What is it about?
Flavonoids are an important group of natural products because they possess various biological activities such as antioxidant, anti-inflammatory, and anti-cancer. The modification of their structure could improve their biological activities. The nitro group is included in diverse pharmaceuticals with various biological activities, such as anti-cancer and anti-inflammatory agents The study aimed to introduce a nitro group into the structure of chrysin, quercetin and naringin in order to observe how their anti-proliferative, antioxidant, and anti-inflammatory activities change. Diverse mild conditions of aromatic nitration were stablished using bismuth (III) nitrate, acetic acid or silica gel, and NOx gases. and 8-nitrochrysin, 5’nitroquercetin, and 3’nitronaringin were obtained. The anti-proliferative activity in CaSki, MDA, and SK-LU-1 cancer cell lines and the anti-inflammatory activity and antioxidant activity of flavonoids and nitro derivatives were evaluated as well. Although chrysin showed higher anti-proliferative activity than quercetin and naringin, the introduction of the nitro group at C-8 did not improve its antiproliferative, antioxidant, and anti-inflammatory activities. On the other hand, the introduction of the nitro group at C-5̍ in quercetin structure was important to improve its antioxidant and antiproliferative activities on cancer cell lines. The introduction of the nitro group at C-3’ in naringin improved its anti-inflammatory activity, but not its antioxidant and anti-proliferative activities. 8-nitrochrysin, quercetin, and 5’-nitroquercetin did not show necrotic activity, so the cell dead could be explained by other mechanism. The introduction of a nitro group into flavonoids structure improved their antiproliferative, antioxidant, and anti-inflammatory activities. These results promote future investigations of structural modification on 2-phenylbenzopyran skeleton to optimize their biological activity.
Photo by National Cancer Institute on Unsplash
Why is it important?
Our work describes a first approach to obtaining nitro derivatives of the flavonoids naringin and quercetin, in addition, the effect of the nitro group on its antioxidant, anti-proliferative and anti-inflammatory activity was determined.
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This page is a summary of: Synthesis of Chrysin, Quercetin and Naringin Nitroderivatives: Antiproliferative, Anti-inflammatory and Antioxidant Activity, Letters in Drug Design & Discovery, August 2021, Bentham Science Publishers, DOI: 10.2174/1570180818666210122162313.
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