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8-Prenylnaringenin

8-Prenylnaringenin
Chemical structure of 8-prenylnaringenin
Names
IUPAC name
(2S)-4′,5,7-Trihydroxy-8-(3-methylbut-2-en-1-yl)flavan-4-one
Systematic IUPAC name
(2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-1-benzopyran-4-one
Other names
Hopein; Flavaprenin; Sophoraflavanone B
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9,18,21-23H,8,10H2,1-2H3/t18-/m0/s1
    Key: LPEPZZAVFJPLNZ-SFHVURJKSA-N
  • InChI=1/C20H20O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9,18,21-23H,8,10H2,1-2H3/t18-/m0/s1
    Key: LPEPZZAVFJPLNZ-SFHVURJKBX
  • CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C[C@H](O2)C3=CC=C(C=C3)O)C
Properties
C20H20O5
Molar mass 340.375 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

8-Prenylnaringenin (8-PN; also known as flavaprenin, (S)-8-dimethylallylnaringenin, hopein, or sophoraflavanone B) is a prenylflavonoid phytoestrogen. It is reported to be the most estrogenic phytoestrogen known.[1] The compound is equipotent at the two forms of estrogen receptors, ERα and ERβ,[2] and it acts as a full agonist of ERα.[3] Its effects are similar to those of estradiol, but it is considerably less potent in comparison.[2]

8-PN is found in hops (Humulus lupulus) and in beer, and is responsible for the estrogenic effects of the former.[2][4] It can be produced from isoxanthohumol in fungal cells cultures,[5] and by flora in the human intestine.[1][6]

  1. ^ a b Keiler AM, Zierau O, Kretzschmar G (2013). "Hop extracts and hop substances in treatment of menopausal complaints". Planta Med. 79 (7): 576–9. doi:10.1055/s-0032-1328330. PMID 23512496.
  2. ^ a b c Hajirahimkhan A, Dietz BM, Bolton JL (2013). "Botanical modulation of menopausal symptoms: mechanisms of action?". Planta Med. 79 (7): 538–53. doi:10.1055/s-0032-1328187. PMC 3800090. PMID 23408273.
  3. ^ Green SE (2015), In Vitro Comparison of Estrogenic Activities of Popular Women's Health Botanicals (thesis), archived from the original on 2016-02-22, retrieved 2016-01-01
  4. ^ Nikolic D, Li Y, Chadwick LR, Grubjesic S, Schwab P, Metz P, Van Breemen RB (2004). "Metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus), by human liver microsomes". Drug Metabolism and Disposition. 32 (2): 272–9. doi:10.1124/dmd.32.2.272. PMID 14744951.
  5. ^ Fu ML, Wang W, Chen F, Dong YC, Liu Xj, Ni H, Chen Qh (2011). "Production of 8-Prenylnaringenin from Isoxanthohumol through Biotransformation by Fungi Cells". Journal of Agricultural and Food Chemistry. 59 (13): 7419–26. doi:10.1021/jf2011722. PMID 21634799.
  6. ^ Cite error: The named reference ix8pren was invoked but never defined (see the help page).
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