Title:Synthesis of Chrysin, Quercetin and Naringin Nitroderivatives: Antiproliferative, Anti-inflammatory and Antioxidant Activity
Volume: 18
Issue: 8
Author(s): Rosario Tavera-Hernández, Manuel Jiménez-Estrada*, Jesús J. Alvarado-Sansininea, Antonio Nieto-Camacho, Hugo López-Muñoz, Luis Sánchez-Sánchez and María L. Escobar
Affiliation:
- Laboratorio 2-10, Departamento de Productos Naturales, Instituto de Química, Universidad Nacional Autonoma de Mexico, Ciudad de Mexico,Mexico
Keywords:
Aromatic nitration, quercetin, naringin, chrysin, anti-proliferative, antioxidant, anti-inflammatory.
Abstract:
Background: 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.
Objective: The study aimed to introduce a nitro group into the structure of flavonoids in order to
observe how their anti-proliferative, antioxidant, and anti-inflammatory activities change.
Methods: In this investigation, we established diverse conditions of aromatic nitration of chrysin (1),
quercetin (2), and naringin (3) flavonoids using bismuth (III) nitrate, acetic acid or silica gel, and
NOx gases. 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.
Results: As a result, mild nitration conditions were established, and 8-nitrochrysin, 5’nitroquercetin,
and 3’nitronaringin were obtained. The number and hydroxyl group position in the flavonoid are
important to carry out the nitration reaction. 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. Chrysin,
8-nitrochrysin, quercetin, and 5’-nitroquercetin did not show necrotic activity.
Conclusion: 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.
