Naringenin is a
flavanone from the
flavonoid group of
polyphenols. It is commonly found in a variety of citrus fruits and is the predominant flavonone in
grapefruit.[2] Naringenin has demonstrated numerous biological activities, including anti-inflammatory properties, antioxidant activity and skin healing.[3][4][5][6] It is used as a cosmetic ingredient and dietary supplement.[7] Naringenin (along with
furanocoumarins presented in citrus fruits) is thought to be responsible for
CYP3A4 suppression in the intestinal wall, that may result in serious
changes of pharmacokinetics in drugs related with this enzyme.[8][9][10]
Structure
Naringenin has the skeleton structure of a flavanone with three
hydroxy groups at the 4′, 5, and 7 carbons. It may be found both in the
aglycol form, naringenin, or in its
glycosidic form,
naringin, which has the addition of the
disaccharideneohesperidose attached via a
glycosidic linkage at carbon 7.
Like the majority of flavanones, naringenin has a single chiral center at carbon 2, although the optical purity is variable.[11][12]Racemization of (S)-(−)-naringenin has been shown to occur fairly quickly.[13]
Grapefruit juice can provide much higher plasma concentrations of naringenin than orange juice.[24] Also found in grapefruit is the related compound
kaempferol, which has a hydroxyl group next to the ketone group.
Naringenin can be absorbed from cooked tomato paste. There are 3.8 mg of naringenin in 150 grams of tomato paste.[25]
Biosynthesis and metabolism
Naringenin can be produced from naringin by the hydrolytic action of the liver enzyme naringinase.[26]
Studies show naringenin has numerous biological activities, including anti-inflammatory, antioxidant, antibacterial, antiviral and anticancer. It is deemed safe for both topical and ingestible use in healthy adults.[7]
Anti-inflammatory
Naringenin’s anti-inflammatory benefits have been well established with multiple in vitro and in vivo studies, revealing it effectively suppresses proinflammatory factors, cytokine and chemokine expressions in inflammation.[3] When taken orally, it has also been shown to reduce inflammatory pain.[29]
Antioxidant
Naringenin has been shown to have significant
antioxidant properties.[30][31] It has been shown to reduce oxidative damage to
DNAin vitro and in animal studies.[32][33] When consumed it has been shown to increase antioxidant markers superoxide dismutase and glutathione.[6]
Endothelium protection
Some human studies and many animal studies have shown the ability of both naringenin and naringin to protect and improve the health of the vascular
endothelium.[26] Naringenin reportedly stimulates
Nrf2 to protect blood vessels.[34]
Naringenin has also been shown to reduce
hepatitis C virus production by infected
hepatocytes (liver cells) in
cell culture. This seems to be secondary to naringenin's ability to inhibit the secretion of
very-low-density lipoprotein by the cells.[40] The antiviral effects of naringenin are currently under clinical investigation.[41] Reports of antiviral effects on
polioviruses,
HSV-1 and
HSV-2 have also been made, though replication of the viruses has not been inhibited.[42][43] In in vitro experiments naringenin also showed a strong antiviral activity against
SARS-CoV-2.
[44]
Skin Healing
When used in topical formulations, naringenin has been shown to be an anti-inflammatory with skin barrier restoration and antioxidant activities.
