Chrysin: Difference between revisions

| verifiedrevid = 407813909

| Name = Chrysin

| ImageFile = Chrysin.png

| ImageSize = 200px

| ImageName = Chrysin

| IUPACName = 5,7-dihydroxy-2-phenyl-4H-chromen-4-one

| OtherNames = 5,7-dihydroxyflavone, Chrysin, 5,7-dihydroxy-2-phenyl-(9CI), NP-005901, galangin flavanone

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| UNII = 3CN01F5ZJ5

| PubChem = 5281607

| InChI = 1/C15H10O4/c16-10-6-11(17)15-12(18)8-13

| Section2 = {{Chembox Properties

| C = 15

| H = 10

| O = 4

| ExactMass = 254.057909 g mol⁻¹

| Density =

| MeltingPt =

| BoilingPt =

'''Chrysin''' is a naturally occurring [[flavone]] chemically extracted from the blue [[passion flower]] (''[[Passiflora caerulea]]''). Honeycomb also contains small amounts. It is also reported in ''[[Oroxylum indicum]]'' or Indian trumpetflower.

==Aromatase inhibition==

Advertised as an [[aromatase]] inhibitor supplement by bodybuilders and athletes.<ref>{{cite journal |author=van Meeuwen JA, Korthagen N, de Jong PC, Piersma AH, van den Berg M. |title=(Anti)estrogenic effects of phytochemicals on human primary mammary fibroblasts, MCF-7 cells and their co-culture |journal=Toxicol Appl Pharmacol. |year=2007 |pmid=17482226 |volume=221 |issue=3 |pages=372–83 |doi=10.1016/j.taap.2007.03.016}}</ref><ref>{{cite journal |author=Kellis JT Jr, Vickery LE. |title=Inhibition of human estrogen synthetase (aromatase) by flavones |journal=Science |year=1984 |pmid=6474163 |doi=10.1126/science.6474163 |volume=225 |pages=1032 |issue=4666}}</ref> However, studies done [[in vivo]] show that orally administered chrysin does not have clinical [[aromatase inhibitor]] activity.<ref>{{cite journal |author=Saarinen N, Joshi SC, Ahotupa M, Li X, Ammälä J, Mäkelä S, Santti R. |title=No evidence for the in vivo activity of aromatase-inhibiting flavonoids |journal=J Steroid Biochem Mol Biol. |year=2001 |pmid=11595503 |doi=10.1016/S0960-0760(01)00098-X |volume=78 |pages=231 |issue=3}}</ref><ref>{{cite journal |author=Int J Sport Nutr Exerc Metab. |title=Effects of anabolic precursors on serum testosterone concentrations and adaptations to resistance training in young men |journal=Int J Sport Nutr Exerc Metab. |year=2000 |pmid=10997957 |volume=10 |issue=3 |pages=340–59}}</ref> This has led to some practitioners administering the drug transdermally(through the skin).

Since chrysin is available as an herbal supplement, some users, for instance body builders, are taking chrysin with the hope of raising testosterone levels or stimulating testosterone production. One study listed below did not find chrysin supplementation to lead to any significant increase in testosterone production.

