Naringin and Grape Fruit Seed Extract.Fascinating Use and Applications!

  seminal trace...Naringin 98%HPLC.CAS.NO:10236-47-2.M.F.:C27H32O14.M.W.:580.54.Names:4'',5,7-trihydroxyflavanone-7-rhamnoglucoside;4'',5,7-trihydroxyflavanone-7-rutinoside;2R-Naringin,Naringoside,NSC5548;4',5,7-Trihydroxyflavanone 7-rhamnoglucoside;Naringenine-7-rhamnosidoglucoside;4',5,7-trihydroxyflavanone-7-rutinoside.MDidea Brand of Naringin Sodium,aurantiin,Cyclorel,naringenin-7-hesperidoside,naringin dihydrochalcone,naringin sodium...

   

   Naringin: Definition and Activity:

  Botanical Name : Citrus paradisi
  Part of Plant Used :Grapefruit.
  Grapefruit got its name from the way it grew in "grape-like" clusters on the tree. Originally it wasn't very desirable with its thick skin, lots of seeds, little juice, and a very sour taste. Growers dramatically improved the flavor and texture so that now you have a fruit that is seedless, with a taste that is both tangy and sweet.
  Nutrition Highlights:Grapefruit (sections; raw, pink and red), 1 cup (230g)
  Calories: 74.Protein: 1.4g.Carbohydrate: 18.6g.Total Fat: 0.23g.Fiber: 2.5g.*Good source of: Vitamin C (79mg).

   Definition: (organic chemistry) C27H32O14 A crystalline bioflavonoid with a melting point of 171 Deg C; soluble in acetone and alcohol; used as a food supplement. Also known as aurantiin.

  Naringin is the major flavonoid glycoside in grapefruit and gives grapefruit juice its bitter taste. It is metabolized to the flavonone naringenin in humans. Both naringin and hesperetin, which are the aglycones of naringin and hesperidin, occur naturally in citrus fruits.

   Activity: Narinigin exerts a variety of pharmacological effects such as antioxidant activity, blood lipid-lowering, anticarcinogenic activity, and inhibition of selected cytochrome P450 enzymes including CYP3A4 and CYP1A2, which may result in several drug interactions in-vitro.
 


 Naringin: Definition and Activity:
 Basic Chemical Info of Naringin:
 Description and Distribution:
 Research Overview and Strudies in Brief:
 Naringin and Fat Burning:
 The fate of naringin in humans: A key to grapefruit juice-drug interactions?
 Research Update of Naringin:
 Safety and Acute toxicity:


   Basic Chemical Info of Naringin:

 Systematic name:Naringin
 Molecular Formula: C27H32O14
 Molecular Weight:580.53
 Chemical Name: (2R)-5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxyhexopyranosyl)hexopyranoside
 (2R)-ISOMER OF NARINGIN
 Synonyms:2R-Naringin,Naringoside,NSC5548;4',5,7-Trihydroxyflavanone 7-rhamnoglucoside;Naringenine-7-rhamnosidoglucoside;4¡ä,5,7-trihydroxyflavanone-7-rutinoside.Alpharma Brand of Naringin Sodium,aurantiin,Cyclorel,naringenin-7-hesperidoside,naringin dihydrochalcone,naringin sodium.
 Other Names: 7-(2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavone; 7-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-5-hydroxy-2(S)-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
 
 Merck Index:13: 6452
 EINECS 233-566-4
 CAS No.: 10236-47-2
 Melting point 166~171 Deg C.
 alpha -91 (c=1, C2H5OH)


   Description and Distribution:

 Naringin is an extract from grapefruit, and has been shown in studies to have a potent effect on the half-life of caffeine in the body (extending the rate at which caffeine is broken down). As such, naringin may effectively prolong the thermogenic activity of caffeine in the body so that it may continue to exert a fat burning effect for a longer period of time.

