Page last updated: 2024-12-08

(2S)-5,7-dihydroxy-6,8-dimethylflavanone

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

Description

(2S)-5,7-dihydroxy-6,8-dimethylflavanone is a natural compound found in various plants, particularly in the genus *Citrus*. It is a flavanone, a type of flavonoid, which are a large group of polyphenolic compounds known for their antioxidant and other beneficial properties.

Here's a breakdown:

**Structure and Properties:**

* **Flavanone:** It belongs to the flavanone subclass of flavonoids, characterized by a specific chemical structure with a 2-phenyl-chroman-4-one core.
* **(2S)-configuration:** This refers to the specific stereochemistry at the 2-position of the flavanone ring. It denotes the spatial arrangement of the molecule.
* **5,7-dihydroxy:** This indicates the presence of two hydroxyl (OH) groups at positions 5 and 7 on the A-ring of the flavanone.
* **6,8-dimethyl:** It means two methyl (CH3) groups are attached at positions 6 and 8 on the A-ring.

**Importance in Research:**

This compound has attracted significant research interest due to its potential biological activities, including:

* **Antioxidant Activity:** (2S)-5,7-dihydroxy-6,8-dimethylflavanone is a potent antioxidant, scavenging free radicals and protecting cells from oxidative damage. This property is linked to its potential benefits in preventing chronic diseases like cancer and cardiovascular disease.
* **Anti-Inflammatory Effects:** Studies suggest that this compound may exhibit anti-inflammatory properties by inhibiting the production of inflammatory mediators. This could be valuable in treating inflammatory conditions such as arthritis.
* **Neuroprotective Potential:** Research is exploring its potential neuroprotective effects, including its ability to protect neurons from damage caused by oxidative stress and inflammation.
* **Anti-Cancer Activity:** Some studies indicate that (2S)-5,7-dihydroxy-6,8-dimethylflavanone may possess anti-cancer properties by inhibiting cell growth and inducing apoptosis (programmed cell death) in cancer cells.
* **Anti-Microbial Activity:** This compound has demonstrated antimicrobial activity against certain bacteria and fungi, suggesting its potential use as a natural antimicrobial agent.

**Current Research:**

Ongoing research focuses on:

* Elucidating the specific mechanisms of action of this compound in various biological systems.
* Evaluating its efficacy and safety in preclinical and clinical studies.
* Investigating its potential applications in drug development and functional foods.

**In summary:** (2S)-5,7-dihydroxy-6,8-dimethylflavanone is a naturally occurring flavanone with a promising range of biological activities, making it a valuable target for research into the development of new therapeutic agents and health-promoting products.

(2S)-5,7-dihydroxy-6,8-dimethylflavanone : A dihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5 and 7 and methyl groups at positions 6 and 8. Isolated from the buds of Cleistocalyx operculatus, it has been shown to exhibit inhibitory effects on the viral neuraminidases from two influenza viral strains, H1N1 and H9N2. [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]

FloraRankFlora DefinitionFamilyFamily Definition
Cleistocalyx operculatusspecies[no description available]MyrtaceaeThe myrtle plant family of the order Myrtales. It includes several aromatic medicinal plants such as EUCALYPTUS.[MeSH]

Cross-References

ID SourceID
PubMed CID180550
CHEMBL ID53439
CHEBI ID70664

Synonyms (25)

Synonym
(2s)-5,7-dihydroxy-6,8-dimethyl-2-phenyl-chroman-4-one
demethoxymatteucinol
CHEMBL53439
6,8-dimethylpinocembrin
chebi:70664 ,
MLS002473099
smr001397201
desmethoxy-matteucinol
(2s)-5,7-dihydroxy-6,8-dimethyl-2-phenyl-2,3-dihydrochromen-4-one
NCGC00247485-01
56297-79-1
(-)-demethoxymatteucinol
4h-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-6,8-dimethyl-2-phenyl-, (s)-
HMS2213L09
(2s)-2,3-dihydro-5,7-dihydroxy-6,8-dimethyl-2-phenyl-4h-1-benzopyran-4-one
(2s)-5,7-dihydroxy-6,8-dimethylflavanone
(2s)-5,7-dihydroxy-6,8-dimethyl-2-phenyl-2,3-dihydro-4h-chromen-4-one
5,7-dihydroxy-6,8-dimethyl-2-phenyl-2,3-dihydro-4h-chromen-4-one #
HAIHGFWQOPJMPV-ZDUSSCGKSA-N
Q27138996
bdbm50278269
5,7-dihydroxy-6,8-dimethyl-2-phenyl-2,3-dihydro-4h-1-benzopyran-4-one
DTXSID10971737
4h-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-6,8-dimethyl-2-phenyl-, (2s)-
AKOS040763206
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC 3.2.1.18 (exo-alpha-sialidase) inhibitorAn antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell.
[role 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]

