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LC–PDA–MS/MS-Based Dereplication Guided Isolation of a New Optical Isomer of 19,20-Epoxycytochalasin-N and Its Cytotoxic Activity

[Image: see text] The Rosellinia sanctae-cruciana extract was subjected to detailed liquid chromatography tandem mass spectrometry studies. A total of 38 peaks were annotated to m/z 508.26, m/z 510.28, m/z 524.26, m/z 526.28, m/z 540.26, m/z 542.27, and m/z 584.28 [M + H](+). The accurate mass, mutu...

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Autores principales: Kushwaha, Manoj, Qayum, Arem, Sharma, Nisha, Abrol, Vidushi, Choudhary, Poonam, Murtaza, Mohd, Singh, Shashank K., Vishwakarma, Ram A., Goutam, Umesh, Jain, Shreyans K., Jaglan, Sundeep
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9404496/
https://www.ncbi.nlm.nih.gov/pubmed/36033687
http://dx.doi.org/10.1021/acsomega.2c03037
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author Kushwaha, Manoj
Qayum, Arem
Sharma, Nisha
Abrol, Vidushi
Choudhary, Poonam
Murtaza, Mohd
Singh, Shashank K.
Vishwakarma, Ram A.
Goutam, Umesh
Jain, Shreyans K.
Jaglan, Sundeep
author_facet Kushwaha, Manoj
Qayum, Arem
Sharma, Nisha
Abrol, Vidushi
Choudhary, Poonam
Murtaza, Mohd
Singh, Shashank K.
Vishwakarma, Ram A.
Goutam, Umesh
Jain, Shreyans K.
Jaglan, Sundeep
author_sort Kushwaha, Manoj
collection PubMed
description [Image: see text] The Rosellinia sanctae-cruciana extract was subjected to detailed liquid chromatography tandem mass spectrometry studies. A total of 38 peaks were annotated to m/z 508.26, m/z 510.28, m/z 524.26, m/z 526.28, m/z 540.26, m/z 542.27, and m/z 584.28 [M + H](+). The accurate mass, mutually supported UV/vis spectra, and database search identified these compounds as cytochalasins. Systematic dereplication helped identify a peak at m/z 540.26 [M + H](+) as the new compound. Further, the identified compound was purified by high-performance liquid chromatography and characterized by 2D NMR to be 19,20-epoxycytochalasin N1, a new optical isomer of 19,20-epoxycytochalasin-N. It exhibited substantial cytotoxicity with IC(50) values ranging from 1.34 to 19.02 μM. This study shows a fast approach for dereplicating and identifying novel cytochalasin metabolites in crude extracts.
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spelling pubmed-94044962022-08-26 LC–PDA–MS/MS-Based Dereplication Guided Isolation of a New Optical Isomer of 19,20-Epoxycytochalasin-N and Its Cytotoxic Activity Kushwaha, Manoj Qayum, Arem Sharma, Nisha Abrol, Vidushi Choudhary, Poonam Murtaza, Mohd Singh, Shashank K. Vishwakarma, Ram A. Goutam, Umesh Jain, Shreyans K. Jaglan, Sundeep ACS Omega [Image: see text] The Rosellinia sanctae-cruciana extract was subjected to detailed liquid chromatography tandem mass spectrometry studies. A total of 38 peaks were annotated to m/z 508.26, m/z 510.28, m/z 524.26, m/z 526.28, m/z 540.26, m/z 542.27, and m/z 584.28 [M + H](+). The accurate mass, mutually supported UV/vis spectra, and database search identified these compounds as cytochalasins. Systematic dereplication helped identify a peak at m/z 540.26 [M + H](+) as the new compound. Further, the identified compound was purified by high-performance liquid chromatography and characterized by 2D NMR to be 19,20-epoxycytochalasin N1, a new optical isomer of 19,20-epoxycytochalasin-N. It exhibited substantial cytotoxicity with IC(50) values ranging from 1.34 to 19.02 μM. This study shows a fast approach for dereplicating and identifying novel cytochalasin metabolites in crude extracts. American Chemical Society 2022-08-10 /pmc/articles/PMC9404496/ /pubmed/36033687 http://dx.doi.org/10.1021/acsomega.2c03037 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Kushwaha, Manoj
Qayum, Arem
Sharma, Nisha
Abrol, Vidushi
Choudhary, Poonam
Murtaza, Mohd
Singh, Shashank K.
Vishwakarma, Ram A.
Goutam, Umesh
Jain, Shreyans K.
Jaglan, Sundeep
LC–PDA–MS/MS-Based Dereplication Guided Isolation of a New Optical Isomer of 19,20-Epoxycytochalasin-N and Its Cytotoxic Activity
title LC–PDA–MS/MS-Based Dereplication Guided Isolation of a New Optical Isomer of 19,20-Epoxycytochalasin-N and Its Cytotoxic Activity
title_full LC–PDA–MS/MS-Based Dereplication Guided Isolation of a New Optical Isomer of 19,20-Epoxycytochalasin-N and Its Cytotoxic Activity
title_fullStr LC–PDA–MS/MS-Based Dereplication Guided Isolation of a New Optical Isomer of 19,20-Epoxycytochalasin-N and Its Cytotoxic Activity
title_full_unstemmed LC–PDA–MS/MS-Based Dereplication Guided Isolation of a New Optical Isomer of 19,20-Epoxycytochalasin-N and Its Cytotoxic Activity
title_short LC–PDA–MS/MS-Based Dereplication Guided Isolation of a New Optical Isomer of 19,20-Epoxycytochalasin-N and Its Cytotoxic Activity
title_sort lc–pda–ms/ms-based dereplication guided isolation of a new optical isomer of 19,20-epoxycytochalasin-n and its cytotoxic activity
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9404496/
https://www.ncbi.nlm.nih.gov/pubmed/36033687
http://dx.doi.org/10.1021/acsomega.2c03037
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