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Chrysin

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Chrysin
Chrysin
Ball-and-stick model of chrysin
Names
IUPAC name
5,7-Dihydroxyflavone
Systematic IUPAC name
5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one
Other names
NP-005901; Galangin flavanone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.864Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17HcheckY
    Key: RTIXKCRFFJGDFG-UHFFFAOYSA-NcheckY
  • InChI=1/C15H10O4/c16-10-6-11(17)15-12(18)8-13 (19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H
    Key: RTIXKCRFFJGDFG-UHFFFAOYAO
  • O=C\1c3c(O/C(=C/1)c2ccccc2)cc(O)cc3O
Properties
C15H10O4
Molar mass 254.241g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Chrysin,also called5,7-dihydroxyflavone,[1]is aflavonefound inhoney,propolis,thepassion flowers,Passiflora caeruleaandPassiflora incarnata,and inOroxylum indicum.[2]It isextractedfrom various plants, such as the blue passion flower (Passiflora caerulea).[1]Following oral intake by humans, chrysin has lowbioavailabilityand rapidexcretion.[1]It is underbasic researchto evaluate its safety and potentialbiological effects.[1]

Chrysin is an ingredient indietary supplements.[3]As of 2016, there was no clinical use of chrysin,[1]and no evidence for its effect ontestosteronelevels.[4]In 2016, the USFood and Drug Administrationdid not recommend chrysin be included on the list of bulk drug substances that can be used incompoundingunder section 503A of theFederal Food, Drug, and Cosmetic Act.[5]

Occurrence[edit]

A component in variousmedicinal plants(e.g.Scutellaria baicalensis), chrysin is adihydroxyflavone,a type offlavonoid.[6]It is also found inhoney,propolis,thepassion flowers,Passiflora caeruleaandPassiflora incarnata,inOroxylum indicum,[2]carrots,[1]chamomile,[7]many fruits, and inmushrooms,such as the mushroomPleurotus ostreatus.[6]It isextractedfrom various plants,[1]such as the blue passion flower (Passiflora caerulea).[1]

The amount of chrysin in honey from various plant sources is about 0.2 mg per 100 g.[8]Chrysin is typically found at higher amounts in propolis than in honey.[9]A 2010 study found the amount of chrysin was 0.10 mg/kg in honeydew honey, and 5.3 mg/kg in forest honeys.[10]A 2010 study found the amount of chrysin in propolis was as much as 28 g/L.[10]A 2013 study found the amount of chrysin in various mushrooms from the island of Lesvos, Greece, varied between 0.17 mg/kg inLactarius deliciosusto 0.34 mg/kg inSuillus bellinii.[10]

Bioavailability[edit]

The effects of chrysin are reliant on itsbioavailabilityandsolubility.[10]Following oral intake by humans, chrysin has low bioavailability and rapidexcretion.[1]As a result, it is poorly absorbed.[1]

A 1998 study determined that the highest amounts inplasmawas from 12 to 64 nM.[10]As of 2015, theserumlevels of chrysin have not been cited in the literature.[10]Following oral intake by humans, the bioavailability was reported to be from 0.003% to 0.02%.[10]

Oral and topical application[edit]

There is insufficient information to determine how long chrysin has been used in pharmacycompounding.[11]Chrysin is used as an ingredient indietary supplements,but there is no information on systemic exposure fromtopical application.[3]As of 2016, there was no evidence to support any effect of oral chrysin ontestosteronelevels,[4]or an any disease-modifying activity with oral or topical formulations.[12]

Safety[edit]

A daily consumed amount of chrysin of 0.5 to 3 g is considered safe.[6]As of 2016, there was no toxicity attributable to chrysin inclinical trialsoradverse eventreporting.[13]As of 2016, clinical safety issues have not been identified.[14]As of 2016, nonclinical data suggest potential concerns.[14]In 2016, the USFood and Drug Administrationdid not recommend chrysin be included on the list of bulk drug substances that can be used in compounding under section 503A of theFederal Food, Drug, and Cosmetic Actbased on consideration of the following criteria: (1) physicochemical characterization; (2) safety; (3) effectiveness; and (4) historical use of the substance in compounding.[5]