UVB radiation is very high energy frequency and wreak havoc on the top layers of the skin by damaging the skin cells and causing DNA mutations that can lead to melanoma and other skin cancers.[45] Naringenin has been proven to reduce UVB-induced skin damage, as well as showing efficacy against oxidative stress and improvement in wound healing.[4][46][6]
Naringenin has also been studied on inflammatory skin conditions such as atopic dermatitis and psoriasis.[3][47][48] For atopic dermatitis, naringenin was found to sharply suppress inflammatory levels and alleviate symptoms and may suppress the development of atopic dermatitis like skin lesions.[3][47] In psoriasis, naringenin has been studied to reduce inflammation in psoriatic plaques.[48]
Anticancer
Cytotoxicity has been reduced reportedly by naringenin in cancer cells from
breast,
stomach,
liver,
cervix,
pancreas, and
colon tissues, along with
leukaemia cells.[49][50] The mechanisms behind inhibition of human
breast carcinoma growth have been examined, and two theories have been proposed.[51] The first theory is that naringenin inhibits
aromatase, thus reducing growth of the tumor.[52] The second mechanism proposes that interactions with
estrogen receptors is the cause behind the modulation of growth.[53] New derivatives of naringenin were found to be active against multidrug-resistant cancer.[54]
Fatty Liver Disease
Naringenin may have some benefits for non-alcoholic fatty liver disease. It was proven to reduce hepatic lipid accumulation and inflammation in the livers of mice with non-alcoholic fatty liver disease.[55]
Alzheimer's disease
Naringenin is being researched as a potential treatment for
Alzheimer's disease. Naringenin has been demonstrated to improve memory and reduce
amyloid and
tau proteins in a study using a mouse model of Alzheimer's disease.[56][57] The effect is believed to be due to a protein present in neurons known as
CRMP2 that naringenin binds to.[58]
Safety
Naringenin has been deemed safe to apply topically and can also be ingested safely by healthy adults in doses of 150 to 900 mg, with 300 mg of naringenin twice a day likely to elicit physiological effect.[7]
^Yáñez JA, Andrews PK, Davies NM (April 2007). "Methods of analysis and separation of chiral flavonoids". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 848 (2): 159–181.
doi:
10.1016/j.jchromb.2006.10.052.
PMID17113835.
^
abYáñez JA, Remsberg CM, Miranda ND, Vega-Villa KR, Andrews PK, Davies NM (March 2008). "Pharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and eriodictyol in rats and their content in fruit juices". Biopharmaceutics & Drug Disposition. 29 (2): 63–82.
doi:
10.1002/bdd.588.
PMID18058792.
S2CID24051610.
^Krause M, Galensa R (July 1991). "Analysis of enantiomeric flavanones in plant extracts by high-performance liquid chromatography on a cellulose triacetate based chiral stationary phase". Chromatographia. 32 (1–2): 69–72.
doi:
10.1007/BF02262470.
ISSN0009-5893.
S2CID95215634.
^Ho PC, Saville DJ, Coville PF, Wanwimolruk S (April 2000). "Content of CYP3A4 inhibitors, naringin, naringenin and bergapten in grapefruit and grapefruit juice products". Pharmaceutica Acta Helvetiae. 74 (4): 379–385.
doi:
10.1016/S0031-6865(99)00062-X.
PMID10812937.
^Gel-Moreto N, Streich R, Galensa R (August 2003). "Chiral separation of diastereomeric flavanone-7-O-glycosides in citrus by capillary electrophoresis". Electrophoresis. 24 (15): 2716–2722.
doi:
10.1002/elps.200305486.
PMID12900888.
S2CID40261445.
^
abMinoggio M, Bramati L, Simonetti P, Gardana C, Iemoli L, Santangelo E, et al. (2003-01-01). "Polyphenol pattern and antioxidant activity of different tomato lines and cultivars". Annals of Nutrition & Metabolism. 47 (2): 64–69.
doi:
10.1159/000069277.
PMID12652057.
S2CID26333030.
^Vallverdú Queralt A, Odriozola Serrano I, Oms Oliu G, Lamuela Raventós RM, Elez Martínez P,
Martín Belloso O (September 2012). "Changes in the polyphenol profile of tomato juices processed by pulsed electric fields". Journal of Agricultural and Food Chemistry. 60 (38): 9667–9672.
doi:
10.1021/jf302791k.
PMID22957841.
^Sánchez Rabaneda F, Jáuregui O, Casals I, Andrés Lacueva C, Izquierdo Pulido M, Lamuela Raventós RM (January 2003). "Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao)". Journal of Mass Spectrometry. 38 (1): 35–42.
Bibcode:
2003JMSp...38...35S.
doi:
10.1002/jms.395.
PMID12526004.
^Exarchou V, Godejohann M, van Beek TA, Gerothanassis IP, Vervoort J (November 2003). "LC-UV-solid-phase extraction-NMR-MS combined with a cryogenic flow probe and its application to the identification of compounds present in Greek oregano". Analytical Chemistry. 75 (22): 6288–6294.
doi:
10.1021/ac0347819.
