ImmunoCR
A repository of plant based immunomodulatory compounds
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Nutraceutical Profile

ImmunCR Id : ICR77
Chemical Name : Geniposide
Plant Source : Zingiber officinale
Nutraceutical information : Gardenia jasminoides, Eucommia ulmoides Oliver, Rehmannia glutinosa
Mode of administration : Oral, intragastric (mice)
Immunomodulatory mechanism : Anti-diabetic (increased ATP levels, GSIS (glucose stimulated insulin secretion), regulates regeneration of β cell, activates Janus kinase 2/STAT3 pathway, upregulates IDE expression, downregulated cerebral amyloid β peptides); Anti-Alzheimer (downregulated TNF-α, IL-1β, BACE1, inhibited iκb (kappa B), NF-κb, suppresses RAGE (receptor for advanced glycation end products) signaling pathway, cerebral amyloid β accumulation, upregulated ADAM10, phosphorylates STAT3 (signal transducer and activator transcriptor 3), Janus kinase 2, Akt308, GSK-3β, Akt 473); Anti-Parkinson (downregulates Bax, Bax/Bcl-2 ratio, mir-21 (microrna-21), α-synuclein expression, upregulated Bcl-2, tyrosine hydroxylase positive neuron, LAMP-2A (lysosome-associated membrane protein)); Hepatoprotective (inhibits AST, ALT, CYP450 2E1, TGF-β1/Smad signaling, upregulates GSH transferase, GSH, cuzn-SOD, GSH-Px, SOD (superoxide dismutase), pparα, downregulates MDA (malondialdehyde); Anti-inflammatory (downregulates TNF-α, IL-1β, IL-1, IL-6, IL-2, phosphorylated JNK expression, TLR4, T helper 17 cell cytokine, prostaglandin E2, upregulates TGF-β1, IL-4); Antioxidant (upregulates HO-1 (heme oxygenase-1) expression, nuclear factor-E2-related factor 2, activates P13K, enhances P13K/Akt signaling pathway); Anti-tumor (upregulates caspase 3,8,9, Bax, p21, p53, fasl, Fas, TIMP-1,2, iκb-α, downregulates MMP-2,9, Bcl-2, Bcl-xl, HIAP-1,2, COX-2, inos, NF-κb, inactivates PI3K/AKT, JNK signaling pathways)
Description : Geniposide is a diverse compound found in more than 50 family of plants. It biosynthetically originated from 8-oxogeranial forming an iridoid glycoside. In a 10 step process ethyl 2,3-butadienoate and enone (S)-3b underwent a [3+2] cycloaddition reaction under phosphine catalyst, then the cis-fused cyclopenta[c]pyran 4 is converted into a natural product known as geniposide.

Chemical Structure Information

IUPAC Name methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
SMILES COC(=O)C1=COC(C2C1CC=C2CO)OC3C(C(C(C(O3)CO)O)O)O
Formula C17H24O10
InchiKey IBFYXTRXDNAPMM-UHFFFAOYSA-N

Chemical Classification

Kingdom Organic compounds
Superclass Lipids and lipid-like molecules
Class Prenol lipids
Subclass Terpene glycosides

Physicochemical properties

LogP -2.066
Molecular weight 388.366
Hydrogen Bond Acceptor 10
Hydrogen Bond Donor 5
Polar surface area 157.098
No. of rotatable bonds 6
Number of Aromatic Rings 0
Number of rings 3

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

  • Antiviral, antibacterial, cardioprotective, anti-tumor, anti-depressant like

References

    1. https://doi: 10.1016/B978-0-12-394591-4.00004-0
    2. https://doi.org/10.1155/2019/4925682
    3. https://doi.org/10.3390/molecules27103319


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