Hyperoside

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Hyperoside

IUPAC name 2-(3,4-dihydroxyphenyl)-3-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-chromene-4,5,7-triol
Other names Hyperozide Hyperasid Hyperosid Hyperin quercetin galactoside Quercetin-3-galactoside Quercetin-3-O-galactoside
Identifiers
CAS number	482-36-0^Y
PubChem	24835331
ChemSpider	9926320^Y
ChEBI	CHEBI:67486
Jmol-3D images	{{#if:O=C2C(\OC1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)CO)=C(/Oc3cc(O)cc(O)c23)c4ccc(O)c(O)c4\|Image 1
SMILES O=C2C(\OC1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)CO)=C(/Oc3cc(O)cc(O)c23)c4ccc(O)c(O)c4
InChI InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15+,17+,18-,21?/m1/s1^Y Key: OVSQVDMCBVZWGM-HBDJNLTOSA-N^Y InChI=1/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15+,17+,18-,21?/m1/s1 Key: OVSQVDMCBVZWGM-HBDJNLTOBV
Properties
Molecular formula	C₂₁H₂₀O₁₂
Molar mass	464.38 g mol⁻¹
Density	1.879 g/mL
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Hyperoside is a chemical compound. It is the 3-O-galactoside of quercetin.

Natural occurrences

Hyperoside has been isolated from Drosera rotundifolia, from the Lamiaceae Stachys sp. and Prunella vulgaris, from Rumex acetosella, Cuscuta chinensis seeds, from St John’s wort and from Camptotheca acuminata.^[1] It is one of the phenolic compounds in the invasive plant Carpobrotus edulis and contributes to the antibacterial^[2] and antioxidant^[3] properties of the plant.

In Rheum nobile and R. rhaponticum, it serves as a UV blocker found in the bracts.

It is also found in Geranium niveum.^[4]

It can have a protective antioxidant effect on cultured PC12 cells.^[5]

↑ Li, Shiyou; Zhang, Zhizhen; Cain, Abigail; Wang, Bo; Long, Melissa; Taylor, Josephine (2005). "Antifungal Activity of Camptothecin, Trifolin, and Hyperoside Isolated fromCamptotheca acuminata". Journal of Agricultural and Food Chemistry 53 (1): 32–7. doi:10.1021/jf0484780. PMID 15631505.
↑ Van Der Watt, Elmarie; Pretorius, Johan C (2001). "Purification and identification of active antibacterial components in Carpobrotus edulis L". Journal of Ethnopharmacology 76 (1): 87–91. doi:10.1016/S0378-8741(01)00197-0. PMID 11378287.
↑ Ibtissem, Bouftira (2012). "Antioxidant and Antibacterial Properties of Mesembryanthemum crystallinum and Carpobrotus edulis Extracts". Advances in Chemical Engineering and Science 02 (3): 359. doi:10.4236/aces.2012.23042.
↑ Calzada, F; Cerda-García-Rojas, CM; Meckes, M; Cedillo-Rivera, R; Bye, R; Mata, R (1999). "Geranins a and B, new antiprotozoal A-type proanthocyanidins from Geranium niveum". Journal of natural products 62 (5): 705–9. doi:10.1021/np980467b. PMID 10346950.
↑ Liu, Zhiyong; Tao, Xinyi; Zhang, Chongwei; Lu, Yanhua; Wei, Dongzhi (2005). "Protective effects of hyperoside (quercetin-3-o-galactoside) to PC12 cells against cytotoxicity induced by hydrogen peroxide and tert-butyl hydroperoxide". Biomedicine & Pharmacotherapy 59 (9): 481. doi:10.1016/j.biopha.2005.06.009.

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Aglycones

Conjugates

Glycosides of herbacetin

Glycosides of kaempferol

Glycosides of myricetin

Conjugates of quercetin

Sulfates	Quercetin 3-O-sulfate Quercetin 3,3'-bissulfate Quercetin 3,4'-bissulfate

Glycosides	Avicularin (quercetin-3-O-α-L-arabinofuranoside) CTN-986 Guaijaverin (quercetin 3-O-arabinoside) Heliosin (quercetin 3-digalactoside) Hyperoside (quercetin 3-O-galactoside) Isoquercetin (quercetin 3-O-glucoside) Miquelianin (quercetin 3-O-glucuronide) Quercetin 3,4'-diglucoside Quercetin-3-sophorodide Quercitrin (quercetin 3-O-rhamnoside) Rutin (quercetin rutinoside) Reinutrin (quercetin-3-D-xyloside) Spiraeoside (quercetin 4'-O-glucoside) Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside

other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)

Derivative flavonols

Aglycones	Noricaritin Dihydronoricaritin

Glycosides	Amurensin Icariin Phelloside Dihydrophelloside Rutin S

Pyranoflavonols

Aglycones	Karanjachromene

Furanoflavonols

Semisynthetic

Glycosides	Hydroxyethylrutosides Monoxerutin Troxerutin

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