PMID14616013.
^Olsen HT, Stafford GI, van Staden J, Christensen SB, Jäger AK (May 2008). "Isolation of the MAO-inhibitor naringenin from Mentha aquatica L". Journal of Ethnopharmacology. 117 (3): 500–502.
doi:
10.1016/j.jep.2008.02.015.
PMID18372132.
^Hungria M, Johnston AW, Phillips DA (1992-05-01). "Effects of flavonoids released naturally from bean (Phaseolus vulgaris) on nodD-regulated gene transcription in Rhizobium leguminosarum bv. phaseoli". Molecular Plant-Microbe Interactions. 5 (3): 199–203.
doi:
10.1094/mpmi-5-199.
PMID1421508.
^Choudhury R, Chowrimootoo G, Srai K, Debnam E, Rice-Evans CA (November 1999). "Interactions of the flavonoid naringenin in the gastrointestinal tract and the influence of glycosylation". Biochemical and Biophysical Research Communications. 265 (2): 410–415.
doi:
10.1006/bbrc.1999.1695.
PMID10558881.
^Wang C, Zhi S, Liu C, Xu F, Zhao A, Wang X, et al. (March 2017). "Characterization of Stilbene Synthase Genes in Mulberry (Morus atropurpurea) and Metabolic Engineering for the Production of Resveratrol in Escherichia coli". Journal of Agricultural and Food Chemistry. 65 (8): 1659–1668.
doi:
10.1021/acs.jafc.6b05212.
PMID28168876.
^Gorinstein S, Leontowicz H, Leontowicz M, Krzemiński R, Gralak M, Delgado-Licon E, et al. (April 2005). "Changes in plasma lipid and antioxidant activity in rats as a result of naringin and red grapefruit supplementation". Journal of Agricultural and Food Chemistry. 53 (8): 3223–3228.
doi:
10.1021/jf058014h.
PMID15826081.
^Yu J, Wang L, Walzem RL, Miller EG, Pike LM, Patil BS (March 2005). "Antioxidant activity of citrus limonoids, flavonoids, and coumarins". Journal of Agricultural and Food Chemistry. 53 (6): 2009–2014.
doi:
10.1021/jf0484632.
PMID15769128.
^Kumar S, Tiku AB (March 2016). "Biochemical and Molecular Mechanisms of Radioprotective Effects of Naringenin, a Phytochemical from Citrus Fruits". Journal of Agricultural and Food Chemistry. 64 (8): 1676–1685.
doi:
10.1021/acs.jafc.5b05067.
PMID26881453.
^Jagetia GC, Reddy TK, Venkatesha VA, Kedlaya R (September 2004). "Influence of naringin on ferric iron induced oxidative damage in vitro". Clinica Chimica Acta; International Journal of Clinical Chemistry. 347 (1–2): 189–197.
doi:
10.1016/j.cccn.2004.04.022.
PMID15313158.
^Rauha JP, Remes S, Heinonen M, Hopia A, Kähkönen M, Kujala T, et al. (May 2000). "Antimicrobial effects of Finnish plant extracts containing flavonoids and other phenolic compounds". International Journal of Food Microbiology. 56 (1): 3–12.
doi:
10.1016/S0168-1605(00)00218-X.
PMID10857921.
^Mandalari G, Bennett RN, Bisignano G, Trombetta D, Saija A, Faulds CB, et al. (December 2007). "Antimicrobial activity of flavonoids extracted from bergamot (Citrus bergamia Risso) peel, a byproduct of the essential oil industry". Journal of Applied Microbiology. 103 (6): 2056–2064.
doi:
10.1111/j.1365-2672.2007.03456.x.
PMID18045389.
S2CID2043029.
^Koru Ö, Toksoy F, Açıkel CH, Tunca YM, Baysallar M, Üsküdar Güçlü A, et al. (2007-06-01). "In vitro antimicrobial activity of propolis samples from different geographical origins against certain oral pathogens". Anaerobe. 13 (3–4): 140–145.
doi:
10.1016/j.anaerobe.2007.02.001.
PMID17475517.
