Hesperidin

Hesperidin
Imena
	IUPAC ime (2S)-5-hidroksi-2-(3-hidroksi-4-metoksifenil)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihidroksi-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihidroksi-6-metiloksan-2-il]oksimetil]oksan-2-il]oksi-2,3-dihidrokromen-4-on
	Druga imena Hesperetin 7-rutinozid
Identifikatorji
Številka CAS	520-26-3;
3D model (JSmol)	Interaktivna slika;
ChEBI	CHEBI:28775;
ChEMBL	ChEMBL449317;
ChemSpider	10176;
ECHA InfoCard	100.007.536
PubChem CID	10621;
UNII	E750O06Y6O;
CompTox Dashboard (EPA)	DTXSID9044328 ;
	InChI InChI=1S/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1 Key: QUQPHWDTPGMPEX-QJBIFVCTSA-N; InChI=1/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1 Key: QUQPHWDTPGMPEX-QJBIFVCTBQ; InChI=1/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1 Key: QUQPHWDTPGMPEX-QJBIFVCTBQ;
	SMILES O=C4c5c(O)cc(O[C@@H]2O[C@H](CO[C@@H]1O[C@H]([C@H](O)[C@@H](O)[C@H]1O)C)[C@@H](O)[C@H](O)[C@H]2O)cc5O[C@H](c3ccc(OC)c(O)c3)C4;
Lastnosti
Kemijska formula	C28H34O15
Molska masa	610,57 g·mol−1
	Če ni navedeno drugače, podatki veljajo za material v standardnem stanju pri 25 °C, 100 kPa).
	Sklici infopolja

Hesperidin je flavanonski glikozid, ki ga najdemo v citrusih. Njegov aglikon se imenuje hesperetin. Ime hesperidina izhaja iz besede "hesperidium", sadež dreves citrusov.

Hesperidin je iz bele notranje plasti olupka citrusov (mezokarp, albedo) prvič izoliral francoski kemik Lebreton leta 1828.^[2]^[3]

Hesperidin naj bi igral vlogo pri rastlinski obrambi in je zanimiv z vidika farmakodinamike pri zdravljenju nekaterih stanj, kot so hemoroidi, limfedem in kronično vensko popuščanje.

Naravni viri

Rutaceae - rutičevke

700–2500 ppm v sadežu rastline Citrus aurantium L. - grenki pomarančevec^[4]
pomarančni sok (Citrus sinensis)
drevo Zanthoxylum gilletii^[5]
limona^[6]
limeta
listi grma Agathosma serratifolia

Lamiaceae - ustnatice

Poprova meta vsebuje hesperidin.^[7]

Ultravijolični kromatogram po UHPLC ločitvi komercialnega pomarančnega soka. Hesperidin ima vrh pri 16.44 min (λ = 280 nm).

Vsebnost v živilih

Približna vsebnost hesperidina na 100 gramov drogeː^[8]

481 mg v posušeni poprovi meti
44 mg v čistem soku rdeče pomaranče
26 mg v čistem soku pomaranče
18 mg v čistem soku limone
14 mg v čistem soku limete
1 mg v čistem soku grenivke

Metabolizem

Hesperidin 6-O-alfa-L-ramnozil-beta-D-glukozidaza, encim, ki uporablja hesperidin in H₂O, da proizvaja hesperetin in rutinozo, se nahaja v vrstah zaprtotrosnic.^[9]

Raziskave

Kot flavanon, ki ga najdemo v citrusih, kot so pomaranče, limone ali pomelo, se hesperidin raziskuje zaradi potencialnih bioloških učinkov.^[10]^[11]^[12] Eno področje raziskav je usmerjeno v morebitne kemopreventivne učinke hesperidina,^[13] vendar trenutno ni dokazov, da bi hesperidin imel tako vlogo v mehanizmu raka pri človeku.

Zdravila

Med zdravili za humano medicino najdemo nekaj primerov, ki vsebujejo hesperidin kot zdravilno učinkovino oziroma rastinske flavonoide, standardizirane glede na hesperidin.

Primer takega zdravila so filmsko obložene tablete Detralex, ki poleg hesperidina vsebujejo tudi diosmin kot glavno učinkovino in se uporabljajo za zdravljenje akutnega hemoroidalnega sindroma, limfedema in simptomov kroničnega venskega popuščanja.^[14]^[15]