Drug Classes (1)

ClassDescription
dihydroxyflavanoneAny hydroxyflavanone carrying two hydroxy substituents.
[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 (7)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TDP1 proteinHomo sapiens (human)Potency29.09290.000811.382244.6684AID686978; AID686979
67.9K proteinVaccinia virusPotency28.18380.00018.4406100.0000AID720579
chromobox protein homolog 1Homo sapiens (human)Potency89.12510.006026.168889.1251AID540317
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency89.12513.548119.542744.6684AID743266
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency79.43280.050127.073689.1251AID588590
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Neuraminidase Influenza A virus (A/Wilson-Smith/1933(H1N1))IC50 (µMol)326.35500.00000.503510.0000AID527157; AID527158
NeuraminidaseInfluenza A virus (A/Puerto Rico/8/1934(H1N1))IC50 (µMol)30.30000.00050.976710.0000AID1502944
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (1)

Processvia Protein(s)Taxonomy
viral release from host cellNeuraminidaseInfluenza A virus (A/Puerto Rico/8/1934(H1N1))
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
exo-alpha-sialidase activityNeuraminidaseInfluenza A virus (A/Puerto Rico/8/1934(H1N1))
peptidase activator activityNeuraminidaseInfluenza A virus (A/Puerto Rico/8/1934(H1N1))
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
extracellular regionNeuraminidaseInfluenza A virus (A/Puerto Rico/8/1934(H1N1))
plasma membraneNeuraminidaseInfluenza A virus (A/Puerto Rico/8/1934(H1N1))
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (43)

