Page last updated: 2024-12-09

(2S)-7-hydroxyflavanone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

## (2S)-7-hydroxyflavanone: A Powerful Antioxidant with Potential Therapeutic Value

(2S)-7-hydroxyflavanone is a naturally occurring flavonoid found in various plants like citrus fruits, tea, and berries. It's a chiral molecule, meaning it exists in two mirror-image forms (enantiomers) - (2S) and (2R). The (2S)-enantiomer is the more biologically active form.

**Here's why it's important for research:**

**1. Powerful Antioxidant Properties:**

* (2S)-7-hydroxyflavanone exhibits potent antioxidant activity, effectively scavenging free radicals and protecting cells from oxidative stress. This is crucial in preventing various diseases linked to oxidative damage, like cancer, cardiovascular disease, and neurodegenerative disorders.

**2. Anti-inflammatory Effects:**

* Studies suggest that (2S)-7-hydroxyflavanone can suppress inflammatory responses, reducing the production of pro-inflammatory mediators like cytokines and chemokines. This makes it a promising candidate for treating inflammatory conditions like arthritis and asthma.

**3. Potential Neuroprotective Activity:**

* Research indicates that (2S)-7-hydroxyflavanone may protect neurons from damage caused by various stressors, including oxidative stress and inflammation. This could be beneficial for managing neurodegenerative disorders like Alzheimer's disease and Parkinson's disease.

**4. Anti-cancer Effects:**

* (2S)-7-hydroxyflavanone has demonstrated anti-cancer properties in various studies. It can inhibit the growth and proliferation of cancer cells, induce apoptosis (programmed cell death), and reduce tumor formation.

**5. Anti-diabetic Potential:**

* Research suggests that (2S)-7-hydroxyflavanone might improve insulin sensitivity and regulate blood sugar levels, making it a potential therapeutic target for diabetes management.

**Ongoing Research:**

* Current research focuses on understanding the detailed mechanisms of action, optimizing its bioavailability, and developing safe and effective therapeutic applications.

**Challenges:**

* One challenge is the development of efficient and cost-effective methods for synthesizing and purifying the (2S)-enantiomer.

**Overall:**

(2S)-7-hydroxyflavanone's promising biological activity and potential therapeutic benefits make it a significant focus in research. Continued investigation into its effects could lead to the development of novel treatments for various diseases.

Cross-References

ID SourceID
PubMed CID688857
CHEMBL ID402744
CHEBI ID41888
SCHEMBL ID1072683

Synonyms (24)

Synonym
BIDD:ER0186
DB04274
(2s)-7-hydroxyflavanone
(-)-7-hydroxyflavanone
7-hydroxy-2-phenyl-chroman-4-one
5,4'-dideoxyflavanone
(2s)-7-hydroxy-2-phenyl-2,3-dihydro-4h-chromen-4-one
CHEBI:41888 ,
CHEMBL402744 ,
(2s)-7-hydroxy-2-phenyl-2,3-dihydrochromen-4-one
2545-13-3
SCHEMBL1072683
J641.665I ,
4h-1-benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-phenyl-, (2s)-
7-hydroxyflavanone, (s)-
(s)-7-hydroxy-2-phenylchroman-4-one
MF98742K2H ,
4h-1-benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-phenyl-, (s)-
flavanone, 7-hydroxy-, (-)-
unii-mf98742k2h
DTXSID90350985
Q27095092
(s)-7-hydroxyflavanone
bdbm50535254
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
7-hydroxyflavanoneA monohydroxyflavanone that is flavanone substituted by a hydroxy group at position 7.
[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)
Proteasome subunit beta type-5Homo sapiens (human)IC50 (µMol)5.21000.00050.939410.0000AID1633148
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
proteolysisProteasome subunit beta type-5Homo sapiens (human)
response to oxidative stressProteasome subunit beta type-5Homo sapiens (human)
proteasome-mediated ubiquitin-dependent protein catabolic processProteasome subunit beta type-5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
threonine-type endopeptidase activityProteasome subunit beta type-5Homo sapiens (human)
protein bindingProteasome subunit beta type-5Homo sapiens (human)
peptidase activityProteasome subunit beta type-5Homo sapiens (human)
endopeptidase activityProteasome subunit beta type-5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
nucleusProteasome subunit beta type-5Homo sapiens (human)
cytoplasmProteasome subunit beta type-5Homo sapiens (human)
proteasome complexProteasome subunit beta type-5Homo sapiens (human)
nucleusProteasome subunit beta type-5Homo sapiens (human)
nucleoplasmProteasome subunit beta type-5Homo sapiens (human)
centrosomeProteasome subunit beta type-5Homo sapiens (human)
cytosolProteasome subunit beta type-5Homo sapiens (human)
extracellular exosomeProteasome subunit beta type-5Homo sapiens (human)
proteasome core complexProteasome subunit beta type-5Homo sapiens (human)
proteasome core complex, beta-subunit complexProteasome subunit beta type-5Homo sapiens (human)
cytosolProteasome subunit beta type-5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID404184Cytotoxicity against human HT1080 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID404180Cytotoxicity against mouse B16-BL6 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID404181Cytotoxicity against mouse LLC cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID502768Cytotoxicity against human MCF7 cells after 72 hrs by MTS reduction assay2010Journal of natural products, Sep-24, Volume: 73, Issue:9
Cytotoxic flavonoids from the leaves of Cryptocarya chinensis.
AID404183Cytotoxicity against human HeLa cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID358173Inhibition of p40 tyrosine kinase1992Journal of natural products, Nov, Volume: 55, Issue:11
Protein-tyrosine kinase inhibition: mechanism-based discovery of antitumor agents.
AID404182Cytotoxicity against human A549 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID313354Cytotoxicity against human PANC1 cells in nutrient deprived medium after 24 hrs2008Bioorganic & medicinal chemistry, Jan-01, Volume: 16, Issue:1
Constituents of Brazilian red propolis and their preferential cytotoxic activity against human pancreatic PANC-1 cancer cell line in nutrient-deprived condition.
AID502769Cytotoxicity against human NCI-H460 cells after 72 hrs by MTS reduction assay2010Journal of natural products, Sep-24, Volume: 73, Issue:9
Cytotoxic flavonoids from the leaves of Cryptocarya chinensis.
AID404179Cytotoxicity against mouse colon 26-L5 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID502770Cytotoxicity against human SF268 cells after 72 hrs by MTS reduction assay2010Journal of natural products, Sep-24, Volume: 73, Issue:9
Cytotoxic flavonoids from the leaves of Cryptocarya chinensis.
AID1633148Inhibition of chymotrypsin-like activity of purified human erythrocyte 20S proteasome assessed as decrease in AMC hydrolysis using Suc-LLVY-AMC as substrate preincubated for 10 mins and measured by fluorescence based method2019European journal of medicinal chemistry, Apr-01, Volume: 167Another look at phenolic compounds in cancer therapy the effect of polyphenols on ubiquitin-proteasome system.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (20.00)18.2507
2000's2 (40.00)29.6817
2010's2 (40.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.87

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.87 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.87)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (40.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other3 (60.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]