A series of aromatic gossypol Schiff bases have been successfully synthesized via a feasible chemical modification. The antiviral activity against tobacco mosaic virus (TMV) of these gossypol Schiff bases has been tested for the first time. The bioassay studies indicated most of these derivatives exhibited excellent anti-TMV activity, in which o-trifluoromethylaniline Schiff base (19) displayed the best antiviral activities. Furthermore, compound 19 exhibited an eminent anti-TMV effect in the field and low toxicity to mice. These results suggest it is a promising candidate for the inhibitor of plant virus.
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http://dx.doi.org/10.1021/jf504411g | DOI Listing |
Molecules
October 2024
N.D. Zelinsky Institute of Organic Chemistry, Leninsky Ave. 47, Moscow 119991, Russia.
Gossypol and its derivatives arouse interest due to their broad spectrum of biological activities. Despite its wide potential application, there is no reported example of gossypol derivatives bearing stable radical functional groups. The first gossypol nitroxide hybrid compound was prepared here via formation of a Schiff base.
View Article and Find Full Text PDFNat Prod Rep
June 2022
School of Materials and Energy, University of Electronic Science and Technology of China, Chengdu 611731, China.
Covering up to 2022Gossypol is a polyphenolic compound isolated from cottonseed. There are two optical enantiomers of gossypol, (-)-gossypol and (+)-gossypol. Gossypol exists as three different tautomers, aldehyde, ketone and lactol.
View Article and Find Full Text PDFCarbohydr Polym
July 2020
Hatay Mustafa Kemal University, Faculty of Arts and Sciences, Department of Chemistry, Hatay, Turkey. Electronic address:
In this work, two new chitosan-Schiff base derivatives (HCS-GSP and LCS-GSP) were synthesized by the condensation reaction of high molecular weight chitosan (HCS) and low molecular weight chitosan (LCS) with (-)-gossypol (GSP), respectively. For this purpose, racemic gossypol was isolated from cotton seeds and it was further enantiomerically purified by diastereomeric resolution technique using l-tryptophan methyl ester hydrochloride. Then, chitosan polymers were derivatized with (-)-gossypol by the condensation reaction.
View Article and Find Full Text PDFMagn Reson Chem
August 2020
Faculty of Chemistry, University of Opole, Opole, Poland.
J( N,H) coupling constants for enaminones and NH-forms of intramolecularly hydrogen-bonded Schiff bases as model compounds for sp -hybridized nitrogen atoms are evaluated using density functional theory (DFT) to find the optimal functionals and basis sets. Ammonia is used as a test molecule and its one-bond coupling constant is compared with experiment. A methylamine Schiff base of a truncated molecule of gossypol is used for checking the performance of selected B3LYP, O3LYP, PBE, BHandH, and APFD density functionals and standard, modified, and dedicated basis sets for coupling constants.
View Article and Find Full Text PDFJ Nat Prod
July 2019
Normandie Université France, UNILEHAVRE, URCOM, EA 3221, FR 3038 CNRS, F-76600 Le Havre , France.
We have recently developed a one-pot process for simultaneous extraction and chemical modification (SECheM) on , a Mauritanian called locally "Izide". On the basis of this innovative methodology that consisted of using ground plant roots as starting material in gossypol Schiff base semisynthesis, we now report how this concept can be used to access enantiomerically pure Schiff base atropisomer derivatives of gossypol in only two steps. This study has been envisioned since enantiomerically pure Schiff base atropisomer derivatives of gossypol are generally more potent biologically when compared to racemic gossypol Schiff bases.
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