Isoflavones oxidants

KERRY N and ABBEY M (1998) The isoflavone genistein inhibits copper and peroxyl radical mediated low density lipoprotein oxidation in vitro. Atherosclerosis. 140 (2) 341-7. 

WEI H, CAO Q AND RAHN R o (1996) Inhibition of UV light- and Fenton reaction-induced oxidative DNA damage by the soybean isoflavone genistein. Carcinogenesis. 17 (1) 73-7. 

Engelman HM, Alekel DL, Hanson LN, Kanthasamy AG and Reddy MB. 2005. Blood lipid and oxidative stress responses to soy protein with isoflavones and phytic acid in postmenopausal women. Am J Clin Nutr 81 590-596. 

Koch-Haaf reaction, 17, 3 Kornblum oxidation, 39, 3 Kostaneki synthesis of chromanes, flavones, and isoflavones, 8, 3... 

Wiseman, H., O Reilly, J.D., Adlercreutz, FI., Mallet, A.I., Bowey, E.A., Rowland, I.R., and Sanders, T.A., Isoflavone phytoestrogens consumed in soy decrease F(2)-isoprostane concentrations and increase resistance of low-density lipoprotein to oxidation in humans, Am. J. Clin. Nutr., 72, 395, 2000. 

This increased resistance of LDL to oxidation is in agreement with the findings of a number of studies with dietary soy, including the increase in lag time in a study in six young healthy male and female subjects who consumed three soy bars per day (providing 57 mg total isoflavones/day 36 mg genistein and 21 mg daidzein) for 2 weeks.Although HDL-derived 17(3-estradiol fatty acid esters have been shown to accumulate in LDL ex v/vo and esterified... 

Djuric Z, Chen G, Doerge DR, Heilbrun LK, Kucuk O. Effect of soy isoflavone supplementation on markers of oxidative stress in men and women. Cancer Lett. 172, 1-6, 2001. 

Similarly, the isoflavone 423a, obtained by dehydrogenation (Mn02) of nepseudin,871 leads to benzofuran (424a) which is oxidized (alkaline H2Oa ) to 6-hydroxybenzofuran-5-carboxylic acid. The same treatment... 

Chromones are readily oxidized by permanganate or dichromate with opening of the pyran ring and the formation of a salicylic acid (402). Flavones and isoflavones are also degradatively oxidized for example oxidation of munetone (403) with alkaline hydrogen peroxide yields 2-methoxybenzoic acid and 4-hydroxy-2-isopropylbenzofuran-5-carboxylic (isotubaic) acid. 

Several groups have described syntheses of chromones which involve the use of enamines. Reaction of salicylaldehyde with 1-morpholinocyclohexene gives the chromanol which is readily oxidized to the chromone (66JOC1232). Other examples include the use of 1-morpholino-l-phenylethylene which gives flavene, whilst N-styrylmorpholine yields isoflavone. The enamine reaction is considered to proceed in the normal manner with subsequent cyclization involving the neighbouring phenolic group (Scheme 163). 

The oxidative rearrangement of chalcones is a valuable route to isoflavones which has been thoroughly investigated. Initially, the conversion was achieved in two distinct steps. Epoxidation of a 2 -benzyloxychalcone, carried out by conventional techniques, is followed by treatment with a Lewis acid, such as boron trifluoride etherate, which brings about the rearrangement. 

Kulling SE, Honig DM, Metzler M. 2001. Oxidative metabolism of the soy isoflavones daidzein and genistein in humans in vitro and in vivo. J Agric Food Chem 49 3024-3033. 

Nitric Oxide Synthesis as a Vascular Target for Dietary Isoflavones 252... 

NITRIC OXIDE SYNTHESIS AS A VASCULAR TARGET FOR DIETARY ISOFLAVONES... 

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