Baraphenazines A-G, Divergent Fused Phenazine-Based Metabolites from a Himalayan Streptomyces

Xiachang Wang; Muhammad Abbas; Yinan Zhang; Sherif I. Elshahawi; Larissa V. Ponomareva; Zheng Cui; Steven G. Van Lanen; Imran Sajid; S. Randal Voss; Khaled A. Shaaban; Jon S. Thorson

doi:10.1021/acs.jnatprod.9b00289

Baraphenazines A-G, Divergent Fused Phenazine-Based Metabolites from a Himalayan Streptomyces

Xiachang Wang, Muhammad Abbas, Yinan Zhang, Sherif I. Elshahawi, Larissa V. Ponomareva, Zheng Cui, Steven G. Van Lanen, Imran Sajid, S. Randal Voss, Khaled A. Shaaban, Jon S. Thorson

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

Abstract

The structures and bioactivities of three unprecedented fused 5-hydroxyquinoxaline/alpha-keto acid amino acid metabolites (baraphenazines A-C, 1-3), two unique diastaphenazine-type metabolites (baraphenazines D and E, 4 and 5) and two new phenazinolin-type (baraphenazines F and G, 6 and 7) metabolites from the Himalayan isolate Streptomyces sp. PU-10A are reported. This study highlights the first reported bacterial strain capable of producing diastaphenazine-type, phenazinolin-type, and izumiphenazine A-type metabolites and presents a unique opportunity for the future biosynthetic interrogation of late-stage phenazine-based metabolite maturation.

Original language	English
Pages (from-to)	1686-1693
Number of pages	8
Journal	Journal of Natural Products
Volume	82
Issue number	6
DOIs	https://doi.org/10.1021/acs.jnatprod.9b00289
State	Published - Jun 28 2019

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society and American Society of Pharmacognosy.

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/acs.jnatprod.9b00289

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title = "Baraphenazines A-G, Divergent Fused Phenazine-Based Metabolites from a Himalayan Streptomyces",

abstract = "The structures and bioactivities of three unprecedented fused 5-hydroxyquinoxaline/alpha-keto acid amino acid metabolites (baraphenazines A-C, 1-3), two unique diastaphenazine-type metabolites (baraphenazines D and E, 4 and 5) and two new phenazinolin-type (baraphenazines F and G, 6 and 7) metabolites from the Himalayan isolate Streptomyces sp. PU-10A are reported. This study highlights the first reported bacterial strain capable of producing diastaphenazine-type, phenazinolin-type, and izumiphenazine A-type metabolites and presents a unique opportunity for the future biosynthetic interrogation of late-stage phenazine-based metabolite maturation.",

author = "Xiachang Wang and Muhammad Abbas and Yinan Zhang and Elshahawi, {Sherif I.} and Ponomareva, {Larissa V.} and Zheng Cui and {Van Lanen}, {Steven G.} and Imran Sajid and Voss, {S. Randal} and Shaaban, {Khaled A.} and Thorson, {Jon S.}",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society and American Society of Pharmacognosy.",

year = "2019",

month = jun,

day = "28",

doi = "10.1021/acs.jnatprod.9b00289",

language = "English",

volume = "82",

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T1 - Baraphenazines A-G, Divergent Fused Phenazine-Based Metabolites from a Himalayan Streptomyces

AU - Wang, Xiachang

AU - Abbas, Muhammad

AU - Zhang, Yinan

AU - Elshahawi, Sherif I.

AU - Ponomareva, Larissa V.

AU - Cui, Zheng

AU - Van Lanen, Steven G.

AU - Sajid, Imran

AU - Voss, S. Randal

AU - Shaaban, Khaled A.

AU - Thorson, Jon S.

PY - 2019/6/28

Y1 - 2019/6/28

N2 - The structures and bioactivities of three unprecedented fused 5-hydroxyquinoxaline/alpha-keto acid amino acid metabolites (baraphenazines A-C, 1-3), two unique diastaphenazine-type metabolites (baraphenazines D and E, 4 and 5) and two new phenazinolin-type (baraphenazines F and G, 6 and 7) metabolites from the Himalayan isolate Streptomyces sp. PU-10A are reported. This study highlights the first reported bacterial strain capable of producing diastaphenazine-type, phenazinolin-type, and izumiphenazine A-type metabolites and presents a unique opportunity for the future biosynthetic interrogation of late-stage phenazine-based metabolite maturation.

AB - The structures and bioactivities of three unprecedented fused 5-hydroxyquinoxaline/alpha-keto acid amino acid metabolites (baraphenazines A-C, 1-3), two unique diastaphenazine-type metabolites (baraphenazines D and E, 4 and 5) and two new phenazinolin-type (baraphenazines F and G, 6 and 7) metabolites from the Himalayan isolate Streptomyces sp. PU-10A are reported. This study highlights the first reported bacterial strain capable of producing diastaphenazine-type, phenazinolin-type, and izumiphenazine A-type metabolites and presents a unique opportunity for the future biosynthetic interrogation of late-stage phenazine-based metabolite maturation.

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JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 6

ER -

Baraphenazines A-G, Divergent Fused Phenazine-Based Metabolites from a Himalayan Streptomyces

Abstract

Bibliographical note

ASJC Scopus subject areas

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