8-Prenylnaringenin

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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

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]

Properties

Estrogenic

8-PN was shown to preserve bone density[1] and has been demonstrated to reduce hot flashes.[1][7] 8-PN also induces the secretion of prolactin, and increases other estrogenic responses.[8] The compound binds to and activates ERα more times[clarification needed] than it does to ERβ.[1][2][9]

This prenylflavanoid has drawn interest in the study of

selective estrogen-receptor modulators.[10][11]

In an in vivo study, 8-PN has activated proliferation of

mammary cells.[8] At the concentration found in beer, it is unlikely to have an estrogenic effect in breast tissue.[12] Similar to other estrogens, 8-PN induces the expression of the progesterone receptor in various tissues.[8]

antigonadotropic properties.[8] 8-PN adversely affects male sperm.[13] The role 8-PN plays in fertility
requires further research.

Other

In an in vitro study, 8-PN and synthetic derivatives demonstrated anticancer properties.[14] More recently, a radioligand binding study showed enhancements in GABAA receptor activity by 8-PN[15]

Prenylflavonoids from hops, including 8-PN, are ingredients in some breast enlargement supplements,[16] though there is no evidence of its effectiveness for this purpose.[17]

Chemistry

The enzyme

dimethylallyl diphosphate and (−)-(2S)-naringenin
to produce diphosphate and sophoraflavanone B (8-prenylnaringenin).

The enzyme 8-dimethylallylnaringenin 2'-hydroxylase uses sophoraflavanone B (8-prenylnaringenin), NADPH, H+ and O2 to produce leachianone G, NADP+ and H2O.

Synthesized derivatives of 8-PN are: 7,4′-di-O-methyl-8-prenylnaringenin; 7-O-pentyl-8-prenylnaringenin; 7,4′-Di-O-allyl-8-prenylnaringenin; 7,4′-Di-O-acetyl-8-prenylnaringenin; and 7,4′-Di-O-palmitoyl-8-prenylnaringenin.[14]

8-Neopentylnaringenin and 8-n-heptylnaringenin are synthetic derivatives of 8-PN.[18]

Etymology

There is another compound, 8-isopentenylnaringenin,[1] also known as sophoraflavanone B, from Sophora flavescens, that could properly be called 8-prenylnaringenin by scientific naming convention.[19]

References

  1. ^
    PMID 23512496
    .
  2. ^
    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. PMID 14744951
    .
  5. PMID 21634799
    .
  6. ^ Possemiers S, Bolca S, Grootaert C, Heyerick A, Decroos K, Dhooge W, De Keukeleire D, Rabot S, Verstraete W, Van de Wiele T (July 2006). "The Prenylflavonoid Isoxanthohumol from Hops (Humulus lupulus L.) Is Activated into the Potent Phytoestrogen 8-Prenylnaringenin In Vitro and in the Human Intestine". Journal of Nutrition. 136 (7). American Society for Nutrition: 1862–1867.
    PMID 16772450
    .
  7. PMID 17088409
    .
  8. ^ a b c d Overk CR, Guo J, Chadwick LR, Lantvit DD, Minassi A, Appendino G, Chen SN, Lankin DC, Farnsworth NR, Pauli GF, Van Breemen RB, Bolton JL (2008). "In vivo estrogenic comparisons of Trifolium pratense (red clover) Humulus lupulus (hops), and the pure compounds isoxanthohumol and 8-prenylnaringenin". Chemico-Biological Interactions. 176 (1): 30–39.
    PMID 18619951
    .
  9. ^ Overk CR, Yao P, Chadwick LR, Nikolic D, Sun Y, Cuendet MA, Deng Y, Hedayat AS, Pauli GF, Farnsworth NR, van Breemen RB, Bolton JL (August 2005). "Comparison of the In Vitro Estrogenic Activities of Compounds from Hops (Humulus lupulus) and Red Clover (Trifolium pratense)". J Agric Food Chem. 53 (16): 6246–6253.
    PMID 16076101
    .
  10. ^ Rad, Hümpel, Schaefer, Schoemaker, Schleuning, Cohen, Burggraaf (September 1, 2006). "Pharmacokinetics and systemic endocrine effects of the phyto-oestrogen 8-prenylnaringenin after single oral doses to postmenopausal women". British Journal of Clinical Pharmacology. 62 (3): 288–296.
    PMID 16934044
    .
  11. PMID 17088409
    .
  12. PMID 20486208
    .
  13. ^ "Environmental 'hormones' wreck sperm". BBC News. July 2, 2002. Retrieved 2013-06-26.
  14. ^
    PMID 23087590
    .
  15. S2CID 73456325
    .
  16. PMID 11134162
    .
  17. PMID 15457059
    .
  18. ^ Breen L, Sugden D, Heyerick A, O'Byrne K, Milligan S (2009). "The effect of synthetic analogues of the phyto-oestrogen 8-prenylnaringenin on tail skin temperature in a rat hot flush model". Proceedings of the Physiological Society. Archived from the original on 3 December 2013.
  19. ^ Chadwick, Pauli, Farnsworth (July 1, 2005). "The pharmacognosy of Humulus lupulus L. (hops) with an emphasis on estrogenic properties". Phytomedicine. 13 (1–2): 119–31.
    PMID 16360942
    .
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