with the hydroxyl on the C2 site of THN. Four compounds were selected and tested for antibacterial activity and cytotoxicity, with 3 and flaviogeranin C2 (5) displaying potent activity against selected bacteria and cancer cell lines. In light of the structure features of isolated compounds and the biosynthetic genes, a biosynthetic pathway of naphthoquinone-based flaviogeranins has been proposed. These isolated compounds not only extend the structural diversity but also represent new insights into the biosynthesis of naphthoquinone-based meroterpenoids. MDPI 2020-08-15 /pmc/articles/PMC7463872/ /pubmed/32824158 http://dx.doi.org/10.3390/biom10081187 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Shen, Xinqian
Wang, Xiaozheng
Huang, Tingting
Deng, Zixin
Lin, Shuangjun
Naphthoquinone-Based Meroterpenoids from Marine-Derived Streptomyces sp. B9173
title Naphthoquinone-Based Meroterpenoids from Marine-Derived Streptomyces sp. B9173
title_full Naphthoquinone-Based Meroterpenoids from Marine-Derived Streptomyces sp. B9173
title_fullStr Naphthoquinone-Based Meroterpenoids from Marine-Derived Streptomyces sp. B9173
title_full_unstemmed Naphthoquinone-Based Meroterpenoids from Marine-Derived Streptomyces sp. B9173
title_short Naphthoquinone-Based Meroterpenoids from Marine-Derived Streptomyces sp. B9173
title_sort naphthoquinone-based meroterpenoids from marine-derived streptomyces sp. b9173
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7463872/
https://www.ncbi.nlm.nih.gov/pubmed/32824158
http://dx.doi.org/10.3390/biom10081187
work_keys_str_mv AT shenxinqian naphthoquinonebasedmeroterpenoidsfrommarinederivedstreptomycesspb9173
AT wangxiaozheng naphthoquinonebasedmeroterpenoidsfrommarinederivedstreptomycesspb9173
AT huangtingting naphthoquinonebasedmeroterpenoidsfrommarinederivedstreptomycesspb9173
AT dengzixin naphthoquinonebasedmeroterpenoidsfrommarinederivedstreptomycesspb9173
AT linshuangjun naphthoquinonebasedmeroterpenoidsfrommarinederivedstreptomycesspb9173