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8-Prenylnaringenin

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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
Identifiers
3D model (JSmol)
ChEBI
  • 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
  • CC(=CCC1=C(C=C(C2=C1OC(CC2=O)C3=CC=C(C=C3)O)O)O)C
Properties
C20H20O5
Molar mass 340.36 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 estradiol at a fraction of the potency.[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.[5]

Properties

8-Prenylnaringenin and its synthesized derivatives of it have anticancer activity.[6] This prenylflavonoid preserves bone density in females.[1]

Estrogenic

8-Prenylnaringenin has been demonstrated to reduce hot flashes in women.[1][7] 8-Prenylnaringenin also influences prolactin, and increases other estrogenic responses.[8] This prenylflavonoid interacts strongly with the prolactin receptor,[8] estrogen receptor beta,[9] and estrogen receptor alpha.[2] 8-prenylnaringenin binds to and activates ER-α more times than it does to ER-β.[10]

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

In a 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.[2]

Luteinizing hormone (LH) and follicle stimulating hormone (FSH) are reduced by 8-prenylnaringenin.[8] 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]

Etymology

There is another compound, 8-isopentenylnaringenin, also known as sophoraflavanone B, from sophora flavescens, that could properly be called 8-prenylnaringenin by scientific naming convention.[13]

References

  1. ^ a b c Keiler; Zierau; Kretzschmar (2013). "Hop Extracts and Hop Substances in Treatment of Menopausal Complaints". Planta Med 2013; 79(07): 576-579. 79 (07): 576–567. doi:10.1055/s-0032-1328330.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ^ a b c S. R. Milligan, J. C. Kalita, V. Pocock, V. Van De Kauter, J. F. Stevens, M. L. Deinzer, H. Rong and D. De Keukeleire (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. ^ Metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus), by human liver microsomes. Drug Metab Dispos., February 2004, volume 32, issue 2, pages 272-279, 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. (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. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)
  6. ^ a b 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. ^ a b c d In vivo estrogenic comparisons of Trifolium pratense (red clover) Humulus lupulus (hops), and the pure compounds isoxanthohumol and 8-prenylnaringenin. {{citation}}: Cite has empty unknown parameter: |1= (help)
  9. ^ Choi, Yongsoo (January 11, 2008). "Development of a screening assay for ligands to the estrogen receptor based on magnetic microparticles and LC-MS". Comb Chem High Throughput Screen. Retrieved 2013-04-07.
  10. ^ Overk; et al. (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. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)
  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. ^ Disposition of hop prenylflavonoids in human breast tissue. Bolca S, Li J, Nikolic D, Roche N, Blondeel P, Possemiers S, De Keukeleire D, Bracke M, Heyerick A, van Breemen RB and Depypere H, Mol Nutr Food Res., July 2010, volume 54, Supplement 2, pages 284-294, doi:10.1002/mnfr.200900519, PMID 20486208
  13. ^ 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.{{cite web}}: CS1 maint: multiple names: authors list (link)

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