Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Hesperidin: Difference between pages

{{short description|Chemical compound}}

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{{distinguish|hesperadin}}

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| verifiedrevid = 461767244

| ImageFile = Hesperidin structure.svg

| ImageSize = 200px

| ImageFile2 = Hesperidin 3D BS.png

| ImageSize2 = 200px

| IUPACName = (2''S'')-3′,5-Dihydroxy-4′-methoxy-7-[α-<small>L</small>-rhamnopyranosyl-(1→6)-β-<small>D</small>-glucopyranosyloxy]flavan-4-one

| SystematicName = (2²''S'',4²''S'',4³''R'',4⁴''S'',4⁵''S'',4⁶''R'',7²''R'',7³''R'',7⁴''R'',7⁵''R'',7⁶''S'')-1³,2⁵,4³,4⁴,4⁵,7³,7⁴,7⁵-Octahydroxy-1⁴-methoxy-7⁶-methyl-2²,2³-dihydro-2⁴''H''-3,6-dioxa-2(2,7)-[1]benzopyrana-4(2,6),7(2)-bis(oxana)-1(1)-benzenaheptaphan-2⁴-one

| OtherNames = Hesperetin, 7-rutinoside,<ref name="pmid24257882">{{cite journal |vauthors=Dakshini KM |title=Hesperetin 7-rutinoside (hesperidin) and taxifolin 3-arabinoside as germination and growth inhibitors in soils associated with the weed, ''[[Pluchea lanceolata]]'' (DC) C.B. Clarke (Asteraceae) |journal=Journal of Chemical Ecology |volume=17 |issue=8 |pages=1585–1591 |date=August 1991 |pmid=24257882 |doi=10.1007/BF00984690 |bibcode=1991JCEco..17.1585I |s2cid=35483504}}</ref> Cirantin, hesperidoside{{!}}heperetin, 7-rhamnoglucoside, hesperitin, 7-O-rutinoside

| Section1 = {{Chembox Identifiers

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

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 449317

| UNII_Ref = {{fdacite|correct|FDA}}

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| KEGG = C09755

| Section2 = {{Chembox Properties

| C=28 | H=34 | O=15

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| Density= 1.65 ± 0.1g/mL (predicted)

| MeltingPt= 262 °C

| BoilingPt= 930.1 ± 65 °C (predicted)

| Solubility=

| Section3 = {{Chembox Hazards

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'''Hesperidin''' is a [[flavanone]] [[glycoside]] found in [[citrus]] fruits. Its [[aglycone]] is [[hesperetin]]. Its name is derived from the word "[[hesperidium]]", for fruit produced by citrus trees.

Hesperidin was first isolated in 1828 by French chemist M. Lebreton from the white inner layer of [[citrus]] peels ([[mesocarp]], albedo).<ref>{{cite journal | vauthors = Lebreton, M | year = 1828 | journal = Journal de Pharmacie et de Sciences Accessories | volume = 14 | page = 377 | title = Sur la matière cristalline des orangettes, et analyse de ces fruits non encore developpés, famille des Hesperidées | url = http://gallica.bnf.fr/ark:/12148/bpt6k214864s/f380.image | access-date = 2016-10-30 | archive-date = 2020-10-20 | archive-url = https://web.archive.org/web/20201020212601/https://gallica.bnf.fr/ark:/12148/bpt6k214864s/f380.image | url-status = live }}</ref><ref>{{cite web |url=http://www.hmdb.ca/metabolites/HMDB03265 |title=Metabocard for Hesperidin (HMDB03265) |publisher=Human Metabolome Database, The Metabolomics Innovation Centre, Genome Canada |date=11 February 2016 |access-date=30 October 2016 |archive-date=30 October 2016 |archive-url=https://web.archive.org/web/20161030204739/http://www.hmdb.ca/metabolites/HMDB03265 |url-status=live }}</ref>

Hesperidin is believed to play a role in [[plant]] defense.

