ImmunoCR
A repository of plant based immunomodulatory compounds
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Nutraceutical Profile

ImmunCR Id : ICR51
Chemical Name : Naringin
Plant Source : Citrus sps.
Nutraceutical information : Edible, High content in citrus fruits Citrus medica, orange.
Mode of administration : Peritoneal injection, oral
Immunomodulatory mechanism : Bone health (inhibit hepatic 3-hydroxy-3-methyl coa (HMG-coa) reductase, modulate ALP, OPG (osteoprotegerin)/RANKL (receptor activator for nuclear factor κ-B ligand) mrna expression, increased proliferation of osteoblastin by upregulating BMP-2 expression through phosphoinositide 3-kinase, Akt, c-Fos/c-Jun and AP-1-dependent signalling pathways, downregulates HMG-coa, NF-κb and ERK expression); Anti-inflammatory (stimulates TNF-α/IFN-γ and increases RANTES (restrain the production of regulated upon activation normal T-cell expressed and secreted), downregulates IL-6, IL-8, inos, Nrf2); Anti-cancer (inhibits β-catenin pathway, G1 phase arrest, increased p53, bax, fas, caspase, mir-126 expression); Metabolic syndrome(upregulates AMPK expression, downregulates pparγ expression, HMG-coa reductase, upregulates pparα, NO metabolite production, in diabetic downregulates glucose-6-phosphatase and phosphoenolpyruvate carboxykinase); Antioxidant (decreased glutathione (GSH), hepatic SOD, GSH peroxidase, catalase, reduced protein glycation, activates Nrf2 pathway, reduced lipid peroxidation, nitrite, elevated TNF-α level); Protects against genetic damage (increase DNA repair, reduce damage and breakage to DNA caused by chemicals or medicines: H2O2); Neuroprotective (upregulates malondialdehyde, NO level, neurotrophic factor, camkii (calmodulin-dependent protein kinase II) autophosphorylation, downregulates GSH reductase, TNF-α, microtubule-associated protein light chain 3 (LC3), acetylcholinesterase expression, reduced seizures).
Description : It is a secondary glycosidic metabolite formed by combination of naringenin and neohesperidose, used in traditional Chinese medicine and found in Drynaria fortunei (Kunze).Its structure comprises of two pentose sugar at one end and a phenol at the other.

Chemical Structure Information

IUPAC Name (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
SMILES CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O
Formula C27H32O14
InchiKey DFPMSGMNTNDNHN-UHFFFAOYSA-N

Chemical Classification

Kingdom Organic compounds
Superclass Phenylpropanoids and polyketides
Class Flavonoids
Subclass Flavonoid glycosides

Physicochemical properties

LogP -0.415
Molecular weight 580.535
Hydrogen Bond Acceptor 14
Hydrogen Bond Donor 8
Polar surface area 228.475
No. of rotatable bonds 6
Number of Aromatic Rings 2
Number of rings 5

ADMET Properties

Absorption level Very low
Solubility level Very Soluble
Blood Brain Barrier Undefined
Plasma protein binding Non-Binder
CYP2D6 inhibition Non-Inhibitor

Other Biological Properties

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References

    1. https://doi.org/10.1002/fft2.129
    2. https://doi.org/10.1016/j.fct.2019.110646


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