Hesperidin
Hesperidin is a flavan-on glycoside found in citrus fruits. Its aglycone form is called hesperetin. Its name is derived from the word "hesperidium", for fruit produced by citrus trees.
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| Names | |
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| IUPAC name
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl}oxan-2-yl]oxy-2,3-dihydrochromen-4-one
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| Other names
Hesperetin 7-rutinoside[1]
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.536 |
PubChem CID
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| UNII | |
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| Properties | |
| C28H34O15 | |
| Molar mass | 610.57 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is  ‹See TfM› ?)
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| Infobox references | |
Hesperidin was first isolated in 1828 by French chemist Lebreton from the white inner layer of citrus peels (mesocarp, albedo).[2][3]
Hesperidin is believed to play a role in plant defense.
Contents
SourcesEdit
RutaceaeEdit
- 700 - 2,500 ppm in fruit of Citrus aurantium L. - Bitter Orange, Petitgrain[4]
- in orange juice (Citrus sinensis)
- in Zanthoxylum gilletii[5]
- in lemon[6]
- in lime[6]
- in leaves of Agathosma serratifolia
LamiaceaeEdit
Peppermint contains hesperidin.[7]
Ultraviolet 280 nm chromatogram after UHPLC separation of commercial orange juice. Hesperidin is peak at 16.44 min.
Content in foodsEdit
Approximate hesperidin content per 100 grams[8]
- 481 mg peppermint, dried
- 44 mg blood orange, pure juice
- 26 mg orange, pure juice
- 18 mg lemon, pure juice
- 14 mg lime, pure juice
- 1 mg grapefruit, pure juice
MetabolismEdit
Hesperidin 6-O-alpha-L-rhamnosyl-beta-D-glucosidase, an enzyme that uses hesperidin and H2O to produce hesperetin and rutinose, is found in the Ascomycetes species.[9]
ResearchEdit
As a flavanone found in citrus fruits (such as oranges, lemons or pummelo fruits), hesperidin is under laboratory research for possible biological properties.[10][11][12] One area of research is focused on the possible chemopreventive effects of hesperidin,[13] but there is no current proof that hesperidin has this role in human cancer mechanisms.
See alsoEdit
ReferencesEdit
- ^ Inderjit, Dakshini KM (August 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 February 2016. Retrieved 30 October 2016.
- ^ "Citrus aurantium L." Dr. Duke's Phytochemical and Ethnobotanical Databases. 6 Oct 2014. Archived from the original on 2004-11-10.
- ^ 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.
- ^ a b 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. Retrieved 15 March 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.
External linksEdit
Media related to Hesperidin at Wikimedia Commons
