Page last updated: 2024-11-10

gentisein

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

Description

gentisein: isolated from the methanol extract of the herb of Hypericum annulatum; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

gentisein : A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3 and 7. [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
HypericumgenusGenus of perennial plants in the family CLUSIACEAE (sometimes classified as Hypericaceae). Herbal and homeopathic preparations are used for depression, neuralgias, and a variety of other conditions. Hypericum contains flavonoids; GLYCOSIDES; mucilage, TANNINS; volatile oils (OILS, ESSENTIAL), hypericin and hyperforin.[MeSH]Hypericaceae[no description available]

Cross-References

ID SourceID
PubMed CID5281635
CHEMBL ID361025
CHEBI ID5323
SCHEMBL ID2315926
MeSH IDM0401753

Synonyms (32)

Synonym
nsc-329491
nsc329491
xanthone deriv
1,3,7-trihydroxyxanthen-9-one
gentisein
1,3,7-trihydroxyxanthone
529-49-7
9h-xanthen-9-one, 1,3,7-trihydroxy-
nsc 329491
xanthen-9-one, 1,3,7-trihydroxy-
ccris 4008
brn 0384687
1,3,7-trihydroxy-9h-xanthen-9-one
bdbm50155446
1,3,7-trihydroxy-xanthen-9-one
CHEMBL361025 ,
chebi:5323 ,
unii-0p3g42tq63
1,3,7-trihydroxy-xanthone
0p3g42tq63 ,
gentisein(nsc 329491)
AKOS022662257
SCHEMBL2315926
DTXSID20200944
1,3,7-trihydroxy-9h-xanthen-9-one, 9ci
9h-xanthen-9-one,1,3,7-trihydroxy-
Q27106719
Y11006
MS-23450
gentisein(nsc329491)
CS-0065353
HY-118166

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" This process leads to trichlormethyl radical (*CCl3) formation, initiation of lipid peroxidation, and measurable toxic effects on the hepatocytes."( Effect of benzophenones from Hypericum annulatum on carbon tetrachloride-induced toxicity in freshly isolated rat hepatocytes.
Kitanov, G; Kondeva, M; Mitcheva, M; Nedialkov, P; Vitcheva, V, 2006
)
0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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 (2)

ClassDescription
xanthonesAny member of the class of xanthenes based on a xanthone skeleton.
polyphenolMembers of the class of phenols that contain 2 or more benzene rings each of which is substituted by at least one hydroxy group.
[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]

Pathways (2)

PathwayProteinsCompounds
superpathway of tetrahydroxyxanthone biosynthesis026
tetrahydroxyxanthone biosynthesis (from benzoate)022

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
UreaseCanavalia ensiformis (jack bean)IC50 (µMol)138.43000.45703.20238.5900AID1802938
Amine oxidase [flavin-containing] AHomo sapiens (human)IC50 (µMol)8.00000.00002.37899.7700AID240726
Fatty acid synthaseHomo sapiens (human)IC50 (µMol)40.98000.00772.46245.8000AID517164
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
biogenic amine metabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
positive regulation of signal transductionAmine oxidase [flavin-containing] AHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
osteoblast differentiationFatty acid synthaseHomo sapiens (human)
glandular epithelial cell developmentFatty acid synthaseHomo sapiens (human)
fatty acid metabolic processFatty acid synthaseHomo sapiens (human)
fatty acid biosynthetic processFatty acid synthaseHomo sapiens (human)
inflammatory responseFatty acid synthaseHomo sapiens (human)
ether lipid biosynthetic processFatty acid synthaseHomo sapiens (human)
neutrophil differentiationFatty acid synthaseHomo sapiens (human)
monocyte differentiationFatty acid synthaseHomo sapiens (human)
mammary gland developmentFatty acid synthaseHomo sapiens (human)
modulation by host of viral processFatty acid synthaseHomo sapiens (human)
cellular response to interleukin-4Fatty acid synthaseHomo sapiens (human)
establishment of endothelial intestinal barrierFatty acid synthaseHomo sapiens (human)
fatty-acyl-CoA biosynthetic processFatty acid synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (20)

