125519-47-3
Chemical Structure
11β,13-Dihydrolactucopicrin
- CAS No.: 125519-47-3
- Formula:C23H24O7
- Molecular Weight:412.44
IUPAC Name: (3S,3aR,4S,9aS,9bR)-9-(hydroxymethyl)-3,6-dimethyl-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydroazuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate
InChIKey: ICJJPTZLMALYBH-ZUQDHHQASA-N
SMILES: C(O)C=1[C@@]2([C@@]3([C@@]([C@@H](OC(CC4=CC=C(O)C=C4)=O)CC(C)=C2C(=O)C1)([C@H](C)C(=O)O3)[H])[H])[H]
Biological Activity: 11β,13-Dihydrolactucopicrin is a sesquiterpene lactone and the main bitter component of chicory root. 11β,13-Dihydrolactucopicrin inhibits yeast α-glucosidase activity (IC50 = 27.49 μM) and inhibits Crz1 activation and nuclear accumulation. 1β,13-Dihydrolactucopicrin possesses blood-brain barrier penetration capacity in an in vitro HBMEC blood-brain barrier model and can generate cysteine-conjugated metabolites within brain microvascular endothelial cells. 11β,13-Dihydrolactucopicrin can regulate the lncRNA H19/miR-21-3p signaling axis; it upregulates the expression of ABCG2 and lncRNA H19, downregulates miR-21-3p, inhibits the release of IL-6, TNF-α, and hs-CRP pro-inflammatory mediators, and alleviates urate-induced inflammatory injury in renal epithelial cells. 11β,13-Dihydrolactucopicrin can be used in research on diabetes and renal urate deposition[1][2][3][4].
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11β,13-Dihydrolactucopicrin | 11β,13-Dihydrolactucopicrin is a sesquiterpene lactone and the main bitter component of chicory root. 11β,13-Dihydrolactucopicrin inhibits yeast α-glucosidase activity (IC50 = 27.49 μM) and inhibits Crz1 activation and nuclear accumulation. 1β,13-Dihydrolactucopicrin possesses blood-brain barrier penetration capacity in an in vitro HBMEC blood-brain barrier model and can generate cysteine-conjugated metabolites within brain microvascular endothelial cells. 11β,13-Dihydrolactucopicrin can regulate the lncRNA H19/miR-21-3p signaling axis; it upregulates the expression of ABCG2 and lncRNA H19, downregulates miR-21-3p, inhibits the release of IL-6, TNF-α, and hs-CRP pro-inflammatory mediators, and alleviates urate-induced inflammatory injury in renal epithelial cells. 11β,13-Dihydrolactucopicrin can be used in research on diabetes and renal urate deposition. | |||||||||||||||||||||
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References
- [1]. Matos MS, et al. Assessing the Intestinal Permeability and Anti-Inflammatory Potential of Sesquiterpene Lactones from Chicory. Nutrients. 2020 Nov 19;12(11):3547.
- [2]. Fan H, et al. Isolation and identification of terpenoids from chicory roots and their inhibitory activities against yeast α-glucosidase. European Food Research and Technology, 2017, 243: 1009-1017.
- [3]. An X Y, et al. Investigation of Pharmacological Mechanisms and Active Ingredients of Cichorium intybus L. in Alleviating Renal Urate Deposition via lncRNA H19/miR-21-3p Regulation to Enhance ABCG2 Expression. International Journal of Molecular Sciences, 2025, 26(16):7892.
- [4]. Ávila-Gálvez MÁ, et al. Costunolide and parthenolide: Novel blood-brain barrier permeable sesquiterpene lactones to improve barrier tightness. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Nov;167:115413.