^Uzel A, Sorkun K, Önçağ Ö, Coǧulu D, Gençay Ö, Salih B (2005-04-25). "Chemical compositions and antimicrobial activities of four different Anatolian propolis samples". Microbiological Research. 160 (2): 189–195.
doi:
10.1016/j.micres.2005.01.002.
hdl:11655/19951.
PMID15881836.
^Bae EA, Han MJ, Kim DH (June 1999). "In vitro anti-Helicobacter pylori activity of some flavonoids and their metabolites". Planta Medica. 65 (5): 442–443.
doi:
10.1055/s-2006-960805.
PMID10454900.
S2CID260284591.
^Mucsi I, Prágai BM (July 1985). "Inhibition of virus multiplication and alteration of cyclic AMP level in cell cultures by flavonoids". Experientia. 41 (7): 930–931.
doi:
10.1007/BF01970018.
PMID2989000.
S2CID6174141.
^Lyu SY, Rhim JY, Park WB (November 2005). "Antiherpetic activities of flavonoids against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in vitro". Archives of Pharmacal Research. 28 (11): 1293–1301.
doi:
10.1007/BF02978215.
PMID16350858.
S2CID34495208.
^Salehi M, Ehterami A, Farzamfar S, Vaez A, Ebrahimi-Barough S (February 2021). "Accelerating healing of excisional wound with alginate hydrogel containing naringenin in rat model". Drug Delivery and Translational Research. 11 (1): 142–153.
doi:
10.1007/s13346-020-00731-6.
PMID32086788.
S2CID211234647.
^
abKim TH, Kim GD, Ahn HJ, Cho JJ, Park YS, Park CS (October 2013). "The inhibitory effect of naringenin on atopic dermatitis induced by DNFB in NC/Nga mice". Life Sciences. 93 (15): 516–524.
doi:
10.1016/j.lfs.2013.07.027.
PMID23933131.
^
abAlalaiwe A, Lin CF, Hsiao CY, Chen EL, Lin CY, Lien WC, Fang JY (May 2020). "Development of flavanone and its derivatives as topical agents against psoriasis: The prediction of therapeutic efficiency through skin permeation evaluation and cell-based assay". International Journal of Pharmaceutics. 581: 119256.
doi:
10.1016/j.ijpharm.2020.119256.
PMID32220586.
S2CID214694347.
^So FV, Guthrie N, Chambers AF, Moussa M, Carroll KK (1996-01-01). "Inhibition of human breast cancer cell proliferation and delay of mammary tumorigenesis by flavonoids and citrus juices". Nutrition and Cancer. 26 (2): 167–181.
doi:
10.1080/01635589609514473.
PMID8875554.
^van Meeuwen JA, Korthagen N, de Jong PC, Piersma AH, van den Berg M (June 2007). "(Anti)estrogenic effects of phytochemicals on human primary mammary fibroblasts, MCF-7 cells and their co-culture". Toxicology and Applied Pharmacology. 221 (3): 372–383.
doi:
10.1016/j.taap.2007.03.016.
PMID17482226.
^Harmon AW, Patel YM (May 2004). "Naringenin inhibits glucose uptake in MCF-7 breast cancer cells: a mechanism for impaired cellular proliferation". Breast Cancer Research and Treatment. 85 (2): 103–110.
doi:
10.1023/B:BREA.0000025397.56192.e2.
PMID15111768.
S2CID24436665.
^Ferreira RJ, Baptista R, Moreno A, Madeira PG, Khonkarn R, Baubichon-Cortay H, et al. (April 2018). "Optimizing the flavanone core toward new selective nitrogen-containing modulators of ABC transporters". Future Medicinal Chemistry. 10 (7): 725–741.
doi:
10.4155/fmc-2017-0228.
PMID29570361.
Wistuba D, Trapp O, Gel-Moreto N, Galensa R, Schurig V (May 2006). "Stereoisomeric separation of flavanones and flavanone-7-O-glycosides by capillary electrophoresis and determination of interconversion barriers". Analytical Chemistry. 78 (10): 3424–3433.
doi:
10.1021/ac0600499.
PMID16689546.
Krause M, Galensa R (1991). "High-performance liquid chromatography of diastereomeric flavanone glycosides in Citrus on a β-cyclodextrin-bonded stationary phase (Cyclobond I)". Journal of Chromatography A. 588 (1–2): 41–45.
doi:
10.1016/0021-9673(91)85005-z.
