Download Связывание свободных радикалов и предохранение от

Связывание свободных радикалов
и предохранение от перикисного окисления
(увеличение срока существования мембраны клеток и клеточных органелл).
Хим.-фарм. журнал, 1995. №9. С.61
Диквертин (дигидрокверцетин) - новое антиоксидантное и капилляропротекторное
средство.
Колхир В.К., Тюкавкина Н.А., Быков В.А. и др.
В результате проведенного экспериментального исследования выявлены
капилляропротекторные
и
антиоксидантные
свойства
дигидрокверцитина
(превосходящие в ряде случаев эффект кверцетина), сочетающиеся с
противовоспалительным, гастро- и гепатопротекторным, гиполипидемическим и
диуретическим действием. Исходя из результатов исследования антиоксидантных
свойств ДКВ, можно предположить, что он обладает прямой антирадикальной
активностью преимущественно за счет взаимодействия с липидными радикалами.
Вместе с тем, нельзя исключить взаимодействия ДКВ (так же, как и КВ) с
супероксидными анионами. Результаты исследований свидетельствуют о том, что
ДКВ тормозит тетрациклин- и тетрахлорметан-индуцированную липидную
пероксидацию микросом печени, приводящую к интенсивному выходу из
поврежденных печеночных клеток трансаминаз (АЛТ, АСТ и др.).
Биофизика, 1996, Т.41, №3. С.620
Антиоксидантные свойства дигидрокверцетина.
Ю.О.Теселкин, Б.А.Жамбалова, И.В.Бабенкова, Г.И.Клебанов, Н.А.Тюкавкина
Изучено влияние дигидрокверцетина на процесс перикисного окисления
липосомальных мембран из яичных фосфолипидов, индуцированный сульфатом
железа или системой Fe+2-аскорбат. Показано, что антиокислительная активность
дигидрокверцитина сравнима с антиокислительной активностью альфа-токоферола.
Предполагается, что механизм антиокислительного действия дигидрокверцетина
заключается в перехвате липидных радикалов.
Вопросы питания, 1996, №2. С.33
Природные флавоноиды как пищевые антиоксиданты и биологически активные
добавки.
Тюкавкина, И.А. Руленко, Ю.А. Колесник
В обзоре обобщены данные литературы о распространении флавоноидных
соединений (ФС) в пищевых растениях, об их антиоксидантной активности (АОА) во
взаимосвязи со структурой и фармакологическим действием. Особое внимание
уделено проблеме использования ФС в роли экзогенных пищевых антиоксидантов.
ФС не являются для человека ксеногенными веществами, отличаются низкой
токсичностью или полным ее отсутствием, по АОА, как правило, превосходят
известные синтетические антиоксиданты. Обсуждено перспективное направление
придания
жизненно
важным
пищевым
продуктам
целевых
лечебнопрофилактических свойств за счет регулируемого добавления ФС. Показано
преимущество применения в качестве добавок индивидуальных флавоноидов
кверцитина и дигидрокверцетина по сравнению со смесями растительных ФС.
Лечебно-профилактические пищевые продукты с добавкой ФС предназначены для
регионов
с
неблагоприятной
экологической
обстановкой
(повышенная
радиоактивность,
загрязненность
промышленными
отходами),
а
также
подверженных воздействию стрессовых факторов или экстремальных климатических
условий.
Biochem Pharmacol, 1988 Mar 15;37(6):989-995
Interaction of flavonoids with 1,1-diphenyl-2-picrylhydrazyl free radical, liposomal
membranes and soybean lipoxygenase-1.
Ratty AK, Sunamoto J, Das NP
The interaction of the antiperoxidative flavonoids namely, quercetin, quercetrin, rutin,
myricetin, phloretin, phloridzin, catechin, morin and taxifolin with the 1,1,-diphenyl-2picrylhydrazyl (DPPH) free radical was demonstrated. Flavonoid-DPPH interaction was
looked at in the absence and presence of liposomes so as to reveal some information on
bilayers. Perturbations in the lipid bilayers were monitored with the fluorescent probe,
dansylhexadecylamine (DSHA). It was observed that the interaction of the flavonoids on
the lipid bilayer occurred in the polar zone of the lipid bilayers. The flavonoids were able to
scavenge free radicals and could do so in biomembranes. It is suggested that the DPPH free
radical abstracts the phenolic hydrogen of the flavonoid molecule and that this could be the
general mechanism of the scavenging action of the antiperoxidative flavonoids. The effects
of the flavonoids on soybean lipoxygenase-1 were investigated both in buffer and also in
liposomal suspension. All the flavonoids studied showed inhibition of the enzyme in both
systems but the inhibition was greater in the liposomal suspension. Quercetin was the most
potent and it inhibited the lipoxygenase in the liposomal suspension by about 42% while
the other flavonoids inhibited the enzyme by about 14-23%. We observed that the effect of
myricetin and quercetin on the enzyme was pH dependent.
Biosci Biotechnol Biochem 1996 Jun;60(6):945-948
Protection against oxidative damage by dihydroflavonols in Engelhardtia chrysolepis.
Haraguchi H, Mochida Y, Sakai S, Masuda H, Tamura Y, Mizutani K, Tanaka O, Chou
WH
Dihydroflavonol taxifolin and its glycoside, astilbin, from Engelhardtia chrysolepis were
evaluated as antioxidants and radical scavengers. These dihydroflavonols inhibited
superoxide anion production in the xanthine/xanthine oxidase system. Microsomal lipid
peroxidation induced by NADPH-cytochrome P-450 reductase was also inhibited by these
flavonoids. Mitochondrial lipid peroxidation was inhibited only by the aglycon. Taxifolin
protected peroxy radical-damaged mitochondria with no effect on enzyme activity.
