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Names | |
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IUPAC name
(2S)-4′,5,7-Trihydroxy-8-(3-methylbut-2-en-1-yl)flavan-4-one
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Systematic IUPAC name
(2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-1-benzopyran-4-one | |
Other names
Hopein; Flavaprenin; Sophoraflavanone B
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Identifiers | |
3D model (
JSmol)
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ChEBI | |
ChemSpider | |
KEGG | |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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Properties | |
C20H20O5 | |
Molar mass | 340.375 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
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 the two forms of estrogen receptors, ERα and ERβ, [2] and it 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]
8-PN was shown to preserve bone density [1] and has been demonstrated to reduce hot flashes. [1] [7] 8-PN also induces the secretion of prolactin, and increases other estrogenic responses. [8] The compound binds to and activates ERα more times[ clarification needed] than it does to ERβ. [1] [2] [9]
This prenylflavanoid has drawn interest in the study of hormone replacement therapy, and it is comparable to some selective estrogen-receptor modulators. [10] [11]
In an in vivo study, 8-PN 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] Similar to other estrogens, 8-PN induces the expression of the progesterone receptor in various tissues. [8]
Luteinizing hormone (LH) and follicle stimulating hormone (FSH) are suppressed by 8-PN, indicating that it possesses antigonadotropic properties. [8] 8-PN adversely affects male sperm. [13] The role 8-PN plays in fertility requires further research.
In an in vitro study, 8-PN and synthetic derivatives demonstrated anticancer properties. [14] More recently, a radioligand binding study showed enhancements in GABAA receptor activity by 8-PN [15]
Prenylflavonoids from hops, including 8-PN, are ingredients in some breast enlargement supplements, [16] though there is no evidence of its effectiveness for this purpose. [17]
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. [14]
8-Neopentylnaringenin and 8-n-heptylnaringenin are synthetic derivatives of 8-PN. [18]
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. [19]
![]() | |
Names | |
---|---|
IUPAC name
(2S)-4′,5,7-Trihydroxy-8-(3-methylbut-2-en-1-yl)flavan-4-one
| |
Systematic IUPAC name
(2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-1-benzopyran-4-one | |
Other names
Hopein; Flavaprenin; Sophoraflavanone B
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChemSpider | |
KEGG | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C20H20O5 | |
Molar mass | 340.375 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
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 the two forms of estrogen receptors, ERα and ERβ, [2] and it 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]
8-PN was shown to preserve bone density [1] and has been demonstrated to reduce hot flashes. [1] [7] 8-PN also induces the secretion of prolactin, and increases other estrogenic responses. [8] The compound binds to and activates ERα more times[ clarification needed] than it does to ERβ. [1] [2] [9]
This prenylflavanoid has drawn interest in the study of hormone replacement therapy, and it is comparable to some selective estrogen-receptor modulators. [10] [11]
In an in vivo study, 8-PN 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] Similar to other estrogens, 8-PN induces the expression of the progesterone receptor in various tissues. [8]
Luteinizing hormone (LH) and follicle stimulating hormone (FSH) are suppressed by 8-PN, indicating that it possesses antigonadotropic properties. [8] 8-PN adversely affects male sperm. [13] The role 8-PN plays in fertility requires further research.
In an in vitro study, 8-PN and synthetic derivatives demonstrated anticancer properties. [14] More recently, a radioligand binding study showed enhancements in GABAA receptor activity by 8-PN [15]
Prenylflavonoids from hops, including 8-PN, are ingredients in some breast enlargement supplements, [16] though there is no evidence of its effectiveness for this purpose. [17]
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. [14]
8-Neopentylnaringenin and 8-n-heptylnaringenin are synthetic derivatives of 8-PN. [18]
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. [19]