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Physical PropertiesWhite powderMolecular weight: 256.26 amuBoiling point: 529.5 C at 1 atmMelting point: 206-208 CSlightly soluble in waterLiquiritigenin (4,7-dihydroxyflavanone)

Licorice Root (Glycyrrhiza uralensis)

Uses of Licoricestomach ulcers, heartburn, colic, and ongoing inflammation of the lining of the stomach (chronic gastritis), Alleviates pre-menopausal syndromeHas aspirin like symptomsCombats hepatitisGlycyrrhizin 50x sweeter than sugar

Other sources of liquiritigeninJacaranda obtusifolia (Bignoniaceae)Sinofranchetia chinensis (Lardizabalaceae)

Biochemical propertiesinhibitor of xanthine oxidase (treatment of gout and hyperuricemia) [Cheng et al, 2000]Estrogen receptor agonist alternatives to estrogen hormone therapy and attenuates Alzheimers like activities in vitro and in vivo [Zou et al, 2009]Neuroprotective effect in glutamate-induced apoptosis [Park et al, 2013]Inhibitor of fulminant hepatitis and hepatoma progress exhibits hepatoprotective activity and protection against liver cancer [Liu, 2014]

Isolation from Licorice RootLicorice root was ground, passed through 60-mesh sieve, soaked overnight in a 1:6 volume of 80% ethanolSolution was filtered then solvent was removed and dried into powder Powder dissolved in water, loaded in a D101 macroporous resin column then eluted with 30% 60% and 90% ethanol solutionElution with 30% ethanol yielded fraction containing liquiritigenin was repeatedly recrystallized with methanol

Spectroscopic data

Positive ion ESI Mass spectrum

Positive ion ESI Mass spectrum

Proposed fragmentation pathway

1H NMR

, 2.3

13C NMR

Significant HMBC correlations

BioChemicalSynthesis

ChemicalSynthesis

Claisen-schmidt Condensation (Acidic)

Claisen-schmidt Condensation (Acidic)

Claisen-schmidt Condensation (basic)

Claisen-schmidt Condensation (basic)

Claisen-schmidt Condensation (basic)

Catalytic cyclization

Reversed Phase HPLCMobile phase: acetonitrile, water, acetic acid (50:50:0.5 v:v:v)Isocratic separation at 25C with a flow rate 0.6 mL/minChiralPak AD-H