Page last updated: 2024-12-08

silychristin

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

Description

silychristin : A flavonolignan isolated from Silybum marianum and has been shown to exhibit inhibitory activities against lipoxygenase and prostaglandin synthetase. [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
Silybumgenus[no description available]AsteraceaeA large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]
Silybum marianumspecies[no description available]AsteraceaeA large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]

Cross-References

ID SourceID
PubMed CID441764
CHEBI ID9143
SCHEMBL ID971442
MeSH IDM0064817

Synonyms (32)

Synonym
(2r,3r)-3,5,7-trihydroxy-2-[(2r,3s)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-4h-chromen-4-one
silychristin
C08717
33889-69-9
silicristine [inn-french]
silicristinum [inn-latin]
silicristin [inn]
2-(2,3-dihydro-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-benzofuranyl)-3,5,7-trihydroxy-4-chromanone
silicristina [inn-spanish]
silicristin
einecs 251-720-9
chebi:9143 ,
(2r,3r)-3,5,7-trihydroxy-2-[(2r,3s)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydrochromen-4-one
silicristina
unii-lk279er14x
lk279er14x ,
silicristinum
silicristine
silymarin ii
silicristin [mart.]
SCHEMBL971442
DTXSID50187512
silychristin, analytical standard
mfcd00883715
AKOS030573535
(2r,3r)-3,5,7-trihydroxy-2-((2r,3s)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydrobenzofuran-5-yl)chroman-4-one
Q27108289
BRD-K16389764-001-01-8
CS-0009673
HY-N0647
AS-79115
AC-34760

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Additionally, the steady-state pharmacokinetic parameters were determined after the subjects were administered one capsule three times daily for 28 consecutive days."( An assessment of pharmacokinetics and antioxidant activity of free silymarin flavonolignans in healthy volunteers: a dose escalation study.
Bernstein, HJ; Brinda, BJ; Chavin, KD; Markowitz, JS; Patrick, KS; Zhu, HJ, 2013
)
0.39
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
radical scavengerA role played by a substance that can react readily with, and thereby eliminate, radicals.
lipoxygenase inhibitorA compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.
prostaglandin antagonistA compound that inhibits the action of prostaglandins.
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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 (5)

ClassDescription
flavonolignanAny lignan condensed with a 2-aryl-1-benzopyran skeleton and its substituted derivatives.
1-benzofuransA member of the class of benzofurans consisting of a 1-benzofuran skeleton and its substituted derivatives thereof.
polyphenolMembers of the class of phenols that contain 2 or more benzene rings each of which is substituted by at least one hydroxy group.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
secondary alpha-hydroxy ketoneAn alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing one hydrogen and one organyl group. Secondary alpha-hydroxy ketones are also known as acyloins, and are formally derived from reductive coupling of two carboxylic acid groups.
[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)
Polyphenol oxidase 2Agaricus bisporusIC50 (µMol)16.00000.03403.987110.0000AID1603425; AID1603430
Polyphenol oxidase 2Agaricus bisporusKi8.70000.00063.28838.8900AID1603426; AID1603428; AID1603431; AID1603433
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Polyphenol oxidase 2Agaricus bisporusKis20.10002.90005.33008.8500AID1603429; AID1603434
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (18)

Assay IDTitleYearJournalArticle
AID462333Inhibition of theophylline-stimulated melanogenesis in mouse B16-4A5 cells at 30 uM after 72 hrs2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells.
AID1603440Binding affinity to mushroom tyrosinase assessed as binding constant by fluorescence spectrophotometry2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle).
AID1705065Inhibition of biotinylated 5-(4-((Z)-3-Carboxy-3-hydroxyacryloyl)-4-(4-chlorobenzyl)piperidine-1-carbonyl)-2-((13,35-dioxo-39-((3aR,4R,6aS)-2-oxohexahydro-1H-thieno[3,4-d]imidazole-4-yl)-3,6,9,16,19,22,25,28,31-nonaoxa-12,34-diazanonatriacontyl)oxy)benzoi2020European journal of medicinal chemistry, Dec-15, Volume: 208Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors.
AID1603435Inhibition of monophenolase activity of mushroom tyrosinase assessed as increase in lag period of monophenolase for oxidation of L-tyrosine substrate at 0.5 to 16 uM by UV-Vis spectrophotometry2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle).
AID1603426Mixed type inhibition of monophenolase activity of mushroom tyrosinase assessed as reduction in dopachrome formation using L-Tyrosine substrate by UV-Vis spectrophotometry based Dixon plot analysis2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle).
AID1603429Inhibition of monophenolase activity of mushroom tyrosinase assessed as inhibition constant for enzyme-substrate-inhibitor complex by measuring reduction in dopachrome formation using L-Tyrosine substrate by UV-Vis spectrophotometry2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle).
AID1603430Inhibition of diphenolase activity of mushroom tyrosinase assessed as reduction in dopachrome formation using L-DOPA substrate by UV-Vis spectrophotometry2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle).
AID462342Toxicity in mouse B16-4A5 cells assessed as inhibition of cell proliferation at 30 uM in presence of 1 mM theophylline after 72 hrs by WST8 dye reduction assay2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells.
AID1603439Binding affinity to mushroom tyrosinase assessed as Stern-Volmer quenching constant by fluorescence spectrophotometry2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle).
AID1603431Mixed type inhibition of diphenolase activity of mushroom tyrosinase assessed as reduction in dopachrome formation using L-DOPA substrate by UV-Vis spectrophotometry based Dixon plot analysis2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle).
AID1603428Inhibition of monophenolase activity of mushroom tyrosinase assessed as inhibition constant for free enzyme-inhibitor complex by measuring reduction in dopachrome formation using L-Tyrosine substrate by UV-Vis spectrophotometry2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle).
AID462336Inhibition of theophylline-stimulated melanogenesis in mouse B16-4A5 cells at 1 uM after 72 hrs2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells.
AID1603433Inhibition of diphenolase activity of mushroom tyrosinase assessed as inhibition constant for free enzyme-inhibitor complex by measuring reduction in dopachrome formation using L-DOPA substrate by UV-Vis spectrophotometry2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle).
AID462335Inhibition of theophylline-stimulated melanogenesis in mouse B16-4A5 cells at 3 uM after 72 hrs2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells.
AID1603425Inhibition of monophenolase activity of mushroom tyrosinase assessed as reduction in dopachrome formation using L-Tyrosine substrate by UV-Vis spectrophotometry2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle).
AID1603437Inhibition of monophenolase activity of mushroom tyrosinase assessed as reduction in steady state rate monophenolase activity for oxidation of L-tyrosine substrate at 0.5 to 16 uM by UV-Vis spectrophotometry2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle).
AID462334Inhibition of theophylline-stimulated melanogenesis in mouse B16-4A5 cells at 10 uM after 72 hrs2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells.
AID1603434Inhibition of diphenolase activity of mushroom tyrosinase assessed as inhibition constant for enzyme-substrate-inhibitor complex by measuring reduction in dopachrome formation using L-DOPA substrate by UV-Vis spectrophotometry2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (44)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (9.09)18.7374
1990's1 (2.27)18.2507
2000's10 (22.73)29.6817
2010's24 (54.55)24.3611
2020's5 (11.36)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.02

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 Index29.02 (24.57)
Research Supply Index3.83 (2.92)
Research Growth Index5.66 (4.65)
Search Engine Demand Index34.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.02)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.22%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other44 (97.78%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]