== Sources ==

===''Rutaceae''===

* 700–2,500 ppm in fruit of ''[[Citrus aurantium]]'' ([[bitter orange]], [[petitgrain]])<ref>{{ cite web | url = http://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=276 | title = ''Citrus aurantium'' L. | date = 6 Oct 2014 | work = Dr. Duke's Phytochemical and Ethnobotanical Databases | url-status = dead | archive-url = https://web.archive.org/web/20041110035619/http://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=276 | archive-date = 2004-11-10 }}</ref>

* in [[orange juice]] (''Citrus sinensis'')

* in ''[[Zanthoxylum gilletii]]''<ref name="Corrado Tringali 2001, Pages 538">{{cite journal |vauthors=Tringali C, Spatafora C, Calì V, Simmonds MS |title=Antifeedant constituents from ''Fagara macrophylla'' |journal=Fitoterapia |volume=72 |issue=5 |pages=538–543 |date=June 2001 |pmid=11429249 |doi=10.1016/S0367-326X(01)00265-9}}</ref>

* in [[lemon]]<ref name="Pearson 2006 S74-S80">{{cite journal |vauthors=Peterson JJ, Beecher GR, Bhagwat SA, Dwyer JT, Gebhardt SE, Haytowitz DB, Holden JM |title=Flavanones in grapefruit, lemons, and limes: A compilation and review of the data from the analytical literature |journal=Journal of Food Composition and Analysis |year=2006 |volume=19 |issue=Supplement |pages=S74–S80 |doi=10.1016/j.jfca.2005.12.009 |url=http://www.ars.usda.gov/SP2UserFiles/Place/12354500/Articles/jfca19_S74-S80.pdf |access-date=2014-01-24 |archive-date=2013-04-02 |archive-url=https://web.archive.org/web/20130402191306/http://www.ars.usda.gov/SP2UserFiles/Place/12354500/Articles/jfca19_S74-S80.pdf |url-status=live }}</ref>

* in [[Lime (fruit)|lime]]<ref name="Pearson 2006 S74-S80"/>

* in leaves of ''[[Agathosma serratifolia]]''

===''Lamiaceae''===

[[Peppermint]] contains hesperidin.<ref>{{cite journal |vauthors=Dolzhenko Y, Bertea CM, Occhipinti A, Bossi S, Maffei ME |title=UV-B modulates the interplay between terpenoids and flavonoids in peppermint (''Mentha × piperita'' L.) |journal=Journal of Photochemistry and Photobiology B: Biology |volume=100 |issue=2 |pages=67–75 |date=August 2010 |pmid=20627615 |doi=10.1016/j.jphotobiol.2010.05.003|hdl=2318/77560 |hdl-access=free }}</ref>

[[File:Orange juice UHPLC UV chromatogram.png|thumb|right|[[Ultraviolet]] 280&nbsp;nm [[chromatogram]] after [[High-performance liquid chromatography|UHPLC]] separation of commercial [[orange juice]]. Hesperidin is the peak at 16.44&nbsp;min.]]

===Content in foods===

Approximate hesperidin content per 100 ml or 100 g<ref>{{cite web |url=http://phenol-explorer.eu/contents/polyphenol/207 |title=Foods in which hesperidin is found |publisher=Phenol-Explorer database, version 3.6 |access-date=15 March 2017 |archive-date=16 March 2017 |archive-url=https://web.archive.org/web/20170316204119/http://phenol-explorer.eu/contents/polyphenol/207 |url-status=live }}</ref>

* 481&nbsp;mg peppermint, dried

* 44&nbsp;mg [[blood orange]], pure juice

* 26&nbsp;mg [[orange (fruit)|orange]], pure juice

* 18&nbsp;mg [[lemon]], pure juice

* 14&nbsp;mg [[lime (fruit)|lime]], pure juice

* 1&nbsp;mg [[grapefruit]], pure juice

== Metabolism ==

[[Hesperidin 6-O-alpha-L-rhamnosyl-beta-D-glucosidase|Hesperidin 6-''O''-α-{{sc|L}}-rhamnosyl-β-{{sc|D}}-glucosidase]], an enzyme that uses hesperidin and water to produce [[hesperetin]] and [[rutinose]], is found in the ''[[Ascomycetes]]'' species.<ref>{{cite journal |vauthors=Mazzaferro L, Piñuel L, Minig M, Breccia JD |title=Extracellular monoenzyme deglycosylation system of 7-''O''-linked flavonoid beta-rutinosides and its disaccharide transglycosylation activity from Stilbella fimetaria |journal=Archives of Microbiology |volume=192 |issue=5 |pages=383–393 |date=May 2010 |pmid=20358178 |doi=10.1007/s00203-010-0567-7 |bibcode=2010ArMic.192..383M |s2cid=25979489|hdl=11336/81705 |hdl-access=free }}</ref>