 As a citrous bioflavonoid found to inhibit cytochrome P450 monooxygenase activirty in mouse liver. It prevents toxin-induced cytoskeletal disruption and apoptotic liver cell death. In addition, it was found to have hypocholesterolemic effect by inhibiting HMG-CoA reductase and ACAT activities. Naringin belongs to the group of flavonoids. Pure naringin is a yellowish powder. Naringin is a conjugate of a sugar molecule with naringenin. The structure of naringin is very similar to that of hesperidin.

  Distribution:

 Naringin is mainly found in grapefruits. It is the compound that gives grapefruit its typical bitter flavour.
 Studies have shown that naringin interferes with enzymatic activity in the intestines and, thus, with the breakdown of certain drugs, resulting in higher blood levels of the drug. A number of drugs that are known to be affected by the naringin in grapefruit include calcium channel blockers, estrogen, sedatives, medications for high blood pressure, allergies, AIDS, and cholesterol-lowering drugs. Caffeine levels and effects of caffeine may also be extended by consuming grapefruit or grapefruit juice. While the effect of naringin on the metabolism of a drug can increase the drug's effectiveness, it can also result in dosages that are inadvertently too high. Therefore, it's best not to take any drugs with grapefruit juice unless the interaction with the drug is known. In addition, the effects of drinking grapefruit juice is cumulative, which means that if you drank a glass of grapefruit juice daily with your medication for a week, the drug interaction would be stronger at the end of the week than at the beginning Naringin can be used as an intermediate in the synthesis of many organic chemicals.
 The best example is the sweeter neohesperidine dihydrochalcone:Naringin is related to other flavanones known to have therapeutic action in influencing capillary permeability. For those pharmaceutical uses the better solubility of naringin in water is an advantage.
 


   Research Overview and Strudies in Brief:

 Research on Naringin shows the following effects:
  1. Protects against toxins in chemotherapy drugs and the environment
  2. Enhances lipid metabolism
  3. Enhances ethanol metabolism
  4. Reduces negative effects of ethanol intake
  5. Acts as a free radical scavenger
  6. Reduces cytotoxicity
  7. Acts as an antioxidant
  8. Acts as an anti-apoptotic
  9. Protect from carcinogenic matter
  10. May reduce risk of atherosclerosis
  11. Significantly inhibits LDL oxidation
  12. Used in the treatment of gastric lesions
  13. Inhibits the Sindbis neurovirulent virus
  14. Reduces total cholesterol levels
  15. Protects plasma vitamin E levels
  16. Prevents hypercholesterolemia
  17. Is anti-atherogenic
 

 Naringin is a flavonoid compound found in grapefruit, naringin gives grapefruit its characteristic bitter flavor. Grapefruit processors attempt to select fruits with a low naringin content, and often blend juices obtained from different grapefruit varieties to obtain the desired degree of bitterness.

 Naringin is believed to enhance our perception of taste by stimulating the taste buds (some people consume a small amount of grapefruit juice before a meal for this reason).

 Naringin may be instrumental in inhibiting cancer-causing compounds and thus may have potential chemotherapeutic value. Studies have also shown that naringin interferes with enzymatic activity in the intestines and, thus, with the breakdown of certain drugs, resulting in higher blood levels of the drug. A number of drugs that are known to be affected by the naringin in grapefruit include calcium channel blockers, estrogen, sedatives, medications for high blood pressure, allergies, AIDS, and cholesterol-lowering drugs. Caffeine levels and effects of caffeine may also be extended by consuming grapefruit or grapefruit juice. While the effect of naringin on the metabolism of a drug can increase the drug's effectiveness, it can also result in dosages that are inadvertently too high. Therefore, it's best not to take any drugs with grapefruit juice unless the interaction with the drug is known. In addition, the effects of drinking grapefruit juice is cumulative, which means that if you drank a glass of grapefruit juice daily with your medication for a week, the drug interaction would be stronger at the end of the week than at the beginning.


