Hesperidin

Hesperidin
	(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-dihidrohromen-4-on
Identifikacija
CAS registarski broj	520-26-3
PubChem	10621
ChemSpider	10176
UNII	E750O06Y6O
ChEBI	28775
ChEMBL	CHEMBL449317
Jmol-3D slike	Slika 1
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
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 ; Kod: 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; Kod: 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; Kod: QUQPHWDTPGMPEX-QJBIFVCTBQ
Svojstva
Molekulska formula	C28H34O15
Molarna masa	610.56 g mol−1
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Hesperidin je flavanonski glikozid koji je izobilan u citrusnom voću. Njegova aglikonska forma se naziva hesperetin. Ime potiče od hesperidnih nimfi iz Grčke mitologije. Za hesperidin se misli da učestvuje u odbrambenom mehanizmu biljki. Sudeći po in vitro ispitivanjima, on deluje kao antioksidans.^[5]

Razna preliminarna ispitivanja indiciraju da on ima specifične farmaceutske osobine, mada nije potvrđeno da su one primenljive kod ljudi. Hesperidin redukuje novo holesterola^[6] i krvnog pritiska^[7] kod pacova. U jednoj studiji na miševima, velike doze hesperidina su snizile gubitak gustine kostiju.^[8] Jedna druga studija na životinjama je pokazala protektivne efekte protiv sepse.^[9] U in vitro i laboratorijskim istraživanjima, hesperidin pokazuje antiinflamatorno dejstvo.^[10]^[11] Hesperidin je isto tako potencijalni sedativ. Moguće je da on deluje putem opioidnih ili adenozinskih receptora.^[12]^[13] Hesperidin pokazuje izraženo antikancerno dejstvo protiv nekih ljudskih karcinomnih ćelijskih linija.^[14]

Deo in vitro rezultata je primenljiv samo na aglikonsku formu. Hesperidin takođe ima sposobnost penetracije krvno moždane barijere u in vitro modelima.^[15]

Reference uredi

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Hirata A, Murakami Y, Shoji M, Kadoma Y, Fujisawa S (2005). „Kinetics of radical-scavenging activity of hesperetin and hesperidin and their inhibitory activity on COX-2 expression”. Anticancer Res. 25 (5): 3367–74. PMID 16101151.
↑ Monforte MT, Trovato A, Kirjavainen S, Forestieri AM, Galati EM, Lo Curto RB (September 1995). „Biological effects of hesperidin, a Citrus flavonoid. (note II): hypolipidemic activity on experimental hypercholesterolemia in rat”. Farmaco 50 (9): 595–9. PMID 7495469.
↑ Ohtsuki K, Abe A, Mitsuzumi H, et al. (December 2003). „Glucosyl hesperidin improves serum cholesterol composition and inhibits hypertrophy in vasculature”. J. Nutr. Sci. Vitaminol. 49 (6): 447–50. PMID 14974738.
↑ Chiba H, Uehara M, Wu J, et al. (June 2003). „Hesperidin, a citrus flavonoid, inhibits bone loss and decreases serum and hepatic lipids in ovariectomized mice”. J. Nutr. 133 (6): 1892–7. PMID 12771335.
↑ Kawaguchi K, Kikuchi S, Hasunuma R, Maruyama H, Yoshikawa T, Kumazawa Y (May 2004). „A citrus flavonoid hesperidin suppresses infection-induced endotoxin shock in mice”. Biol. Pharm. Bull. 27 (5): 679–83. DOI:10.1248/bpb.27.679. PMID 15133244.
↑ Emim JA, Oliveira AB, Lapa AJ (February 1994). „Pharmacological evaluation of the anti-inflammatory activity of a citrus bioflavonoid, hesperidin, and the isoflavonoids, duartin and claussequinone, in rats and mice”. J. Pharm. Pharmacol. 46 (2): 118–22. PMID 8021799.
↑ Galati EM, Monforte MT, Kirjavainen S, Forestieri AM, Trovato A, Tripodo MM (November 1994). „Biological effects of hesperidin, a citrus flavonoid. (Note I): antiinflammatory and analgesic activity”. Farmaco 40 (11): 709–12. PMID 7832973.
↑ Loscalzo LM, Wasowski C, Paladini AC, Marder M (February 2008). „Opioid receptors are involved in the sedative and antinociceptive effects of hesperidin as well as in its potentiation with benzodiazepines”. Eur. J. Pharmacol. 580 (3): 306–13. DOI:10.1016/j.ejphar.2007.11.011. PMID 18048026.
↑ Guzmán-Gutiérrez SL, Navarrete A (March 2009). „Pharmacological exploration of the sedative mechanism of hesperidin identified as the active principle of Citrus sinensis flowers”. Planta Med. 75 (4): 295–301. DOI:10.1055/s-0029-1185306. PMID 19219759.
↑ Al-Ashaal HA, El-Sheltawy ST"Antioxidant capacity of hesperidin from citrus peel using electron spin resonance and cytotoxic activity against human carcinoma cell lines. Pharm Biol. 2011 Mar;49(3):276-82
↑ Youdim KA, Dobbie MS, Kuhnle G, Proteggente AR, Abbott NJ, Rice-Evans C (April 2003). „Interaction between flavonoids and the blood-brain barrier: in vitro studies”. J. Neurochem. 85 (1): 180–92. DOI:10.1046/j.1471-4159.2003.01652.x. PMID 12641740.