Processvia Protein(s)Taxonomy
protein bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
RNA bindingFatty acid synthaseHomo sapiens (human)
[acyl-carrier-protein] S-acetyltransferase activityFatty acid synthaseHomo sapiens (human)
[acyl-carrier-protein] S-malonyltransferase activityFatty acid synthaseHomo sapiens (human)
3-oxoacyl-[acyl-carrier-protein] synthase activityFatty acid synthaseHomo sapiens (human)
3-oxoacyl-[acyl-carrier-protein] reductase (NADPH) activityFatty acid synthaseHomo sapiens (human)
(3R)-3-hydroxypalmitoyl-[acyl-carrier-protein] dehydratase activityFatty acid synthaseHomo sapiens (human)
protein bindingFatty acid synthaseHomo sapiens (human)
(3R)-3-hydroxymyristoyl-[acyl-carrier-protein] dehydratase activityFatty acid synthaseHomo sapiens (human)
(3R)-3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase activityFatty acid synthaseHomo sapiens (human)
fatty acyl-[ACP] hydrolase activityFatty acid synthaseHomo sapiens (human)
phosphopantetheine bindingFatty acid synthaseHomo sapiens (human)
cadherin bindingFatty acid synthaseHomo sapiens (human)
(3R)-3-hydroxybutanoyl-[acyl-carrier-protein] hydratase activityFatty acid synthaseHomo sapiens (human)
(3R)-3-hydroxyoctanoyl-[acyl-carrier-protein] dehydratase activityFatty acid synthaseHomo sapiens (human)
enoyl-[acyl-carrier-protein] reductase (NADPH) activityFatty acid synthaseHomo sapiens (human)
fatty acid synthase activityFatty acid synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] AHomo sapiens (human)
cytosolAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
Golgi apparatusFatty acid synthaseHomo sapiens (human)
cytosolFatty acid synthaseHomo sapiens (human)
plasma membraneFatty acid synthaseHomo sapiens (human)
membraneFatty acid synthaseHomo sapiens (human)
melanosomeFatty acid synthaseHomo sapiens (human)
glycogen granuleFatty acid synthaseHomo sapiens (human)
extracellular exosomeFatty acid synthaseHomo sapiens (human)
cytoplasmFatty acid synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (36)

