Page last updated: 2024-11-11

trilinolein

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

Description

trilinolein: RN given refers to (Z,Z)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1,2,3-trilinoleoylglycerol : A triglyceride formed by acylation of the three hydroxy groups of glycerol with linoleic acid. [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]

Cross-References

ID SourceID
PubMed CID5322095
CHEMBL ID3343985
CHEBI ID75844
SCHEMBL ID114944
MeSH IDM0054381

Synonyms (69)

Synonym
v5lj52ogs7 ,
unii-v5lj52ogs7
9,12-octadecadienoic acid (z,z)-, 1,2,3-propanetriyl ester
tg(18:2/18:2/18:2)
1,2,3-tri-(9z,12z-octadecadienoyl)-glycerol
LMGL03010371
tg(18:2(9z,12z)/18:2(9z,12z)/18:2(9z,12z))
trilinolein
glyceryl trilinoleate, >=98% (tlc), liquid
(z,z)-9,12-octadecadienoic acid, 1,2,3-propanetriyl ester
glyceryl trilinoleate
linoleic acid, 1,2,3-propanetriyl ester
1,2,3-propenetriol tri(9,12-octadecaienoate)
1,2,3-propanetriol trilinoleate
einecs 208-666-6
propane-1,2,3-triyl tris((9z,12z)-octadeca-9,12-dienoate)
trilinoelaidate
9,12-octadecadienoic acid, 1,2,3-propanetriyl ester
trilinoleic glycerol
trilinolein c18:2
propane-1,2,3-triyl (9z,12z,9'z,12'z,9''z,12''z)tris-octadeca-9,12-dienoate
537-40-6
glycerol trilinoleate
1,2,3-tri(cis,cis-9,12-octadecadienoyl) glycerol
T1388
2,3-bis[[(9z,12z)-octadeca-9,12-dienoyl]oxy]propyl (9z,12z)-octadeca-9,12-dienoate
1,2,3-tri-(cis,cis-9,12-octadecadienoyl)glycerol
trilinolelaidin
1,2,3-trilinoleoylglycerol
S6125
tg(18:2omega6/18:2omega6/18:2omega6)
1,2,3-tri-(9z,12z)-octadecadienoylglycerol
linoleoyl triglyceride
tg [18:2(omega-6)/18:2(omega-6)/18:2(omega-6)]
1,2,3-propenetriol tri(9,12-octadecadienoate)
tag(18:2/18:2/18:2)
triacylglycerol(54:6)
tag(54:6)
1,2,3-tri-(9z,12z-octadecadienoyl)glycerol
tracylglycerol(18:2omega6/18:2omega6/18:2omega6)
CHEBI:75844 ,
triacylglycerol(18:2/18:2/18:2)
SCHEMBL114944
linolein, tri-
efaderma-f
9,12-octadecadienoic acid (9z,12z)-, 1,2,3-propanetriyl ester
9,12-octadecadienoic acid (9z,12z)-, 1,1',1''-(1,2,3-propanetriyl) ester
trilinolein [inci]
2,3-bis[(9z,12z)-9,12-octadecadienoyloxy]propyl (9z,12z)-9,12-octadecadienoate #
DTXSID1042653
CHEMBL3343985 ,
glyceryl trilinoleate, analytical standard
mfcd00042909
tag(18:2n6/18:2n6/18:2n6)
tag(18:2w6/18:2w6/18:2w6)
tracylglycerol(18:2n6/18:2n6/18:2n6)
tracylglycerol(18:2/18:2/18:2)
tracylglycerol(18:2w6/18:2w6/18:2w6)
tg(18:2n6/18:2n6/18:2n6)
1-linoleoyl-2-linoleoyl-3-linoleoyl-glycerol
tg 54:6
HY-128393
tg(18:2w6/18:2w6/18:2w6)
propane-1,2,3-triyl (9z,9'z,9''z,12z,12'z,12''z)-tris(octadeca-9,12-dienoate)
CS-0099524
T72589
tg 18:2_18:2_18:2
AKOS040758726
BP-29845

Research Excerpts

Overview

Trilinolein is a triacylglycerol recently purified from the traditional Chinese medicinal plant Panax pseudo-ginseng. It has linoleic acid as the only type of fatty acid in all three esterified positions of glycerol.

