Lactucopicrin

Product NameLactucopicrin
CAS65725-11-3
MFC23H22O7
MW410.42
EINECS
MOL File65725-11-3.mol

Chemical Properties

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)

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids
Hazard Classifications	Skin Sens. 1

Usage And Synthesis

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).

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.

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.

References

[1] Wesoowska 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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