== Research ==

As a [[flavanone]] found in the [[peel (fruit)|rinds]] of [[citrus]] fruits (such as oranges or lemons), hesperidin is under preliminary research for its possible biological properties [[in vivo]]. One review did not find evidence that hesperidin affected [[blood lipid]] levels or [[hypertension]].<ref name="Mohammadi">{{cite journal |vauthors=Mohammadi M, Ramezani-Jolfaie N, Lorzadeh E, Khoshbakht Y, Salehi-Abargouei A |title=Hesperidin, a major flavonoid in orange juice, might not affect lipid profile and blood pressure: A systematic review and meta-analysis of randomized controlled clinical trials |journal=Phytotherapy Research |volume=33 |issue=3 |pages=534–545 |date=March 2019 |pmid=30632207 |doi=10.1002/ptr.6264 |s2cid=58564512}}</ref> Another review found that hesperidin may improve [[endothelium|endothelial function]] in humans, but the overall results were inconclusive.<ref>{{cite journal |vauthors=Pla-Pagà L, Companys J, Calderón-Pérez L, Llauradó E, Solà R, Valls RM, Pedret A |title=Effects of hesperidin consumption on cardiovascular risk biomarkers: a systematic review of animal studies and human randomized clinical trials |journal=Nutrition Reviews |volume=77 |issue=12 |pages=845–864 |date=December 2019 |pmid=31271436 |doi=10.1093/nutrit/nuz036 | doi-access = free}}</ref>

== Biosynthesis ==

[[File:SVG-CDX-HesperidinFromLPhe-Final.svg|alt=Chemical drawing scheme depicting the successive chemoenzymatic transformations from L-phenylalanine to arrive at hesperidin.|thumb|The biosynthesis of hesperidin proceeds from {{sc|L}}-phenylalanine in nine steps.]]