   Naringin and Fat Burning:

 Naringin is a citrus flavanoid commonly found in grapefruit, and is responsible for grapefruit's distinctive bitter taste.Most of us have heard how it's important to be careful consuming grapefruit juice along with certain medications -- studies reveal that naringin interferes with some digestive enzymes which can affect the metabolism and breakdown of these drugs. This can in effect lead to an inadvertantly higher dose of the drug, which may pose the threat of adverse reactions in some cases.
 However, naringin displays many other interesting properties, some of which make it suitable for inclusion into the ingredients list of many popular fat burners.Naringin is Grapefruit's Fat Burning Accelerator.
 For one, there is some evidence that the effects and levels of caffeine can be extended when consumed with naringin. Since virtually 99% of the fat burners on the market contain caffeine (often derived from natural sources like Kola nut, Yerba mate, Green tea, and so on), and since caffeine does exhibit thermogenic (fat burning) properties, naringin is an obvious "no brainer" way to improve and extend its effects.

 Naringin has also been shown to exhibit cholesterol-lowering effects, which is always a good thing for dieters. It's also an aldose reductase inhibitor,which means it may also have a role to play battling retinal disease in diabetics.
 While naringin may not be the most "sexy" ingredient in your favorite fat burner,it is a worthwhile one.
 


   The fate of naringin in humans: A key to grapefruit juice-drug interactions?

 The increase of concentrations observed for many drugs when administered concomitantly with grapefruit juice was attributed to inhibition of cytochrome P450 enzymes by naringenin, the aglycone of the grapefruit flavonoid naringin.

 However, this explanation is equivocal, and formation of naringenin after ingestion of grapefruit juice has not been proved. We investigated renal excretion of naringin, naringenin, and its glucuronides after administration of 20 ml grapefruit juice (621 mol/L naringin) per kilogram of body weight to six healthy adults. Urine was collected for 24 hours, and flavonoids were measured by HPLC in aliquots with and without glucuronidase pretreatment. Naringin or naringin glucuronides were not found. Naringenin and its glucuronides appeared in urine after a median lag-time of 2 hours and reached 0.012% to 0.37% and 5.0% to 57%, respectively, of the molar naringin dose. In additional investigations, low concentrations (<4 mol/L) of naringenin glucuronides, but neither naringin nor naringenin were found in plasma samples from previous grapefruit juice interaction studies, and metabolization of naringin to naringenin occurred during 24 hours of incubation (37¡ã C) in three of five feces samples tested.
 

 The data suggest that cleavage of the sugar moiety, presumably by intestinal bacteria, is the first step of naringin metabolism.Naringenin formation is thought to be the crucial step in determination of bioavailability of the compound, which undergoes rapid glucuronidation. The pronounced interindividual variability of naringin kinetics provides a possible explanation for some of the apparently contradictory results of drug interaction studies with grapefruit and naringin.


  Safety and Acute toxicity:

 Naringin

 Chemical name: Naringin
 CAS No.: 10236-47-2. Molecular Formula:C27-H32-O14. Molecular Weight:580.59
 Synonmys: Naringenin-7-beta-neohesperidoside;Naringoside.

 Acute toxicity(LD50):Naringin
 LD50-Lethal dose,50 percent kill. Intraperitoneal.Rodent-rat.2 gm(2000 mgs)/kg.
 Details of toxic effects not reported other than lethal dose value.

 LD50-Lethal dose,50 percent kill. Intraperitoneal.Rodent-guinea pig.2 gm(2000 mgs)/kg.
 Details of toxic effects not reported other than lethal dose value.
 Reference:EKMMA8 Eksperimentalna Meditsina i Morfologiya.(Hemus,Blvd.Russki 6,Sofia,Bulgaria)V.1-1962-Volume(issue)/page/year:19,207,1980.


  Scientific References:

  1.Naringin and Grape Fruit Seed Extract.Fascinating Use and Applications!