ImmunoCR
A repository of plant based immunomodulatory compounds
ImmunoCR
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Nutraceutical Profile

ImmunCR Id : ICR15
Chemical Name : Punicalagin
Plant Source : Punica granatum
Nutraceutical information : Edible, Highest occurance in Punica granatum, Terminalia catappa, fruits, peel (pericarp), seeds, flowers, leaves and bark, as well as in the fruits of myrobalan (Terminalia chebula), leaves of yellow wood (Terminalia oblongata)
Mode of administration : Orally
Immunomodulatory mechanism : Antiproliferative activity against tumor cells through inhibition of cell proliferation and induction of apoptosis via upregulation of Bax; Casp-3 and 9; cytochrome C; ROS; cytosolic STAT-3, p53; cytosolic NF-κb-p65, downregulation of Bcl-2; Jak-1; nuclear STAT-3, nuclear NF-κb-p65; Induction of apoptosis-independent cell death via autophagy through the activation of MAPK and inhibition of mtor signaling via upregulating LC3-II conversion, beclin-1; phosphorylated ERK 1/2 and p38 and downregulating p62; phosphorylated p70, S6, and 4E-BP1 ; anti-inflammatory action through inhibiting the production of tumor necrosis factor alpha (TNF)-α and interleukin (IL)-1β or IL-6 by macrophages in primary human chondrocytes; suppresses NF-kb and MAPK signaling pathways to suppress NO, TNF-α and IL-6; suppresses various signaling pathways, including NF-kβ, MAPK, Bcl-XL and LKB1-AMPK-p27
Description : It is an ellagitannin polyphenolic compound existing as alpha and beta forms in pomegranate, Indian Almond capable of immunosuppresive actions and anti-cancer abilities through different signalling pathways.

Chemical Structure Information

IUPAC Name (1R,35R,38R,55S)-6,7,8,11,12,23,24,27,28,29,37,43,44,45,48,49,50-heptadecahydroxy-2,14,21,33,36,39,54-heptaoxaundecacyclo[33.20.0.04,9.010,19.013,18.016,25.017,22.026,31.038,55.041,46.047,52]pentapentaconta-4,6,8,10,12,16,18,22,24,26,28,30,41,43,45,47,49,51-octadecaene-3,15,20,32,40,53-hexon
SMILES C1C2C(C3C(C(O2)O)OC(=O)C4=CC(=C(C(=C4C5=C(C(=C(C=C5C(=O)O3)O)O)O)O)O)O)OC(=O)C6=CC(=C(C(=C6C7=C(C(=C8C9=C7C(=O)OC2=C(C(=C(C3=C(C(=C(C=C3C(=O)O1)O)O)O)C(=C92)C(=O)O8)O)O)O)O)O)O)O
Formula C48H28O30
InchiKey ZJVUMAFASBFUBG-UHFFFAOYSA-N

Chemical Classification

Kingdom Organic compounds
Superclass Phenylpropanoids and polyketides
Class Tannins
Subclass Hydrolyzable tannins

Physicochemical properties

LogP 3.405
Molecular weight 1084.72
Hydrogen Bond Acceptor 30
Hydrogen Bond Donor 17
Polar surface area 520.179
No. of rotatable bonds 0
Number of Aromatic Rings 6
Number of rings 11

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

  • Antioxidant, chemopreventive, hepatoprotective, anti-atherosclerotic, cardioprotective,diabetes

References

    1. https://doi.org/10.1016/j.biopha.2020.110959
    2. https://doi.org/10.3390/nu13072150
    3. https://doi.org/10.3390/nu13082733
    4. https://doi.org/10.3390/nu13072150
    5. https://doi.org/10.3390/nu13072150


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