8-Prenylnaringenin

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
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
ChEBI CHEBI:50207 YesY
ChemSpider 421848
Jmol 3D model Interactive image
PubChem 480764
  • 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 340.38 g·mol−1
Vapor pressure {{{value}}}
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

<templatestyles src="Reflist/styles.css" />

Cite error: Invalid <references> tag; parameter "group" is allowed only.

Use <references />, or <references group="..." />
  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ 2.0 2.1 2.2 2.3 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ 7.0 7.1 Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ 9.0 9.1 9.2 9.3 Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
Retrieved from "https://infogalactic.com/w/index.php?title=8-Prenylnaringenin&oldid=720713957"