Discover The Health Benefits Of Naringenin

The structure of naringenin:

Naringenin has a flavanone skeleton structure with three hydroxyl groups at the 4', 5 and 7 carbon atoms. Naringenin can exist as a monomer, and also in the form of glycosides, that is, naringin, which has the added disaccharide neohesperidose connected to the 7th carbon atom.

Like most flavanones, naringenin has a chiral center at carbon 2, although the optical purity is variable. Racemization of S(-)-naringenin has been shown to occur rather rapidly.


Sources and Bioavailability of Naringenin:

Naringenin and its glycosides are found in a variety of herbs and fruits, including grapefruit, bergamot, lime, sour cherry, and beans. The ratio of naringenin to naringin varies by source, as does the ratio of enantiomers.

The bioavailability of the naringin-7-glucoside form appears to be lower than that of the polyethylene glycol form.

Naringenin plasma concentrations were higher after consumption of grapefruit juice than after consumption of orange juice. The related compound kaempferol is also found in grapefruit, with the hydroxyl group next to the ketone group.

Naringenin can be absorbed from cooked tomato paste. Tomato paste contains 253 mg of naringenin per 10 grams.

Biosynthesis and metabolism of naringenin:

It is derived from malonyl CoA and 4-coumaroyl CoA. The latter is derived from phenylalanine. The obtained butenone acts on chalcone synthase to obtain chalcone. The chalcone then undergoes ring closure to produce naringenin.

Naringenin-8-dimethylallyl transferase uses dimethylallyl diphosphate and (−)-(2S)-naringenin to produce diphosphate and 8-pentylnaringenin. Cunninghamella elegans is a fungal model organism of mammalian metabolism, which can be used to study the sulfation of naringenin.

The difference between hesperetin and naringenin:

Citrus extracts mainly contain hesperetin and naringenin.

Both products have antioxidant effects. The former can reduce the harm caused by oxidation reactions, while the latter has a good scavenging effect on free radicals, can effectively inhibit lipid peroxidation, and can also enhance superoxide dismutase (SOD). , The activity of catalase plays an antioxidant role.

In terms of anti-inflammation, hesperetin can interfere with the release of arachidonic acid metabolites and histamine inflammatory mediators, indirectly inhibiting inflammation; naringenin has anti-allergic, anti-inflammatory, antibacterial and other effects.

Hesperetin mainly comes from Rutaceae plants, such as citrus, chrysanthemum and so on. The content in ordinary orange juice and grapefruit juice is 200-590mg/L, and the content in the peel is rich.

Naringenin is mainly derived from Rutaceae plants, such as pomelo fruits, grapefruit fruits, tangerine fruits and leaves. The pomelo peel has a higher content of naringin than the pulp, about 1% to 6%.

A method for extracting naringenin from grapefruit, the steps are as follows:

1) Take the dried grapefruit fruit, crush it, pass it through a 10-mesh sieve, and set aside the residue;

2) Take the undersieve and put it into hot water at 80-90°C, heat it to above 95°C to extract for 1-2 hours, filter, and put the filtrate for later use, put the filter residue into hot water at 80-90°C, heat it to above 95°C for extraction 1-2 hours, filter, combine the two filtrate to get the total filtrate;

3) Pass the total filtrate through a decanter centrifuge, the speed of the decanter centrifuge is 12000R/min, after removing mechanical impurities, cool the total filtrate to below 60°C, separate and purify it with an ultrafiltration membrane, and remove most of the total filtrate Subcategories of substances to obtain membrane-passing liquid;

4) Concentrate the membrane-passing liquid, the pressure of the inlet solution is 0.9 Mpa, and the pressure of the outlet solution is 0.45Mpa, and then transfer the membrane-passing liquid to a decompression concentration tank, after concentration, the extract is obtained, and the extract is put into a clean crystallization container Cool to below 10°C to crystallize for 1-2 days, wait until the crystallization is saturated, filter to obtain crystals, wash the crystals with pure water twice the weight of the crystals, and dry the crystals to obtain product I;

5) Product I was hydrolyzed with aqueous hydrochloric acid solution with a concentration of 1.5 mol/L, then rapidly cooled to 25-28°C and allowed to stand for crystallization for 10 hours, and the crude crystals were separated by suction filtration, and the crude crystals of naringenin were obtained after drying;

6) Add ethanol with a mass fraction of 60%-85% to the crude crystals of naringenin, heat to 80°C to completely dissolve the crude crystals of naringenin, cool to below 10°C to crystallize for 2-3 days, and completely crystallize The material is subjected to suction filtration, and the filter cake is washed with purified water twice the weight of the filter cake until the filtrate is colorless to obtain crystals, which are vacuum-dried at 80°C to obtain naringenin.

The method is simple and easy to operate, and the raw materials are easy to obtain, the time consumption is short, the energy consumption is small, the extraction rate is high, no column is required, it is suitable for industrial mass production, less organic solvent is used, the cost is saved and the environmental pollution is reduced. The obtained naringenin The crude product has few impurities, and higher quality naringenin can be obtained through only one recrystallization.

Determination method of naringenin:

Note: Before the formal measurement, select 2-3 samples with large expected differences for pre-determination.

Product Introduction: Naringenin is a dihydroflavonoid compound, and its unique spatial structure makes it the flavone skeleton substance with the most derivatives. Naringenin has a wide range of pharmacological activities, including antioxidant, anti-inflammatory and other activities. Naringenin has an absorption peak at 270 nm, and its content can be determined by high performance liquid chromatography.

Instruments and reagents required in the experiment: High-performance liquid chromatography (C18 column (4.6×250 mm), ultraviolet detector (VWD)), desktop centrifuge, adjustable pipette, mortar/homogenizer, brown EP tube, syringe filter (50 pieces, organic system, 0.45 µm), syringe, suction filter, filter membrane (organic system, water system), brown injection bottle (50 pieces, 1.5 mL), acetonitrile (chromatographically pure, 500 mL), ultrapure water, phosphoric acid (analytical grade), methanol (analytical grade), 5 mL white plastic reagent bottle, 2 mL EP tube.

product content:

Extract: liquid 90 mL × 1 bottle, store at 4°C.

Standard product: powder x 1 stick, stored at 4°C in the dark. Before use, add 2 mL of methanol to prepare a 1 mg/mL naringenin standard solution, and store in a sealed container at 4°C, avoiding direct sunlight.

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