Immunomodulatory Function of Nutritionals and Nutraceuticals for Health and Wellness

Nutraceutical Profile


ImmunCR Id :	ICR73
Chemical Name :	Shikonin (R)
Plant Source :	Lithospermum erythrorhizon
Nutraceutical information :	---
Mode of administration :	Cream, Ointment, Oral, Intramuscular


Immunomodulatory mechanism :	Anti-inflammatory (inhibits COX-2, inos, TNF-α, downregulates NF-κb, ERK1/2); Anti-arthritic (downregulates TH1 cytokines IL-12, TNF-α, inhibits IL-6, elevates expression of GATA-binding protein-3); Anti-asthma (inhibits histamine release, supresses phosphorylation of iκbα, iκb kinase β, p38); Neuroprotective (upregulates Bcl2, glutathione-independent superoxide dismutase mrna, downregulates Bax); Cardioprotective (inhibits NOS); Anti-cancer (inhibits NF-κb, tumor specific pyruvate kinase-M2, regulates ROS production, reduces glutathione, G1 phase cycle arrest, activates p38 MAPK, ASK1, downregulates p21, integrin β1 mrna and protein expression, ERK1/2); Anti-bacterial (effective against gram positive bacteria, inhibits NAT-mediates N-acetylation, biofilm formation); Wound healing (increases cell proliferation, tgfβ1, reduces cell migration)
Description :	Shikonin (5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-pentenyl]-1,4-naphthoquinone) is a highly lipophilic compound which is extracted from the roots of Lithospermum erythrorhizon and is among the main active compound in the traditional Chinese medicine Zicao. It can also be found in the roots of other plants of Boraginaceae family.

Immunomodulatory mechanism :

Anti-inflammatory (inhibits COX-2, inos, TNF-α, downregulates NF-κb, ERK1/2); Anti-arthritic (downregulates TH1 cytokines IL-12, TNF-α, inhibits IL-6, elevates expression of GATA-binding protein-3); Anti-asthma (inhibits histamine release, supresses phosphorylation of iκbα, iκb kinase β, p38); Neuroprotective (upregulates Bcl2, glutathione-independent superoxide dismutase mrna, downregulates Bax); Cardioprotective (inhibits NOS); Anti-cancer (inhibits NF-κb, tumor specific pyruvate kinase-M2, regulates ROS production, reduces glutathione, G1 phase cycle arrest, activates p38 MAPK, ASK1, downregulates p21, integrin β1 mrna and protein expression, ERK1/2); Anti-bacterial (effective against gram positive bacteria, inhibits NAT-mediates N-acetylation, biofilm formation); Wound healing (increases cell proliferation, tgfβ1, reduces cell migration)

Description :

Shikonin (5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-pentenyl]-1,4-naphthoquinone) is a highly lipophilic compound which is extracted from the roots of Lithospermum erythrorhizon and is among the main active compound in the traditional Chinese medicine Zicao. It can also be found in the roots of other plants of Boraginaceae family.

Chemical Structure Information


IUPAC Name	5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
SMILES	CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
Formula	C16H16O5
InchiKey	NEZONWMXZKDMKF-UHFFFAOYSA-N

Chemical Classification


Kingdom	Organic compounds
Superclass	Benzenoids
Class	Naphthalenes
Subclass	Naphthoquinones

Physicochemical properties


LogP	2.444
Molecular weight	288.295
Hydrogen Bond Acceptor	5
Hydrogen Bond Donor	3
Polar surface area	97.048
No. of rotatable bonds	3
Number of Aromatic Rings	1
Number of rings	2

ADMET Properties


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

Other Biological Properties