Daidzein chemical structure

Fig. 2.86. Chemical structures of the iosflavones daidzein, genistein, O-desmethylangolensin, equol, and the lignans enterolactone and enterodiol. Reprinted with permission from Z. Kuklenyik el al. [209].

FIGURE 7.2 Chemical structures of the main soy (genistein and daidzein) and red clover (biochanin A and formononetin) isoflavonoids (aglycones and glucosides). 

As previously mentioned, certain flavonoids can penetrate into the hydrophobic core of membranes, a feature that mainly relies on their hydrophobic character, which is dictated by flavanoid chemical structure and spatial conformation. When flavonoid hydrophobicity was assessed from the partition coefficient between ra-octanol and an aqueous solution, the following order of hydrophobicity was observed flavone, genistein > eriodictyol, myricetin, quercetin, kaempferol, hesperetin, daidzein > > galangin, morin, flavanone, naringenin, taxifolin (Table 4.1). 

Figure 4.1 Chemical structures of the principal classes of polyphenols. The examples shown are of polyphenols with hydroxyl groups in the 7- and 4"-positions. Anthocyanins may also be found in oligomeric forms. The coumestane is coumestrol, The isoflavone (daidzein) differs from the flavonoid h the substitution of the phenolic group. For the flavonoid it is in the 2-position, whereas it is in the 3-position in the isoflavone.

Figure 2 Chemical structures of selected plant polyphenols. Structures include a flavonol (quercetin), isoflavone (daidzein), cinnamic acid (chlorogenic acid), flavan-3-ol (catechin), a lignan microbial metabolite (enterodiol), and a stilbene (resveratrol).

Figure 1 Chemical structures of two major isoflavones and an estrogen. The structures of genistein (4H-henzopyran-4-one-5, 7-dihydroxy-3-(4-hydroxyphenyl) or 4, 5,7-trihy-droxyisoflavone), daidzein (4H-henzopyran-4-one-7-hydroxy-3-(4-hydroxyphenyl) or 4, 7-dihydroxyisoflavone), and estradiol are shown. The purification schemes of the isoflavones and their physical properties are reported in Ref. 98.

Figure 8.1 A diagram t)T ihc chemical structures of the isoflavone aglycones found in soybean as well as conjugates of daidzein. Similar conjugates arc fornicd of genistein and glycitein.

The most important members of the flavonoid family include anthocyanidins (e.g., cyanidin, delphinidin, malvidin), flavonols (e.g., quercetin, kaempferol), flavones (e.g., luteolin, apigenin), flavanones (e.g., myricetin, naringin, hesperetin, naringenin), flavan-3-ols (e.g., catechin, epicatechin, gallocatechin) and, although sometimes classified separately, the isoflavones (e.g., genistein, daidzein). For chemical structures see Figure 1. All these phytochemical are frequently referred to as bioflavonoids due to well established effects in human health maintenance. 

Figure 3. Chemical structures of daidzein, genistein, resorcinol and resveratrol. All agents have a common resorcin moiety, except for daidzein,...

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