Microbial metabolism of 1-aminoanthracene by Beauveria bassiana

Jixun Zhan; A. A.Leslie Gunatilaka

doi:10.1016/j.bmc.2008.03.030

Microbial metabolism of 1-aminoanthracene by Beauveria bassiana

Jixun Zhan, A. A.Leslie Gunatilaka

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

13 Scopus citations

Abstract

The carcinogen and mutagen, 1-aminoanthracene, was efficiently metabolized by the fungal strain Beauveria bassiana ATCC 7159 to yield three new metabolites identified as 1-acetamido-5-[(4′-O-methyl-β-d-glucopyranosyl)oxy]anthracene, 1-acetamido-8-[(4′-O-methyl-β-d-glucopyranosyl)oxy]anthraquinone, and 1-acetamido-6-[(4′-O-methyl-β-d-glucopyranosyl)oxy]anthraquinone, together with 1-acetamidoanthracene and 1-acetamidoanthraquinone. Formation of these metabolites suggests that the metabolic pathways of 1-aminoanthracene in B. bassiana ATCC 7159 involve acetylation, oxidation, hydroxylation, and O-methylglucosylation.

Original language	English (US)
Pages (from-to)	5085-5089
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry
Volume	16
Issue number	9
DOIs	https://doi.org/10.1016/j.bmc.2008.03.030
State	Published - May 1 2008

Keywords

1-Aminoanthracene
Acetylation
Beauveria bassiana
Biotransformaion
Hydroxylation
Microbial metabolism
O-Methylglucosylation
Oxidation

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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title = "Microbial metabolism of 1-aminoanthracene by Beauveria bassiana",

abstract = "The carcinogen and mutagen, 1-aminoanthracene, was efficiently metabolized by the fungal strain Beauveria bassiana ATCC 7159 to yield three new metabolites identified as 1-acetamido-5-[(4′-O-methyl-β-d-glucopyranosyl)oxy]anthracene, 1-acetamido-8-[(4′-O-methyl-β-d-glucopyranosyl)oxy]anthraquinone, and 1-acetamido-6-[(4′-O-methyl-β-d-glucopyranosyl)oxy]anthraquinone, together with 1-acetamidoanthracene and 1-acetamidoanthraquinone. Formation of these metabolites suggests that the metabolic pathways of 1-aminoanthracene in B. bassiana ATCC 7159 involve acetylation, oxidation, hydroxylation, and O-methylglucosylation.",

keywords = "1-Aminoanthracene, Acetylation, Beauveria bassiana, Biotransformaion, Hydroxylation, Microbial metabolism, O-Methylglucosylation, Oxidation",

author = "Jixun Zhan and Gunatilaka, {A. A.Leslie}",

note = "Funding Information: Financial support from the NCI/NIH (Grant R01 CA 90265) and Arizona Biomedical Research Commission is gratefully acknowledged. We thank Mr. C. J. Seliga for technical assistance.",

year = "2008",

month = may,

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doi = "10.1016/j.bmc.2008.03.030",

language = "English (US)",

volume = "16",

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AU - Zhan, Jixun

AU - Gunatilaka, A. A.Leslie

N1 - Funding Information: Financial support from the NCI/NIH (Grant R01 CA 90265) and Arizona Biomedical Research Commission is gratefully acknowledged. We thank Mr. C. J. Seliga for technical assistance.

PY - 2008/5/1

Y1 - 2008/5/1

N2 - The carcinogen and mutagen, 1-aminoanthracene, was efficiently metabolized by the fungal strain Beauveria bassiana ATCC 7159 to yield three new metabolites identified as 1-acetamido-5-[(4′-O-methyl-β-d-glucopyranosyl)oxy]anthracene, 1-acetamido-8-[(4′-O-methyl-β-d-glucopyranosyl)oxy]anthraquinone, and 1-acetamido-6-[(4′-O-methyl-β-d-glucopyranosyl)oxy]anthraquinone, together with 1-acetamidoanthracene and 1-acetamidoanthraquinone. Formation of these metabolites suggests that the metabolic pathways of 1-aminoanthracene in B. bassiana ATCC 7159 involve acetylation, oxidation, hydroxylation, and O-methylglucosylation.

AB - The carcinogen and mutagen, 1-aminoanthracene, was efficiently metabolized by the fungal strain Beauveria bassiana ATCC 7159 to yield three new metabolites identified as 1-acetamido-5-[(4′-O-methyl-β-d-glucopyranosyl)oxy]anthracene, 1-acetamido-8-[(4′-O-methyl-β-d-glucopyranosyl)oxy]anthraquinone, and 1-acetamido-6-[(4′-O-methyl-β-d-glucopyranosyl)oxy]anthraquinone, together with 1-acetamidoanthracene and 1-acetamidoanthraquinone. Formation of these metabolites suggests that the metabolic pathways of 1-aminoanthracene in B. bassiana ATCC 7159 involve acetylation, oxidation, hydroxylation, and O-methylglucosylation.

KW - 1-Aminoanthracene

KW - Acetylation

KW - Beauveria bassiana

KW - Biotransformaion

KW - Hydroxylation

KW - Microbial metabolism

KW - O-Methylglucosylation

KW - Oxidation

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ER -

Microbial metabolism of 1-aminoanthracene by Beauveria bassiana

Abstract

Keywords

ASJC Scopus subject areas

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