Prunin - Misplaced Pages

Prunin
Names


IUPAC name (2S)-7-(β-D-Glucopyranosyloxy)-4′,5-dihydroxyflavan-4-one
Systematic IUPAC name (2S)-5-Hydroxy-2-(4-hydroxyphenyl)-7-{oxy}-2,3-dihydro-4H-1-benzopyran-4-one
Other names Naringenin-7-O-glucoside
Identifiers
CAS Number	529-55-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28327
ChemSpider	83766
ECHA InfoCard	100.007.696
KEGG	C09099
PubChem CID	92794
UNII	LSB8HDX4E5
CompTox Dashboard (EPA)	DTXSID40967365
InChI InChI=1S/C21H22O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-6,14,16,18-24,26-28H,7-8H2/t14-,16+,18+,19-,20+,21+/m0/s1Key: DLIKSSGEMUFQOK-SFTVRKLSSA-N InChI=1/C21H22O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-6,14,16,18-24,26-28H,7-8H2/t14-,16+,18+,19-,20+,21+/m0/s1Key: DLIKSSGEMUFQOK-SFTVRKLSBO
SMILES C1(OC2=CC(=CC(=C2C1=O)O)O3((((O3)CO)O)O)O)C4=CC=C(C=C4)O
Properties
Chemical formula	C₂₁H₂₂O₁₀
Molar mass	434.397 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Prunin is a flavanone glycoside found in immature citrus fruits and in tomatoes. Its aglycone form is called naringenin.

Metabolism

Glucosidase breaks prunin into glucose and naringenin.

Berhow, Mark A.; Vandercook, Carl E. (1989). "Biosynthesis of naringin and prunin in detached grapefruit". Phytochemistry. 28 (6): 1627–1630. doi:10.1016/S0031-9422(00)97813-0. ISSN 0031-9422.
Castillo, Julian.; Benavente, Obdulio.; del Rio, Jose A. (1993). "Hesperetin 7-O-glucoside and prunin in Citrus species (C. aurantium and C. paradisi). A study of their quantitative distribution in immature fruits and as immediate precursors of neohesperidin and naringin in Citrus aurantium". Journal of Agricultural and Food Chemistry. 41 (11): 1920–1924. doi:10.1021/jf00035a021. ISSN 0021-8561.
Improved characterization of tomato polyphenols using liquid chromatography/electrospray ionization linear ion trap quadrupole Orbitrap mass spectrometry and liquid hromatography/electrospray ionization tandem mass spectrometry. Anna Vallverdu´-Queralt, Olga Jauregui, Alexander Medina-Remon, Cristina Andres-Lacueva and Rosa M. Lamuela-Raventos, Rapid Commun. Mass Spectrom., 2010, volume 24, pages 2986–2992, doi:10.1002/rcm.4731

v t e Flavanones and their glycosides
Flavanones	Butin Eriodictyol Naringenin Pinocembrin
O-methylated flavanones	Alpinetin Hesperetin Homoeriodictyol Isosakuranetin Pinostrobin (Pinocembrin-7-methylether) Sakuranetin Sterubin
C-methylated flavanones	Poriol
Glycosides	Eriocitrin Neoeriocitrin Hesperidin Liquiritin Naringin (Narigenin 7-O-neohesperidoside) Narirutin (Naringenin 7-O-rutinoside) Poncirin Prunin (Naringenin-7-O-glucoside) Sakuranin
Acetylated	8-Prenylnaringenin Isoxanthohumol Sophoraflavanone G
Acetylated glycosides	Nirurin

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