Furthermore, taxifolin and astilbin protected red cells against oxidative hemolysis. These
dihydroflavonols were found to be effective for protecting subcellular systems and red
blood cells against oxidative stress in vitro.
Biochem Med Metab Biol 1988 Feb;39(1):69-79
Effects of flavonoids on nonenzymatic lipid peroxidation: structure-activity relationship.
Ratty AK, Das NP
The in vitro effects of several flavonoids on nonenzymatic lipid peroxidation in the rat
brain mitochondria was studied. The lipid peroxidation was indexed by measuring the
MDA production using the 2-thiobarbituric acid TBA test. The flavonoids, apigenin,
flavone, flavanone, hesperidin, naringin, and tangeretin promoted the ascorbic acid-induced
lipid peroxidation, the extent of which depended upon the concentration of the flavonoid
and ascorbic acid. The other flavonoids studied, viz., quercetin, quercetrin, rutin, taxifolin,
myricetin, myricetrin, phloretin, phloridzin, diosmetin, diosmin, apiin, hesperetin,
naringenin, (+)-catechin, morin, fisetin, chrysin, and 3-hydroxyflavone, all showed varying
extents of inhibition of the nonenzymatic lipid peroxidation, induced by either ascorbic acid
or ferrous sulfate. The flavonoid aglycones were more potent in their antiperoxidative
action than their corresponding glycosides. Structure-activity analysis revealed that the
flavonoid molecule with polyhydroxylated substitutions on rings A and B, a 2,3-double
bond, a free 3-hydroxyl substitution and a 4-keto moiety, would confer upon the compound
potent antiperoxidative properties.
- ингибирование ферментов (миелопероксидазы), способствующих перикисному
окислению
Chem Biol Interact 1990;73(2-3):323-335
How flavonoids inhibit the generation of luminol-dependent chemiluminescence by
activated human neutrophils.
Hart BA, Ip Via Ching TR, Van Dijk H, Labadie RP
The mechanism by which (a panel of) flanonoids inhibit the production of luminoldependent chemiluminescence (CLlum) by activated human neutrophils is subject to this
study. CLlum is frequently used as a bio-assay to quantify the effect of xenobiotics on the
production of reactive oxygen species (ROS). Most of the flavonoids decreased CLlum by
inhibition of ROS production by the cells. Four selected flavonoids (Taxifolin, Eriodictyol,
Hesperetin and Luteolin), inhibited myeloperoxidase (MPO) release, while two of these
(Taxifolin and Eriodictyol) strongly inhibited MPO activity. Because CLlum is a MPOdependent process these activities might mask effects of the flavonoids on ROS production.
Finally, our results provide evidence that essential determinants for inhibition of O2(-)release are the OH-groups located in the B-ring of the flavonoid molecule. Flavonoids
methylated at a single OH-group in the B-ring are only inhibitory when they react with
activated neutrophils in the presence of myeloperoxidase.
- повышение устойчивости кожи к воздействию групп с активным кислородом и
продуктам окисления липопронеинов
Environ Mutagen 1981;3(4): 401-419
Mutagenicities of 61 flavonoids and 11 related compounds.
Nagao M, Morita N, Yahagi T, Shimizu M, Kuroyanagi M, Fukuoka M, Yoshihira K,
Natori S, Fujino T, Sugimura T
The mutagenicities of 61 flavonoids (naturally occurring flavonoid aglycones and flavonal
glycosides and synthetic flavonoids) and those of 11 compounds structurally related to
flavonoids were tested with Salmonella typhimurium strains TA100 and TA98. Among the
22 flavone derivatives tested, only wogonin was strongly mutagenic, while five derivatives,
apigenin triacetate, acacetin, chrysoeriol, pedalitin, and pedalitin tetraacetate, were only
weakly mutagenic. Two bisflavonyl derivatives, neither of which has a 3-hydroxyl group,
were not mutagenic. Of the 16 flavonol derivatives tested, all except 3-hydroxyflavone and
the tetra- and penta-methyl ethers of quercetin were mutagenic. Of the five flavanone
derivatives tested, only 7,4-dihydroxyflavanone was mutagenic, showing weak activity. Of
the four flavanolol derivatives tested, hydrorobinetin and taxifolin were weakly mutagenic.
Of the six isoflavone derivatives tested, tectorigenin was weakly mutagenic. Of the 11
compounds in the miscellaneous group structurally related to flavonoids, only
isoliquiritigenin was mutagenic, showing weak activity. For the emergence of strong
mutagenicity, the double bond between positions 2 and 3 and the hydroxyl group at
position 3 are required, except in wogonin, which does not have a hydroxyl group at
position 3 but is strongly mutagenic to TA100. The 3-O-acetyl ester of flavonol, quercetin,
was mutagenic with S9 mix, but 3-O-methyl ethers were not. Six flavonol glycosides, three
quercetin glycosides and three kaempferol glycosides were mutagenic after preincubation
with "hesperidinase," a crude extract of Aspergillus niger. Of 66 flavonoid agylcones and
compounds structurally related to flavonoids, quercetin was the strongest mutagen. The
carcinogenicity of this compound should be clarified because it is ubiquitously found in
vegetables.