Glej tudi

Viri

↑ Inderjit, Dakshini KM (Avgust 1991). »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 of Chemical Ecology. 17 (8): 1585–91. doi:10.1007/BF00984690. PMID 24257882.
↑ Lebreton, M (1828). »Sur la matiere cristalline des orangettes, et analyse de ces fruits non encore developpes, famille des Hesperidees«. Journal de Pharmacie et de Sciences Accessories. 14: 377ff.
↑ »Metabocard for Hesperidin (HMDB03265)«. Human Metabolome Database, The Metabolomics Innovation Centre, Genome Canada. 11. februar 2016. Pridobljeno 30. oktobra 2016.
↑ »Citrus aurantium L.«. Dr. Duke's Phytochemical and Ethnobotanical Databases. 6. oktober 2014. Arhivirano iz prvotnega spletišča dne 10. novembra 2004.
↑ Tringali, C.; Spatafora, C.; Calì, V.; Simmonds, M. S. (2001). »Antifeedant constituents from Fagara macrophylla«. Fitoterapia. 72 (5): 538–43. doi:10.1016/S0367-326X(01)00265-9. PMID 11429249.
↑ Peterson, J. J.; Beecher, G. R.; Bhagwat, S. A.; Dwyer, J. T.; Gebhardt, S. E.; Haytowitz, D. B.; Holden, J. M. (2006). »Flavanones in grapefruit, lemons, and limes: A compilation and review of the data from the analytical literature« (PDF). Journal of Food Composition and Analysis. 19 (Supplement): S74–S80. doi:10.1016/j.jfca.2005.12.009.
↑ Dolzhenko, Y.; Bertea, C. M.; Occhipinti, A.; Bossi, S.; Maffei, M. E. (2010). »UV-B modulates the interplay between terpenoids and flavonoids in peppermint (Mentha × piperita L.)«. Journal of Photochemistry and Photobiology B: Biology. 100 (2): 67–75. doi:10.1016/j.jphotobiol.2010.05.003.
↑ »Foods in which hesperidin is found«. Phenol-Explorer database, version 3.6. Pridobljeno 15. marca 2017.
↑ Mazzaferro, L; Piñuel, L; Minig, M; Breccia, J. D. (2010). »Extracellular monoenzyme deglycosylation system of 7-O-linked flavonoid beta-rutinosides and its disaccharide transglycosylation activity from Stilbella fimetaria«. Archives of Microbiology. 192 (5): 383–93. doi:10.1007/s00203-010-0567-7. PMID 20358178.
↑ Benavente-García, O.; Castillo, J. (2008). »Update on Uses and Properties of Citrus Flavonoids: New Findings in Anticancer, Cardiovascular, and Anti-inflammatory Activity«. Journal of Agricultural and Food Chemistry. 56 (15): 6185–205. doi:10.1021/jf8006568. PMID 18593176.
↑ Hwang, S. L.; Shih, P. H.; Yen, G. C. (2012). »Neuroprotective Effects of Citrus Flavonoids«. Journal of Agricultural and Food Chemistry. 60 (4): 877–85. doi:10.1021/jf204452y. PMID 22224368.
↑ Roohbakhsh, A.; Parhiz, H.; Soltani, F.; Rezaee, R.; Iranshahi, M. (2014). »Neuropharmacological properties and pharmacokinetics of the citrus flavonoids hesperidin and hesperetin — A mini-review«. Life Sciences. 113 (1–2): 1–6. doi:10.1016/j.lfs.2014.07.029. PMID 25109791.
↑ Tanaka, T.; Tanaka, T.; Tanaka, M.; Kuno, T. (2012). »Cancer Chemoprevention by Citrus Pulp and Juices Containing High Amounts of β-Cryptoxanthin and Hesperidin«. Journal of Biomedicine and Biotechnology. 2012: 1–10. doi:10.1155/2012/516981. PMC 3228311. PMID 22174562.
↑ d.o.o., Modra Jagoda. »DETRALEX filmsko obložene tablete — Mediately Register zdravil«. mediately.co. Pridobljeno 18. marca 2018.
↑ »Navodila za uporabo zdravila Detralex« (PDF). Pridobljeno 18. marca 2018.^{[mrtva povezava]}

Zunanje povezave

Predstavnosti o temi Hesperidin v Wikimedijini zbirki

[pmid24257882-1] Inderjit, Dakshini KM (Avgust 1991). »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 of Chemical Ecology. 17 (8): 1585–91. doi:10.1007/BF00984690. PMID 24257882.

[2] Lebreton, M (1828). »Sur la matiere cristalline des orangettes, et analyse de ces fruits non encore developpes, famille des Hesperidees«. Journal de Pharmacie et de Sciences Accessories. 14: 377ff.

[3] »Metabocard for Hesperidin (HMDB03265)«. Human Metabolome Database, The Metabolomics Innovation Centre, Genome Canada. 11. februar 2016. Pridobljeno 30. oktobra 2016.

[4] »Citrus aurantium L.«. Dr. Duke's Phytochemical and Ethnobotanical Databases. 6. oktober 2014. Arhivirano iz prvotnega spletišča dne 10. novembra 2004.

