Compounds > (8)-shogaol
Page last updated: 2024-12-11

(8)-shogaol

Description

(8)-Shogaol is a bioactive compound found in ginger (Zingiber officinale Roscoe). It's a pungent, spicy molecule closely related to another well-known ginger compound, gingerol.

Here's why (8)-shogaol is important for research:

**1. Potential Health Benefits:**

* **Anti-inflammatory:** Studies show that (8)-shogaol has powerful anti-inflammatory properties, potentially rivaling or even exceeding gingerol's effects. This is crucial for understanding its potential role in managing inflammatory conditions like arthritis, inflammatory bowel disease, and even cancer.
* **Antioxidant:** (8)-shogaol acts as a potent antioxidant, helping to neutralize free radicals and reduce oxidative stress in the body. This contributes to its potential role in protecting cells from damage and promoting overall health.
* **Anti-cancer:** Some research suggests that (8)-shogaol may inhibit the growth of certain cancer cells. It's being investigated for its potential to prevent or even treat some cancers.
* **Neuroprotective:** Research indicates that (8)-shogaol might offer neuroprotective effects, potentially protecting neurons from damage and contributing to improved cognitive function.
* **Cardioprotective:** (8)-shogaol may possess cardioprotective properties, helping to lower blood pressure and improve heart health.

**2. Unique Properties:**

* **Heat stability:** Unlike gingerol, which breaks down easily with heat, (8)-shogaol is remarkably stable even at high temperatures. This makes it more suitable for use in processed foods and supplements.
* **Bioavailability:** (8)-shogaol is readily absorbed by the body, potentially contributing to its effectiveness in delivering therapeutic benefits.

**3. Research Focus:**

* **Drug development:** Researchers are investigating the potential of (8)-shogaol as a drug candidate for treating various diseases, including inflammatory conditions, cancer, and neurological disorders.
* **Food science:** Its heat stability and potential health benefits make it a promising ingredient in food products, particularly those marketed for health benefits.
* **Mechanism of action:** Scientists are actively studying the mechanisms by which (8)-shogaol exerts its beneficial effects to better understand its full therapeutic potential.

Overall, (8)-shogaol is a promising natural compound with a range of potential health benefits. Ongoing research is crucial to further understand its mechanisms, validate its efficacy, and develop safe and effective applications for promoting human health.

(8)-shogaol: isolated from ginger; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6442560
CHEMBL ID25893
CHEBI ID174643
SCHEMBL ID4886648
SCHEMBL ID4886657
MeSH IDM0589810

Synonyms (40)

Synonym
CHEBI:174643
[8]-shogaol
(e)-1-(4-hydroxy-3-methoxyphenyl)dodec-4-en-3-one
36700-45-5
MEGXP0_001220
ACON1_001127
NCGC00169651-01
CHEMBL25893 ,
8-shogaol
BRD-K03628532-001-01-5
bdbm50317424
(e)-1-(4-hydroxy-3-methoxy-phenyl)-dodec-4-en-3-one
SCHEMBL4886648
SCHEMBL4886657
LGZSMXJRMTYABD-MDZDMXLPSA-N
4-dodecen-3-one, 1-(4-hydroxy-3-methoxyphenyl)
1-(4-hydroxy-3-methoxyphenyl)dodec-4-en-3-one
unii-av4ik2hcnt
AC-34352
104186-07-4
(e)-(8)-shogaol
4-dodecen-3-one, 1-(4-hydroxy-3-methoxyphenyl)-, (4e)-
AV4IK2HCNT ,
8-shogaol (constituent of ginger) [dsc]
4-dodecen-3-one, 1-(4-hydroxy-3-methoxyphenyl)-
trans-(8)-shogaol
(8)-shogaol
(4e)-1-(4-hydroxy-3-methoxyphenyl)dodec-4-en-3-one
cis-[8]-shogaol
AKOS030530374
cis-8-shogaol
mfcd21333718
ncgc00169651-02!(e)-1-(4-hydroxy-3-methoxyphenyl)dodec-4-en-3-one
CS-0022653
HY-N2435
Q27274135
shogaol, 8-(p)
MS-24401
(e)-1-(4-hydroxy-3-methoxyphenyl) dodec-4-en-3-one
8-shogaol (constituent of ginger)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
monomethoxybenzeneCompounds containing a benzene skeleton substituted with one methoxy group.
enoneAn alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 1AHomo sapiens (human)Ki13.05000.00010.532610.0000AID480937
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (15)

