Cargando…

Antibacterial effect of 3-p-trans-coumaroyl-2-hydroxyquinic acid, a phenolic compound from needles of Cedrus deodara, on cellular functions of Staphylococcus aureus

A natural phenolic compound, 3-p-trans-coumaroyl-2-hydroxyquinic acid (CHQA) from needles of Cedrus deodara, has been reported to exhibit strong antibacterial activity. In this study, the molecular structural requirements of CHQA for the antibacterial activity and its effect on the cellular function...

Descripción completa

Detalles Bibliográficos
Autores principales: Wu, Yanping, Bai, Jinrong, Liu, Xiaoyan, Liu, Lijin, Zhong, Kai, Huang, Yina, Gao, Hong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9077780/
https://www.ncbi.nlm.nih.gov/pubmed/35539522
http://dx.doi.org/10.1039/c7ra13457f
_version_ 1784702185874915328
author Wu, Yanping
Bai, Jinrong
Liu, Xiaoyan
Liu, Lijin
Zhong, Kai
Huang, Yina
Gao, Hong
author_facet Wu, Yanping
Bai, Jinrong
Liu, Xiaoyan
Liu, Lijin
Zhong, Kai
Huang, Yina
Gao, Hong
author_sort Wu, Yanping
collection PubMed
description A natural phenolic compound, 3-p-trans-coumaroyl-2-hydroxyquinic acid (CHQA) from needles of Cedrus deodara, has been reported to exhibit strong antibacterial activity. In this study, the molecular structural requirements of CHQA for the antibacterial activity and its effect on the cellular functions of Staphylococcus aureus were investigated. The structure–activity relationship analysis revealed that the p-coumaric acid moiety of CHQA was critical for the antibacterial activity, while the esterification between p-coumaric acid and 2-hydroxyquinic acid was unfavorable. Studies of the cellular metabolism demonstrated that CHQA induced a significant decrease in the intracellular ATP concentration but no proportional increase in the extracellular ATP. It was also found that CHQA slightly increased the respiratory activity and succinate dehydrogenase activity of S. aureus. Meanwhile, CHQA decreased the DNA synthesis of S. aureus and directly interacted with DNA through the groove binding mode.
format Online
Article
Text
id pubmed-9077780
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90777802022-05-09 Antibacterial effect of 3-p-trans-coumaroyl-2-hydroxyquinic acid, a phenolic compound from needles of Cedrus deodara, on cellular functions of Staphylococcus aureus Wu, Yanping Bai, Jinrong Liu, Xiaoyan Liu, Lijin Zhong, Kai Huang, Yina Gao, Hong RSC Adv Chemistry A natural phenolic compound, 3-p-trans-coumaroyl-2-hydroxyquinic acid (CHQA) from needles of Cedrus deodara, has been reported to exhibit strong antibacterial activity. In this study, the molecular structural requirements of CHQA for the antibacterial activity and its effect on the cellular functions of Staphylococcus aureus were investigated. The structure–activity relationship analysis revealed that the p-coumaric acid moiety of CHQA was critical for the antibacterial activity, while the esterification between p-coumaric acid and 2-hydroxyquinic acid was unfavorable. Studies of the cellular metabolism demonstrated that CHQA induced a significant decrease in the intracellular ATP concentration but no proportional increase in the extracellular ATP. It was also found that CHQA slightly increased the respiratory activity and succinate dehydrogenase activity of S. aureus. Meanwhile, CHQA decreased the DNA synthesis of S. aureus and directly interacted with DNA through the groove binding mode. The Royal Society of Chemistry 2018-01-29 /pmc/articles/PMC9077780/ /pubmed/35539522 http://dx.doi.org/10.1039/c7ra13457f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Wu, Yanping
Bai, Jinrong
Liu, Xiaoyan
Liu, Lijin
Zhong, Kai
Huang, Yina
Gao, Hong
Antibacterial effect of 3-p-trans-coumaroyl-2-hydroxyquinic acid, a phenolic compound from needles of Cedrus deodara, on cellular functions of Staphylococcus aureus
title Antibacterial effect of 3-p-trans-coumaroyl-2-hydroxyquinic acid, a phenolic compound from needles of Cedrus deodara, on cellular functions of Staphylococcus aureus
title_full Antibacterial effect of 3-p-trans-coumaroyl-2-hydroxyquinic acid, a phenolic compound from needles of Cedrus deodara, on cellular functions of Staphylococcus aureus
title_fullStr Antibacterial effect of 3-p-trans-coumaroyl-2-hydroxyquinic acid, a phenolic compound from needles of Cedrus deodara, on cellular functions of Staphylococcus aureus
title_full_unstemmed Antibacterial effect of 3-p-trans-coumaroyl-2-hydroxyquinic acid, a phenolic compound from needles of Cedrus deodara, on cellular functions of Staphylococcus aureus
title_short Antibacterial effect of 3-p-trans-coumaroyl-2-hydroxyquinic acid, a phenolic compound from needles of Cedrus deodara, on cellular functions of Staphylococcus aureus
title_sort antibacterial effect of 3-p-trans-coumaroyl-2-hydroxyquinic acid, a phenolic compound from needles of cedrus deodara, on cellular functions of staphylococcus aureus
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9077780/
https://www.ncbi.nlm.nih.gov/pubmed/35539522
http://dx.doi.org/10.1039/c7ra13457f
work_keys_str_mv AT wuyanping antibacterialeffectof3ptranscoumaroyl2hydroxyquinicacidaphenoliccompoundfromneedlesofcedrusdeodaraoncellularfunctionsofstaphylococcusaureus
AT baijinrong antibacterialeffectof3ptranscoumaroyl2hydroxyquinicacidaphenoliccompoundfromneedlesofcedrusdeodaraoncellularfunctionsofstaphylococcusaureus
AT liuxiaoyan antibacterialeffectof3ptranscoumaroyl2hydroxyquinicacidaphenoliccompoundfromneedlesofcedrusdeodaraoncellularfunctionsofstaphylococcusaureus
AT liulijin antibacterialeffectof3ptranscoumaroyl2hydroxyquinicacidaphenoliccompoundfromneedlesofcedrusdeodaraoncellularfunctionsofstaphylococcusaureus
AT zhongkai antibacterialeffectof3ptranscoumaroyl2hydroxyquinicacidaphenoliccompoundfromneedlesofcedrusdeodaraoncellularfunctionsofstaphylococcusaureus
AT huangyina antibacterialeffectof3ptranscoumaroyl2hydroxyquinicacidaphenoliccompoundfromneedlesofcedrusdeodaraoncellularfunctionsofstaphylococcusaureus
AT gaohong antibacterialeffectof3ptranscoumaroyl2hydroxyquinicacidaphenoliccompoundfromneedlesofcedrusdeodaraoncellularfunctionsofstaphylococcusaureus