Gaggeri R, Rossi D, Collina S, Mannucci B, Baierl M, Juza M (August 2011). "Quick development of an analytical enantioselective high performance liquid chromatography separation and preparative scale-up for the flavonoid Naringenin". Journal of Chromatography A. 1218 (32): 5414–5422.
doi:
10.1016/j.chroma.2011.02.038.
PMID21397238.
Naringenin also produces
BDNF-dependent antidepressant-like effects in mice.Yi LT, Liu BB, Li J, Luo L, Liu Q, Geng D, et al. (January 2014). "BDNF signaling is necessary for the antidepressant-like effect of naringenin". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 48: 135–141.
doi:
10.1016/j.pnpbp.2013.10.002.
PMID24121063.
S2CID24620048.
Gao K, Henning SM, Niu Y, Youssefian AA, Seeram NP, Xu A, Heber D (February 2006). "The citrus flavonoid naringenin stimulates DNA repair in prostate cancer cells". The Journal of Nutritional Biochemistry. 17 (2): 89–95.
doi:
10.1016/j.jnutbio.2005.05.009.
PMID16111881.
Naringenin has been reported to induce apoptosis in
preadipocytes.Hsu CL, Huang SL, Yen GC (June 2006). "Inhibitory effect of phenolic acids on the proliferation of 3T3-L1 preadipocytes in relation to their antioxidant activity". Journal of Agricultural and Food Chemistry. 54 (12): 4191–4197.
doi:
10.1021/jf0609882.
PMID16756346.
Naringenin lowers the plasma and hepatic
cholesterol concentrations by suppressing HMG-CoA reductase and ACAT in rats fed a high-cholesterol diet.Lee SH, Park YB, Bae KH, Bok SH, Kwon YK, Lee ES, Choi MS (1999). "Cholesterol-lowering activity of naringenin via inhibition of 3-hydroxy-3-methylglutaryl coenzyme A reductase and acyl coenzyme A:cholesterol acyltransferase in rats". Annals of Nutrition & Metabolism. 43 (3): 173–180.
doi:
10.1159/000012783.
PMID10545673.
S2CID5685548.
Naringenin is a
flavanone from the
flavonoid group of
polyphenols. It is commonly found in a variety of citrus fruits and is the predominant flavonone in
grapefruit.[2] Naringenin has demonstrated numerous biological activities, including anti-inflammatory properties, antioxidant activity and skin healing.[3][4][5][6] It is used as a cosmetic ingredient and dietary supplement.[7] Naringenin (along with
furanocoumarins presented in citrus fruits) is thought to be responsible for
CYP3A4 suppression in the intestinal wall, that may result in serious
changes of pharmacokinetics in drugs related with this enzyme.[8][9][10]
Structure
Naringenin has the skeleton structure of a flavanone with three
hydroxy groups at the 4′, 5, and 7 carbons. It may be found both in the
aglycol form, naringenin, or in its
glycosidic form,
naringin, which has the addition of the
disaccharideneohesperidose attached via a
glycosidic linkage at carbon 7.
Like the majority of flavanones, naringenin has a single chiral center at carbon 2, although the optical purity is variable.[11][12]Racemization of (S)-(−)-naringenin has been shown to occur fairly quickly.[13]
Grapefruit juice can provide much higher plasma concentrations of naringenin than orange juice.[24] Also found in grapefruit is the related compound
kaempferol, which has a hydroxyl group next to the ketone group.