Processvia Protein(s)Taxonomy
behavioral fear response5-hydroxytryptamine receptor 1AHomo sapiens (human)
G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
adenylate cyclase-inhibiting serotonin receptor signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
gamma-aminobutyric acid signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
positive regulation of cell population proliferation5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of serotonin secretion5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of vasoconstriction5-hydroxytryptamine receptor 1AHomo sapiens (human)
exploration behavior5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of dopamine metabolic process5-hydroxytryptamine receptor 1AHomo sapiens (human)
serotonin metabolic process5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of hormone secretion5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of behavior5-hydroxytryptamine receptor 1AHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 1AHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 1AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 1AHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 1AHomo sapiens (human)
receptor-receptor interaction5-hydroxytryptamine receptor 1AHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 1AHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 1AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
plasma membrane5-hydroxytryptamine receptor 1AHomo sapiens (human)
synapse5-hydroxytryptamine receptor 1AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 1AHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 1AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID480937Displacement of [3H]8-OH-DPAT from 5HT1A receptor expressed in HEK293 cells after 2 hrs by liquid scintillation counting2010Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9
Identification of serotonin 5-HT1A receptor partial agonists in ginger.
AID480938Displacement of [3H]8-OH-DPAT from 5HT1A receptor expressed in HEK293 cells at 25 ug/ml after 2 hrs by liquid scintillation counting2010Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9
Identification of serotonin 5-HT1A receptor partial agonists in ginger.
AID1527555Inhibition of NLRP3 inflammasome activation in LPS-primed human THP1 cells assessed as reduction in IL-1beta level at 20 uM preincubated for 1 hr followed by addition of ATP and measured after 3 hrs by ELISA method relative to control2020European journal of medicinal chemistry, Jan-01, Volume: 185Development of small molecule inhibitors targeting NLRP3 inflammasome pathway for inflammatory diseases.
AID156507Effective dose to protect PC12 cells from beta-Amyloid (BA) insult was determined using MTT reduction assay2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Side-chain length is important for shogaols in protecting neuronal cells from beta-amyloid insult.
AID91529Effective dose to protect IMR-32 cells from beta-Amyloid (BA) insult was determined using MTT reduction assay2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Side-chain length is important for shogaols in protecting neuronal cells from beta-amyloid insult.
AID480942Antagonist activity at 5HT1A receptor expressed in HEK293 cells assessed as inhibition of serotonin-induced [S35]GTPgammaS binding by scintillation counting2010Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9
Identification of serotonin 5-HT1A receptor partial agonists in ginger.
AID480944Inhibition of human MDR1 expressed in MDCK cells assessed as fluorescence activity at 30 uM after 1.5 hrs by rhodamine 123 efflux test2010Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9
Identification of serotonin 5-HT1A receptor partial agonists in ginger.
AID480941Antagonist activity at 5HT1A receptor expressed in HEK293 cells assessed as inhibition of 8-OH-DPAT-induced [S35]GTPgammaS binding by scintillation counting2010Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9
Identification of serotonin 5-HT1A receptor partial agonists in ginger.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (14.29)29.6817
2010's3 (42.86)24.3611
2020's3 (42.86)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.03

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index22.03 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.81 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.03)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
guaiacol
Guaiacol: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747). methylcatechol : Any member of the class of catechols carrying one or more methyl substituents.. guaiacol : A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.		2.8630guaiacolsdisinfectant;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
expectorant;
plant metabolite
verapamil
Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.		2.0510aromatic ether;
nitrile;
polyether;
tertiary amino compound
glyburide
Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.		3.3510monochlorobenzenes;
N-sulfonylurea		anti-arrhythmia drug;
EC 2.7.1.33 (pantothenate kinase) inhibitor;
EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor;
hypoglycemic agent
mefenamic acid
Mefenamic Acid: A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase.. mefenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to be minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis.		3.3510aminobenzoic acid;
secondary amino compound		analgesic;
antipyretic;
antirheumatic drug;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
environmental contaminant;
non-steroidal anti-inflammatory drug;
xenobiotic
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		2.0810acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
vinblastine
[no description available]		2.0510
zingerone
zingerone: pungent principle of ginger; structure. zingerone : A methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger.		2.0210methyl ketone;
monomethoxybenzene;
phenols		anti-inflammatory agent;
antiemetic;
antioxidant;
flavouring agent;
fragrance;
plant metabolite;
radiation protective agent
8-gingerol
8-gingerol: isolated from Zingiber officinale		2.0510beta-hydroxy ketone;
monomethoxybenzene;
phenols
10-gingerol
[no description available]		2.0510beta-hydroxy ketone;
monomethoxybenzene;
phenols
gingerol
gingerol: an active ingredient in GINGER along with SHOGAOL. a nonvolatile methoxy phenyl decanone. gingerol : A beta-hydroxy ketone that is 5-hydroxydecan-3-one substituted by a 4-hydroxy-3-methoxyphenyl moiety at position 1; believed to inhibit adipogenesis. It is a constituent of fresh ginger.		2.520beta-hydroxy ketone;
guaiacols		antineoplastic agent;
plant metabolite
3,4-methylenedioxy-beta-nitrostyrene
3,4-methylenedioxy-beta-nitrostyrene: tyrosine kinase inhibitor that prevents platelet glycoprotein IIb/IIIa activation; structure in first source		3.3510
apigenin
Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.		3.3510trihydroxyflavoneantineoplastic agent;
metabolite
shogaol
shogaol: from ginger, ZINGIBER OFFICINALE; less mutagenic than GINGEROL; structure given in first source		4.2850enone;
monomethoxybenzene;
phenols
bay 11-7082
(E)-3-tosylacrylonitrile : A nitrile that is acrylonitrile in which the hydrogen located beta,trans to the cyano group is replaced by a tosyl group. It is an inhibitor of cytokine-induced IkappaB-alpha phosphorylation in cells.		3.3510nitrile;
sulfone		apoptosis inducer;
EC 2.7.11.10 (IkappaB kinase) inhibitor;
EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor;
non-steroidal anti-inflammatory drug;
platelet aggregation inhibitor
(10)-shogaol
(10)-shogaol: isolated from ginger; structure in first source		2.9840enone;
monomethoxybenzene;
phenols
mcc-950
[no description available]		3.3510
2-(4-methoxyphenyl)-1H-quinazolin-4-one
[no description available]		3.3510quinazolines
ConditionIndicatedRelationship StrengthStudiesTrials
Innate Inflammatory Response
[description not available]		03.1710
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		03.1710
Rheumatoid Arthritis
[description not available]		02.4110
Arthritis, Rheumatoid
A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.		02.4110
Aging
The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.		02.610
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