8-Prenylnaringenin

8-Prenylnaringenin
Chemical structure of 8-prenylnaringenin.
Names
IUPAC name
(2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Other names
Hopein; Flavaprenin; Sophoraflavanone B
Identifiers
3D model (Jmol) Interactive image
ChEBI CHEBI:50207 YesY
ChemSpider 421848
PubChem 480764
Properties
C20H20O5
Molar mass 340.38 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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 ERα and ERβ,[2] and 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]

Properties

In an in vitro study, 8-PN and its synthesized derivatives of it demonstrated to have anticancer activity.[7]

Estrogenic

8-PN was shown to preserve bone density[1] and has been demonstrated to reduce hot flashes.[1][8] 8-PN also induces the secretion of prolactin, and increases other estrogenic responses.[9] The compound binds to and activates ERα more times than it does to ERβ.[1][2][10]

This prenylflavanoid has drawn interest in the study of hormone replacement therapy, and it is comparable to selective estrogen-receptor modulators.[11][12]

In an in vivo study, 8-PN has activated proliferation of mammary cells.[9] At the concentration found in beer, it is unlikely to have an estrogenic effect in breast tissue.[13] Prenylflavonoids from hops, namely 8-PN, are common in herbal breast enlargement preparations.[14]

Similarly to other estrogens, 8-PN induces the expression of the progesterone receptor in various tissues.[9]

Luteinizing hormone (LH) and follicle stimulating hormone (FSH) are suppressed by 8-PN, indicating that it possesses antigonadotropic properties.[9] 8-PN adversely affects male sperm.[15] The role 8-PN plays in fertility requires further research.

Chemistry

The enzyme naringenin 8-dimethylallyltransferase uses 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.[7]

8-Neopentylnaringenin and 8-n-heptylnaringenin are synthetic derivatives of 8-PN.[16]

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.[17]

References

  1. 1 2 3 4 5 6 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. 1 2 3 4 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 3800090Freely accessible. PMID 23408273.
  3. ↑ Green, Sarah E (2015), In Vitro Comparison of Estrogenic Activities of Popular Women’s Health Botanicals
  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: the biological fate of chemicals. 32 (2): 272–9. doi:10.1124/dmd.32.2.272. PMID 14744951.
  5. ↑ Fu, Ming-Liang; Wang, Wei; Chen, Feng; Dong, Ya-Chen; Liu, Xiao-jie; Ni, Hui; Chen, Qi-he (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. ↑ Possemiers, S.; et al. (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. American Society for Nutrition. 136 (7): 1862–1867. PMID 16772450.
  7. 1 2 Anioł, Mirosław (January 7, 2012). "Antiproliferative activity and synthesis of 8-prenylnaringenin derivatives by demethylation of 7-O- and 4′-O-substituted isoxanthohumols". Med Chem Res. doi:10.1007/s00044-011-9967-8. Retrieved 2013-04-07.
  8. ↑ Bowe, James (November 15, 2012). "The hop phytoestrogen, 8-prenylnaringenin, reverses the ovariectomy-induced rise in skin temperature in an animal model of menopausal hot flushes.". Journal of Endocrinology. doi:10.1677/joe.1.06919. Retrieved 2013-04-07.
  9. 1 2 3 4 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. doi:10.1016/j.cbi.2008.06.005. PMC 2574795Freely accessible. PMID 18619951.
  10. ↑ Overk, C. R.; et al. (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. doi:10.1021/jf050448p. PMC 1815392Freely accessible. PMID 16076101.
  11. ↑ 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. doi:10.1111/j.1365-2125.2006.02656.x. PMC 1885137Freely accessible. PMID 16934044.
  12. ↑ Bowe (November 2006). "The hop phytoestrogen, 8-prenylnaringenin, reverses the ovariectomy-induced rise in skin temperature in an animal model of menopausal hot flushes.". Journal of Endocrinology. doi:10.1677/joe.1.06919. Retrieved 2013-04-08.
  13. ↑ Bolca, Selin; Li, Jinghu; Nikolic, Dejan; Roche, Nathalie; Blondeel, Phillip; Possemiers, Sam; De Keukeleire, Denis; Bracke, Marc; Heyerick, Arne; Van Breemen, Richard B.; Depypere, Herman (2010). "Disposition of hop prenylflavonoids in human breast tissue". Molecular Nutrition & Food Research. 54: S284–94. doi:10.1002/mnfr.200900519. PMC 3856213Freely accessible. PMID 20486208.
  14. ↑ S. R. Milligan; J. C. Kalita; V. Pocock; V. Van De Kauter; J. F. Stevens; M. L. Deinzer; H. Rong & D. De Keukeleire (December 2000). "The Endocrine Activities of 8-Prenylnaringenin and Related Hop (Humulus lupulus L.) Flavonoids" (PDF). Journal of Clinical Endocrinology & Metabolism. 85 (12): 4912–4915. doi:10.1210/jcem.85.12.7168. PMID 11134162.
  15. ↑ "Environmental 'hormones' wreck sperm". BBC News. July 2, 2002. Retrieved 2013-06-26.
  16. ↑ Breen, L.; et al. (2009). "The effect of synthetic analogues of the phyto-oestrogen 8-prenylnaringenin on tail skin temperature in a rat hot flush model". The Physiological Society.
  17. ↑ Chadwick; Pauli; Farnsworth (July 1, 2005). "The pharmacognosy of Humulus lupulus L. (hops) with an emphasis on estrogenic properties". Phytomedicine. doi:10.1016/j.phymed.2004.07.006. Retrieved 2013-04-12.
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