Coumestrol structure

KULLING s E, ROSENBERG B, JACOBS E, METZLER M (1999) The phytoestrogens coumestrol and genistein induce structural and chromosomal aberrations in cultured human peripheral blood lympocytes. Arch Toxicol. Ti 50-54. 

The basic structures of flavanones, flavones, and isoflavones together with coumestrol, an intermediate in the phenylpropane metabolism, are given in Fig. 2. The 3,5,7,3 -tetrahydroxy-4 -methoxyflavanone is a nod gene inducer in Rhizo-bium leguminosarum bv. viciae the 3, 4, 5,7-tetrahydroxyflavone, in Rhizobium ineliloti and 4,7-dihydroxyisoflavone, in Bradyrhizobium japonicum. Coumestrol, an intermediate in phenylpropane metabolism, is only a weak inducer (7). 

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.

Fig. (3). Chemical structures of major isoflavones, metabolic derivatives, coumestrol and estradiol.

FIGURE 25.1 Structures of nonsteroidal phytoestrogens. The most prevalent classes of phytoestrogens are (1) flavones apigenin (2) kaempferol (3) isoflavones daidzein (4) genistein (5) formononetin (6) biochanin A (7) lignans enterolactone (8) coumestans coumestrol (9) flavanones 8-prenylnaringenin. 

Fig. 60.2 Structures of the estrogen estradiol, the androgen testosterone, and the Isoflavonoids -daidzein, genistein, and coumestrol...

According to the structure, pterocarpans are divided into simple pterocarpans (an example is medicarpin with a methoxyl group and maackiain with a methylenedioxy group), pterocarpans (such as coumestrol) and 6-hydroxypterocarpans (such as pisatin), some of which, such as glyceollin III (10-103) with a prenylated substituent on the furan ring, have a more complex structure. 

FIGURE 2 The coumestan skeleton, and the structures of wedelolactone and coumestrol. 

Figure 1.11 Structures of the oestrogen oestradiol, the androgen testosterone and the isoflavonoids daidzein, genistein and coumestrol.

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