Efficient identification of fungal antimicrobial principles by tandem MS and NMR database

Ming Shian Lee, Yu Liang Yang, Chia Yen Wu, Ying Lien Chen, Ching Kuo Lee, Shean Shong Tzean, Tzong Huei Lee

研究成果: 雜誌貢獻文章

摘要

The continuous re-isolation of the known and non-applicable compounds that is time-consuming and wasting resources is still a critical problem in the discovery of bioactive entities from natural resources. To efficiently address the problem, high performance liquid chromatography-diode array detector-microfractionation (HPLC-DAD-microfractionation) guided by disk agar diffusion assay was developed, and the active compounds were further identified using the tandem mass spectrometry (MS/MS)-based molecular networking. Of 150 fungal strains screened, the methanolic extracts of Phoma herbarum PPM7487, Cryptosporiopsis ericae PPM7405, and Albifimbria verrucaria PPM945 exhibited potent antimicrobial activity against Candida albicans SC5314 and Cryptococcus neoformans H99 in the preliminary agar diffusion assay. The concept of OSMAC (one strain many compounds) was employed in the fungal cultures in order to enrich the diversity of the 2nd metabolites in this study. HPLC coupled with off-line bioactivity-directed profiling of the extracts enabled a precise localization of the compounds responsible for the conspicuous antimicrobial activity. The purified active compounds were identified based mainly on MS/MS database, and further supported by 13C nuclear magnetic resonance (NMR) spectral data compared to the literatures. In addition to nineteen known compounds, a new trichothecene derivative 1, namely trichoverrin D, was isolated and identified through this protocol. The antifungal activities of all the pure isolates were evaluated, and the structure activity relationships were also inferred. This report has demonstrated the combination of HPLC microfractination and MS/MS coupled by NMR spectral dereplication for speeding up the antimicrobial natural products discovery process.

原文英語
期刊Journal of Food and Drug Analysis
DOIs
出版狀態已發佈 - 一月 1 2019

指紋

nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
anti-infective agents
High Pressure Liquid Chromatography
Databases
Agar
high performance liquid chromatography
Trichothecenes
Cryptococcus neoformans
Cryptosporiopsis
agar
Verrucaria
Structure-Activity Relationship
Tandem Mass Spectrometry
Biological Products
Candida albicans
Phoma
trichothecenes
extracts
assays

ASJC Scopus subject areas

  • Food Science
  • Pharmacology

引用此文

Efficient identification of fungal antimicrobial principles by tandem MS and NMR database. / Lee, Ming Shian; Yang, Yu Liang; Wu, Chia Yen; Chen, Ying Lien; Lee, Ching Kuo; Tzean, Shean Shong; Lee, Tzong Huei.

於: Journal of Food and Drug Analysis, 01.01.2019.

研究成果: 雜誌貢獻文章

Lee, Ming Shian ; Yang, Yu Liang ; Wu, Chia Yen ; Chen, Ying Lien ; Lee, Ching Kuo ; Tzean, Shean Shong ; Lee, Tzong Huei. / Efficient identification of fungal antimicrobial principles by tandem MS and NMR database. 於: Journal of Food and Drug Analysis. 2019.
@article{ee240d834f8b472392e6f26a39a8542c,
title = "Efficient identification of fungal antimicrobial principles by tandem MS and NMR database",
abstract = "The continuous re-isolation of the known and non-applicable compounds that is time-consuming and wasting resources is still a critical problem in the discovery of bioactive entities from natural resources. To efficiently address the problem, high performance liquid chromatography-diode array detector-microfractionation (HPLC-DAD-microfractionation) guided by disk agar diffusion assay was developed, and the active compounds were further identified using the tandem mass spectrometry (MS/MS)-based molecular networking. Of 150 fungal strains screened, the methanolic extracts of Phoma herbarum PPM7487, Cryptosporiopsis ericae PPM7405, and Albifimbria verrucaria PPM945 exhibited potent antimicrobial activity against Candida albicans SC5314 and Cryptococcus neoformans H99 in the preliminary agar diffusion assay. The concept of OSMAC (one strain many compounds) was employed in the fungal cultures in order to enrich the diversity of the 2nd metabolites in this study. HPLC coupled with off-line bioactivity-directed profiling of the extracts enabled a precise localization of the compounds responsible for the conspicuous antimicrobial activity. The purified active compounds were identified based mainly on MS/MS database, and further supported by 13C nuclear magnetic resonance (NMR) spectral data compared to the literatures. In addition to nineteen known compounds, a new trichothecene derivative 1, namely trichoverrin D, was isolated and identified through this protocol. The antifungal activities of all the pure isolates were evaluated, and the structure activity relationships were also inferred. This report has demonstrated the combination of HPLC microfractination and MS/MS coupled by NMR spectral dereplication for speeding up the antimicrobial natural products discovery process.",
keywords = "Albifimbria verrucaria, Cryptosporiopsis ericae, Dereplication, Molecular networking, Phoma herbarum",
author = "Lee, {Ming Shian} and Yang, {Yu Liang} and Wu, {Chia Yen} and Chen, {Ying Lien} and Lee, {Ching Kuo} and Tzean, {Shean Shong} and Lee, {Tzong Huei}",
year = "2019",
month = "1",
day = "1",
doi = "10.1016/j.jfda.2019.06.003",
language = "English",
journal = "Journal of Food and Drug Analysis",
issn = "1021-9498",
publisher = "Elsevier Taiwan LLC",

