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Details

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

SHOW SMILES / InChI
Structure of SHOGAOL

SMILES

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

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

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).