Page last updated: 2024-12-10

ladanein

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

Description

ladanein: from Marrubium peregrinum; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ladanein : A dimethoxyflavone that is scutellarein in which the hydroxy groups at positions 4' and 7 are replaced by methoxy groups. It is an effective anti-HCV agent. [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
MarrubiumgenusA plant genus of the LAMIACEAE family that contains marrubiin (a labdane diterpene). It is known as a traditional medicinal for sore throat.[MeSH]LamiaceaeThe mint plant family. They are characteristically aromatic, and many of them are cultivated for their oils. Most have square stems, opposite leaves, and two-lipped, open-mouthed, tubular corollas (united petals), with five-lobed, bell-like calyxes (united sepals).[MeSH]

Cross-References

ID SourceID
PubMed CID3084066
CHEMBL ID209257
CHEBI ID192702
SCHEMBL ID737069
MeSH IDM0546587

Synonyms (22)

Synonym
5,6-dihydroxy-7-methoxy-2-(4-methoxyphenyl)-4h-1-benzopyran-4-one
4h-1-benzopyran-4-one, 5,6-dihydroxy-7-methoxy-2-(4-methoxyphenyl)-
CHEMBL209257
ladanein
LMPK12111165
bj486k
5,6-dihydroxy-7-methoxy-2-(4-methoxyphenyl)-4h-chromen-4-one
5,6-dihydroxy-7,4'-dimethoxyflavone
CHEBI:192702
4',7-dimethylscutellarein
10176-71-3
5,6-dihydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one
SCHEMBL737069
UUQJTIHOVGMQIH-UHFFFAOYSA-N
5,6-dihydroxy-4',7-dimethoxyflavone
ladanine; scutellarein 4',7-dimethyl ether
DTXSID00144175
AKOS032962667
FS-8782
A910427
HY-N3409
CS-0024154

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" We tested the bioavailability of the compound in mice."( A plant-derived flavonoid inhibits entry of all HCV genotypes into human hepatocytes.
Bailleul, F; Bankwitz, D; Bartenschlager, R; Chhatwal, P; Davioud-Charvet, E; Gentzsch, J; Geuenich, S; Grethe, C; Haid, S; Hennebelle, T; Hernandez, C; Jannack, B; Keppler, OT; Lemasson, M; Novodomská, A; Pietschmann, T; Poenisch, M; Rosenberg, AR; Wong-Staal, F, 2012
)
0.38
"We identified a flavonoid, ladanein (BJ486K), with unreported antiviral activity and established its oral bioavailability in mice."( A plant-derived flavonoid inhibits entry of all HCV genotypes into human hepatocytes.
Bailleul, F; Bankwitz, D; Bartenschlager, R; Chhatwal, P; Davioud-Charvet, E; Gentzsch, J; Geuenich, S; Grethe, C; Haid, S; Hennebelle, T; Hernandez, C; Jannack, B; Keppler, OT; Lemasson, M; Novodomská, A; Pietschmann, T; Poenisch, M; Rosenberg, AR; Wong-Staal, F, 2012
)
0.68
"BJ486K has oral bioavailability and interferes with entry of HCV into cultured human hepatocytes."( A plant-derived flavonoid inhibits entry of all HCV genotypes into human hepatocytes.
Bailleul, F; Bankwitz, D; Bartenschlager, R; Chhatwal, P; Davioud-Charvet, E; Gentzsch, J; Geuenich, S; Grethe, C; Haid, S; Hennebelle, T; Hernandez, C; Jannack, B; Keppler, OT; Lemasson, M; Novodomská, A; Pietschmann, T; Poenisch, M; Rosenberg, AR; Wong-Staal, F, 2012
)
0.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antiviral agentA substance that destroys or inhibits replication of viruses.
radical scavengerA role played by a substance that can react readily with, and thereby eliminate, radicals.
[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
dimethoxyflavoneAny methoxyflavone with two methoxy substituents.
dihydroxyflavoneAny hydroxyflavone in which two ring hydrogens are replaced by 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]

Pathways (1)

PathwayProteinsCompounds
salvigenin biosynthesis713

Bioassays (21)

