Isoflavonoid

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3-phenylchromen-4-one
3-phenylchroman (isoflavan) backbone of the isoflavanes

Isoflavonoids are a class of flavonoid phenolic compounds, many of which are biologically active. Isoflavonoids and their derivatives are sometimes referred to as phytoestrogens, as many isoflavonoid compounds have biological effects via the estrogen receptor.

Medically, isoflavonoids and related compounds have been used in many dietary supplements, but the medical and scientific community is generally skeptical of their use. Recently, some natural isoflavonoids have been identified as toxins, including biliatresone which may cause biliary atresia when infants are exposed to the plant product.[1]

The isoflavonoid group is broad, and includes many structurally similar groups, including:

Isoflavonoids are derived from the flavonoid biosynthesis pathway via liquiritigenin or naringenin.[3]

Chemical makeup[edit]

While flavonoids (in the narrow sense) have the 2-phenylchromen-4-one backbone, isoflavonoids have the 3-phenylchromen-4-one backbone (Number 574-12-9, chemical formula C15H10O2, exact mass : 222.0680792) with no hydroxyl group substitution at position 2 (case of the isoflavones) or the 3-phenylchroman (isoflavan, CAS number : 4737-26-2) backbone (case of isoflavanes, e.g. : equol).

See also[edit]

References[edit]

  1. ^ Lorent, Kristin; Gong, Weilong; Koo, Kyung A.; Waisbourd-Zinman, Orith; Karjoo, Sara; Zhao, Xiao; Sealy, Ian; Kettleborough, Ross N.; Stemple, Derek L. (2015-05-06). "Identification of a plant isoflavonoid that causes biliary atresia". Science Translational Medicine 7 (286): 286ra67–286ra67. doi:10.1126/scitranslmed.aaa1652. ISSN 1946-6234. PMID 25947162. Retrieved 2015-05-12. 
  2. ^ superpathway of pterocarpan biosynthesis (via formononetin) on metacyc.org
  3. ^ Isoflavonoid biosynthesis on www.ncbi.nlm.nih.gov/biosystems/