Table 5.

Characteristic Downfield NMR Data of Major Detectable Metabolites in Glycyrrhiza Extracts (DMSO-d₆ with 5% v/v D₂O and 2.05 mM of Calibrant, at 600 MHz)

compound	no.	position	δH, mult. (J in Hz)a
liquiritin	1F	H-3′/5′	7.052, XX′ type (8.58/2.46/0.31)
liquiritin apioside	3F	H-3′/5′	7.028, XX′ type (8.58/2.46/0.31)
liquiritin and liquiritin apioside	1/3F	H-5	7.637, d (8.67/0.16)
		H-2′/6′	7.446, AA′ type (8.58/2.46/0.31)
		H-6	6.511, dd (8.67/2.21)
		H-8	6.354, d (2.21)
		H-2	5.507, dd (12.84/2.91)
liquiritin-isoliquiritin	1F, 1C	1″-O-Glc	4.936, d (7.46)
liquiritin apioside and isoliquiritin apioside	3F/3C	1″-O-Glc	4.957, d (7.75)
		1″-O-Api	5.328, d (1.20)
isoliquiritin and isoliquiritin apioside	1/2C	H-6′	8.166, dd (8.93/0.53)
		H-2/6	7.838, AA′ type (8.70/2.04/0.18)
		H-β	7.830, d (15.44)
		H-α	7.740, d (15.44)
		H-3/5	7.063, XX′ type (8.70/2.04/0.18)
		H-3′	6.296, d (2.33)
licuraside	2C	H-6′	8.240, d (9.02)
		H-3/5	6.848, XX′ type (8.51/2.72/0.15)
		H-5′	6.598, dd (9.02/2.41)
		H-3′	6.547, d (2.41)
liquiritigenin-7-O-apiosylglucoside	2F	H-2′/6′	7.340 AA′ type (8.14/ 1.81/0.33)
		H-3′/5′	6.795 XX′ type (8.14/1.81/0.33)
liquiritigenin	4F	H-2′/6′	7.332 AA′ type (8.41/2.63/0.33)
		H-3′/5′	6.822, XX′ type (8.41/2.63/0.33)
		H-6	6.486, dd (8.68/2.18)
		H-8	6.315, d (2.18)
glycyrrhizin	5	H-12	5.381, s
glabridin	6	H-6′	6.848, d (8.21)
		H-5	6.827, d (8.32)
		H-4″	6.574, d (9.89)
		H-3″	5.635, d (9.89)
		H-3′	6.313, d (2.42)
		H-6	6.268, d (8.21)
		H-5′	6.183, dd (8.32/2.42)
licochalcone A	7	H-2′/6′	7.949, AA′ type (8.59/2.43/0.27)
		H-β	7.870, d (15.54)
		H-α	7.557, d (15.54)
		H-3	6.526, s
		H-3′/5′	6.887, XX′ type (8.59/2.43/0.27)
		H-6	7.526, s
		H-2″	6.221, dd (17.49/ 10.62)
HBMA	8	H-2′/6′	6.911, AA′ type (8.33/2.65/0.32)
		H-3′/5′	6.574, XX′ type (8.33/2.65/0.32)

^aExact values obtained through ¹H iterative full-spin analysis (HiFSA) using Perch NMR software (v.2011.1, PERCH Solutions Ltd., Kuopio, Finland).