Naringenin can be absorbed from cooked tomato paste. There are 3.8 mg of naringenin in 150 grams of tomato paste.[25]
Biosynthesis and metabolism
Naringenin can be produced from naringin by the hydrolytic action of the liver enzyme naringinase.[26]
Studies show naringenin has numerous biological activities, including anti-inflammatory, antioxidant, antibacterial, antiviral and anticancer. It is deemed safe for both topical and ingestible use in healthy adults.[7]
Anti-inflammatory
Naringenin’s anti-inflammatory benefits have been well established with multiple in vitro and in vivo studies, revealing it effectively suppresses proinflammatory factors, cytokine and chemokine expressions in inflammation.[3] When taken orally, it has also been shown to reduce inflammatory pain.[29]
Antioxidant
Naringenin has been shown to have significant
antioxidant properties.[30][31] It has been shown to reduce oxidative damage to
DNAin vitro and in animal studies.[32][33] When consumed it has been shown to increase antioxidant markers superoxide dismutase and glutathione.[6]
Endothelium protection
Some human studies and many animal studies have shown the ability of both naringenin and naringin to protect and improve the health of the vascular
endothelium.[26] Naringenin reportedly stimulates
Nrf2 to protect blood vessels.[34]
Naringenin has also been shown to reduce
hepatitis C virus production by infected
hepatocytes (liver cells) in
cell culture. This seems to be secondary to naringenin's ability to inhibit the secretion of
very-low-density lipoprotein by the cells.[40] The antiviral effects of naringenin are currently under clinical investigation.[41] Reports of antiviral effects on
polioviruses,
HSV-1 and
HSV-2 have also been made, though replication of the viruses has not been inhibited.[42][43] In in vitro experiments naringenin also showed a strong antiviral activity against
SARS-CoV-2.
[44]
Skin Healing
When used in topical formulations, naringenin has been shown to be an anti-inflammatory with skin barrier restoration and antioxidant activities.
UVB radiation is very high energy frequency and wreak havoc on the top layers of the skin by damaging the skin cells and causing DNA mutations that can lead to melanoma and other skin cancers.[45] Naringenin has been proven to reduce UVB-induced skin damage, as well as showing efficacy against oxidative stress and improvement in wound healing.[4][46][6]
Naringenin has also been studied on inflammatory skin conditions such as atopic dermatitis and psoriasis.[3][47][48] For atopic dermatitis, naringenin was found to sharply suppress inflammatory levels and alleviate symptoms and may suppress the development of atopic dermatitis like skin lesions.[3][47] In psoriasis, naringenin has been studied to reduce inflammation in psoriatic plaques.[48]
Anticancer
Cytotoxicity has been reduced reportedly by naringenin in cancer cells from
breast,
stomach,
liver,
cervix,
pancreas, and
colon tissues, along with
leukaemia cells.[49][50] The mechanisms behind inhibition of human
breast carcinoma growth have been examined, and two theories have been proposed.[51] The first theory is that naringenin inhibits
aromatase, thus reducing growth of the tumor.[52] The second mechanism proposes that interactions with
estrogen receptors is the cause behind the modulation of growth.[53] New derivatives of naringenin were found to be active against multidrug-resistant cancer.[54]
Fatty Liver Disease
Naringenin may have some benefits for non-alcoholic fatty liver disease. It was proven to reduce hepatic lipid accumulation and inflammation in the livers of mice with non-alcoholic fatty liver disease.[55]
Alzheimer's disease
Naringenin is being researched as a potential treatment for
Alzheimer's disease. Naringenin has been demonstrated to improve memory and reduce
amyloid and
tau proteins in a study using a mouse model of Alzheimer's disease.[56][57] The effect is believed to be due to a protein present in neurons known as
CRMP2 that naringenin binds to.[58]
Safety
Naringenin has been deemed safe to apply topically and can also be ingested safely by healthy adults in doses of 150 to 900 mg, with 300 mg of naringenin twice a day likely to elicit physiological effect.[7]
^Yáñez JA, Andrews PK, Davies NM (April 2007). "Methods of analysis and separation of chiral flavonoids". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 848 (2): 159–181.
doi:
10.1016/j.jchromb.2006.10.052.
PMID17113835.
^
abYáñez JA, Remsberg CM, Miranda ND, Vega-Villa KR, Andrews PK, Davies NM (March 2008). "Pharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and eriodictyol in rats and their content in fruit juices". Biopharmaceutics & Drug Disposition. 29 (2): 63–82.
doi:
10.1002/bdd.588.
PMID18058792.
S2CID24051610.
^Krause M, Galensa R (July 1991). "Analysis of enantiomeric flavanones in plant extracts by high-performance liquid chromatography on a cellulose triacetate based chiral stationary phase". Chromatographia. 32 (1–2): 69–72.
doi:
10.1007/BF02262470.
