Naringin, structure

FIGURE 13.4 Typical structures for main classes of flavonoids naringin chalcone, 4,6,4 -trihydroxyaurone, apigenin (flavone), and pelargonidin (anthocyanidin). 

Fronza, G. et al.. Structural features of the (3-CD complexes with naringin and its dihydrochalcone and aglycone derivatives by IH NMR, J. Inclusion Phenom. Macrocyclic Chem., 44, 225, 2002. 

Figure 1 Chemical structure of polyphenolics in citrus. (A) Bergamottin, (B) 6 7 dihydroxybergamottin, (C) Naringenin, (D) Naringin, (E) Rutin, (F) Tangeretin, and (G) Nobiletin.

Figure 3. Structural isomers of naringenin illustrating the two possible configurations of the sugars attached at the 7 position. Naringin is bitter whereas narirutin...

Ribeiro, I.A. Ribeiro, M.H.L. 2008. Naringin and naringenin determination and control in grapefruit juice by a validated HPLC method. Food Control 19 432-438. Rice-Evans, C.A. Miller, N.J. Paganga, G. 1996. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 20 933-956. Rietjens, I.M.C.M. Boersma, M.G. Haan, L.D. Spenkelink, B. Awad, H.M. Cnubhen, N.H.P. van Zanden, J.J. Woude, H.V.D. Alink, G.M. Koeman, J.H. 

Fig-1 Structures of naringenin (flavanone, 1), naringin (flavanone O-glycoside, 2) and rutin (flavonol O-glycoside, 3), ketoconazole (4), 7/3-hydroxycholesterol (5) and 25-hydroxycholesterol (6), resveratrol (7) and etoposide (8, VP-16)... 

The reduction in signal density and hence overlap made possible the distinction of the flavonoids hesperidin and naringin, that are present in citrus fruits. They occur as diastereoisomers whose proportions depend on the ripeness of the fiuit. Aguilar et al. predicted that the most common 2D NMR experiments could be adapted to decoupling methods of Zangger— Sterk of constant-time type such that pure-shift 2D correlation spectra could be produced. They would be of enormous value in structure elucidation and analyses of mixtures. 

The most important members of the flavonoid family include anthocyanidins (e.g., cyanidin, delphinidin, malvidin), flavonols (e.g., quercetin, kaempferol), flavones (e.g., luteolin, apigenin), flavanones (e.g., myricetin, naringin, hesperetin, naringenin), flavan-3-ols (e.g., catechin, epicatechin, gallocatechin) and, although sometimes classified separately, the isoflavones (e.g., genistein, daidzein). For chemical structures see Figure 1. All these phytochemical are frequently referred to as bioflavonoids due to well established effects in human health maintenance. 

Fig. 7.4 Chemical structures and DPP-IV inhibitory activity for the most relevant natural compounds of non-peptide nature a sulphostin b berberine c trigonelline d compound 4 e curcumin f resveratrol g luteolin h apigenin i flavone j naringin and kZINC02132035...

Figure 1.10 Structures of the flavanones hesperidin, neohesperidin and naringin.

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