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Brutieridin

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Brutieridin
Names
IUPAC name
5-[[(2R,3S,4S,5R,6S)-3,4-Dihydroxy-6-[[(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
Identifiers
3D model (JSmol)
  • InChI=1S/C34H42O19/c1-13-26(41)28(43)30(45)32(49-13)53-31-29(44)27(42)22(12-48-24(40)11-34(2,46)10-23(38)39)52-33(31)50-15-7-17(36)25-18(37)9-20(51-21(25)8-15)14-4-5-19(47-3)16(35)6-14/h4-8,13,20,22,26-33,35-36,41-46H,9-12H2,1-3H3,(H,38,39)/t13-,20-,22+,26-,27+,28+,29-,30+,31+,32-,33+,34?/m0/s1
    Key: SHCWOSSXLGIQEQ-CZFUJNBSSA-N
  • C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC(=C(C=C5)OC)O)O)COC(=O)CC(C)(CC(=O)O)O)O)O)O)O)O
Properties
C34H42O19
Molar mass 754.691 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Brutieridin is a flavanone glycoside. Brutieridin was discovered in bergamot orange juice and exhibits statin-like properties in preclinical research,[1][2][3][4] as well as an anticholesterolaemic effect.[1][5]

See also

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References

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  1. ^ a b Di Donna, Leonardo; De Luca, Giuseppina; Mazzotti, Fabio; Napoli, Anna; Salerno, Raffaele; Taverna, Domenico; Sindona, Giovanni (2009). "Statin-like Principles of Bergamot Fruit: Isolation of 3-Hydroxymethylglutaryl Flavonoid Glycosides". Journal of Natural Products. 72 (7): 1352–1354. doi:10.1021/np900096w. PMID 19572741.
  2. ^ Natalizia Miceli; M. R. Mondello; M. T. Monforte; V. Sdrafkakis; P. Dugo; M. L. Crupi; M. F. Taviano; R. De Pasquale & A. Trovato (2007). "Hypolipidemic Effects of Citrus bergamia Risso et Poiteau Juice in Rats Fed a Hypercholesterolemic Diet". J. Agric. Food Chem. 55 (27): 10671–10677. doi:10.1021/jf071772i. PMID 18038978.
  3. ^ Monica Leopoldini; N. Malaj; M. Toscano; G. Sindona & N. Russo (2010). "On the Inhibitor Effects of Bergamot Juice Flavonoids Binding to the 3-Hydroxy-3-methylglutaryl-CoA Reductase (HMGR) Enzyme". J. Agric. Food Chem. 58 (19): 10768–10773. doi:10.1021/jf102576j. PMID 20843083.
  4. ^ Vincenzo Mollace; I. Sacco; E. Janda; C. Malara; D. Ventrice; C. Colica; V. Visalli; S. Muscoli; S. Ragusa; C. Muscoli; D. Rotirotia; F. Romeo (2011). "Hypolipemic and hypoglycaemic activity of bergamot polyphenols: From animal models to human studies". Fitoterapia. 82 (3): 309–316. doi:10.1016/j.fitote.2010.10.014. PMID 21056640. PDF Archived 2012-04-02 at the Wayback Machine
  5. ^ Di Donna, Leonardo; Gallucci, Giselda; Malaj, Naim; Romano, Elvira; Tagarelli, Antonio; Sindona, Giovanni (2011). "Recycling of industrial essential oil waste: Brutieridin and Melitidin, two anticholesterolaemic active principles from bergamot albedo". Food Chemistry. 125 (2): 438–441. doi:10.1016/j.foodchem.2010.09.025. ISSN 0308-8146.

Bibliography

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  • Di Donna, Leonardo; Taverna, Domenico; Mazzotti, Fabio; Benabdelkamel, Hicham; Attya, Mohamed; Napoli, Anna; Sindona, Giovanni (2013). "Comprehensive assay of flavanones in citrus juices and beverages by UHPLC–ESI-MS/MS and derivatization chemistry". Food Chemistry. 141 (3): 2328–2333. doi:10.1016/j.foodchem.2013.05.034. ISSN 0308-8146. PMID 23870965.
  • Mencherini, Teresa; Campone, Luca; Piccinelli, Anna Lisa; García Mesa, Milagros; Sánchez, Dulce María; Aquino, Rita Patrizia; Rastrelli, Luca (2013). "HPLC-PDA-MS and NMR Characterization of a Hydroalcoholic Extract of Citrus aurantium L. var.amara Peel with Antiedematogenic Activity". Journal of Agricultural and Food Chemistry. 61 (8): 1686–1693. doi:10.1021/jf302815t. ISSN 0021-8561. PMID 22957519.
  • Barreca, Davide; Bellocco, Ersilia; Caristi, Corrado; Leuzzi, Ugo; Gattuso, Giuseppe (2011). "Distribution of C- and O-glycosyl flavonoids, (3-hydroxy-3-methylglutaryl)glycosyl flavanones and furocoumarins in Citrus aurantium L. juice". Food Chemistry. 124 (2): 576–582. doi:10.1016/j.foodchem.2010.06.076. ISSN 0308-8146.
  • Di Donna, Leonardo; Taverna, Domenico; Mazzotti, Fabio; Benabdelkamel, Hicham; Attya, Mohamed; Napoli, Anna; Sindona, Giovanni (2013). "Comprehensive assay of flavanones in citrus juices and beverages by UHPLC–ESI-MS/MS and derivatization chemistry". Food Chemistry. 141 (3): 2328–2333. doi:10.1016/j.foodchem.2013.05.034. ISSN 0308-8146. PMID 23870965.
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