Systematic Identification, Fragmentation Pattern, And Metabolic Pathways of Hyperoside in Rat Plasma, Urine, And Feces by UPLC-Q-Exactive Orbitrap MS

Table 1

Characterization of hyperoside and its metabolites in rats using UPLC-Q-exactive orbitrap MS.

No.	Formula	Calculated (m/z)	Observed (m/z)	Error (ppm)	tR (min)	Major fragments (m/z)	Metabolic reactions	P	U	F
M0	C21H20O12	463.0871	463.0887	3.46	5.28	301.0353, 300.0276, 271.0247, 255.0297, 243.0299, 227.0351, 151.0039, 149.0249	Parent	+	+	+
M1	C27H28O18	639.1192	639.1223	4.85	4.95	463.0877, 301.0352, 271.0244, 255.0300, 243.0297, 227.0352, 151.0038, 149.0244	Glucuronide conjugation	−	+	−
M2-1	C22H22O12	477.1028	477.1047	3.98	5.52	315.0881, 301.0713, 255.0659, 227.0342, 151.0038,149.0249	Methylation	+	+	+
M2-2	C22H22O12	477.1028	477.1042	2.93	5.84	315.0878, 301.0355, 255.0301, 243.0292, 227.0353, 151.0038, 149.0246	Methylation	+	+	−
M3	C28H30O18	653.1348	653.1375	4.13	4.07	477.1042, 315.0511, 301.0356, 271.0247, 255.0299, 243.0301, 227.0350, 151.0037	Methylation, glucuronide	−	+	−
M4	C21H20O11	447.0922	447.0939	3.80	6.41	285.0403, 255.0298, 227.0350, 151.0037, 149.0611	Dehydroxylation	+	+	+
M5	C21H20O13	479.082	479.0834	2.92	4.53	317.0283, 301.0251, 271.0244, 243.0283, 227.0348, 151.0039	Hydroxylation	−	−	+
M6	C27H28O19	655.1141	655.1157	2.44	4.03	479.1103, 317.0567, 301.0316, 271.0246, 255.0295, 243.0300, 227.0348, 151.0039	Hydroxylation, glucuronide	−	+	−
M7	C23H22O13	505.0977	505.099	2.57	6.19	301.0277, 271.0247, 255.0298, 243.0298, 227.0357, 151.0042	Acetylation	−	−	+
M8	C29H32O18	667.1504	667.1555	7.64	3.53	301.0276, 271.0247, 255.0298, 243.0299, 227.0351, 151.0038,149.9955	Acetylation, glucoside	−	+	−
M9	C15H10O7	301.0343	301.0355	3.99	7.75	273.0406, 257.0450, 151.0038, 149.0245, 121.0295, 107.0139, 65.0032	Glycoside hydrolysis	+	+	+
M10	C15H12O8	319.0448	319.0458	3.13	7.02	301.0328, 273.0894, 151.9274, 149.0975, 121.0296, 107.0503, 65.0396	Glycoside hydrolysis, hydration	+	+	+
M11	C15H10O10S	380.9911	380.9928	4.46	6.21	301.0354, 273.0407, 151.0038, 149.0248, 121.0296, 107.0139, 65.0033	Glycoside hydrolysis, sulfation	−	+	+
M12-1	C21H18O13	477.0664	477.0678	2.93	5.26	301.0354, 273.0392, 257.0462, 151.0038, 149.0244, 121.0296, 107.0139, 65.0032	Glycoside hydrolysis, glucuronide	+	+	−
M12-2	C21H18O13	477.0664	477.0678	2.93	6.36	301.0355, 273.0401, 257.0460, 151.0038, 149.0243, 121.0296, 107.0139, 65.0033	Glycoside hydrolysis, glucuronide	+	+	−
M13-1	C27H26O19	653.0985	653.1015	4.59	4.63	477.0639, 301.0356, 273.0403, 151.0038, 149.0243, 121.0296, 107.0140, 65.0032	Glycoside hydrolysis, glucuronide × 2	−	+	−