The biosynthesis of hesperidin stems from the [[phenylpropanoid pathway]], in which the natural amino acid {{sc|L}}-[[phenylalanine]] undergoes a deamination by [[Phenylalanine ammonia-lyase|phenylalanine ammonia lyase]] to afford [[Cinnamic acid|(''E'')-cinnamate]].<ref>{{cite journal |vauthors=Wanner LA, Li G, Ware D, Somssich IE, Davis KR |title=The phenylalanine ammonia-lyase gene family in ''Arabidopsis thaliana'' |journal=Plant Molecular Biology |volume=27 |issue=2 |pages=327–338 |date=January 1995 |pmid=7888622 |doi=10.1007/BF00020187 |s2cid=25919229}}</ref> The resulting monocarboxylate undergoes an [[Redox|oxidation]] by [[Trans-cinnamate 4-monooxygenase|cinnamate 4-hydroxylase]] to afford (''E'')-4-coumarate,<ref>{{cite journal |vauthors=Mizutani M, Ohta D, Sato R |title=Isolation of a cDNA and a genomic clone encoding cinnamate 4-hydroxylase from Arabidopsis and its expression manner in planta |journal=Plant Physiology |volume=113 |issue=3 |pages=755–763 |date=March 1997 |pmid=9085571 |pmc=158193 |doi=10.1104/pp.113.3.755}}</ref> which is transformed into [[Coumaroyl-CoA|(''E'')-4-coumaroyl-CoA]] by [[4-Coumarate-CoA ligase|4-coumarate-CoA ligase]].<ref>{{cite journal |vauthors=Costa MA, Bedgar DL, Moinuddin SG, Kim KW, Cardenas CL, Cochrane FC, Shockey JM, Helms GL, Amakura Y, Takahashi H, Milhollan JK, Davin LB, Browse J, Lewis NG |title=Characterization in vitro and in vivo of the putative multigene 4-coumarate:CoA ligase network in ''Arabidopsis'': syringyl lignin and sinapate/sinapyl alcohol derivative formation |journal=Phytochemistry |volume=66 |issue=17 |pages=2072–2091 |date=September 2005 |pmid=16099486 |doi=10.1016/j.phytochem.2005.06.022| bibcode = 2005PChem..66.2072C }}</ref> (''E'')-4-coumaroyl-CoA is then subjected to the [[Polyketide synthase|type III polyketide synthase]] [[Chalcone synthase|naringenin chalcone synthase]], undergoing successive [[condensation reaction]]s and ultimately a [[Ring closing reaction|ring-closing]] [[Claisen condensation]] to afford [[naringenin chalcone]].<ref>{{cite journal |vauthors=Leyva A, Jarillo JA, Salinas J, Martinez-Zapater JM |title=Low Temperature Induces the Accumulation of Phenylalanine Ammonia-Lyase and Chalcone Synthase mRNAs of ''Arabidopsis thaliana'' in a Light-Dependent Manner |journal=Plant Physiology |volume=108 |issue=1 |pages=39–46 |date=May 1995 |pmid=12228452 |pmc=157303 |doi=10.1104/pp.108.1.39}}</ref> The corresponding [[chalcone]] undergoes an [[isomerization]] by [[chalcone isomerase]] to afford [[Naringenin|(2''S'')-naringenin]],<ref>{{cite journal |vauthors=Jez JM, Noel JP |title=Reaction mechanism of chalcone isomerase. pH dependence, diffusion control, and product binding differences |journal=The Journal of Biological Chemistry |volume=277 |issue=2 |pages=1361–1369 |date=January 2002 |pmid=11698411 |doi=10.1074/jbc.m109224200 | doi-access = free}}</ref> which is oxidized to [[Eriodictyol|(2''S'')-eriodictyol]] by [[Flavonoid 3'-monooxygenase|flavonoid 3′-hydroxylase]].<ref>{{cite journal |vauthors=Schoenbohm C, Martens S, Eder C, Forkmann G, Weisshaar B |title=Identification of the ''Arabidopsis thaliana'' flavonoid 3′-hydroxylase gene and functional expression of the encoded P450 enzyme |journal=Biological Chemistry |volume=381 |issue=8 |pages=749–753 |date=August 2000 |pmid=11030432 |doi=10.1515/BC.2000.095 |s2cid=22010146}}</ref> After ''O''-methylation by [[Caffeoyl-CoA O-methyltransferase|caffeoyl-CoA ''O''-methyltransferase]],<ref>{{cite journal |vauthors=Lin Y, Sun X, Yuan Q, Yan Y |title=Combinatorial biosynthesis of plant-specific coumarins in bacteria |journal=Metabolic Engineering |volume=18 |pages=69–77 |date=July 2013 |pmid=23644174 |doi=10.1016/j.ymben.2013.04.004}}</ref> the [[Hesperetin|hesperitin]] product undergoes a [[glycosylation]] by [[Flavanone 7-O-beta-glucosyltransferase|flavanone 7-''O''-glucosyltransferase]] to afford hesperitin-7-''O''-β-{{sc|D}}-glucoside.<ref>{{cite journal |vauthors=Durren RL, McIntosh CA |title=Flavanone-7-''O''-glucosyltransferase activity from ''Petunia hybrida'' |journal=Phytochemistry |volume=52 |issue=5 |pages=793–798 |date=November 1999 |pmid=10626374 |doi=10.1016/S0031-9422(99)00307-6|bibcode=1999PChem..52..793D }}</ref> Finally, a [[Rhamnose|rhamnosyl]] moiety is introduced to the monoglycosylated product by 1,2-rhamnosyltransferase, forming hesperidin.<ref>{{cite journal |vauthors=Bar-Peled M, Lewinsohn E, Fluhr R, Gressel J |title=UDP-rhamnose:flavanone-7-''O''-glucoside-2″-''O''-rhamnosyltransferase |journal=The Journal of Biological Chemistry |volume=266 |issue=31 |pages=20953–20959 |date=November 1991 |pmid=1939145 |doi=10.1016/s0021-9258(18)54803-1 | doi-access = free}}</ref>

== See also ==

* [[Diosmin]]

* [[List of phytochemicals in food]]

* [[List of MeSH codes (D03)]]

* [[List of food additives]]

== References ==

{{Reflist|2}}

== External links ==

*{{Commons category-inline}}

{{Flavanone}}

{{Glycosides}}

[[Category:Flavanone glycosides]]

[[Category:Flavonoid antioxidants]]

[[Category:Bitter compounds]]

[[Category:Flavonoids found in Rutaceae]]