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Details

Stereochemistry ACHIRAL
Molecular Formula C17H24O3
Molecular Weight 276.3707
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SHOGAOL

SMILES

CCCCC\C=C\C(=O)CCC1=CC(OC)=C(O)C=C1

InChI

InChIKey=OQWKEEOHDMUXEO-BQYQJAHWSA-N
InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+

HIDE SMILES / InChI

Molecular Formula C17H24O3
Molecular Weight 276.3707
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Shogaol (6-Shogaol) is a bioactive ingredient of ginger root (Zingiber officinale), a medicinal plant having anti-nausea, anti-inflammatory, and anti-carcinogenic properties and a carminative effect. 6-Shogaol inhibits LPS-induced inflammation by activating PPAR-γ. As one of the main bioactive compounds of dried ginger, 6-shogaol has been widely used to alleviate many ailments. It is also a major pungent flavor component, and its precursor prior to dehydration is 6-gingerol, which is reported to be responsible for the pungent flavor and biological activity of fresh ginger. The conjugation of the α,β-unsaturated ketone skeleton in the chemical structure of 6-shogaol explicates its higher potency and efficacy than 6-gingerol in terms of antioxidant, anti-inflammatory, anticancer, antiemetic and other bioactivities. 6-Shogaol not only scavenges free radicals, such as superoxide radicals and hydroxyl radicals, but also effectively suppresses the activity of xanthine oxidase, which is an important generator of oxygen containing free radicals. 6-shogaol possesses strong metal-binding capacity to inhibit lipid peroxidation and AAPH-induced DNA damage. 6-shogaol exhibits an excellent anti-inflammatory activity in downregulation of pro-inflammatory cytokines and prevention of excessive oxidants in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells, human kidney epithelial cell 293T, mouse microglia, rat astrocytes, human keratinocytes as well as 12-O-tetradecanoylphorbol-13-acetate (TPA)-treated mouse skin. 6-Shogaol also exerts a strong anti-inflammatory influence on acute gouty arthritis. The increased lipid peroxidation, lysosomal enzymes, inflammatory mediator tumor necrosis factor-α (TNF-α) as well as enlarged paw volume induced by monosodium urate crystals in mice can be reduced to nearly normal levels upon consuming 6-shogaol. Various molecular targets are involved in the anti-inflammatory effect of 6-shogoal. Some molecules such as TLR4 receptor and Keap1 are directly targeted by 6-shogaol, while others are indirectly mediated by various pathways. 6-shogaol also exhibits neuroprotective effects on dopaminergic neurons in both in vitro and in vivo Parkinson's disease (PD) models. In addition to anti-oxidative stress, anti-neuroinflammation and anti-Aβ toxicity activities, 6-shogaol also shows capacities to resist neuronal apoptosis and to modulate synaptic and cholinergic functions. 6-shogaol has been treated as a potent anticancer agent against multitudinous cancers including liver, colon, lung, breast, gastric, skin, kidney, ovarian, prostate, laryngeal and pancreatic cancers as well as leukemia. The anticancer activity of 6-shogaol is attributed to its ability to modulate a series of signaling molecules such as MAPK, PI3K, Akt, NF-κB, signal transducer and activator of transcription-3 (STAT3), TNF-ɑ, COX-2, cyclin D1, CDK, MMP-9, survivin, cellular inhibitor of apoptosis protein 1 (cIAP-1), X-linked inhibitor-of-apoptosis protein (XIAP), Bcl-2, and caspases. 6-Shogaol can trigger autophagy of human non-small cell lung cancer A549 cells by blocking the activation of Akt and its downstream targets, such as mTOR, forkhead in rhabdomyosarcoma (FKHR), and glycogen synthase kinase-3β (GSK-3β).

