Prunin

Names
IUPAC name

(2S)-7-(β-D-Glucopyranosyloxy)-4′,5-dihydroxyflavan-4-one

Systematic IUPAC name

(2S)-5-Hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]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 Y

PubChem CID

* 92794

UNII |

* LSB8HDX4E5 Y

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/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 | 434.397 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

Chemical compound

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

## Metabolism

[edit]

Glucosidase breaks prunin into glucose and naringenin.

## References

[edit]

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

[edit]

* 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. PMID 6418025.

## External links

[edit]

* Media related to Prunin at Wikimedia Commons

* v
* t
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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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