M13-2	C27H26O19	653.0985	653.1014	4.44	5.15	477.0671, 301.0353, 273.0392, 257.0452, 151.0038, 149.0244, 121.0296, 107.0139, 65.0033	Glycoside hydrolysis, glucuronide × 2	−	+	−
M14	C21H18O16S	557.0232	557.0253	3.77	6.63	477.0679, 380.9921, 301.0352, 273.0405, 151.0037, 149.0243, 121.02965, 107.0139, 65.0032	Glycoside hydrolysis, sulfation, glucuronide	−	+	−
M15	C15H10O6	285.0394	285.0406	4.21	8.92	257.0453, 241.0500, 151.0038, 121.0295, 65.0033	Glycoside hydrolysis, dehydroxylation	+	+	+
M16	C15H10O8	317.0292	317.0313	6.62	7.56	289.1573, 257.0264, 151.1128, 149.1339, 121.0296, 65.3057	Glycoside hydrolysis, hydroxylation	−	+	+
M17	C15H10O11S	396.986	396.9881	5.29	7.15	317.0305, 289.1569, 151.0039, 149.1339, 121.0296, 65.4439	Glycoside hydrolysis, hydroxylation, sulfation	−	+	−
M18	C21H18O14	493.0613	493.0627	2.84	6.34	317.0573, 289.0638, 273.0349, 151.0039, 149.9958	Glycoside hydrolysis, hydroxylation, glucuronide	−	+	−
M19	C15H12O7	303.0499	303.0513	4.62	5.74	275.0442, 259.1820, 151.0402, 149.0245, 121.0295, 107.0139	Glycoside hydrolysis, hydrogenation	−	+	+
M20	C15H12O10S	383.0067	383.0079	3.13	5.06	303.0514, 285.0403, 275.1660, 151.0036, 123.0691, 109.0533,	Glycoside hydrolysis, hydrogenation, sulfation	+	+	−
M21	C21H20O13	479.082	479.0834	2.92	3.42	303.0873, 285.0763, 275.0457, 257.0373, 151.0098, 123.0455, 109.0295	Glycoside hydrolysis, hydrogenation, glucuronide	−	+	−
M22	C27H28O19	655.1141	655.1157	2.44	3.38	479.1103, 303.0405, 151.0039	Glycoside hydrolysis, hydrogenation, glucuronide × 2	−	+	−
M23	C21H20O16S	559.0388	559.04	2.15	3.54	479.0675, 303.0414, 151.0038, 109.0295	Glycoside hydrolysis, hydrogenation, sulfation, glucuronide	−	+	−
M24	C16H12O7	315.0499	315.0511	3.81	9	300.0275, 283.0241, 271.0246, 255.0296, 243.0299, 227.0354, 151.0038, 149.9958, 121.6068, 107.0139,	Glycoside hydrolysis, methylation	+	+	−
M25	C16H12O10S	395.0067	395.0084	4.30	8.02	315.0511, 300.0277, 283.0244, 271.0247, 255.0306, 243.0300, 227.0345, 151.0038, 149.9956, 121.6540, 107.0139	Glycoside hydrolysis, methylation, sulfation	+	+	+
M26	C22H20O13	491.082	491.0833	2.65	6.56	315.0511, 300.0276, 283.0251, 271.0247, 255.0300, 243.0297, 227.0353, 151.0038, 149.9959, 121.6044, 107.0139	Glycoside hydrolysis, methylation, glucuronide	+	+	−
M27	C22H20O16S	571.0388	571.0408	3.50	6.26	315.0511, 300.0278, 271.0247, 255.0299, 243.0292, 227.0346, 151.0037, 149.9953, 107.0139	Glycoside hydrolysis, methylation, sulfation, glucuronide	+	+	−
M28	C8H8O4	167.0339	167.0348	5.39	5.54	123.0452, 109.0217, 93.0346	Decomposition	+	+	+
M29	C7H6O4	153.0182	153.0191	5.88	4.5	109.0659, 93.0346	Decomposition	+	+	+

Notes. P represents plasma samples, U represents urine samples and F refers to feces samples.