ISSN0009-5893.
S2CID95215634.
^Ho PC, Saville DJ, Coville PF, Wanwimolruk S (April 2000). "Content of CYP3A4 inhibitors, naringin, naringenin and bergapten in grapefruit and grapefruit juice products". Pharmaceutica Acta Helvetiae. 74 (4): 379–385.
doi:
10.1016/S0031-6865(99)00062-X.
PMID10812937.
^Gel-Moreto N, Streich R, Galensa R (August 2003). "Chiral separation of diastereomeric flavanone-7-O-glycosides in citrus by capillary electrophoresis". Electrophoresis. 24 (15): 2716–2722.
doi:
10.1002/elps.200305486.
PMID12900888.
S2CID40261445.
^
abMinoggio M, Bramati L, Simonetti P, Gardana C, Iemoli L, Santangelo E, et al. (2003-01-01). "Polyphenol pattern and antioxidant activity of different tomato lines and cultivars". Annals of Nutrition & Metabolism. 47 (2): 64–69.
doi:
10.1159/000069277.
PMID12652057.
S2CID26333030.
^Vallverdú Queralt A, Odriozola Serrano I, Oms Oliu G, Lamuela Raventós RM, Elez Martínez P,
Martín Belloso O (September 2012). "Changes in the polyphenol profile of tomato juices processed by pulsed electric fields". Journal of Agricultural and Food Chemistry. 60 (38): 9667–9672.
doi:
10.1021/jf302791k.
PMID22957841.
^Sánchez Rabaneda F, Jáuregui O, Casals I, Andrés Lacueva C, Izquierdo Pulido M, Lamuela Raventós RM (January 2003). "Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao)". Journal of Mass Spectrometry. 38 (1): 35–42.
Bibcode:
2003JMSp...38...35S.
doi:
10.1002/jms.395.
PMID12526004.
^Exarchou V, Godejohann M, van Beek TA, Gerothanassis IP, Vervoort J (November 2003). "LC-UV-solid-phase extraction-NMR-MS combined with a cryogenic flow probe and its application to the identification of compounds present in Greek oregano". Analytical Chemistry. 75 (22): 6288–6294.
doi:
10.1021/ac0347819.
PMID14616013.
^Olsen HT, Stafford GI, van Staden J, Christensen SB, Jäger AK (May 2008). "Isolation of the MAO-inhibitor naringenin from Mentha aquatica L". Journal of Ethnopharmacology. 117 (3): 500–502.
doi:
10.1016/j.jep.2008.02.015.
PMID18372132.
^Hungria M, Johnston AW, Phillips DA (1992-05-01). "Effects of flavonoids released naturally from bean (Phaseolus vulgaris) on nodD-regulated gene transcription in Rhizobium leguminosarum bv. phaseoli". Molecular Plant-Microbe Interactions. 5 (3): 199–203.
doi:
10.1094/mpmi-5-199.
PMID1421508.
^Choudhury R, Chowrimootoo G, Srai K, Debnam E, Rice-Evans CA (November 1999). "Interactions of the flavonoid naringenin in the gastrointestinal tract and the influence of glycosylation". Biochemical and Biophysical Research Communications. 265 (2): 410–415.
doi:
10.1006/bbrc.1999.1695.
PMID10558881.
^Wang C, Zhi S, Liu C, Xu F, Zhao A, Wang X, et al. (March 2017). "Characterization of Stilbene Synthase Genes in Mulberry (Morus atropurpurea) and Metabolic Engineering for the Production of Resveratrol in Escherichia coli". Journal of Agricultural and Food Chemistry. 65 (8): 1659–1668.
doi:
10.1021/acs.jafc.6b05212.
PMID28168876.
^Gorinstein S, Leontowicz H, Leontowicz M, Krzemiński R, Gralak M, Delgado-Licon E, et al. (April 2005). "Changes in plasma lipid and antioxidant activity in rats as a result of naringin and red grapefruit supplementation". Journal of Agricultural and Food Chemistry. 53 (8): 3223–3228.
doi:
10.1021/jf058014h.
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Naringenin lowers the plasma and hepatic
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