[Corrado_Tringali_2001,_Pages_538-5] Tringali, C.; Spatafora, C.; Calì, V.; Simmonds, M. S. (2001). »Antifeedant constituents from Fagara macrophylla«. Fitoterapia. 72 (5): 538–43. doi:10.1016/S0367-326X(01)00265-9. PMID 11429249.

[Pearson_2006_S74-S80-6] Peterson, J. J.; Beecher, G. R.; Bhagwat, S. A.; Dwyer, J. T.; Gebhardt, S. E.; Haytowitz, D. B.; Holden, J. M. (2006). »Flavanones in grapefruit, lemons, and limes: A compilation and review of the data from the analytical literature« (PDF). Journal of Food Composition and Analysis. 19 (Supplement): S74–S80. doi:10.1016/j.jfca.2005.12.009.

[7] Dolzhenko, Y.; Bertea, C. M.; Occhipinti, A.; Bossi, S.; Maffei, M. E. (2010). »UV-B modulates the interplay between terpenoids and flavonoids in peppermint (Mentha × piperita L.)«. Journal of Photochemistry and Photobiology B: Biology. 100 (2): 67–75. doi:10.1016/j.jphotobiol.2010.05.003.

[8] »Foods in which hesperidin is found«. Phenol-Explorer database, version 3.6. Pridobljeno 15. marca 2017.

[9] Mazzaferro, L; Piñuel, L; Minig, M; Breccia, J. D. (2010). »Extracellular monoenzyme deglycosylation system of 7-O-linked flavonoid beta-rutinosides and its disaccharide transglycosylation activity from Stilbella fimetaria«. Archives of Microbiology. 192 (5): 383–93. doi:10.1007/s00203-010-0567-7. PMID 20358178.

[10] Benavente-García, O.; Castillo, J. (2008). »Update on Uses and Properties of Citrus Flavonoids: New Findings in Anticancer, Cardiovascular, and Anti-inflammatory Activity«. Journal of Agricultural and Food Chemistry. 56 (15): 6185–205. doi:10.1021/jf8006568. PMID 18593176.

[11] Hwang, S. L.; Shih, P. H.; Yen, G. C. (2012). »Neuroprotective Effects of Citrus Flavonoids«. Journal of Agricultural and Food Chemistry. 60 (4): 877–85. doi:10.1021/jf204452y. PMID 22224368.

[12] Roohbakhsh, A.; Parhiz, H.; Soltani, F.; Rezaee, R.; Iranshahi, M. (2014). »Neuropharmacological properties and pharmacokinetics of the citrus flavonoids hesperidin and hesperetin — A mini-review«. Life Sciences. 113 (1–2): 1–6. doi:10.1016/j.lfs.2014.07.029. PMID 25109791.

[13] Tanaka, T.; Tanaka, T.; Tanaka, M.; Kuno, T. (2012). »Cancer Chemoprevention by Citrus Pulp and Juices Containing High Amounts of β-Cryptoxanthin and Hesperidin«. Journal of Biomedicine and Biotechnology. 2012: 1–10. doi:10.1155/2012/516981. PMC 3228311. PMID 22174562.

[14] .o.o., Modra Jagoda. »DETRALEX filmsko obložene tablete — Mediately Register zdravil«. mediately.co. Pridobljeno 18. marca 2018.

[15] »Navodila za uporabo zdravila Detralex« (PDF). Pridobljeno 18. marca 2018.^{[mrtva povezava]}

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Imena

IUPAC ime (2S)-5-hidroksi-2-(3-hidroksi-4-metoksifenil)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihidroksi-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihidroksi-6-metiloksan-2-il]oksimetil]oksan-2-il]oksi-2,3-dihidrokromen-4-on
Druga imena Hesperetin 7-rutinozid^[1]
Identifikatorji
Številka CAS	520-26-3
3D model (JSmol)	Interaktivna slika
ChEBI	CHEBI:28775
ChEMBL	ChEMBL449317
ChemSpider	10176
ECHA InfoCard	100.007.536
PubChem CID	10621
UNII	E750O06Y6O
CompTox Dashboard (EPA)	DTXSID9044328
InChI InChI=1S/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1 Key: QUQPHWDTPGMPEX-QJBIFVCTSA-N InChI=1/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1 Key: QUQPHWDTPGMPEX-QJBIFVCTBQ InChI=1/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1 Key: QUQPHWDTPGMPEX-QJBIFVCTBQ
SMILES O=C4c5c(O)cc(O[C@@H]2O[C@H](CO[C@@H]1O[C@H]([C@H](O)[C@@H](O)[C@H]1O)C)[C@@H](O)[C@H](O)[C@H]2O)cc5O[C@H](c3ccc(OC)c(O)c3)C4
Lastnosti
Kemijska formula	C₂₈H₃₄O₁₅
Molska masa	610,57 g·mol⁻¹
Če ni navedeno drugače, podatki veljajo za material v standardnem stanju pri 25 °C, 100 kPa).
Sklici infopolja