}

TY - JOUR

T1 - Efficient identification of fungal antimicrobial principles by tandem MS and NMR database

AU - Lee, Ming Shian

AU - Yang, Yu Liang

AU - Wu, Chia Yen

AU - Chen, Ying Lien

AU - Lee, Ching Kuo

AU - Tzean, Shean Shong

AU - Lee, Tzong Huei

PY - 2019/1/1

Y1 - 2019/1/1

N2 - The continuous re-isolation of the known and non-applicable compounds that is time-consuming and wasting resources is still a critical problem in the discovery of bioactive entities from natural resources. To efficiently address the problem, high performance liquid chromatography-diode array detector-microfractionation (HPLC-DAD-microfractionation) guided by disk agar diffusion assay was developed, and the active compounds were further identified using the tandem mass spectrometry (MS/MS)-based molecular networking. Of 150 fungal strains screened, the methanolic extracts of Phoma herbarum PPM7487, Cryptosporiopsis ericae PPM7405, and Albifimbria verrucaria PPM945 exhibited potent antimicrobial activity against Candida albicans SC5314 and Cryptococcus neoformans H99 in the preliminary agar diffusion assay. The concept of OSMAC (one strain many compounds) was employed in the fungal cultures in order to enrich the diversity of the 2nd metabolites in this study. HPLC coupled with off-line bioactivity-directed profiling of the extracts enabled a precise localization of the compounds responsible for the conspicuous antimicrobial activity. The purified active compounds were identified based mainly on MS/MS database, and further supported by 13C nuclear magnetic resonance (NMR) spectral data compared to the literatures. In addition to nineteen known compounds, a new trichothecene derivative 1, namely trichoverrin D, was isolated and identified through this protocol. The antifungal activities of all the pure isolates were evaluated, and the structure activity relationships were also inferred. This report has demonstrated the combination of HPLC microfractination and MS/MS coupled by NMR spectral dereplication for speeding up the antimicrobial natural products discovery process.

AB - The continuous re-isolation of the known and non-applicable compounds that is time-consuming and wasting resources is still a critical problem in the discovery of bioactive entities from natural resources. To efficiently address the problem, high performance liquid chromatography-diode array detector-microfractionation (HPLC-DAD-microfractionation) guided by disk agar diffusion assay was developed, and the active compounds were further identified using the tandem mass spectrometry (MS/MS)-based molecular networking. Of 150 fungal strains screened, the methanolic extracts of Phoma herbarum PPM7487, Cryptosporiopsis ericae PPM7405, and Albifimbria verrucaria PPM945 exhibited potent antimicrobial activity against Candida albicans SC5314 and Cryptococcus neoformans H99 in the preliminary agar diffusion assay. The concept of OSMAC (one strain many compounds) was employed in the fungal cultures in order to enrich the diversity of the 2nd metabolites in this study. HPLC coupled with off-line bioactivity-directed profiling of the extracts enabled a precise localization of the compounds responsible for the conspicuous antimicrobial activity. The purified active compounds were identified based mainly on MS/MS database, and further supported by 13C nuclear magnetic resonance (NMR) spectral data compared to the literatures. In addition to nineteen known compounds, a new trichothecene derivative 1, namely trichoverrin D, was isolated and identified through this protocol. The antifungal activities of all the pure isolates were evaluated, and the structure activity relationships were also inferred. This report has demonstrated the combination of HPLC microfractination and MS/MS coupled by NMR spectral dereplication for speeding up the antimicrobial natural products discovery process.

KW - Albifimbria verrucaria

KW - Cryptosporiopsis ericae

KW - Dereplication

KW - Molecular networking

KW - Phoma herbarum

UR - http://www.scopus.com/inward/record.url?scp=85068027050&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85068027050&partnerID=8YFLogxK

U2 - 10.1016/j.jfda.2019.06.003

DO - 10.1016/j.jfda.2019.06.003

M3 - Article

JO - Journal of Food and Drug Analysis

JF - Journal of Food and Drug Analysis

SN - 1021-9498

ER -