Assay IDTitleYearJournalArticle
AID657723Antibacterial activity against Staphylococcus aureus ATCC 29213 after 20 to 22 hrs by broth microdilution method2012Bioorganic & medicinal chemistry, May-15, Volume: 20, Issue:10
An efficient and convenient microwave-assisted chemical synthesis of (thio)xanthones with additional in vitro and in silico characterization.
AID661913Inhibition of Influenza A virus H1N1 neuraminidase using 4-MU-NANA as substrate by fluorescence assay2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
Xanthones from Polygala karensium inhibit neuraminidases from influenza A viruses.
AID657724Antibacterial activity against Streptococcus pneumoniae ATCC 49619 after 20 to 22 hrs by broth microdilution method2012Bioorganic & medicinal chemistry, May-15, Volume: 20, Issue:10
An efficient and convenient microwave-assisted chemical synthesis of (thio)xanthones with additional in vitro and in silico characterization.
AID661912Selectivity ratio of IC50 for wild type H1N1 swine influenza virus neuraminidase to IC50 for oseltamivir-resistant H1N1 swine influenza virus neuraminidase H274Y mutant2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
Xanthones from Polygala karensium inhibit neuraminidases from influenza A viruses.
AID1525034Cytotoxicity in human MCF7 cells incubated for 72 hrs by MTT assay2019Journal of natural products, 05-24, Volume: 82, Issue:5
Tetrandraxanthones A-I, Prenylated and Geranylated Xanthones from the Stem Bark of Garcinia tetrandra.
AID1434700Cytotoxicity against human MCF7/ADR cells measured after 48 hrs by MTT assay2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Structure-activity relationships of diverse xanthones against multidrug resistant human tumor cells.
AID1478625Antiproliferative activity against human K562 cells after 48 hrs by CCK8 assay2017European journal of medicinal chemistry, Jun-16, Volume: 133Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them.
AID657727Antibacterial activity against Haemophilus influenzae ATCC 49247 after 20 to 22 hrs by broth microdilution method2012Bioorganic & medicinal chemistry, May-15, Volume: 20, Issue:10
An efficient and convenient microwave-assisted chemical synthesis of (thio)xanthones with additional in vitro and in silico characterization.
AID661916Inhibition of oseltamivir-resistant H1N1 swine influenza virus neuraminidase H274Y mutant using 4-MU-NANA as substrate by fluorescence assay2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
Xanthones from Polygala karensium inhibit neuraminidases from influenza A viruses.
AID1328100Neuroprotective activity in human SK-N-SH cells assessed as inhibition of glutamate-induced injury by measuring increase in cell viability at 10 uM preincubated for 4 hrs followed by glutamate addition measured after 4 hrs by MTT assay2016Journal of natural products, 08-26, Volume: 79, Issue:8
Regiospecific Prenylation of Hydroxyxanthones by a Plant Flavonoid Prenyltransferase.
AID657728Antibacterial activity against Escherichia coli ATCC 25922 after 20 to 22 hrs by broth microdilution method2012Bioorganic & medicinal chemistry, May-15, Volume: 20, Issue:10
An efficient and convenient microwave-assisted chemical synthesis of (thio)xanthones with additional in vitro and in silico characterization.
AID1434698Cytotoxicity against Taxol-resistant human SMMC7721 cells measured after 48 hrs by MTT assay2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Structure-activity relationships of diverse xanthones against multidrug resistant human tumor cells.
AID1357474Growth inhibition of human MCF7 cells after 24 hrs by MTT assay2018European journal of medicinal chemistry, May-10, Volume: 151Incorporation of nitric oxide donor into 1,3-dioxyxanthones leads to synergistic anticancer activity.
AID1478626Antiproliferative activity against human COLO320 cells after 48 hrs by CCK8 assay2017European journal of medicinal chemistry, Jun-16, Volume: 133Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them.
AID1434699Cytotoxicity against Taxol-resistant human A549 cells measured after 48 hrs by MTT assay2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Structure-activity relationships of diverse xanthones against multidrug resistant human tumor cells.
AID1525032Cytotoxicity in human KB cells incubated for 72 hrs by MTT assay2019Journal of natural products, 05-24, Volume: 82, Issue:5
Tetrandraxanthones A-I, Prenylated and Geranylated Xanthones from the Stem Bark of Garcinia tetrandra.
AID1357473Growth inhibition of human MDA-MB-231 cells after 24 hrs by MTT assay2018European journal of medicinal chemistry, May-10, Volume: 151Incorporation of nitric oxide donor into 1,3-dioxyxanthones leads to synergistic anticancer activity.
AID1357472Growth inhibition of human HepG2 cells after 24 hrs by MTT assay2018European journal of medicinal chemistry, May-10, Volume: 151Incorporation of nitric oxide donor into 1,3-dioxyxanthones leads to synergistic anticancer activity.
AID517164Inhibition of FAS2010Bioorganic & medicinal chemistry letters, Oct-15, Volume: 20, Issue:20
Fatty acid synthase inhibitors of phenolic constituents isolated from Garcinia mangostana.
