LACTUCIN

Product NameLACTUCIN
CAS1891-29-8
MFC15H16O5
MW276.28
EINECS
MOL File1891-29-8.mol

Chemical Properties

Melting point	228-233°
alpha	D +49° (c = 0.90 in methanol), +77.9° (c = 3.44 in pyridine)
Boiling point	575.6±50.0 °C(Predicted)
Density	1.39±0.1 g/cm3(Predicted)
storage temp.	2-8°C
pka	13.53±0.60(Predicted)
form	solid
InChI	1S/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3/t9-,12+,13-,14-/m0/s1
InChIKey	VJQAFLAZRVKAKM-VZLIPTOUSA-N
SMILES	O1[C@H]2[C@@H]([C@H](CC(=C3[C@@H]2C(=CC3=O)CO)C)O)C(=C)C1=O
LogP	0.330 (est)
CAS DataBase Reference	1891-29-8

Safety Information

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

Usage And Synthesis

Description

Lactucin, as lactucopicrin, is a sesquiterpene lactone contained in lettuce (Lactuca sativa).

Uses

Lactucin is an anti-inflammatory agent. Lactucin induces cancer cell apoptosis. Lactucin also shows analgesic, anticancer and antimalarial activities[1][2][3][4].

Definition

ChEBI: An azulenofuran that is 3-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione carrying additional hydroxy, methyl and hydroxymethyl substituents at positions 4, 6 and 9 respectively (the 3aR,4S,9 S,9bR-diastereomer). Found in chicory.

Contact allergens

Lactucin, as lactucopicrin, is a sesquiterpene lactone contained in lettuce (Lactuca sativa L.)

in vivo

Lactucin (15 and 30 mg/kg; i.p.; once) decreases the spontaneous locomotor activity and shows analgesic properties in mice^[2].

Animal Model:	Male Albino-Swiss mice (18-24 g)^[2]
Dosage:	15 and 30 mg/kg
Administration:	Intraperitoneal injection, once
Result:	Decreased the spontaneous locomotor activity and showed analgesic properties in the hot plate test.

References

[1] Dang T, et al. Sesquiterpenoids with diverse carbon skeletons from the roots of Cichorium glandulosum and their anti-inflammatory activities. Fitoterapia. 2019 Jul;136:104170. DOI:10.1016/j.fitote.2019.104170
[2] Gromek D, et al. Biologically active preparations from Lactuca virosa L. Phytotherapy Research, 1992, 6(5): 285-287.
[3] Zhang F H, et al. Lactucin induces potent anti-cancer effects in HL-60 human leukemia cancer cells by inducing apoptosis and sub-G1 cell cycle arrest. Bangladesh Journal of Pharmacology, 2016, 11(2): 478-484.
[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

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