Assay IDTitleYearJournalArticle
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1502945Inhibition of neuraminidase activity in H9N2 A/chicken/Korea/01210/2001 infected in MDCK cells using 4-MU-NANA as substrate pretreated for 30 mins followed by substrate addition measured after 2 hrs by fluorescence assay2017Journal of natural products, 10-27, Volume: 80, Issue:10
C-Methylated Flavonoid Glycosides from Pentarhizidium orientale Rhizomes and Their Inhibitory Effects on the H1N1 Influenza Virus.
AID377053Cytotoxicity against mouse J774A1 cells after 72 hrs by cell-titer assay2005Journal of natural products, Jan, Volume: 68, Issue:1
Antiprotozoal compounds from Psorothamnus polydenius.
AID287083Antimalarial activity against multidrug-resistant Plasmodium falciparum K1 by micro culture radioisotope technique2007Journal of natural products, May, Volume: 70, Issue:5
Bioactive compounds from Bauhinia purpurea possessing antimalarial, antimycobacterial, antifungal, anti-inflammatory, and cytotoxic activities.
AID377052Cytotoxicity against african green monkey Vero cells after 72 hrs by cell-titer assay2005Journal of natural products, Jan, Volume: 68, Issue:1
Antiprotozoal compounds from Psorothamnus polydenius.
AID502566Antitumor activity against human Bel7402 cells2010Bioorganic & medicinal chemistry letters, Sep-15, Volume: 20, Issue:18
Synthesis and biological activity of flavanone derivatives.
AID502567Antitumor activity against human HL60 cells2010Bioorganic & medicinal chemistry letters, Sep-15, Volume: 20, Issue:18
Synthesis and biological activity of flavanone derivatives.
AID502571Antivegetative activity against rat VSMC2010Bioorganic & medicinal chemistry letters, Sep-15, Volume: 20, Issue:18
Synthesis and biological activity of flavanone derivatives.
AID287087Cytotoxicity against KB cells by colorimetric method2007Journal of natural products, May, Volume: 70, Issue:5
Bioactive compounds from Bauhinia purpurea possessing antimalarial, antimycobacterial, antifungal, anti-inflammatory, and cytotoxic activities.
AID502572Cytoprotectant activity against H2O2-induced injury in HUVEC cells2010Bioorganic & medicinal chemistry letters, Sep-15, Volume: 20, Issue:18
Synthesis and biological activity of flavanone derivatives.
AID235739Therapeutic index determined by ratio of IC50 to EC502003Bioorganic & medicinal chemistry letters, May-19, Volume: 13, Issue:10
Anti-AIDS agents 54. A potent anti-HIV chalcone and flavonoids from genus Desmos.
AID79287Concentration that inhibits uninfected H9 cell growth by 50%.2003Bioorganic & medicinal chemistry letters, May-19, Volume: 13, Issue:10
Anti-AIDS agents 54. A potent anti-HIV chalcone and flavonoids from genus Desmos.
AID527158Inhibition of Influenza A virus (A/Sw/Kor/CAH1/04 (H1N1) KCTC 11165BP neuraminidase after 30 mins by spectrofluorimetric analysis2010Journal of natural products, Oct-22, Volume: 73, Issue:10
C-Methylated Flavonoids from Cleistocalyx operculatus and Their Inhibitory Effects on Novel Influenza A (H1N1) Neuraminidase.
AID377050Antileishmanial activity against Leishmania donovani MHOM/SD/62/1S-CL2D axenic amastigotes after 3 days by tetrazolium dye method2005Journal of natural products, Jan, Volume: 68, Issue:1
Antiprotozoal compounds from Psorothamnus polydenius.
AID287085Inhibition of COX1 by radioimmunoassay method2007Journal of natural products, May, Volume: 70, Issue:5
Bioactive compounds from Bauhinia purpurea possessing antimalarial, antimycobacterial, antifungal, anti-inflammatory, and cytotoxic activities.
AID1502944Inhibition of neuraminidase activity in Influenza A virus (A/PR/8/34 (H1N1)) infected in MDCK cells using 4-MU-NANA as substrate pretreated for 30 mins followed by substrate addition measured after 2 hrs by fluorescence assay2017Journal of natural products, 10-27, Volume: 80, Issue:10
C-Methylated Flavonoid Glycosides from Pentarhizidium orientale Rhizomes and Their Inhibitory Effects on the H1N1 Influenza Virus.
AID287084Antifungal activity against Candida albicans by colorimetric method2007Journal of natural products, May, Volume: 70, Issue:5
Bioactive compounds from Bauhinia purpurea possessing antimalarial, antimycobacterial, antifungal, anti-inflammatory, and cytotoxic activities.
AID527157Inhibition of Influenza A virus (A/chicken/Korea/01310/2001 (H9N2)) neuraminidase after 30 mins by spectrofluorimetric analysis2010Journal of natural products, Oct-22, Volume: 73, Issue:10
C-Methylated Flavonoids from Cleistocalyx operculatus and Their Inhibitory Effects on Novel Influenza A (H1N1) Neuraminidase.
AID1713999Inhibition of monophenolase activity of mushroom tyrosinase using L-Tyrosine substrate incubated for 10 mins followed by substrate addition and measured for 20 mins
AID377051Antitrypanosomal activity against blood stream-form of Trypanosoma brucei brucei MITat1.2 after 72 hrs by MTT assay2005Journal of natural products, Jan, Volume: 68, Issue:1
Antiprotozoal compounds from Psorothamnus polydenius.
AID287088Cytotoxicity against BC cells by colorimetric method2007Journal of natural products, May, Volume: 70, Issue:5
Bioactive compounds from Bauhinia purpurea possessing antimalarial, antimycobacterial, antifungal, anti-inflammatory, and cytotoxic activities.
AID1502946Antiviral activity against Influenza A virus (A/PR/8/34 (H1N1)) infected in MDCK cells assessed as reduction in virus-induced cytopathic effect after 3 days by MTT assay2017Journal of natural products, 10-27, Volume: 80, Issue:10
C-Methylated Flavonoid Glycosides from Pentarhizidium orientale Rhizomes and Their Inhibitory Effects on the H1N1 Influenza Virus.
AID1502947Cytotoxicity against MDCK cells after 2 days by MTT assay2017Journal of natural products, 10-27, Volume: 80, Issue:10
C-Methylated Flavonoid Glycosides from Pentarhizidium orientale Rhizomes and Their Inhibitory Effects on the H1N1 Influenza Virus.
AID287086Inhibition of COX2 by radioimmunoassay method2007Journal of natural products, May, Volume: 70, Issue:5
Bioactive compounds from Bauhinia purpurea possessing antimalarial, antimycobacterial, antifungal, anti-inflammatory, and cytotoxic activities.
AID502568Antitumor activity against human BGC823 cells2010Bioorganic & medicinal chemistry letters, Sep-15, Volume: 20, Issue:18
Synthesis and biological activity of flavanone derivatives.
AID502569Antitumor activity against human KB cells2010Bioorganic & medicinal chemistry letters, Sep-15, Volume: 20, Issue:18
Synthesis and biological activity of flavanone derivatives.
AID79284Effective concentration against HIV-1 replication in H9 lymphocytic cells2003Bioorganic & medicinal chemistry letters, May-19, Volume: 13, Issue:10
Anti-AIDS agents 54. A potent anti-HIV chalcone and flavonoids from genus Desmos.
AID287082Antimycobacterial activity against Mycobacterium tuberculosis H37Ra by microplate Alamar Blue assay2007Journal of natural products, May, Volume: 70, Issue:5
Bioactive compounds from Bauhinia purpurea possessing antimalarial, antimycobacterial, antifungal, anti-inflammatory, and cytotoxic activities.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (30.77)29.6817
2010's7 (53.85)24.3611
2020's2 (15.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.65

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 Index11.65 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.29 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.65)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]