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
6-Shogaol and 6-gingerol, the pungent of ginger, inhibit TNF-alpha mediated downregulation of adiponectin expression via different mechanisms in 3T3-L1 adipocytes.
2008 Aug 29
6-Shogaol suppressed lipopolysaccharide-induced up-expression of iNOS and COX-2 in murine macrophages.
2008 Dec
6-Shogaol induces apoptosis in human colorectal carcinoma cells via ROS production, caspase activation, and GADD 153 expression.
2008 May
Synthesis of a new [6]-gingerol analogue and its protective effect with respect to the development of metabolic syndrome in mice fed a high-fat diet.
2011 Sep 22
Effects of [6]-shogaol on cholinergic signaling in HT22 cells following neuronal damage induced by hydrogen peroxide.
2012 May
A novel shogaol analog suppresses cancer cell invasion and inflammation, and displays cytoprotective effects through modulation of NF-κB and Nrf2-Keap1 signaling pathways.
2013 Nov 1
Ginger compound [6]-shogaol and its cysteine-conjugated metabolite (M2) activate Nrf2 in colon epithelial cells in vitro and in vivo.
2014 Sep 15
6-Shogaol enhances renal carcinoma Caki cells to TRAIL-induced apoptosis through reactive oxygen species-mediated cytochrome c release and down-regulation of c-FLIP(L) expression.
2015 Feb 25
Patents

Sample Use Guides

In Vivo Use Guide
In the case of humans, when healthy volunteers were orally administrated with ginger extract (containing 0.37% of 6-shogaol) at dosage ranging from 100 mg to 2.0 g, no free 6-shogaol and 6-shogaol sulfate were detectable in plasma within the dose range investigated, while 6-shogaol glucuronide was detected at dosage of 2.0 g (containing 7.4 mg of 6-shogaol). These findings indicate that 6-shogaol is also severely metabolized in human body.
Route of Administration: Oral
In Vitro Use Guide
In vitro study has confirmed that 6-shogaol at a concentration of 6 uM can almost completely inhibit N-formyl-methionyl-leucyl-phenylalanine (f-MLP)-induced ROS production in human polymorphonuclear neutrophils (PMN).
Substance Class Chemical
Created
by admin
on Tue Oct 22 08:11:24 UTC 2019
Edited
by admin
on Tue Oct 22 08:11:24 UTC 2019
Record UNII
83DNB5FIRF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SHOGAOL
Common Name English
ENEXASOGAOL [INN]
Common Name English
4-DECEN-3-ONE, 1-(4-HYDROXY-3-METHOXYPHENYL)-, (E)
Common Name English
(6)-SHOGAOL
Common Name English
ENEXASOGAOL
Official Name English
(E)-1-(4-HYDROXY-3- METHOXYPHENYL)DEC-4-EN-3-ONE
Systematic Name English
4-DECEN-3-ONE, 1-(4-HYDROXY-3-METHOXYPHENYL)-
Systematic Name English
6-SHOGAOL (CONSTITUENT OF GINGER) [DSC]
Common Name English
Code System Code Type Description
MESH
C040115
Created by admin on Tue Oct 22 08:11:24 UTC 2019 , Edited by admin on Tue Oct 22 08:11:24 UTC 2019
PRIMARY
INN
10763
Created by admin on Tue Oct 22 08:11:24 UTC 2019 , Edited by admin on Tue Oct 22 08:11:24 UTC 2019
PRIMARY
PUBCHEM
5281794
Created by admin on Tue Oct 22 08:11:24 UTC 2019 , Edited by admin on Tue Oct 22 08:11:24 UTC 2019
PRIMARY
CAS
555-66-8
Created by admin on Tue Oct 22 08:11:24 UTC 2019 , Edited by admin on Tue Oct 22 08:11:24 UTC 2019
NON-SPECIFIC STEREOCHEMISTRY
WIKIPEDIA
SHOGAOL
Created by admin on Tue Oct 22 08:11:24 UTC 2019 , Edited by admin on Tue Oct 22 08:11:24 UTC 2019
PRIMARY
CAS
23513-13-5
Created by admin on Tue Oct 22 08:11:24 UTC 2019 , Edited by admin on Tue Oct 22 08:11:24 UTC 2019
PRIMARY
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