Spoljašnje veze uredi

Portal Hemija

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[5] Hirata A, Murakami Y, Shoji M, Kadoma Y, Fujisawa S (2005). „Kinetics of radical-scavenging activity of hesperetin and hesperidin and their inhibitory activity on COX-2 expression”. Anticancer Res. 25 (5): 3367–74. PMID 16101151.

[6] Monforte MT, Trovato A, Kirjavainen S, Forestieri AM, Galati EM, Lo Curto RB (September 1995). „Biological effects of hesperidin, a Citrus flavonoid. (note II): hypolipidemic activity on experimental hypercholesterolemia in rat”. Farmaco 50 (9): 595–9. PMID 7495469.

[7] Ohtsuki K, Abe A, Mitsuzumi H, et al. (December 2003). „Glucosyl hesperidin improves serum cholesterol composition and inhibits hypertrophy in vasculature”. J. Nutr. Sci. Vitaminol. 49 (6): 447–50. PMID 14974738.

[8] Chiba H, Uehara M, Wu J, et al. (June 2003). „Hesperidin, a citrus flavonoid, inhibits bone loss and decreases serum and hepatic lipids in ovariectomized mice”. J. Nutr. 133 (6): 1892–7. PMID 12771335.

[9] Kawaguchi K, Kikuchi S, Hasunuma R, Maruyama H, Yoshikawa T, Kumazawa Y (May 2004). „A citrus flavonoid hesperidin suppresses infection-induced endotoxin shock in mice”. Biol. Pharm. Bull. 27 (5): 679–83. DOI:10.1248/bpb.27.679. PMID 15133244.

[10] Emim JA, Oliveira AB, Lapa AJ (February 1994). „Pharmacological evaluation of the anti-inflammatory activity of a citrus bioflavonoid, hesperidin, and the isoflavonoids, duartin and claussequinone, in rats and mice”. J. Pharm. Pharmacol. 46 (2): 118–22. PMID 8021799.

[11] Galati EM, Monforte MT, Kirjavainen S, Forestieri AM, Trovato A, Tripodo MM (November 1994). „Biological effects of hesperidin, a citrus flavonoid. (Note I): antiinflammatory and analgesic activity”. Farmaco 40 (11): 709–12. PMID 7832973.

[12] Loscalzo LM, Wasowski C, Paladini AC, Marder M (February 2008). „Opioid receptors are involved in the sedative and antinociceptive effects of hesperidin as well as in its potentiation with benzodiazepines”. Eur. J. Pharmacol. 580 (3): 306–13. DOI:10.1016/j.ejphar.2007.11.011. PMID 18048026.

[13] Guzmán-Gutiérrez SL, Navarrete A (March 2009). „Pharmacological exploration of the sedative mechanism of hesperidin identified as the active principle of Citrus sinensis flowers”. Planta Med. 75 (4): 295–301. DOI:10.1055/s-0029-1185306. PMID 19219759.

[14] Al-Ashaal HA, El-Sheltawy ST"Antioxidant capacity of hesperidin from citrus peel using electron spin resonance and cytotoxic activity against human carcinoma cell lines. Pharm Biol. 2011 Mar;49(3):276-82

[15] Youdim KA, Dobbie MS, Kuhnle G, Proteggente AR, Abbott NJ, Rice-Evans C (April 2003). „Interaction between flavonoids and the blood-brain barrier: in vitro studies”. J. Neurochem. 85 (1): 180–92. DOI:10.1046/j.1471-4159.2003.01652.x. PMID 12641740.

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