ExcerptReferenceRelevance
"Trilinolein (TriL) is a natural triacylglycerol presented in several plants."( Trilinolein, a Natural Triacylglycerol, Protects Cerebral Ischemia through Inhibition of Neuronal Apoptosis and Ameliorates Intimal Hyperplasia via Attenuation of Migration and Modulation of Matrix Metalloproteinase-2 and RAS/MEK/ERK Signaling Pathway in
Chen, YF; Siao, LR; Tsai, HY; Wu, KJ, 2022
)
2.89
"Trilinolein is a triacylglycerol purified from a commonly used traditional Chinese medicine Panax notoginseng. "( Protective effects of trilinolein extracted from panax notoginseng against cardiovascular disease.
Chan, P; Thomas, GN; Tomlinson, B, 2002
)
2.07
"Trilinolein is a triacylglycerol recently purified from the well known traditional Chinese herb Panax pseudoginseng, which has been used in treating circulatory disorders among Chinese for hundreds of years; it has linoleate as the only fatty acid residue in all three esterified positions of glycerol."( Trilinolein preserves mitochondria ultrastructure in isolated rat heart subjected to global ischemia through antioxidant activity as measured by chemiluminescence.
Chan, P; Cheng, JT; Hong, CY; Niu, CS; Tsai, SK; Tsao, CW, 1996
)
2.46
"Trilinolein is a triacylglycerol recently purified from the traditional Chinese medicinal plant Panax pseudo-ginseng."( Effect of trilinolein on superoxide dismutase activity and left ventricular pressure in isolated rat hearts subjected to hypoxia and normoxic perfusion.
Chan, P; Chen, JP; Cheng, JT; Hong, CT; Hong, CY; Niu, CS; Tomlinson, B; Tsai, SK, 1997
)
1.42
"1. Trilinolein is a triacylglycerol with linoleic acid as the only type of fatty acid in all three esterified positions of glycerol. "( Trilinolein inhibits the adhesion of neutrophils to endothelial cells.
Hong, CY; Huang, SS; Kwok, CF; Sung, YJ; Wang, R, 1998
)
2.36
"Trilinolein is a lipophilic antioxidant purified from the herb of Panax pseudoginseng."( Effect of trilinolein on the activity and gene expression of superoxide dismutase in cultured rat brain astrocytes.
Chan, P; Cheng, JT; Chiu, WT; Liao, SS; Liou, JR, 1999
)
1.43

Effects

Trilinolein has been identified as one of the active constituents isolated from Panax notoginseng used widely in traditional Chinese medicine. It has been reported to provide a number of beneficial effects including reducing thrombogenicity and arrhythmias.

ExcerptReferenceRelevance
"Trilinolein has been identified as one of the active constituents isolated from Panax notoginseng used widely in traditional Chinese medicine. "( Trilinolein inhibits proliferation of human non-small cell lung carcinoma A549 through the modulation of PI3K/Akt pathway.
Chen, YY; Cheng, HC; Chien, YC; Chou, PY; Huang, GJ; Pan, CH; Sheu, MJ; Wu, CH, 2011
)
3.25
"Trilinolein has been reported to provide a number of beneficial effects including reducing thrombogenicity and arrhythmias and increasing erythrocyte deformability."( Protective effects of trilinolein extracted from panax notoginseng against cardiovascular disease.
Chan, P; Thomas, GN; Tomlinson, B, 2002
)
1.35
"Trilinolein, which has recently been isolated from natural products, as well as the well-known water soluble analogue of vitamin E-Trolox, were used as control."( The in vitro antioxidant activity of trilinolein and other lipid-related natural substances as measured by enhanced chemiluminescence.
Chan, P; Cheng, JT; Hong, CY; Niu, CS; Tsao, CW, 1996
)
1.29

Treatment

Pretreatment with trilinolein was associated with better preservation of left ventricular function during hypoxia and more rapid return to recovery during normoxic perfusion. Pretreatment of tril inolein with 10 microM d-sphingosine before being incubated with PMNs attenuated the occurrence of ventricular tachycardia.

