Isolation of 6-methoxy gossypol and 6,6'-dimethoxy gossypol from Gossypium barbadense Sea Island cotton

Journal of Agricultural and Food Chemistry
Michael K Dowd, Scott M Pelitire

Abstract

6-methoxy gossypol and 6,6'-dimethoxy gossypol were isolated from the seeds and root bark of a St. Vincent Sea Island variety of cotton (AZK-267, GRIN# PI 528406). Crude mixtures of gossypol and the methoxy compounds were obtained by extraction of the tissue with acetone and precipitation with acetic acid. After recrystallization, the preparations were treated with 3-amino-1-propanol to form gossypol Schiff's bases, which were separated by preparative reverse phase chromatography. The separated Schiff's bases were then hydrolyzed with acid, extracted into diethyl ether, concentrated, and precipitated with acetic acid. From the above procedure, both methoxy gossypol compounds were obtained as 1:1 molar acetic acid solvates. Each compound was prepared in sufficient amounts to determine its physical properties and begin testing for bioactivity. Light absorbance differed significantly for the di-3-amino-1-propanol derivatives of gossypol and the methoxy gossypol compounds at 254 nm. Relative response factors were developed, which can be used for determining or correcting analytical measurements of these methylated gossypol forms.

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Citations

Jun 19, 2013·Applied Microbiology and Biotechnology·Meiliang ZhouYixiong Tang
Nov 23, 2007·Natural Product Reports·Braulio M Fraga
Feb 5, 2011·Letters in Applied Microbiology·J E MellonM K Dowd
Oct 6, 2010·Acta Crystallographica. Section C, Crystal Structure Communications·Carlos A ZelayaMichael K Dowd
Dec 12, 2019·Phytotherapy Research : PTR·Pratik ShriwasYulin Ren
Apr 10, 2014·Letters in Applied Microbiology·J E MellonG G Moore
Jan 25, 2016·Science China. Life Sciences·Xiu TianChangqing Yang
Jul 12, 2018·Scientific Reports·Heping CaoJohn M Bland
Jul 12, 2019·Journal of Natural Products·Mohamed V Sidi BouneAta M Lawson
Jun 4, 2008·Journal of Agricultural and Food Chemistry·Xi WangJ David Gangemi

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