Chrysin was once believed to be an effective aromatase inhibitor, decreasing the levels of estrogen in the body. However, there is growing consensus that chrysin has no effect on estrogen levels in either animals or humans.<ref>Dean, W.Chrysin: Is It An Effective Aromatase Inhibitor? http://www.vrp.com/articles.aspx?page=LIST&ProdID=1208&qid=&zTYPE=2</ref> Early evidence was reported in the early 1980s through in vitro studies (in the laboratory, as opposed to in the body).<ref>{{cite journal |author=Kellis JT, Vickery LE |title=Inhibition of human estrogen synthetase (aromatase) by flavones |journal=Science |volume=225 |issue=4666 |pages=1032–4 |year=1984 |month=September |pmid=6474163 |url=http://www.sciencemag.org/cgi/pmidlookup?view=long&pmid=6474163 |doi=10.1126/science.6474163}}</ref><ref>{{cite journal |author=Ibrahim AR, Abul-Hajj YJ |title=Aromatase inhibition by flavonoids |journal=J. Steroid Biochem. Mol. Biol. |volume=37 |issue=2 |pages=257–60 |year=1990 |month=October |pmid=2268557 |doi=10.1016/0960-0760(90)90335-I }}</ref><ref>{{cite journal |author=Campbell DR, Kurzer MS |title=Flavonoid inhibition of aromatase enzyme activity in human preadipocytes |journal=J. Steroid Biochem. Mol. Biol. |volume=46 |issue=3 |pages=381–8 |year=1993 |month=September |pmid=9831487 |doi=10.1016/0960-0760(93)90228-O }}</ref><ref>{{cite journal |author=Wang C, Mäkelä T, Hase T, Adlercreutz H, Kurzer MS |title=Lignans and flavonoids inhibit aromatase enzyme in human preadipocytes |journal=J. Steroid Biochem. Mol. Biol. |volume=50 |issue=3-4 |pages=205–12 |year=1994 |month=August |pmid=8049151 |doi=10.1016/0960-0760(94)90030-2 }}</ref><ref>{{cite journal |author=Pelissero C, Lenczowski MJ, Chinzi D, Davail-Cuisset B, Sumpter JP, Fostier A |title=Effects of flavonoids on aromatase activity, an in vitro study |journal=J. Steroid Biochem. Mol. Biol. |volume=57 |issue=3-4 |pages=215–23 |year=1996 |month=February |pmid=8645631 |url=http://linkinghub.elsevier.com/retrieve/pii/0960-0760(95)00261-8 |doi=10.1016/0960-0760(95)00261-8}}</ref><ref>{{cite journal |author=Le Bail JC, Laroche T, Marre-Fournier F, Habrioux G |title=Aromatase and 17β-hydroxysteroid dehydrogenase inhibition by flavonoids |journal=Cancer Lett. |volume=133 |issue=1 |pages=101–6 |year=1998 |month=November |pmid=9929167 |url=http://linkinghub.elsevier.com/retrieve/pii/S0304-3835(98)00211-0 |doi=10.1016/S0304-3835(98)00211-0}}</ref><ref>{{cite journal |author=Jeong HJ, Shin YG, Kim IH, Pezzuto JM |title=Inhibition of aromatase activity by flavonoids |journal=Arch. Pharm. Res. |volume=22 |issue=3 |pages=309–12 |year=1999 |month=June |pmid=10403137 |doi=10.1007/BF02976369 }}</ref> Unfortunately, follow-up studies determined that cell membranes effectively block chrysin from entering the cells and having any effect at all on estrogen levels in biological organisms.<ref>{{cite journal |author=Campbell DR, Kurzer MS |title=Flavonoid inhibition of aromatase enzyme activity in human preadipocytes |journal=J. Steroid Biochem. Mol. Biol. |volume=46 |issue=3 |pages=381–8 |year=1993 |month=September |pmid=9831487 |doi=10.1016/0960-0760(93)90228-O }}</ref><ref>{{cite journal |author=King DS, Sharp RL, Vukovich MD, ''et al.'' |title=Effect of oral androstenedione on serum testosterone and adaptations to resistance training in young men: a randomized controlled trial |journal=JAMA |volume=281 |issue=21 |pages=2020–8 |year=1999 |month=June |pmid=10359391 |url=http://jama.ama-assn.org/cgi/pmidlookup?view=long&pmid=10359391 |doi=10.1001/jama.281.21.2020}}> [see comments]</ref><ref>{{cite journal |author=Saarinen N, Joshi SC, Ahotupa M, Li X, Ammälä J, Mäkelä S, Santti R. |title=No evidence for the in vivo activity of aromatase-inhibiting flavonoids |journal=J Steroid Biochem Mol Biol. |year=2001 |pmid=11595503 |doi=10.1016/S0960-0760(01)00098-X |volume=78 |pages=231 |issue=3}}</ref> In vivo (in the body) studies involving biological organisms lend support to the observation that chrysin has no effect on estrogen levels, but may have other detrimental effects to the body, particularly to thyroid function.<ref>{{cite journal |author=Koehrle J, Auf'mkolk M, Spanka M, Irmscher K, Cody V, Hesch RD |title=Iodothyronine deiodinase is inhibited by plant flavonoids |journal=Prog. Clin. Biol. Res. |volume=213 |pages=359–71 |year=1986 |pmid=3086894 }}</ref> For instance, a 30 day study administered chrysin to four groups of mice both orally and via injection to examine chrysin's effect on serum estrogen levels. The results showed that chrysin had no effect on estrogen levels. Further, the mice treated with chrysin became considerably fatter, possibly due to chrysin's ability to disrupt thyroid function.<ref>Shibayama, J. The Oral Bioavailability and In Vivo Activity of Chrysin in Exercising and Non-Exercising Mice. Submitted for publication, as reported by VRP article (by W. Dean)</ref> Another study on rats administered 50 mg of chrysin per kg body weight, considerably more than found in dietary supplements. Chrysin was found to have no ability to inhibit aromatase, possibly due to poor absorption or bioavailability.<ref>{{cite journal |author=Saarinen N, Joshi SC, Ahotupa M, Li X, Ammälä J, Mäkelä S, Santti R. |title=No evidence for the in vivo activity of aromatase-inhibiting flavonoids |journal=J Steroid Biochem Mol Biol. |year=2001 |pmid=11595503 |doi=10.1016/S0960-0760(01)00098-X |volume=78 |pages=231 |issue=3}}</ref>

