Prunin

Prunin

Names
Other names Naringenin-7-O-glucoside
Identifiers
ChEBI	CHEBI:28327
ChemSpider	83766
Jmol interactive 3D	Image
PubChem	92794
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/s1 Key: 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/s1 Key: DLIKSSGEMUFQOK-SFTVRKLSBO
SMILES C1[C@H](OC2=CC(=CC(=C2C1=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C4=CC=C(C=C4)O
Properties
Chemical formula	C21H22O10
Molar mass	434.40 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Prunin is a flavanone glycoside found in immature citrus fruits^[1][2] and in tomatoes.^[3] Its aglycone form is called naringenin.

Metabolism

Alpha-L-rhamnosidase breaks naringin into prunin and rhamnose. Glucosidase breaks prunin into glucose and naringenin.

References

1. 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.
2. 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.
3. 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

Bibliography

• Habelt, Konrad; Pittner, Fritz (1983). "A rapid method for the determination of naringin, prunin, and naringenin applied to the assay of naringinase". Analytical Biochemistry 134 (2): 393–397. doi:10.1016/0003-2697(83)90314-7. ISSN 0003-2697.