Assay IDTitleYearJournalArticle
AID1265082Aqueous solubility of the compound in water after 1 hr by UV-vis spectrophotometer analysis2015European journal of medicinal chemistry, Dec-01, Volume: 106Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo.
AID1265075Antithrombotic activity in New Zealand white rabbit platelet-poor plasma assessed as increase of thrombin time at 100 uM after 3 mins (Rvb = 20.25 +/- 1.02 seconds)2015European journal of medicinal chemistry, Dec-01, Volume: 106Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo.
AID1265085N-octanol/0.15 M NaHCO3 partition coefficient, log P of the compound after 5 hrs by spectrophotometric analysis2015European journal of medicinal chemistry, Dec-01, Volume: 106Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo.
AID1265076Antithrombotic activity in New Zealand white rabbit platelet-poor plasma assessed as increase of prothrombin time at 100 uM after 3 mins (Rvb = 4.99 +/- 0.18 seconds)2015European journal of medicinal chemistry, Dec-01, Volume: 106Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo.
AID494832Antimalarial activity against chloroquine-sensitive Plasmodium falciparum NF542010Bioorganic & medicinal chemistry letters, Aug-15, Volume: 20, Issue:16
Integrated ligand and structure based studies of flavonoids as fatty acid biosynthesis inhibitors of Plasmodium falciparum.
AID1265077Antithrombotic activity in New Zealand white rabbit platelet-poor plasma assessed as increase of activated partial thromboplastin time at 100 uM after 3 mins (Rvb = 30.58 +/- 1.55 seconds)2015European journal of medicinal chemistry, Dec-01, Volume: 106Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo.
AID265763Inhibition of FabZ at 100 uM2006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.
AID1265079Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins2015European journal of medicinal chemistry, Dec-01, Volume: 106Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo.
AID360320Antiproliferative activity against human HT1080 cells after 4 days by MTT assay2001Journal of natural products, May, Volume: 64, Issue:5
Five novel highly oxygenated diterpenes of Orthosiphon stamineus from Myanmar.
AID1265081Antioxidant activity in rat PC12 cells assessed as inhibition of H2O2-induced cytotoxicity at 25 uM after 4 hrs by MTT assay2015European journal of medicinal chemistry, Dec-01, Volume: 106Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo.
AID265762Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum K12006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.
AID494831Inhibition of Plasmodium falciparum FabI at 100 uM2010Bioorganic & medicinal chemistry letters, Aug-15, Volume: 20, Issue:16
Integrated ligand and structure based studies of flavonoids as fatty acid biosynthesis inhibitors of Plasmodium falciparum.
AID265761Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum NF542006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.
AID1265083N-octanol/0.1 M HCl partition coefficient, log P of the compound after 5 hrs by spectrophotometric analysis2015European journal of medicinal chemistry, Dec-01, Volume: 106Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo.
AID1265084N-octanol/0.15 M NaCl partition coefficient, log P of the compound after 5 hrs by spectrophotometric analysis2015European journal of medicinal chemistry, Dec-01, Volume: 106Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo.
AID1265078Antithrombotic activity in New Zealand white rabbit platelet-poor plasma assessed as increase of fibrinogen at 100 uM after 3 mins (Rvb = 7.02+/- 0.16 g/L)2015European journal of medicinal chemistry, Dec-01, Volume: 106Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo.
AID360319Antiproliferative activity against mouse Colon 26-L5 cells after 4 days by MTT assay2001Journal of natural products, May, Volume: 64, Issue:5
Five novel highly oxygenated diterpenes of Orthosiphon stamineus from Myanmar.
AID1265080Antioxidant activity in rat PC12 cells assessed as inhibition of H2O2-induced cytotoxicity at 50 uM after 4 hrs by MTT assay2015European journal of medicinal chemistry, Dec-01, Volume: 106Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo.
AID265765Inhibition of FabG at 100 uM2006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.
AID265764Inhibition of FabI at 100 uM2006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.
AID294158Inhibition of diphenolase activity of mushroom tyrosinase at 0.053 mM2007Bioorganic & medicinal chemistry, Apr-01, Volume: 15, Issue:7
Identification of tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (27.27)29.6817
2010's8 (72.73)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: 21.28

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 Index21.28 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.28)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (9.09%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]