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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2019
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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. |
format | Online Article Text |
id | pubmed-6479638 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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