Research[edit]

As of 2016, there is no evidence for chrysin being used in human clinical applications.[1]Research showed that orally administered chrysin does not have clinical activity as anaromataseinhibitor.[1][15] Nanoformulationsofpolyphenols,including chrysin, are made using various carrier methods, such asliposomesandnanocapsules.[16]

Bibliography[edit]

  • Brave M (23 June 2016)."Chrysin"(PDF).Pharmacy Compounding Advisory Committee, Division of Oncology Products, US Food and Drug Administration. pp. 1–13.Public DomainThis article incorporates text from this source, which is in thepublic domain.

References[edit]

  1. ^abcdefghijkl"Chrysin: Compound Summary for CID 5281607".PubChem, National Center for Biotechnology Information, US National Institutes of Health. 14 July 2018.
  2. ^abMorissette M, Litim N, Di Paolo T (18 May 2017)."Chapter 2 – Natural Phytoestrogens: A Class of Promising Neuroprotective Agents for Parkinson Disease".In Brahmachari G (ed.).Discovery and Development of Neuroprotective Agents from Natural Products.Elsevier Science. p. 32.doi:10.1016/B978-0-12-809593-5.00002-1.ISBN978-0-12-809769-4.
  3. ^abFDA 2016,p. 3.
  4. ^abFDA 2016,p. 8.
  5. ^abFDA 2016,p. 13.
  6. ^abcSamarghandian S, Farkhondeh T, Azimi-Nezhad M (2017)."Protective Effects of Chrysin Against Drugs and Toxic Agents".Dose-response.15(2): 1559325817711782.doi:10.1177/1559325817711782.PMC5484430.PMID28694744.
  7. ^Zhandi, M; Ansari, M; Roknabadi, P; Zare Shahneh, A; Sharafi, M (2017). "Orally administered Chrysin improves post-thawed sperm quality and fertility of rooster".Reproduction in Domestic Animals.52(6): 1004–1010.doi:10.1111/rda.13014.ISSN0936-6768.PMID28695606.S2CID28744455.
  8. ^Istasse T, Jacquet N, Berchem T, Haubruge E, Nguyen BK, Richel A (2016)."Extraction of Honey Polyphenols: Method Development and Evidence of Cis Isomerization".Analytical Chemistry Insights.11:49–57.doi:10.4137/ACI.S39739.PMC4981221.PMID27547032.
  9. ^Premratanachai P, Chanchao C (2014)."Review of the anticancer activities of bee products".Asian Pacific Journal of Tropical Biomedicine.4(5): 337–44.doi:10.12980/APJTB.4.2014C1262.PMC3985046.PMID25182716.
  10. ^abcdefgNabavi SF, Braidy N, Habtemariam S, Orhan IE, Daglia M, Manayi A, Gortzi O, Nabavi SM (2015). "Neuroprotective effects of chrysin: From chemistry to medicine".Neurochemistry International.90:224–31.doi:10.1016/j.neuint.2015.09.006.PMID26386393.S2CID24391203.
  11. ^FDA 2016,p. 11.
  12. ^FDA 2016,p. 9.
  13. ^FDA 2016,p. 10.
  14. ^abFDA 2016,p. 12.
  15. ^Saarinen N, Joshi SC, Ahotupa M, Li X, Ammälä J, Mäkelä S, Santti R (September 2001). "No evidence for the in vivo activity of aromatase-inhibiting flavonoids".The Journal of Steroid Biochemistry and Molecular Biology.78(3): 231–9.doi:10.1016/S0960-0760(01)00098-X.PMID11595503.S2CID25787862.
  16. ^Davatgaran-Taghipour Y, Masoomzadeh S, Farzaei MH, Bahramsoltani R, Karimi-Soureh Z, Rahimi R, Abdollahi M (2017)."Polyphenol nanoformulations for cancer therapy: experimental evidence and clinical perspective".International Journal of Nanomedicine.12:2689–2702.doi:10.2147/IJN.S131973.PMC5388197.PMID28435252.
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