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Isoflavonoid

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Class of chemical compound
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.

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

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

Chemical makeup

While flavonoids (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 as equol).

See also

References

  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.
Xenoestrogens
Phytoestrogens
Flavanones
Flavones
Prenylflavonoids
Isoflavones
Isoflavanes
Dihydrochalcones
IsoflavenesGlabrene
Coumestans
Lignans
Flavonolignans
Flavonols
Others
Mycoestrogens
Derivatives
Synthetic
Metalloestrogens
  • Aluminium
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  • Arsenite
  • Barium
  • Cadmium
  • Chromium
  • Cobalt
  • Copper
  • Lead
  • Mercury
  • Nickel
  • Selenite
  • Tin
  • Vanadate
Types of flavonoids
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
Flavonoid biosynthesis
Types of isoflavonoids
Isoflavonoids:
Misc.
GABA receptor modulators
Ionotropic
GABAATooltip γ-Aminobutyric acid A receptor
GABAATooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABABTooltip γ-Aminobutyric acid B receptor
See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators
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