Metabolic bioprofiling of different Glycyrrhiza glabra solvent fractions for the identification of anti-adenoviral compounds using LC-HRMS/MS and in-vitro cytopathic assay coupled with chemometry

Mahrous, Rahma SR.; Fathy, Hoda; Ibrahim, Reham S.

doi:10.1186/s12906-023-04063-z

BMC Complementary Medicine and Therapies

Table 2 LC-HRMS/MS data of compounds identified in EtOAc fractions of G. glabra roots

From: Metabolic bioprofiling of different Glycyrrhiza glabra solvent fractions for the identification of anti-adenoviral compounds using LC-HRMS/MS and in-vitro cytopathic assay coupled with chemometry

NO	R_t (min)	Identification	Class	[M + H]⁺	Mass error (ppm)	Molecular formula	MSⁿ ions	EtOAc Fraction No^b						Ref
NO	R_t (min)	Identification	Class	[M + H]⁺	Mass error (ppm)	Molecular formula	MSⁿ ions	1	2	3	4	5	6	Ref
1	10.269	Licoagroside B	Saccharolipids	433.1136	0.202	C18H24O12	163, 157, 127, 99	+	+	+	+	+	-	[21]
2	10.469	Kaempferol-3-O-rutinoside	Flavone O-glycosides	595.1663	-0.02	C27H30O15	286	+	+	+	+	+	+	[21]
3	10.563	Liquiritin apioside	Flavanone O-glycoside	551.1765	-0.01	C26H30O13	419, 257	+	-	+	-	+	+	[21, 25]
4	10.679	Liquiritin	Flavanone O-glycoside	441.1161^a	-0.01	C21H22O9	280, 262	-	-	-	+	-	-	[9, 25]
5	10.918	Violanthin	Flavone C-glycoside	579.1707	-1.15	C27H30O14	561, 505, 489, 475, 459, 385, 355	+	+	+	+	+	+	[25]
6	11.304	Liquiritigenin 4'-[3-acetylapiosyl-(1–2)] glucoside	Flavanone O-glycoside	593.187	-0.15	C28H32O14	550, 533, 473, 461, 299, 257	+	+	+	+	+	+	[20]
7	11.377	Rhamnoliquiritin	Flavanone O-glycoside	565.1909	-2.12	C27H32O13	505, 445, 433, 419, 257	+	+	+	+	+	+	[20]
8	11.393	Esculin	Coumarin glycoside	341.1747	-1.79	C15H16O9	179, 163, 135, 124, 111	+	+	+	+	+	+	[21]
9	11.404	Licorice glycoside C2/A	Flavanone O-glycoside	727.2228	-1.35	C36H38O16	550, 532, 257, 137	-	-	-	+	-	-	[22, 25]
10	11.521	Licorice glycoside B/D1/D2	Flavanone O-glycoside	697.2121	-1.63	C35H36O15	651, 550, 532, 418, 257, 137	+	+	+	+	+	+	(22, 25)
11	11.667	3,3',4,4'-Tetrahydroxy-2 methoxychalcone	Chalcone	303.0862	-2.07	C16H14O6	288, 275, 152, 110	+	+	+	+	+	+	[22]
12	12.129	2',3',4',7-Tetrahydroxyisoflavan; (R)-form, 3',4'-dimethylether	Isoflavan	325.106^a	2.671	C17H18O5	310, 295	+	+	+	+	+	+	[42]
13	12.314	Prunetin	Isoflavone	285.0757	-2.05	C16H12O5	269, 241, 137, 121	-	+	+	+	+	+	[43]
14	12.54	Kumatakenin	Flavone	315.086	-2.54	C17H14O6	300, 285, 287, 271, 149, 167	+	+	-	-	+	+	[32, 43]
15	12.57	Licochalcone B	Chalcone	287.0917	-0.92	C16H14O5	245, 193, 167, 147, 121	+	+	-	+	+	-	[30]
16	12.589	Licoagrochalcone D	Chalcone	355.1543	-0.78	C21H22O5	340, 337, 327, 234, 122	+	-	-	-	+	-	[22]
17	12.615	Liquirtigenin/ Isoliquiritigenin isomer	Chalcone	257.081	-1.64	C15H12O6	137, 121, 93	+	-	-	-	-	-	[21, 22]
