| Identification | Back Directory | [Name]
Lactucopicrin | [CAS]
65725-11-3 | [Synonyms]
Lactupicrin
[(3aR,4S,9aS,9bR)-9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-(4-hydroxyphenyl)acetate
Benzeneacetic acid, 4-hydroxy-, (3aR,4S,9aS,9bR)-2,3,3a,4,5,7,9a,9b-octahydro-9-(hydroxymethyl)-6-methyl-3-methylene-2,7-dioxoazuleno[4,5-b]furan-4-yl ester | [Molecular Formula]
C23H22O7 | [MOL File]
65725-11-3.mol | [Molecular Weight]
410.42 |
| Chemical Properties | Back Directory | [Melting point ]
146 °C | [Boiling point ]
686.0±55.0 °C(Predicted) | [density ]
1.40±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
Solid | [pka]
9.79±0.15(Predicted) | [color ]
White to off-white | [InChIKey]
UMVSOHBRAQTGQI-XGARDCMYSA-N | [SMILES]
C1(CC(O[C@@H]2[C@@]3([H])C(=C)C(=O)O[C@]3([H])[C@]3([H])C(C(=O)C=C3CO)=C(C)C2)=O)=CC=C(O)C=C1 | [LogP]
2.240 (est) |
| Hazard Information | Back Directory | [Uses]
Lactupicrin (Lactucopicrin) exhibits analgesic, sedative, antimalarial activities and atheroprotective effect. Lactupicrin inhibits acetylcholinesterase (AChE) with an IC50 of 150.3 μM. Lactupicrin is an orally active characteristic bitter sesquiterpene lactone[1][2][3][4][5]. | [Definition]
ChEBI: Lactucopicrin is an azulenofuran, a cyclic terpene ketone, an enone, a member of phenols, a sesquiterpene lactone and a primary alcohol. It has a role as a plant metabolite, a sedative and an antimalarial. It is functionally related to a 4-hydroxyphenylacetic acid and a lactucin. | [in vivo]
Lactupicrin (15-30 mg/kg, i.p.) shows analgesic activities and sedative properties in mice[1].
Lactupicrin (1.2-120 mg/kg, p.o., daily, 12 weeks) limits macrophage foam cell formation through a reduction of LOX-1 in lipid rafts, contributing to its atheroprotective effect in ApoE-/- mice[2].
Lactupicrin (1.2-120 mg/kg, p.o., daily, 12 weeks) inhibits early atherosclerosis formation in ApoE-/-mice[3].
Lactupicrin (1.2-120 mg/kg, p.o., daily, 12 weeks) reduces ApoE-/-mice serum levels of IL-1β and TNF-α but not IL-6 dose-dependently[3].
| Animal Model: | Male Albino Swiss mice, weighing 24-28 g[1]. | | Dosage: | 15, 30 mg/kg | | Administration: | i.p. | | Result: | Prolonged the latency towards a noxious stimulus by 142 %.
Showed significant antinociceptive activities.
Decreased the spontaneous locomotor activity at a dose of 30 mg/kg (but not 15 mg/kg).
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| Animal Model: | ApoE-/- mice (C57BL/6), 8 weeks old, male, were fed with a high-fat diet (21% milk fat, 0.15% cholesterol)[2]. | | Dosage: | 1.2, 12, 120 mg/kg | | Administration: | p.o., daily, 12 weeks | | Result: | Reduced the percentage of F4/80 (a marker to identify macrophage) positive derived foam cells within plaques at the aortic sinus dose-dependently.
Reduced the mRNA levels of Lox1 and F4/80 in aortic arches dose-dependently.
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| Animal Model: | Male ApoE-/- mice (C57BL/6), 6-8 weeks old, were fed a high fat diet (21% milk fat, 0.15% cholesterol)[3]. | | Dosage: | 12, 120 mg/kg | | Administration: | p.o., daily, 12 weeks | | Result: | Reduced the atherosclerotic plaque area at the sites of both aortic sinus and thoracic and abdominal aortas.
Reduced the percentage of CD68 and F4/80 (two widely used markers to identify macrophages) positive
cells within plaques at the aortic sinus.
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| [References]
[1] Weso?owska A, et, al. Analgesic and sedative activities of lactucin and some lactucin-like guaianolides in mice. J Ethnopharmacol. 2006 Sep 19;107(2):254-8. DOI:10.1016/j.jep.2006.03.003
[2] Li Q, et, al. Terpene Lactucopicrin Limits Macrophage Foam Cell Formation by a Reduction of Lectin-Like Oxidized Low-Density Lipoprotein Receptor-1 in Lipid Rafts. Mol Nutr Food Res. 2022 Feb;66(4):e2100905. DOI:10.1002/mnfr.202100905
[3] He L, et al. Lactupicrin Inhibits Cytoplasmic Dynein-Mediated NF-κB Activation in Inflammated Macrophages and Alleviates Atherogenesis in Apolipoprotein E-Deficient Mice. Mol Nutr Food Res. 2021 Feb;65(4):e2000989. DOI:10.1002/mnfr.202000989
[4] Bischoff TA, et al. Antimalarial activity of lactucin and lactucopicrin: sesquiterpene lactones isolated from Cichorium intybus L. J Ethnopharmacol. 2004 Dec;95(2-3):455-7. DOI:10.1016/j.jep.2004.06.031
[5] Rollinger JM, et al. Application of the in combo screening approach for the discovery of non-alkaloid acetylcholinesterase inhibitors from Cichorium intybus. Curr Drug Discov Technol. 2005 Sep;2(3):185-93. DOI:10.2174/1570163054866855 |
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