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Isoflavonoid

From Wikipedia, the free encyclopedia
Class of chemical compound
3-phenylchromen-4-one
3-phenylchroman (isoflavan) backbone of the isoflavanes

Isoflavonoids are a class offlavonoid phenolic compounds, many of which are biologically active. Isoflavonoids and their derivatives are sometimes referred to asphytoestrogens, as many isoflavonoid compounds have biological effects via theestrogen receptor.

Medically, isoflavonoids and related compounds have been used in manydietary supplements but the medical and scientific community[who?] is generally skeptical of their use. Recently, some natural isoflavonoids have been identified as toxins, includingbiliatresone which may causebiliary 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 vialiquiritigenin ornaringenin.[3]

Chemical makeup

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Whileflavonoids (in the narrow sense) have the 2-phenylchromen-4-one backbone, isoflavonoids have the 3-phenylchromen-4-one backbone with no hydroxyl group substitution at position 2 (case of the isoflavones) or the 3-phenylchroman (isoflavan) backbone (case of isoflavanes, such asequol).

See also

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References

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  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.doi:10.1126/scitranslmed.aaa1652.ISSN 1946-6234.PMC 4784984.PMID 25947162.
  2. ^superpathway of pterocarpan biosynthesis (via formononetin) on metacyc.org
  3. ^"Isoflavonoid biosynthesis".BioSystems. U.S. National Library of Medicine.
Phytoestrogens
Flavanones
Flavones
Prenylflavonoids
Isoflavones
Isoflavanes
Dihydrochalcones
Isoflavenes
Coumestans
Lignans
Flavonolignans
Flavonols
Others
Mycoestrogens
Derivatives
Synthetic
Metalloestrogens
Types offlavonoids
Flavonoids
Anthoxanthins
Flavones
Flavonols
Isoflavones
Neoflavonoids
Flavans
Flavan
Flavan-3-ols
(flavanols)
Flavan-4-ols
(flavanols)
Flavan-3,4-diols
Flavanones
Flavanonols
Anthocyanidins
3-deoxyanthocyanidins
3-hydroxyanthocyanidin
Aurones
Chalcones
Chalcones
Dihydrochalcone
Miscellaneous
Types of isoflavonoids
Isoflavonoids:
Misc.
Ionotropic
GABAATooltip γ-Aminobutyric acid A receptor
GABAATooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABABTooltip γ-Aminobutyric acid B receptor
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