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Investigating Stability and Tautomerization of Gossypol—A Spectroscopy Study

The stability of gossypol was investigated by the spectroscopic method. Gossypol was dissolved in three different solvents (CHCl(3), DMSO, and CH(3)OH) under different storage conditions (dark and with nitrogen protection, natural light and with nitrogen protection, ambient air conditions) for diffe...

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Autores principales: Wang, Lulu, Liu, Yanxia, Zhang, Yagang, Yasin, Akram, Zhang, Letao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6479638/
https://www.ncbi.nlm.nih.gov/pubmed/30987000
http://dx.doi.org/10.3390/molecules24071286
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author Wang, Lulu
Liu, Yanxia
Zhang, Yagang
Yasin, Akram
Zhang, Letao
author_facet Wang, Lulu
Liu, Yanxia
Zhang, Yagang
Yasin, Akram
Zhang, Letao
author_sort Wang, Lulu
collection PubMed
description The stability of gossypol was investigated by the spectroscopic method. Gossypol was dissolved in three different solvents (CHCl(3), DMSO, and CH(3)OH) under different storage conditions (dark and with nitrogen protection, natural light and with nitrogen protection, ambient air conditions) for different time intervals (0 days, 3 days, 5 days, 7 days, 15 days, 30 days, and 45 days) at room temperature. Then, the stability of gossypol was investigated by (1)H NMR, UV-vis, and HPLC-QTOF-MS spectrometry. Results showed that gossypol existed in aldehyde–aldehyde form in chloroform within five days. Then, both aldehyde–aldehyde and lactol–lactol tautomeric forms existed and maintained a stable solution for 45 days. Gossypol dissolved in methanol mainly existed in aldehyde–aldehyde form. Only a tiny amount of lactol–lactol was found in freshly prepared methanol solution. Gossypol was found to only exist in lactol–lactol form between 30–45 days. Gossypol existed in aldehyde–aldehyde, lactol–lactol, and ketol–ketol forms in dimethyl sulfoxide, and there was a competitive relationship between aldehyde–aldehyde and lactol–lactol form during the 45 days. Among all the solvents and conditions studied, gossypol was found to be highly stable in chloroform. Under the tested conditions, the natural light and atmospheric oxygen had little effect on its stability. Although the spectroscopy data seemed to be changed over time in the three different solvents, it was actually due to the tautomeric transformation rather than molecular decomposition.
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spelling pubmed-64796382019-04-30 Investigating Stability and Tautomerization of Gossypol—A Spectroscopy Study Wang, Lulu Liu, Yanxia Zhang, Yagang Yasin, Akram Zhang, Letao Molecules Article The stability of gossypol was investigated by the spectroscopic method. Gossypol was dissolved in three different solvents (CHCl(3), DMSO, and CH(3)OH) under different storage conditions (dark and with nitrogen protection, natural light and with nitrogen protection, ambient air conditions) for different time intervals (0 days, 3 days, 5 days, 7 days, 15 days, 30 days, and 45 days) at room temperature. Then, the stability of gossypol was investigated by (1)H NMR, UV-vis, and HPLC-QTOF-MS spectrometry. Results showed that gossypol existed in aldehyde–aldehyde form in chloroform within five days. Then, both aldehyde–aldehyde and lactol–lactol tautomeric forms existed and maintained a stable solution for 45 days. Gossypol dissolved in methanol mainly existed in aldehyde–aldehyde form. Only a tiny amount of lactol–lactol was found in freshly prepared methanol solution. Gossypol was found to only exist in lactol–lactol form between 30–45 days. Gossypol existed in aldehyde–aldehyde, lactol–lactol, and ketol–ketol forms in dimethyl sulfoxide, and there was a competitive relationship between aldehyde–aldehyde and lactol–lactol form during the 45 days. Among all the solvents and conditions studied, gossypol was found to be highly stable in chloroform. Under the tested conditions, the natural light and atmospheric oxygen had little effect on its stability. Although the spectroscopy data seemed to be changed over time in the three different solvents, it was actually due to the tautomeric transformation rather than molecular decomposition. MDPI 2019-04-02 /pmc/articles/PMC6479638/ /pubmed/30987000 http://dx.doi.org/10.3390/molecules24071286 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wang, Lulu
Liu, Yanxia
Zhang, Yagang
Yasin, Akram
Zhang, Letao
Investigating Stability and Tautomerization of Gossypol—A Spectroscopy Study
title Investigating Stability and Tautomerization of Gossypol—A Spectroscopy Study
title_full Investigating Stability and Tautomerization of Gossypol—A Spectroscopy Study
title_fullStr Investigating Stability and Tautomerization of Gossypol—A Spectroscopy Study
title_full_unstemmed Investigating Stability and Tautomerization of Gossypol—A Spectroscopy Study
title_short Investigating Stability and Tautomerization of Gossypol—A Spectroscopy Study
title_sort investigating stability and tautomerization of gossypol—a spectroscopy study
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6479638/
https://www.ncbi.nlm.nih.gov/pubmed/30987000
http://dx.doi.org/10.3390/molecules24071286
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