A chromatographic-fluorometric method for determination of naringin, naringenin rutinoside, and related flavanone glycosides in grapefruit juice and juice sacs

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

doi:10.1016/0003-2697(65)90213-7

Cited by 27 publications

(2 citation statements)

References 8 publications

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“…60 Thus, naringenin is a safe flavanone with known pharmacokinetics and bioavailability. Naringenin can be found in grapefruit juice at 306 mg/ L. 61 Grapefruit juice was reported to enhance antinociception after morphine administration with a potential to reverse or delay morphine tolerance in rats. 62 We cannot conclude whether these effects were related directly to naringenin.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

The Natural Flavonoid Naringenin Elicits Analgesia through Inhibition of NaV1.8 Voltage-Gated Sodium Channels

Zhou

Cai

Moutal

et al. 2019

ACS Chem. Neurosci.

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Naringenin (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one is a natural flavonoid found in fruits from the citrus family. Because (2S)-naringenin is known to racemize, its bioactivity might be related to one or both enantiomers. Computational studies predicted that (2R)-naringenin may act on voltage-gated ion channels, particularly the N-type calcium channel (CaV2.2) and the NaV1.7 sodium channelboth of which are key for pain signaling. Here we set out to identify the possible mechanism of action of naringenin. Naringenin inhibited depolarization-evoked Ca 2+ influx in acetylcholine-, ATP-, and capsaicin-responding rat dorsal root ganglion (DRG) neurons. This was corroborated in electrophysiological recordings from DRG neurons. Pharmacological dissection of each of the voltage-gated Ca 2+ channels subtypes could not pinpoint any selectivity of naringenin. Instead, naringenin inhibited NaV1.8-dependent and tetrodotoxin (TTX)-resistant while sparing tetrodotoxin sensitive (TTX-S) voltage-gated Na + channels as evidenced by the lack of further inhibition by the NaV1.8 blocker A-803467. The effects of the natural flavonoid were validated ex vivo in spinal cord slices where naringenin decreased both the frequency and amplitude of sEPSC recorded in neurons within the substantia gelatinosa. The antinociceptive potential of naringenin was evaluated in male and female mice. Naringenin had no effect on the nociceptive thresholds evoked by heat. Naringenin's reversed allodynia was in mouse models of postsurgical and neuropathic pain. Here, driven by a call by the National Center for Complementary and Integrative Health's strategic plan to advance fundamental research into basic biological mechanisms of the action of natural products, we advance the antinociceptive potential of the flavonoid naringenin.

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Section: ■ Results and Discussionmentioning

confidence: 99%

The Natural Flavonoid Naringenin Elicits Analgesia through Inhibition of NaV1.8 Voltage-Gated Sodium Channels

Zhou

Cai

Moutal

et al. 2019

ACS Chem. Neurosci.

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“…Chromatographic analysis of the extracts were done using 5x concentrated samples after published procedures (6,7). RESULTS …”

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Naringin Levels in Citrus Tissues

Jourdan¹,

McIntosh²,

Mansell³

1985

Plant Physiol.

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ABSTRACIThe quantitative distribution of the flavanone-7-neohesperidoside, naringin, in seeds, seedlings, young plants, branches, flowers, and fruit of Citrusparadisi Macfad, cv 'Duncan' was analyzed by radioimmunoassay. High levels of naringin were associated with very young tissue and lower levels were found in older tissues. Seed coats of ungerminated seeds and young shoots had high naringin concentrations whereas cotyledons and roots had very low concentrations. Light-grown seedlings contained nearly twice as much naringin as etiolated seedlings and, in young plants and branches, the naringin content was highest in developing leaves and stem tissue. In flowers, the ovary had the highest levels of nari accounting for nearly 11% of the fresh weight. There was a net increase in the total naringin content of fruits during growth. However, due to the large increase in fruit size, there was a concomitant decrease in the narinn concentration as the fruit matured.The flavonoid pigments of plants have been intensively investigated over the past three decades and it is clear that this group of secondary metabolites is one of the largest and most diverse from both structural and functional standpoints (9) MATERIALS AND METHODS Plant Material. Fruits were obtained from grapefruit trees (var Duncan) grown at the Agricultural Experimental Station, Lake Alfred, FL. Seeds were removed from mature (November) fruit, placed on 1% agar, and were germinated under continuous illumination or in darkness. After 3 weeks, some seedlings were transferred to soil and were grown in a phytotron (25°C, 50% RH) under a 16-h light/8-h dark cycle. The 1-year-old plant used in this study was grown under the same conditions. Buds and flowers at various stages of development were collected from a single mature tree. Stages were defined according to the fresh weight and degree of development of the flowers.Extraction of Plant Tissues. For seeds, the outer seed coat, inner seed coat, and the cotyledons/embryo were separated before extraction. All tissues were cut into small pieces, placed in 5 ml methanol and boiled for 2 h. Tissues weighing more than 500 mg fresh weight were extracted in 10 ml methanol. After extraction, samples were filtered, brought to the original volume, diluted 50% with water, and stored at -20°C until assay. Fruits and fruit parts were extracted by maceration in a volume of 0.1 M Tris-HCI (pH 8.0) sufficient to prevent gelation ofendogenous pectins and the extracts stored at -20°C.Radioimmunoassay Procedure. The procedures for the naringin RIA have been described elsewhere (15; and part I of this series). Samples were diluted with water and assayed by the [3H] naringinol/oxime-hapten antiserum RIA described in part I.TLC and HPLC. Chromatographic analysis of the extracts were done using 5x concentrated samples after published procedures (6, 7). RESULTS AND DISCUSSIONThe genus Citrus is characterized by the accumulation of flavanone glycosides rather than the more common flavone, flavonol, or anthocyanin glycosides (I 1)...

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