Isolation and identification of some flavanone rutinosides of the grapefruit

Mizelle, J.W.; Dunlap, W. J.; Hagen, R. E.; Wender, Simon H.; Lime, Bruce J.; Albach, Roger F.; Griffiths, Francis P.

doi:10.1016/0003-2697(65)90097-7

Cited by 30 publications

(5 citation statements)

References 11 publications

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“…The specific activity of PPO decreased by approximately 50% during 7 days of ripening. Mizelle et al, 1965; 3-6, Stahl and and Schorn, 1961. Nt = not tested.…”

Section: Resultsmentioning

confidence: 99%

Relationship between polyphenols and browning in avocado mesocarp. Comparison between the Fuerte and Lerman cultivars

Golan¹,

Kahn²,

Sadovski³

1977

J. Agric. Food Chem.

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“…The specific activity of PPO decreased by approximately 50% during 7 days of ripening. Mizelle et al, 1965; 3-6, Stahl and and Schorn, 1961. Nt = not tested.…”

Section: Resultsmentioning

confidence: 99%

Relationship between polyphenols and browning in avocado mesocarp. Comparison between the Fuerte and Lerman cultivars

Golan¹,

Kahn²,

Sadovski³

1977

J. Agric. Food Chem.

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“…The major aglycones of flavanones include naringenin, hesperetin, and eriodictyol (Brett et al., 2009), and the glycosylation mainly occurs at the C‐7 position through O ‐glycosylation by the disaccharide of rutinose (rhamnosyl‐α−1,6‐glucose) or neohesperidose (rhamnosyl‐α−1,2‐glucose) (Ke et al., 2015). The glycosylated flavanones with neohesperidoside ligands including naringin, neohesperidin, and neoeriocitrin confer the bitter taste and are primarily found in grapefruit and bitter oranges (Frydman et al., 2013; Mizelle et al., 1965; Owens & McIntosh, 2011). On the other hand, the glycosylation forms with a rutinoside such as narirutin and hesperidin are tasteless and are mainly present in sweet orange, mandarin, and lemon (Owens & McIntosh, 2011).…”

Section: Structural Classification Of Citrus Flavonoidsmentioning

confidence: 99%

A comprehensive review of the metabolism of citrus flavonoids and their binding to bitter taste receptors

Yan

Chen

et al. 2023

Comp Rev Food Sci Food Safe

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Citrus is an important source of flavonoids in our daily diet. Citrus flavonoids have antioxidant, anticancer, anti-inflammatory, and cardiovascular disease prevention functions. Studies have shown that some pharmaceutical values of flavonoids may be related to their binding to bitter taste receptors, thus activating downstream signal transduction pathways; however, the underlying mechanism has not been systematically elucidated. In this paper, the biosynthesis pathway and the absorption and metabolism of citrus flavonoids were briefly reviewed, and the relationship between flavonoid structure and bitter taste intensity was investigated. In addition, the pharmacological effects of bitter flavonoids and the activation of bitter taste receptors in combating various diseases were discussed.This review provides an important basis for the targeted design of citrus flavonoid structures to make them more biologically active and more attractive as powerful drugs for the effective treatment of chronic diseases such as obesity, asthma, and neurological diseases.

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“…Eriocitrin is also a citrus flavonoid found in lemon peel which has antioxidant and enzyme inhibitory activity [ 9 ]. Narirutin is a flavanone originally isolated from C. paradisi that has anti-inflammatory and antidepressant-like activities [ 10 ]. These natural flavonoids have several benefits over other therapeutic agents (a) available as dietary supplements, (b) rarely have side effects (c), cost-effective, (d) can be easily absorbed in the intestine, and (e) can be used effectively for home care patients with mild symptoms.…”

Section: Introductionmentioning

confidence: 99%

Identification of some dietary flavonoids as potential inhibitors of TMPRSS2 through protein–ligand interaction studies and binding free energy calculations

Varughese

Kavitha

et al. 2022

Struct Chem

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The continuing threat of COVID-19 and deaths need an urgent cost-effective pharmacological approach. Here, we examine the inhibitory activity of a group of dietary bioactive flavonoids against the human protease TMPRSS2, which plays a major role in SARS CoV-2 viral entry. After the molecular docking studies of a large number of flavonoids, four compounds with high binding scores were selected and studied in detail. The binding affinities of these four ligands, Amentoflavone, Narirutin, Eriocitrin, and Naringin, at the active site of the TMPRSS2 target, were investigated using MD simulations followed by MM-PBSA binding energy calculations. From the studies, a number of significant hydrophobic and hydrogen bonding interactions between the ligands and binding site amino residues of TMPRSS2 are identified which showcase their excellent inhibitory activity against TMPRSS2. Among these ligands, Amentoflavone and Narirutin showed MM-PBSA binding energy values of −155.57 and −139.71 kJ/mol, respectively. Our previous studies of the inhibitory activity of these compounds against the main protease of SARS-COV2 and the present study on TMPRSS2 strongly highlighted that Amentoflavone and Naringin can exhibit promising multi-target activity against SARS-CoV-2. Moreover, due to their wide availability, no side effects, and low cost, these compounds could be recommended as dietary supplements for COVID patients or for the development of SARS-CoV-2 treatments. Supplementary Information The online version contains supplementary material available at 10.1007/s11224-022-01955-7.

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Isolation and identification of some flavanone rutinosides of the grapefruit

Cited by 30 publications

References 11 publications

Relationship between polyphenols and browning in avocado mesocarp. Comparison between the Fuerte and Lerman cultivars

Relationship between polyphenols and browning in avocado mesocarp. Comparison between the Fuerte and Lerman cultivars

A comprehensive review of the metabolism of citrus flavonoids and their binding to bitter taste receptors

Identification of some dietary flavonoids as potential inhibitors of TMPRSS2 through protein–ligand interaction studies and binding free energy calculations

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