8-Prenylnaringenin

From Wikipedia, the free encyclopedia
8-Prenylnaringenin
Chemical structure of 8-prenylnaringenin.
Identifiers
PubChem 480764
ChEBI CHEBI:50207 YesY
Jmol-3D images Image 1
Properties
Molecular formula C20H20O5
Molar mass 340.36 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

8-Prenylnaringenin known as flavaprenin, (S)-8-dimethylallylnaringenin, hopein or 8-PN is a prenylflavonoid. It is the most estrogenic phytoestrogen known.[1] Its effects are similar to, but weaker than estradiol.[2]

8-Prenylnaringenin is found in hops (Humulus lupulus).[3] It can be produced from isoxanthohumol in fungal cells cultures,[4] and by flora in the human intestine.[1][5]

Properties

In an in vitro study, 8-Prenylnaringenin and its synthesized derivatives of it demonstrated to have anticancer activity.[6] This prenylflavonoid was shown to preserve bone density.[1]

Estrogenic

8-Prenylnaringenin has been demonstrated to reduce hot flashes.[1][7] 8-Prenylnaringenin also influences prolactin, and increases other estrogenic responses.[8] 8-prenylnaringenin binds to and activates ER-α more times than it does to ER-β.[1][2][9] This prenylflavonoid also interacts with the progesterone receptor.[8]

This prenylflavanoid has drawn interest in the study of hormone replacement therapy, and it is comparable to selective estrogen-receptor modulators.[10][11]

In an in vivo study, 8-prenylnaringenin 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] Prenylflavonoids from hops, namely 8-prenylnaringenin, are common in herbal breast enlargement preparations.[13]

Luteinizing hormone (LH) and follicle stimulating hormone (FSH) are reduced by 8-prenylnaringenin.[8] 8-Prenylnaringenin adversely affects male sperm.[14] The role 8-prenylnaringenin 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-prenylnaringenin 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.[6]

8-neopentylnaringenin and 8-n-heptylnaringenin are synthetic forms of 8-Prenylnaringenin.[15]

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.[16]

References

  1. 1.0 1.1 1.2 1.3 1.4 1.5 Keiler; Zierau; Kretzschmar (2013). "Hop Extracts and Hop Substances in Treatment of Menopausal Complaints". Planta Medica 2013; 79(07): 576-579 79 (7): 576–567. doi:10.1055/s-0032-1328330. 
  2. 2.0 2.1 Hajirahimkhan; Dietz; Bolton (2013). "Botanical Modulation of Menopausal Symptoms: Mechanisms of Action?". Planta Med 79 (07): 538–553. doi:10.1055/s-0032-1328187. 
  3. 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. 
  4. Production of 8-Prenylnaringenin from Isoxanthohumol through Biotransformation by Fungi Cells. Ming-liang Fu, Wei Wang, Feng Chen, Ya-chen Dong, Xiao-jie Liu, Hui Ni and Qi-he Chen, J. Agric. Food Chem., 2011, volume 59, issue 13, pages 7419–7426, doi:10.1021/jf2011722
  5. Possemiers 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. 
  6. 6.0 6.1 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. 
  7. 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. 
  8. 8.0 8.1 8.2 8.3 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 2574795. PMID 18619951 
  9. Overk 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. 
  10. Rad, Hümpel, 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 1885137. PMID 16934044. 
  11. 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. 
  12. 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. PMID 20486208. 
  13. S. R. Milligan, J. C. Kalita, V. Pocock, V. Van De Kauter, J. F. Stevens, M. L. Deinzer, H. Rong and D. De Keukeleire (December 2000). "The Endocrine Activities of 8-Prenylnaringenin and Related Hop (Humulus lupulus L.) Flavonoids". Journal of Clinical Endocrinology & Metabolism 85 (12): 4912–4915. doi:10.1210/jc.85.12.4912. 
  14. "Environmental 'hormones' wreck sperm". BBC News. July 2, 2002. Retrieved 2013-06-26. 
  15. Breen 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 
  16. 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. 
This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.