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'''8-Prenylnaringenin''' known as '''sophoraflavanone B''', '''flavaprenin''', '''(S)-8-dimethylallylnaringenin''' or '''8-PN''' is a [[prenylflavonoid]], and it is one of the most estrogenic [[phytoestrogen]]s known. Its effects are similar to [[estradiol]] at fraction of the potency.<ref name="endocrine 8pren">{{cite journal | url=http://jcem.endojournals.org/content/85/12/4912.full.pdf+html | title=The Endocrine Activities of 8-Prenylnaringenin and Related Hop (Humulus lupulus L.) Flavonoids | author=S. R. Milligan, J. C. Kalita, V. Pocock, V. Van De Kauter, J. F. Stevens, M. L. Deinzer, H. Rong and D. De Keukeleire | journal=Journal of Clinical Endocrinology & Metabolism | year=2000 | month=December | volume=85 | issue=12 | pages=4912–4915 | doi=10.1210/jc.85.12.4912}}</ref>
'''8-Prenylnaringenin''' known as '''sophoraflavanone B''', '''flavaprenin''', '''(S)-8-dimethylallylnaringenin''', '''hopein''' or '''8-PN''' is a [[prenylflavonoid]], and it is one of the most estrogenic [[phytoestrogen]]s known. Its effects are similar to [[estradiol]] at fraction of the potency.<ref name="endocrine 8pren">{{cite journal | url=http://jcem.endojournals.org/content/85/12/4912.full.pdf+html | title=The Endocrine Activities of 8-Prenylnaringenin and Related Hop (Humulus lupulus L.) Flavonoids | author=S. R. Milligan, J. C. Kalita, V. Pocock, V. Van De Kauter, J. F. Stevens, M. L. Deinzer, H. Rong and D. De Keukeleire | journal=Journal of Clinical Endocrinology & Metabolism | year=2000 | month=December | volume=85 | issue=12 | pages=4912–4915 | doi=10.1210/jc.85.12.4912}}</ref>


It is found in hops (''[[Humulus lupulus]]'').<ref>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}}</ref> It can be produced from [[isoxanthohumol]] in fungal cells cultures.,<ref>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}}</ref> and by flora in the human intestine.<ref name="ix8pren">{{cite journal|title=The Prenylflavonoid Isoxanthohumol from Hops (Humulus lupulus L.) Is Activated into the Potent Phytoestrogen 8-Prenylnaringenin In Vitro and in the Human Intestine|url=http://jn.nutrition.org/content/136/7/1862.long |journal=Journal of Nutrition|author=Possemiers et al|year=2006|month=July |volume=136| issue= 7| pages=1862–1867|publisher=American Society for Nutrition }}</ref> At the concentration found in beer, it is unlikely to have an estrogenic effect in breast tissue.<ref>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}}</ref>
8-Prenylnaringenin is found in hops (''[[Humulus lupulus]]'').<ref>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}}</ref> It can be produced from [[isoxanthohumol]] in fungal cells cultures.,<ref>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}}</ref> and by flora in the human intestine.<ref name="ix8pren">{{cite journal|title=The Prenylflavonoid Isoxanthohumol from Hops (Humulus lupulus L.) Is Activated into the Potent Phytoestrogen 8-Prenylnaringenin In Vitro and in the Human Intestine|url=http://jn.nutrition.org/content/136/7/1862.long |journal=Journal of Nutrition|author=Possemiers et al|year=2006|month=July |volume=136| issue= 7| pages=1862–1867|publisher=American Society for Nutrition }}</ref>

8-Prenylnaringenin and synthesized derivatives of it have anticancer activity.<ref>{{cite web | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3474914/ | title=Antiproliferative activity and synthesis of 8-prenylnaringenin derivatives by demethylation of 7-O- and 4′-O-substituted isoxanthohumols | publisher=Med Chem Res | date=January 7, 2012 | accessdate=2013-04-07 | author=Anioł, Mirosław | doi=10.1007/s00044-011-9967-8}}</ref>

At the concentration found in beer, it is unlikely to have an estrogenic effect in breast tissue.<ref>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}}</ref> 8-Prenylnaringenin has been demonstrated to reduce hot flashes in women.<ref>{{cite web | url=http://joe.endocrinology-journals.org/content/191/2/399.long | title=The hop phytoestrogen, 8-prenylnaringenin, reverses the ovariectomy-induced rise in skin temperature in an animal model of menopausal hot flushes. | publisher=Journal of Endocrinology | date=November 15, 2012 | accessdate=2013-04-07 | author=Bowe, James | doi=10.1677/joe.1.06919}}</ref> This prenylflavonoid interacts strongly with [[estrogen receptor beta]].<ref>{{cite web | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2736128/ | title=Development of a screening assay for ligands to the estrogen receptor based on magnetic microparticles and LC-MS | publisher=Comb Chem High Throughput Screen | date=January 11, 2008 | accessdate=2013-04-07 | author=Choi, Yongsoo}}</ref>


The enzyme [[naringenin 8-dimethylallyltransferase]] uses [[dimethylallyl diphosphate]] and (-)-(2S)-[[naringenin]] to produce diphosphate and sophoraflavanone B (8-Prenylnaringenin).
The enzyme [[naringenin 8-dimethylallyltransferase]] uses [[dimethylallyl diphosphate]] and (-)-(2S)-[[naringenin]] to produce diphosphate and sophoraflavanone B (8-Prenylnaringenin).

Revision as of 09:50, 7 April 2013

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
Sophoraflavanone B
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 sophoraflavanone B, flavaprenin, (S)-8-dimethylallylnaringenin, hopein or 8-PN is a prenylflavonoid, and it is one of the most estrogenic phytoestrogens known. Its effects are similar to estradiol at fraction of the potency.[1]

8-Prenylnaringenin is found in hops (Humulus lupulus).[2] It can be produced from isoxanthohumol in fungal cells cultures.,[3] and by flora in the human intestine.[4]

8-Prenylnaringenin and synthesized derivatives of it have anticancer activity.[5]

At the concentration found in beer, it is unlikely to have an estrogenic effect in breast tissue.[6] 8-Prenylnaringenin has been demonstrated to reduce hot flashes in women.[7] This prenylflavonoid interacts strongly with estrogen receptor beta.[8]

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.

References

  1. ^ 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)
  2. ^ 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
  3. ^ 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
  4. ^ 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)
  5. ^ 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.
  6. ^ 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
  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. ^ 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.

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