Prunin

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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.696 Edit this at Wikidata
KEGG
UNII
  • 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
  • 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
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).

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

Biosynthesis

Flavonoid biosynthesis in plants uses a phenylpropanoid metabolic pathway in which the amino acid phenylalanine is converted to 4-coumaroyl-CoA. This is combined with three units of malonyl-CoA to yield a group of compounds called chalcones, which contain two phenyl rings. In the main pathway, the enzymes chalcone synthase and chalcone isomerase produce (S)-naringenin which is the immediate precursor for prunin.

Flavanone 7-O-beta-glucosyltransferase uses UDP-glucose to transfer a sugar group to one of the phenolic hydroxyl groups of (S)-naringenin.

2D representation of the chemical structure of naringenin .
naringenin
+ UDP-glucose
 
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of prunin.
prunin
+ UDP
 

In some citrus fruits, the product prunin is converted to naringin, a compound which is responsible for the bitter taste of grapefruit.

2D representation of the chemical structure of prunin .
prunin
+ UDP-rhamnose
 
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of naringin .
naringin
+ UDP
 

Flavanone 7-O-glucoside 2"-O-beta-L-rhamnosyltransferase uses UDP-rhamnose to add the second sugar component.

Metabolism in the human gut

Glucosidase breaks dietary prunin back 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
  4. 1 2 Ververidis Filippos, F; Trantas Emmanouil; Douglas Carl; Vollmer Guenter; Kretzschmar Georg; Panopoulos Nickolas (October 2007). "Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health". Biotechnology Journal. 2 (10): 1214–34. doi:10.1002/biot.200700084. PMID 17935117.
  5. ↑ Wang C, Zhi S, Liu C, Xu F, Zhao A, Wang X, et al. (March 2017). "Characterization of Stilbene Synthase Genes in Mulberry (Morus atropurpurea) and Metabolic Engineering for the Production of Resveratrol in Escherichia coli". Journal of Agricultural and Food Chemistry. 65 (8): 1659–1668. Bibcode:2017JAFC...65.1659W. doi:10.1021/acs.jafc.6b05212. PMID 28168876.
  6. ↑ Moustafa E, Wong E (1967). "Purification and properties of chalcone-flavanone isomerase from soya bean seed". Phytochemistry. 6 (5): 625–632. Bibcode:1967PChem...6..625M. doi:10.1016/S0031-9422(00)86001-X.
  7. 1 2 McIntosh CA; Mansell RL (1990). "Biosynthesis of naringin in Citrus paradisi - UDP-glucosyl-transferase activity in grapefruit seedlings". Phytochemistry. 29 (5): 1533–1538. Bibcode:1990PChem..29.1533M. doi:10.1016/0031-9422(90)80115-W.
  8. ↑ Alam MA, Subhan N, Rahman MM, Uddin SJ, Reza HM, Sarker SD (July 2014). "Effect of Citrus Flavonoids, Naringin and Naringenin, on Metabolic Syndrome and Their Mechanisms of Action". Advances in Nutrition. 5 (4): 404–417. doi:10.3945/an.113.005603. ISSN 2156-5376. PMC 4085189. PMID 25022990.
  9. ↑ Bar-Peled M, Lewinsohn E, Fluhr R, Gressel J (1991). "UDP-rhamnose:flavanone-7-O-glucoside-2''-O-rhamnosyltransferase Purification and characterization of an enzyme catalyzing the production of bitter compounds in citrus". J. Biol. Chem. 266 (31): 20953–9. doi:10.1016/S0021-9258(18)54803-1. PMID 1939145.
  10. ↑ 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.
  11. ↑ Goris, Tobias; Cuadrat, Rafael R. C.; Braune, Annett (2021). "Flavonoid-Modifying Capabilities of the Human Gut Microbiome—An in Silico Study". Nutrients. 13 (8): 2688. doi:10.3390/nu13082688. PMC 8398226. PMID 34444848.