4547-72-2Relevant articles and documents
Gossypolhemiquinone, a dimeric sesquiterpenoid identified in cotton (Gossypium)
Stipanovic, Robert,Puckhaber, Lorraine,Frelichowski, James,Esquivel, Jesus,Westbrook, John,O'Neil, Mike,Bell, Alois,Dowd, Michael,Hake, Kater,Duke, Sara
, p. 165 - 171 (2016)
The report that the cotton leaf perforator, Bucculatrix thurberiella, is one of the few insect herbivores to attack Gossypium thurberi prompted an investigation of the terpenoids present in the leaves of this wild species of cotton. Members of Gossypium produce subepidermal pigment glands in their leaves that contain the dimeric sesquiterpenoid gossypol as well as other biosynthetically related terpenoids. In addition to gossypol, a previously unknown dimeric sesquiterpenoid, gossypolhemiquinone (GHQ), was identified in trace amounts in G. thurberi, a member of the D genome. Other members of the D genome of Gossypium were subsequently found to contain this compound, but GHQ was not detected in commercial cotton cultivars. When fed to Helicoverpa zea in an artificial diet, GHQ delayed days-to-pupation, reduced pupal weights, and survival to adulthood to a lesser or equal extent than gossypol in comparison to the control diet. However, GHQ had a synergistic effect on survival and days-to-pupation when combined with gossypol at the highest dosage tested (0.18%; 15.5:84.5 GHQ:gossypol). Because gossypol exhibits anti-cancer activity, GHQ was also evaluated for its anti-cancer activity against the National Cancer Institute's 60-Human Tumor Cell Line Screen. Significant inhibitory activity against most of these cell lines was not observed, but the results may offer some promise against leukemia cancer cell lines.
Inhibitory effects of gossypol, gossypolone, and apogossypolone on a collection of economically important filamentous fungi
Mellon, Jay E.,Zelaya, Carlos A.,Dowd, Michael K.,Beltz, Shannon B.,Klich, Maren A.
, p. 2740 - 2745 (2012)
Racemic gossypol and its related derivatives gossypolone and apogossypolone demonstrated significant growth inhibition against a diverse collection of filamentous fungi that included Aspergillus flavus, Aspergillus parasiticus, Aspergillus alliaceus, Aspergillus fumigatus, Fusarium graminearum, Fusarium moniliforme, Penicillium chrysogenum, Penicillium corylophilum, and Stachybotrys atra. The compounds were tested in a Czapek agar medium at a concentration of 100 μg/mL. Racemic gossypol and apogossypolone inhibited growth by up to 95%, whereas gossypolone effected 100% growth inhibition in all fungal isolates tested except A. flavus. Growth inhibition was variable during the observed time period for all tested fungi capable of growth in these treatment conditions. Gossypolone demonstrated significant aflatoxin biosynthesis inhibition in A. flavus AF13 (B1, 76% inhibition). Apogossypolone was the most potent aflatoxin inhibitor, showing greater than 90% inhibition against A. flavus and greater than 65% inhibition against A. parasiticus (B1, 67%; G 1, 68%). Gossypol was an ineffectual inhibitor of aflatoxin biosynthesis in both A. flavus and A. parasiticus. Both gossypol and apogossypolone demonstrated significant inhibition of ochratoxin A production (47%; 91%, respectively) in cultures of A. alliaceus.
New thioderivatives of gossypol and gossypolone, as prodrugs of cytotoxic agents
Dao, Vi-Thuy,Dowd, Michael K.,Gaspard, Christiane,Martin, Marie-Therese,Hemez, Julie,Laprevote, Olivier,Mayer, Michel,Michelot, Robert J.
, p. 2001 - 2006 (2003)
New dithiane or dithiolane derivatives of gossypol and gossypolone were synthesized with dithiolethane or dithiolpropane in the presence of BF3/Et2O. These thioderivatives exhibited low toxicity on KB cells (human epidermoid carcinom
