Antioxidant and apoptotic activity of cocoa bean husk extract on prostate cancer cells was written by Choi, Jinhee;Yang, Changwon;Lim, Whasun;Song, Gwonhwa;Choi, Haeyeon. And the article was included in Molecular & Cellular Toxicology in 2022.Safety of (2R,2’R,3R,3’R,4R)-2,2′-Bis(3,4-dihydroxyphenyl)-[4,8′-bichromane]-3,3′,5,5′,7,7′-hexaol The following contents are mentioned in the article:
Although prostate cancer is the most commonly diagnosed cancer in men, its incidence among Asians, who consume foods rich in phenols, is relatively low compared with that in other populations. Cocoa bean husk (CBH) is an important byproduct of the cocoa industry; its polyphenol content (catechin, epicatechin, and procyanidin B) is as high as that of cocoa beans. However, there are no studies on the anticancer effect of CBH. Herein, we assessed the antioxidant and anticancer effects of CBH on prostate cancer cells. We fractionated CBH ethanol crude extract and compared the total polyphenol content, total flavonoid content, and DPPH and ABTS+ radical scavenging activities of the fractions. Catechin, epicatechin, and procyanidin B were analyzed by HPLC in the Et acetate (EAF) and butanol (BF) fractions, which had the highest physiol. content and antioxidant activity. PC3 and DU145 cells were treated with the two fractions, and annexin V/propidium iodide, and TUNEL assays were performed to assess apoptosis and DNA fragmentation, resp. The highest phytochem. content and antioxidant activity were observed in EAF, followed by those in BF. HPLC anal. revealed high content of phenolic compounds in both these fractions. Notably, catechin (5.64 mg/g), epicatechin (20.47 mg/g), and procyanidin B (20.29 mg/g) were abundant in EAF. Both fractions induced apoptosis in a concentration-dependent manner in PC3 and DU145 cells, and DNA fragmentation at a concentration of 200 μg/mL. CBH, a byproduct of cocoa processing, contains large amounts of phenolic compounds and exhibits high antioxidant activity and anticancer effects on prostate cancer cells. CBH has potential applications as a functional food material. This study involved multiple reactions and reactants, such as (2R,2’R,3R,3’R,4R)-2,2′-Bis(3,4-dihydroxyphenyl)-[4,8′-bichromane]-3,3′,5,5′,7,7′-hexaol (cas: 29106-49-8Safety of (2R,2’R,3R,3’R,4R)-2,2′-Bis(3,4-dihydroxyphenyl)-[4,8′-bichromane]-3,3′,5,5′,7,7′-hexaol).
(2R,2’R,3R,3’R,4R)-2,2′-Bis(3,4-dihydroxyphenyl)-[4,8′-bichromane]-3,3′,5,5′,7,7′-hexaol (cas: 29106-49-8) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. A multistep synthesis may use Grignard-like reactions to form an alcohol with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the desired functionality.Safety of (2R,2’R,3R,3’R,4R)-2,2′-Bis(3,4-dihydroxyphenyl)-[4,8′-bichromane]-3,3′,5,5′,7,7′-hexaol
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts