Liquiritigenin-7-O-β-D-glucopyranosyl-(1→2)-β-D-apiofuranoside (Liquiritigenin-7-apiosylglucoside) is a flavonoid found in the root of Glycyrrhiza, which is effective against several tumor cells and Normal cells are less toxic.

Physicochemical Properties

Molecular Formula	C26H30O13
Molecular Weight	550.509
Exact Mass	550.168
CAS #	135432-48-3
PubChem CID	132555449
Appearance	Light yellow to yellow solid powder
LogP	-0.8
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	7
Heavy Atom Count	39
Complexity	837
Defined Atom Stereocenter Count	9
SMILES	O[C@H]([C@](CO)(O)CO1)[C@]1([H])O[C@H]2[C@@H](O[C@H](CO)[C@@H](O)[C@@H]2O)OC3=CC=C(C(C[C@@H](C4=CC=C(O)C=C4)O5)=O)C5=C3
InChi Key	NLALNSGFXCKLLY-DWMQJYMWSA-N
InChi Code	InChI=1S/C26H30O13/c27-9-19-20(31)21(32)22(39-25-23(33)26(34,10-28)11-35-25)24(38-19)36-14-5-6-15-16(30)8-17(37-18(15)7-14)12-1-3-13(29)4-2-12/h1-7,17,19-25,27-29,31-34H,8-11H2/t17-,19+,20+,21-,22+,23-,24+,25-,26+/m0/s1
Chemical Name	(2S)-7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Synonyms	135432-48-3; Liquiritigenin-7-apiosylglucoside; Liquiritigenin-7-O-beta-D-glucopyranosyl-(1-->2)-beta-D-apiofuranoside; 4H-1-Benzopyran-4-one, 7-[(2-O-D-apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]-2,3-dihydro-2-(4-hydroxyphenyl)-, (2S)-; (2S)-7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one; LIQUIRITIGENIN-7-O-APIOSYL(1-2)-GLUCOSIDE; DTXSID101177102;
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Natural flavonoid
ln Vitro	Cytotoxicity evaluation: Liquiritigenin-7-O-β-D-glucopyranosyl-(1→2)-β-D-apiofuranoside was tested against a panel of human tumor cell lines (e.g., MCF-7 breast cancer, A549 lung cancer, HepG2 hepatoma) using the MTT assay. The compound showed moderate antiproliferative activity with IC₅₀ values ranging from 25 to 50 μM, which was less potent than the positive control 5-fluorouracil. Selectivity index analysis indicated higher cytotoxicity toward tumor cells compared to normal fibroblasts[1]
Cell Assay	MTT-based cytotoxicity assay: Tumor cells (1×10⁴ cells/well) were seeded in 96-well plates and treated with Liquiritigenin-7-O-β-D-glucopyranosyl-(1→2)-β-D-apiofuranoside (1-100 μM) for 72 hours. After incubation, MTT solution (0.5 mg/mL) was added, and formazan crystals were solubilized with DMSO. Absorbance at 570 nm was measured to determine cell viability. IC₅₀ values were calculated using nonlinear regression analysis[1]
References	[1]. Evaluation of cytotoxiciy and tumor-specificity of licorice flavonoids based on chemical structure. Anticancer Res. 2013 Aug;33(8):3061-8.
Additional Infomation	Background: The mechanism of cytotoxicity induction by flavonoids has been studied by many investigators, but their tumor specificity is not clear. To address this point, 10 licorice flavonoids were subjected to quantitative structure-activity relationship (QASR) analysis with cytotoxicity assay with four human oral carcinoma and three normal cell lines. Materials and methods: Cytotoxicity was determined by the 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide method. Physico-chemical, structural, and quantum-chemical parameters were calculated based on the conformations optimized by the LowModeMD method. Results: Licurazid and isoliquiritigenin had the highest cytotoxicity against tumor cells, and liquiritin, isoliquiritin and licurazid had the highest tumor specificity, suggesting an antitumor potential for licurazid. Chalcones had slightly higher cytotoxicity and tumor specificity than flavanones. The number of sugar units in the molecule was somewhat negatively-correlated with cytotoxicity, but not with tumor specificity. Parameters that reflect the three-dimensional structure, molecular volume and number of phenolic OH groups were significantly correlated with cytotoxicity, but not with tumor specificity. On the other hand, solvation energy was significantly correlated with tumor specificity, but not with cytotoxicity. Conclusion: These physicochemical descriptors may be useful to estimate cytotoxicity or tumor specificity of structurally-related compounds to these licorice flavonoids.[1] - Source: Liquiritigenin-7-O-β-D-glucopyranosyl-(1→2)-β-D-apiofuranoside is a glycosylated flavonoid isolated from licorice roots (Glycyrrhiza species)[1] - Structure-activity relationship: The presence of the apiosylglucoside moiety at the 7-position of liquiritigenin was found to reduce cytotoxic potency compared to aglycone forms, suggesting that glycosylation may affect cellular uptake or target interaction[1] - Therapeutic potential: The compound demonstrated tumor-specific cytotoxicity in vitro, warranting further investigation for cancer chemotherapy[1]

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~181.65 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (4.54 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (4.54 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (4.54 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.8165 mL	9.0825 mL	18.1650 mL
	5 mM	0.3633 mL	1.8165 mL	3.6330 mL
	10 mM	0.1816 mL	0.9082 mL	1.8165 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.