18	12.664	Pinocembrin	Falvanone	257.0809	-1.78	C15H12O5	153, 131	-	+	+	+	+	+	[21, 25]
19	12.968	Echinatin	Chalcone	271.0967	-1.44	C16H14O4	256, 239, 151, 122	+	+	-	-	-	-	[21]
20	13.39	Echinatin isomer	Chalcone	271.0602	-1.65	C16H14O4	256, 227, 153, 135	+	+	+	+	+	-	[21]
21	13.449	Isoliquiritigenin isomer	Flavanone	257.081	-1.52	C15H12O7	137, 121, 93	+	-	-	+	+	-	[21, 22]
22	13.634	Formononetin	Isoflavone	269.0809	-2.01	C16H12O4	254, 237, 213, 107	+	-	-	+	+	+	[30]
23	13.718	Kanzonol U	2-arylbenzofuran flavonoid	309.1122	-1.52	C19H16O4	294, 172, 105	-	+	+	-	-	-	[8]
24	13.873	Hispaglabridin A	Pyranoisoflavan	393.2062	-0.92	C25H28O4	337, 191, 189	+	-	-	-	-	-	[21, 30]
25	14.069	Licoagrocarpin	Pterocarpan	339.1592	-1.19	C21H22O4	283, 255	+	-	-	-	-	-	[44]
26	14.237	3’-hydroxy-4’-O- methyl- glabridin	Pyranoisoflavan	355.1542	-1.13	C21H22O5	215, 189, 153, 147	+	-	-	-	-	-	[30]
27	14.406	Kanzonol X	Prenyl Isoflavan	395.2211	-2.92	C25H30O4	375, 349, 324, 215, 203	+	-	-	-	-	-	[21]
28	14.569	Erythrinin B	Prenyl Isoflavone	339.1229	-1.16	C20H18O5	321, 311, 295, 221, 119	+	+	-	+	+	-	[21]
29	14.69	Isoangustone A	Prenyl isoflavanones	423.1807	-0.11	C25H26O6	379, 367, 311, 176	+	+	+	+	+	-	[23]
30	14.983	Hispaglabridin B	Pyranoisoflavan	391.1907	-0.53	C25H26O4	335, 203, 189, 147	+	+	+	+	+	+	[21, 30]
31	15.279	Glycycoumarin	Coumarin	369.1336	0.628	C21H20O6	313, 285, 191,149	+	+	+	+	+	-	[21]
32	15.79	Glabrone	Pyranoisoflavone	337.107	-1.89	C20H16O5	319, 309, 295, 283, 137	-	-	-	+	-	+	[21, 25]
33	15.806	Glabridin	Pyranoisoflavan	325.1431	-2.87	C20H20O4	269, 203, 189, 123	+	-	-	-	-	-	[21, 25]
34	15.961	Glabrene	Pyranoisoflavene	323.1274	-2.77	C20H18O4	267, 213, 189, 123	+	-	-	-	-	-	[21, 25]
35	16.017	Kanzonol Y	Chalcone	411.2166	-1.4	C25H30O5	355, 235, 217, 189, 177, 161, 148	+	+	+	+	+	-	[9, 21]
36	16.051	Glabrol	Prenyl flavanone	393.2001	3.417	C25H28O4	351, 337, 205, 203	+	+	+	+	+	-	[29, 30]
37	16.225	Kanzonol Y isomer	Chalcone	411.2167	-1.18	C25H30O5	235, 217, 205, 177, 161, 135, 122	+	+	+	-	+	-	[21]
38	16.602	Licoisoflavone B	Pyranoisoflavone	353.1022	-1.05	C20H16O6	338, 335, 325, 311, 309, 201, 153	+	+	+	+	+	-	[22]
39	17.956	Licoisoflavone A	Prenyl isoflavone	355.1181	-0.27	C20H18O6	340, 337, 327, 311, 299, 203, 153	+	+	+	+	-	-	[22]
40	26.109	Kanzonol W; 4'-methylether	Pyranoisoflavone	351.123	-0.86	C21H18O5	336, 333, 323, 307	-	-	+	-	+	+	[45]
41	26.723	Glisoflavanone	Prenyl isoflavanones	425.196	-0.92	C25H28O6	369, 247, 231, 195, 111	-	-	-	-	+	-	[24]

^am/z values of [M + Na] + ions
^b( +) meaning the presence of the metabolite in the investigated fraction, (-) meaning the absence of the metabolite in the investigated fraction

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ISSN: 2662-7671

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