ISSN 1070-4272, Russian Journal of Applied Chemistry, 2014, Vol. 87, No. 12, pp. 1877−1883. © Pleiades Publishing, Ltd., 2014.
Original Russian Text © A.F. Gogotov, L.V. Kanitskaya, Dam Thi Thanh Hai, L.A. Ostroukhova, Do Chiem Tai, E.A. Bitukheeva, A.N. Shaposhnikova, V.A. Babkin,
V.K. Stankevich, 2014, published in Zhurnal Prikladnoi Khimii, 2014, Vol. 87, No. 12, pp. 1801−1808.
ORGANIC SYNTHESIS AND INDUSTRIAL
Enhancement of Antiradical Properties
of Dihydroquercetin by Nitrosation
A. F. Gogotov
, L. V. Kanitskaya
, Dam Thi Thanh Hai
, L. A. Ostroukhova
, Do Chiem Tai
E. A. Bitukheeva
, A. N. Shaposhnikova
, V. A. Babkin
, and V. K. Stankevich
Favorskii Institute of Chemistry, Siberian Branch, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
Baikal State University of Economy and Law, ul. Lenina 11, k. 1, Irkutsk, 664025 Russia
Рetrovietnam University (PVU), Petroleum Institute Tower, Hanoi, Vietnam
Received December 25, 2014
Abstract—Abstract—Dihydroquercetin was converted to nitroso derivative by treatment with nascent nitrous
acid in aqueous solution. The chemical structure of the synthesized compound was determined by quantitative
С NMR spectroscopy. As shown by the NMR spectra, the nitroso group is incorporated at the catechol
ring of the ﬂ avonoid. The antiradical properties of nitrosated dihydroquercetin were evaluated by inhibition of the
pyrocondensate formed in ethylene and propylene production, which readily polymerizes upon heat treatment.
Nitrosated dihydroquercetin is 10–15% more active than the initial compound. The probable mechanisms of the
radical-scavenging action of nitrosated dihydroquercetin are considered.
; taxifolin; DHQ] belongs to the group of
ﬂ avanones. It exhibits a broad spectrum of biological
activity and is one of the most effective natural anti-
oxidants . A study of the antioxidant activity of
DHQ has shown that it is comparable with the known
antioxidant, α-tocopherol, and is two times more active
than β-carotene. It is assumed  that the mechanism of
the antioxidant action of DHQ consists in scavenging and
deactivation of lipid radicals. The DHQ molecule consists
of two aromatic rings (А and В) and one heterocyclic
oxygen-containing fragment С, which bears a carbonyl
group and a free alcoholic group and is fused with ring A.
The antioxidant activity of flavonoids and, in
particular, of DHQ is believed to be associated with the
structure of the heterocyclic fragment of the molecule
(fragment С), namely with the presence or absence of
the carbonyl group, free alcoholic group, and double
bond, whereas the rate of alkyl radical deactivation,
which depends on the number of free hydroxy groups, is
believed to be determined by ring В. The catechol moiety
exhibits the highest activity .
Flavonoids are capable to prevent the generation
and neutralize the effect of active oxygen and nitrogen
molecules by preventing peroxidation of lipids and
forming chelates with metals. Owing to the phenolic
structure, flavonoid molecules act as free radical
scavengers and cause their detoxiﬁ cation [4–6]. The
inhibiting effect of dihydroquercetin on the development
of apoptosis (programmed cell death) was noted.