Structural Diversification of Pyrazinone Metabolites via Spontaneous Oxa-Michael Addition in Staphylococcus xylosus

Ju Ryeong Lee; Su Jung Hwang; Yukyung Choi; Jonghwan Kim; Gyu Sung Lee; Bum Soo Lee; Ki Hyun Kim; Kyo Bin Kang; Hyo Jong Lee; Chung Sub Kim

doi:10.1021/acs.jnatprod.4c00252

Structural Diversification of Pyrazinone Metabolites via Spontaneous Oxa-Michael Addition in Staphylococcus xylosus

Ju Ryeong Lee
, Su Jung Hwang
, Yukyung Choi
, Jonghwan Kim
, Gyu Sung Lee
, Bum Soo Lee
, Ki Hyun Kim
, Kyo Bin Kang
, Hyo Jong Lee
, Chung Sub Kim

Department of Pharmacy

Sungkyunkwan University
Sookmyung Women's University

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

1 Scopus citations

Abstract

A family of pyrazinone metabolites (1-11) were characterized from Staphylococcus xylosus ATCC 29971. Six of them were hydroxylated or methoxylated, which were proposed to be produced by the rare noncatalytic oxa-Michael addition reaction with a water or methanol molecule. It was confirmed that isopropyl alcohol can also be the Michael donor of the reaction. 1-7 and the synthetic precursor 2a showed significant inhibition of breast cancer cell migration.

Original language	English
Pages (from-to)	1881-1887
Number of pages	7
Journal	Journal of Natural Products
Volume	87
Issue number	7
DOIs	https://doi.org/10.1021/acs.jnatprod.4c00252
State	Published - 26 Jul 2024

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10.1021/acs.jnatprod.4c00252

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title = "Structural Diversification of Pyrazinone Metabolites via Spontaneous Oxa-Michael Addition in Staphylococcus xylosus",

abstract = "A family of pyrazinone metabolites (1-11) were characterized from Staphylococcus xylosus ATCC 29971. Six of them were hydroxylated or methoxylated, which were proposed to be produced by the rare noncatalytic oxa-Michael addition reaction with a water or methanol molecule. It was confirmed that isopropyl alcohol can also be the Michael donor of the reaction. 1-7 and the synthetic precursor 2a showed significant inhibition of breast cancer cell migration.",

author = "Lee, \{Ju Ryeong\} and Hwang, \{Su Jung\} and Yukyung Choi and Jonghwan Kim and Lee, \{Gyu Sung\} and Lee, \{Bum Soo\} and Kim, \{Ki Hyun\} and Kang, \{Kyo Bin\} and Lee, \{Hyo Jong\} and Kim, \{Chung Sub\}",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society and American Society of Pharmacognosy.",

year = "2024",

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day = "26",

doi = "10.1021/acs.jnatprod.4c00252",

language = "English",

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AU - Lee, Ju Ryeong

AU - Hwang, Su Jung

AU - Choi, Yukyung

AU - Kim, Jonghwan

AU - Lee, Gyu Sung

AU - Lee, Bum Soo

AU - Kim, Ki Hyun

AU - Kang, Kyo Bin

AU - Lee, Hyo Jong

AU - Kim, Chung Sub

PY - 2024/7/26

Y1 - 2024/7/26

N2 - A family of pyrazinone metabolites (1-11) were characterized from Staphylococcus xylosus ATCC 29971. Six of them were hydroxylated or methoxylated, which were proposed to be produced by the rare noncatalytic oxa-Michael addition reaction with a water or methanol molecule. It was confirmed that isopropyl alcohol can also be the Michael donor of the reaction. 1-7 and the synthetic precursor 2a showed significant inhibition of breast cancer cell migration.

AB - A family of pyrazinone metabolites (1-11) were characterized from Staphylococcus xylosus ATCC 29971. Six of them were hydroxylated or methoxylated, which were proposed to be produced by the rare noncatalytic oxa-Michael addition reaction with a water or methanol molecule. It was confirmed that isopropyl alcohol can also be the Michael donor of the reaction. 1-7 and the synthetic precursor 2a showed significant inhibition of breast cancer cell migration.

UR - https://www.scopus.com/pages/publications/85197466380

U2 - 10.1021/acs.jnatprod.4c00252

DO - 10.1021/acs.jnatprod.4c00252

M3 - Article

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SN - 0163-3864

VL - 87

SP - 1881

EP - 1887

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 7

ER -

Structural Diversification of Pyrazinone Metabolites via Spontaneous Oxa-Michael Addition in Staphylococcus xylosus

Abstract

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