AID657730Cytotoxicity against human Jurkat T cells assessed as NADH level after overnight incubation by MTS assay2012Bioorganic & medicinal chemistry, May-15, Volume: 20, Issue:10
An efficient and convenient microwave-assisted chemical synthesis of (thio)xanthones with additional in vitro and in silico characterization.
AID661914Inhibition of Influenza A virus H9N2 neuraminidase using 4-MU-NANA as substrate by fluorescence assay2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
Xanthones from Polygala karensium inhibit neuraminidases from influenza A viruses.
AID657725Antibacterial activity against Streptococcus pyogenes ATCC 700294 after 20 to 22 hrs by broth microdilution method2012Bioorganic & medicinal chemistry, May-15, Volume: 20, Issue:10
An efficient and convenient microwave-assisted chemical synthesis of (thio)xanthones with additional in vitro and in silico characterization.
AID1478623Antiproliferative activity against human MCF7 cells after 48 hrs by CCK8 assay2017European journal of medicinal chemistry, Jun-16, Volume: 133Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them.
AID1520336Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay2019European journal of medicinal chemistry, Mar-15, Volume: 166All that glitters is not gold: Panning cytotoxic natural products and derivatives with a fused tricyclic backbone by the estimation of their leadlikeness for cancer treatment.
AID240726Concentration required to inhibit monoamine oxidase activity by 50%2004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
QSAR modeling of the MAO inhibitory activity of xanthones derivatives.
AID361498Inhibition of yeast alpha glucosidase in phosphate buffer after 0.5 hrs by spectrophotometry2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Synthesis, inhibitory activities, and QSAR study of xanthone derivatives as alpha-glucosidase inhibitors.
AID657729Cytotoxicity against human HepG2 cells assessed as NADH level after overnight incubation by MTS assay2012Bioorganic & medicinal chemistry, May-15, Volume: 20, Issue:10
An efficient and convenient microwave-assisted chemical synthesis of (thio)xanthones with additional in vitro and in silico characterization.
AID1525035Cytotoxicity in human HepG2 cells incubated for 72 hrs by MTT assay2019Journal of natural products, 05-24, Volume: 82, Issue:5
Tetrandraxanthones A-I, Prenylated and Geranylated Xanthones from the Stem Bark of Garcinia tetrandra.
AID661918Antiviral activity against Influenza A virus PR/8/34 H1N1 infected in dog MDCK cells assessed as reduction in virus-induced cytopathic effect at 5 ug/mL2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
Xanthones from Polygala karensium inhibit neuraminidases from influenza A viruses.
AID1525036Cytotoxicity in human HT-29 cells incubated for 72 hrs by MTT assay2019Journal of natural products, 05-24, Volume: 82, Issue:5
Tetrandraxanthones A-I, Prenylated and Geranylated Xanthones from the Stem Bark of Garcinia tetrandra.
AID1478624Antiproliferative activity against human HepG2 cells after 48 hrs by CCK8 assay2017European journal of medicinal chemistry, Jun-16, Volume: 133Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them.
AID1525033Cytotoxicity in human HeLaS3 cells incubated for 72 hrs by MTT assay2019Journal of natural products, 05-24, Volume: 82, Issue:5
Tetrandraxanthones A-I, Prenylated and Geranylated Xanthones from the Stem Bark of Garcinia tetrandra.
AID1478622Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by CCK8 assay2017European journal of medicinal chemistry, Jun-16, Volume: 133Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them.
AID661915Inhibition of wild type H1N1 swine influenza virus neuraminidase using 4-MU-NANA as substrate by fluorescence assay2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
Xanthones from Polygala karensium inhibit neuraminidases from influenza A viruses.
AID657726Antibacterial activity against Moraxella catarrhalis ATCC 23246 after 20 to 22 hrs by broth microdilution method2012Bioorganic & medicinal chemistry, May-15, Volume: 20, Issue:10
An efficient and convenient microwave-assisted chemical synthesis of (thio)xanthones with additional in vitro and in silico characterization.
AID1802938Urease Inhibition Assay from Article 10.3109/14756360903179385: \\Urease inhibitors from Hypericum oblongifolium WALL.\\2010Journal of enzyme inhibition and medicinal chemistry, Apr, Volume: 25, Issue:2
Urease inhibitors from Hypericum oblongifolium WALL.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's6 (33.33)29.6817
2010's12 (66.67)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: 46.17

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

MetricThis Compound (vs All)
Research Demand Index46.17 (24.57)
Research Supply Index3.00 (2.92)
Research Growth Index4.57 (4.65)
Search Engine Demand Index69.20 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (46.17)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (5.26%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other18 (94.74%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]