==Pharmacokinetics==

* Peak plasma chrysin concentrations after oral dose of 400 mg = 3–16 ng mL−1 <ref name="Waile">{{cite journal |author=Walle T, Otake Y, Brubaker JA, Walle UK, Halushka PV |title=Disposition and metabolism of the flavonoid chrysin in normal volunteers |journal=Br J Clin Pharmacol |volume=51 |issue=2 |pages=143–6 |year=2001 |month=February |pmid=11259985 |pmc=2014445 }}</ref>

* AUC = 5–193 ng mL−1 h <ref name="Waile" />

* Plasma chrysin sulfate concentrations were 30-fold higher (AUC 450–4220 ng mL−1 h).<ref name="Waile" />

* Excretion: urine peak concentration = 0.2–3.1 mg. Most of the dose appeared in faeces as chrysin.<ref name="Waile" />

==Inflammation==

Chrysin has been shown to induce an anti-inflammatory effect, most likely by inhibition of COX-2 expression and via IL-6 signaling.<ref>{{cite journal |author=Woo KJ, Jeong YJ, Inoue H, Park JW, Kwon TK |title=Chrysin suppresses lipopolysaccharide-induced cyclooxygenase-2 expression through the inhibition of nuclear factor for IL-6 (NF-IL6) DNA-binding activity |journal=FEBS Lett. |volume=579 |issue=3 |pages=705–11 |year=2005 |month=January |pmid=15670832 |doi=10.1016/j.febslet.2004.12.048 }}</ref>

==Anxiety==

In rodent in vivo studies, chrysin was found anxiolytic.<ref>{{cite journal |author=Brown E, Hurd NS, McCall S, Ceremuga TE |title=Evaluation of the anxiolytic effects of chrysin, a Passiflora incarnata extract, in the laboratory rat |journal=AANA J |volume=75 |issue=5 |pages=333–7 |year=2007 |month=October |pmid=17966676 }}</ref><ref>{{cite journal |author=Wolfman C, Viola H, Paladini A, Dajas F, Medina JH |title=Possible anxiolytic effects of chrysin, a central benzodiazepine receptor ligand isolated from Passiflora coerulea |journal=Pharmacol. Biochem. Behav. |volume=47 |issue=1 |pages=1–4 |year=1994 |month=January |pmid=7906886 |doi=10.1016/0091-3057(94)90103-1 }}</ref>

In herbal medicine, chrysin is recommended as a remedy for anxiety,<ref>{{cite book |author=Balch, Phyllis A. |title=Prescription for herbal healing: [an easy-to-use A-to-Z reference to hundreds of common disorders and their herbal remedies] |publisher=Avery |location=New York |year=2002 |isbn=0-89529-869-4 }}</ref> but there are no controlled data in humans available.

Many herbal remedies that contain chrysin promote their value as a libido-increasing supplement. There is some in-vivo evidence for chrysin's libido-enhancing effects in rats.<ref>{{cite journal |author=Dhawan K, Kumar S, Sharma A |title=Beneficial effects of chrysin and benzoflavone on virility in 2-year-old male rats |journal=J Med Food |volume=5 |issue=1 |pages=43–8 |year=2002 |pmid=12511112 |doi=10.1089/109662002753723214 }}</ref>

Chrysin demonstrated cell toxicity and inhibition of DNA synthesis at very low concentrations in a normal trout liver cell line.<ref>{{cite journal |author=Tsuji PA, Walle T. |title=Cytotoxic effects of the dietary flavones chrysin and apigenin in a normal trout liver cell line |journal=[[Chem Biol Interact]] |year=2008 |pmid=17884029 |doi=10.1016/j.cbi.2007.08.007 |volume=171 |pages=37 |issue=1 |pmc=2219546}}</ref>

==References==

{{reflist|2}}

{{Flavone}}

[[fr:Chrysine]]

[[pt:Crisina]]