| Identification | Back Directory | [Name]
licoricidin | [CAS]
30508-27-1 | [Synonyms]
licoricidin
Licorisoflavan B
LICORICIDIN (LCD)
7-O-Demethyllicorisoflavan A
1,3-Benzenediol,4-[(3R)-3,4-dihydro-7-hydroxy-5-methoxy-6-(3-methyl-2-buten-1-yl)-2H-1-benzopyran-3-yl]-2-(3-methyl-2-buten-1-yl)- | [Molecular Formula]
C26H32O5 | [MDL Number]
MFCD32182601 | [MOL File]
30508-27-1.mol | [Molecular Weight]
424.53 |
| Chemical Properties | Back Directory | [Melting point ]
161.0-162.5℃ | [Boiling point ]
610.8±55.0 °C(Predicted) | [density ]
1.171±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [form ]
Solid | [pka]
10.10±0.40(Predicted) | [color ]
White to off-white | [biological source]
plant | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [InChI]
1S/C26H32O5/c1-15(2)6-8-19-22(27)11-10-18(25(19)29)17-12-21-24(31-14-17)13-23(28)20(26(21)30-5)9-7-16(3)4/h6-7,10-11,13,17,27-29H,8-9,12,14H2,1-5H3/t17-/m0/s1 | [InChIKey]
GBRZTUJCDFSIHM-KRWDZBQOSA-N | [SMILES]
O1C[C@H](Cc3c1cc(c(c3OC)CC=C(C)C)O)c2c(c(c(cc2)O)CC=C(C)C)O |
| Hazard Information | Back Directory | [Uses]
Licoricidin is a natural product derived from plant source th at finds application in compound screening libraries, metabolomics, phytochemical, and pharmaceutical research. | [Definition]
ChEBI: Licoricidin is a member of the class of hydroxyisoflavans that is R-isoflavan with hydroxy groups at positions 7, 2' and 4', a methoxy group at position 5 and prenyl groups at positions 6 and 3'. Isolated from Glycyrrhiza uralensis, it exhibits antibacterial activity. It has a role as an antibacterial agent and a plant metabolite. It is a member of hydroxyisoflavans, an aromatic ether and a methoxyisoflavan. | [Biological Activity]
Licoricidin (LCD), isolated from Glycyrrhiza uralensis Fisch, has anticancer activity. It (LCD) can be used in the study of colorectal cancer by inducing cycle arrest, apoptosis and autophagy. Licoricidin (LCD) inhibits lung metastasis by inhibiting tumor angiogenesis and lymphangiogenesis and changes in the local microenvironment of tumor tissue. Licoricidin (LCD) enhances gemcitabine-induced cytotoxicity of osteosarcoma (OS) cells through inactivation of Akt and NF-κB pathways in vitro and in vivo. | [in vitro]
Licoricidin (LCD) (0-20 μM; 24 hours) dose-dependently inhibits the viability of colon cancer cell lines with various pathological and genetic characters, namely SW480, HCT116, SW620 and LoVo cells, with IC < sub> 50 values of 7.2, 5.4, 4.5 and 5.1 μM, respectively. Licoricidin (LCD) (0-20 μM; 0-12 hours) induces cell apoptosis was accompanied with the activation of caspase-3 by cleavage in a time- and dose-dependent manner. Licoricidin (LCD) (0-20 μM; 0-12 hours) induces autophagy of SW480 cells, increases the cleavage of LC3-I to LC3-II and the degradation of p62 in a time and Dose dependent manner. Licoricidin (LCD) (0-5 μg/ml; 18 hours) inhibits cell migration, MMP-9 secretion, and VCAM expression in 4T1 cells. < /p> Cell Viability Assay | Cell Line: | SW480, HCT116, SW620 and LoVo cells | < tr> Concentration: | 0-20 μM | | Incubation Time: | 24 hours | | Result: | Decreased colon cancer cell lines viability. | Western Blot Analysis < /p> | Cell Line: | SW480 cells | | Concentration: | 0 μM, 2.5 μM, 5 μM, 10 μM, 20 μM | | Incubation Time: | 0 hours, 1 hour, 3 hours, 6 hours, 12 hours | | Result: | Induced cell apoptosis. | | [in vivo]
Licoricidin (LCD) (intraperitoneal injection; 5, 10, or 20 mg/kg; once daily; 15 days) significantly inhibited the growth of SW480 xenografts in nude mice with an inhibitory rate of 43.5%. Licoricidin ( LCD) (intraperitoneal injection; 5, 10, or 20 mg/kg; once daily; 32 days) reduces pulmonary metastasis and the expression of CD45, CD31, HIF-1α, iNOS, COX-2, and VEGF-A in tumor tissues , additionally, decreased protein expression of VEGF-R2, VEGF-C, VEGF-R3, and LYVE-1 in tumor tissues of licoricidin-treated mice. | Animal Model: | SW480 xenografted tumor growth in nude mice | | Dosage: | 5, 10, or 20 mg/kg | | Administration: | Intraperitoneal injection; once daily; 15 days | | Result: | Decreased tumor volumes. | | Animal Model: | BALB/c mouse orthotopic model | | Dosage: | 5, 10, or 20 mg/kg | | Administration: | Intraperitoneal injection; 5, 10, or 20 mg/kg; once daily; 32 days | | Result: | Inhibited Lung Metastasis of 4T1 Murine Mammary Carcinoma cells. | |
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