Hesperidin

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Not to be confused with hesperadin.
Hesperidin
Hesperidin structure.svg
Identifiers
CAS number 520-26-3 YesY
PubChem 10621
ChemSpider 10176 YesY
UNII E750O06Y6O YesY
ChEBI CHEBI:28775 YesY
ChEMBL CHEMBL449317 YesY
Jmol-3D images Image 1
Properties
Molecular formula C28H34O15
Molar mass 610.56 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Hesperidin is a flavanone 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.

Hesperidin was first isolated in 1828 by French chemist Lebreton from the white inner layer of citrus peels (mesocarp, albedo).[2]

Hesperidin is believed to play a role in plant defense.

Sources[edit]

in Rutaceae
in Lamiaceae

Peppermint also contains hesperidin.[6]

Metabolism[edit]

Hesperidin 6-O-alpha-L-rhamnosyl-beta-D-glucosidase is an enzyme that uses hesperidin and H2O to produce hesperetin and rutinose. It is found in the hyphomycetes species Stilbella fimetaria.

Research[edit]

As a flavanone found in citrus fruits (such as oranges, lemons or pummelo fruits), hesperidin is under laboratory research for possible biological properties.[7][8][9]

One area of research is focused on the chemopreventive effects of hesperidin.[10] Hesperidin has been linked as a natural product that inhibits tumor metastasis and is cytotoxic to certain cancer cell lines. [11][12] Hesperidin's interaction with Aurora B kinase, a mitotic kinase protein that is essential to proper chromosome alignment and cytokinesis, is being studied as it has been identified as a candidate small molecule inhibitor of over-expression of this kinase.[13][14] Hesperidin also is proving to have an apoptotic effect on some cancer cell lines, like colon cancer, through Caspase 3 activation to induce cell dealth.[15]

See also[edit]

References[edit]

  1. ^ Inderjit, Dakshini, K. M. (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)". J Chem Ecol 17 (8): 1585–91. doi:10.1007/BF00984690. PMID 24257882. 
  2. ^ Lebreton (1828). Journal de Pharmacie et de sciences accessories 14: 377ff. 
  3. ^ "Citrus aurantium L.". Dr. Duke's Phytochemical and Ethnobotanical Databases. 6 Oct 2014. 
  4. ^ 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. 
  5. ^ 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". Journal of Food Composition and Analysis 19 (Supplement): S74–S80. doi:10.1016/j.jfca.2005.12.009. 
  6. ^ 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. 
  7. ^ 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.  edit
  8. ^ 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.  edit
  9. ^ 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.  edit
  10. ^ 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. doi:10.1155/2012/516981.  edit
  11. ^ Zeng, W. F.; Navaratne, K.; Prayson, R. A.; Weil, R. J. (2006). "Aurora B expression correlates with aggressive behaviour in glioblastoma multiforme". Journal of Clinical Pathology 60 (2): 218. doi:10.1136/jcp.2006.036806.  edit
  12. ^ Febriansah, R; Putri, D. D.; Sarmoko; Nurulita, N. A.; Meiyanto, E; Nugroho, A. E. (2014). "Hesperidin as a preventive resistance agent in MCF-7 breast cancer cells line resistance to doxorubicin". Asian Pacific journal of tropical biomedicine 4 (3): 228–33. doi:10.1016/S2221-1691(14)60236-7 (inactive 2014-11-18). PMC 3868794. PMID 25182442.  edit
  13. ^ Fu, J.; Bian, M.; Jiang, Q.; Zhang, C. (2007). "Roles of Aurora Kinases in Mitosis and Tumorigenesis". Molecular Cancer Research 5: 1. doi:10.1158/1541-7786.MCR-06-0208.  edit
  14. ^ Zeng, W. F.; Navaratne, K.; Prayson, R. A.; Weil, R. J. (2006). "Aurora B expression correlates with aggressive behaviour in glioblastoma multiforme". Journal of Clinical Pathology 60 (2): 218. doi:10.1136/jcp.2006.036806.  edit
  15. ^ Park, H. J.; Kim, M. -J.; Ha, E.; Chung, J. -H. (2008). "Apoptotic effect of hesperidin through caspase3 activation in human colon cancer cells, SNU-C4". Phytomedicine 15: 147. doi:10.1016/j.phymed.2007.07.061.  edit