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Open AccessArticle

Investigating Stability and Tautomerization of Gossypol—A Spectroscopy Study

by 1,2, 1,2, 1,2,3,*, 1 and 1
1
Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China
2
University of Chinese Academy of Sciences, Beijing 100049, China
3
Department of chemical and environmental engineering, Xinjiang Institute of Engineering, Urumqi 830026, China
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(7), 1286; https://doi.org/10.3390/molecules24071286
Received: 20 February 2019 / Revised: 27 March 2019 / Accepted: 29 March 2019 / Published: 2 April 2019
(This article belongs to the Section Physical Chemistry)
The stability of gossypol was investigated by the spectroscopic method. Gossypol was dissolved in three different solvents (CHCl3, DMSO, and CH3OH) 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 1H 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. View Full-Text
Keywords: gossypol; tautomerization; 1H NMR; UV-vis; HPLC-QTOF-MS gossypol; tautomerization; 1H NMR; UV-vis; HPLC-QTOF-MS
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MDPI and ACS Style

Wang, L.; Liu, Y.; Zhang, Y.; Yasin, A.; Zhang, L. Investigating Stability and Tautomerization of Gossypol—A Spectroscopy Study. Molecules 2019, 24, 1286.

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