ExcerptReferenceRelevance
"Trilinolein treatment induced the upregulation of pro-apoptotic Bax, downregulation of anti-apoptotic Bcl-2 expression, which was associated with the proteolytic activation of caspases and the concomitant degradation of poly(ADP-ribose) polymerase (PARP) protein."( Trilinolein inhibits proliferation of human non-small cell lung carcinoma A549 through the modulation of PI3K/Akt pathway.
Chen, YY; Cheng, HC; Chien, YC; Chou, PY; Huang, GJ; Pan, CH; Sheu, MJ; Wu, CH, 2011
)
2.53
"Treatment with trilinolein or triolein on oxidized low-density lipoprotein -stimulated endothelial cells inhibited the expression of ICAM-1 and E-selectin mRNA."( Triolein and trilinolein ameliorate oxidized low-density lipoprotein-induced oxidative stress in endothelial cells.
Deng, ZY; Fan, YW; Li, XP; Luo, T; Rao, H, 2014
)
1.11
"Pretreatment with trilinolein was associated with better preservation of left ventricular function during hypoxia and more rapid return to recovery during normoxic perfusion."( Effect of trilinolein on superoxide dismutase activity and left ventricular pressure in isolated rat hearts subjected to hypoxia and normoxic perfusion.
Chan, P; Chen, JP; Cheng, JT; Hong, CT; Hong, CY; Niu, CS; Tomlinson, B; Tsai, SK, 1997
)
1.02
"Pretreatment with trilinolein before strophanthidin administration did not prevent the occurrence of ventricular tachycardia; the doses of strophanthidin required to induce arrhythmias (ventricular extrasystole and ventricular tachycardia) were similar in guinea pigs pretreated with trilinolein or control."( Effect of trilinolein on strophanthidin-induced ventricular tachycardia in guinea pigs.
Chang, M; Chen, S; Chen, Y; Chiang, C; Hong, C; Tai, C, 1999
)
1.03
"Pretreatment of trilinolein with 10 microM d-sphingosine, before being incubated with PMNs, attenuated the stimulatory effect of trilinolein on cyclic GMP formation, and pretreatment of 10 microM d-sphingosine also attenuated the aggregation induced by PMA and trilinolein."( Trilinolein potentiates the pro-aggregating effect of phorbol-12-myristate 13-acetate in human polymorphonuclear leukocytes.
Hong, CY; Yang, SH, 1999
)
2.08

Toxicity

ExcerptReferenceRelevance
" Trilinolenin (18:3; omega-3) was toxic only after prolonged incubation."( Toxicity of polyunsaturated fatty acid esters for human monocyte-macrophages: the anomalous behaviour of cholesteryl linolenate.
Carpenter, KL; Hardwick, SJ; Hird, R; Law, NS; Marchant, CE; Mitchinson, MJ; Van Der Veen, C, 1997
)
0.3

Compound-Compound Interactions

ExcerptReferenceRelevance
"High-purity trilinolein and triolein were prepared by Novozym 435-catalyzed esterification reaction combined with column chromatography purification in this study."( Preparation of High-Purity Trilinolein and Triolein by Enzymatic Esterification Reaction Combined with Column Chromatography.
Chen, Z; Lan, T; Li, H; Pan, L; Wu, D; Zhao, B, 2019
)
1.19

Dosage Studied

ExcerptRelevanceReference
" These data emphasize the importance of choosing an optimal dosage for supplementation with anti-oxidants in humans for the scavenging of oxygen free radicals."( Effects of trilinolein on superoxide dismutase activity and mrna levels in aortic smooth muscle cells.
Chan, P; Chang, JJ; Chen, FC; Cheng, JT; Tomlinson, B; Wu, MS, 2000
)
0.7
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[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
triglycerideAny glyceride resulting from the condensation of all three hydroxy groups of glycerol (propane-1,2,3-triol) with fatty acids.
TG(18:2/18:2/18:2)
linoleoyl containing 1,2,3-triacyl-sn-glycerol
1,2-diacyl-3-linoleoylglycerol
1,3-diacyl-2-linoleoylglycerol
[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 (3)

PathwayProteinsCompounds
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))511
De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))513
Thermogenesis018

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Polyphenol oxidase 2Agaricus bisporusIC50 (µMol)8.40000.03403.987110.0000AID1167964
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1167964Non-competitive inhibition of mushroom tyrosinase2014Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21
Structure-activity relationships of the thujaplicins for inhibition of human tyrosinase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (81)

TimeframeStudies, This Drug (%)All Drugs %
pre-199010 (12.35)18.7374
1990's24 (29.63)18.2507
2000's25 (30.86)29.6817
2010's19 (23.46)24.3611
2020's3 (3.70)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 46.76

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 Index46.76 (24.57)
Research Supply Index4.43 (2.92)
Research Growth Index4.74 (4.65)
Search Engine Demand Index69.83 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (46.76)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (2.41%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other81 (97.59%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]