Table 2.

Metabolites identified in C. annua crude extract using LC-ESI/TOF/MS/MS.

Compound No	Rt (Min.)	Proposed Compound	Molecular Formula	Precursor Type	Calcd. m/z for Precursor	Obs. m/z for Precursor	MS/MS	Ref.
1	1.05	Citric acid	C6H8O7	[M−H]−	191.0192	191.0193	173, 111	[42]
2	1.18	Malic acid	C4H6O5	[M−H]−	133.0137	133.0141	155, 71	[42,43]
3	1.24	Methanesulfonic acid	CH4O3S	[M−H]−	94.9803	94.9807	80	[44]
4	1.39	Trigonilline	C7H7NO2	[M+H]+	138.0550	138.0551	94, 92	[45]
5	1.44	D-(-)-Quinic acid	C7H12O6	[M−H]−	191.0556	191.0556	173, 147, 85	[46,47]
6	2.02	Caffeoyl-quinic acid	C16H18O9	[M−H]−	353.0872	353.0868	191, 179, 135	[42]
7	2.23	Glucotropaeolin	C14H19NO9S2	[M−H]−	408.0423	408.0268	408, 162, 195, 246, 228	[48]
8	2.98	1H-indole-3 carboxylic acid	C9H7NO2	[M−H]−	160.0399	160.0399	116, 142, 143	[40,49]
9	3.22	Progoitrin	C11H19NO10S2	[M−H]−	388.0372	388.0370	388, 274, 259, 210, 192	[50,51]
10	4.18	3-formylindole	C9H7NO	[M+H]+	146.0606	146.0608	118	[40,49]
11	4.60 *	Quercetin-3-O-arabinoglucoside	C26H28O16	[M−H]−	595.1299	595.1303	462, 433, 301, 300, 299	[21,52]
12	4.68 *	Quercetin 3-O-β-D-glucopyranosyl-(1→2)-arabinopyranoside	C26H28O16	[M−H]−	595.1299	595.1306	301, 311, 433	[19,52]
13	4.75	2-(1H-indol-3-yl) acetic acid	C10H9NO2	[M+H]+	176.0712	176.0736	176, 159, 158 130, 118	[40,49]
14	5.10	Sinigrin	C10H17NO9S2	[M−H]−	358.0266	358.0569	358, 278, 275, 259, 241	[50]
15	5.29	Kaempferol 3, 7 di-glucoside	C27H30O16	[M−H]−	609.1456	609.1460	489, 447, 285	[42]
16	5.69	Quercetin3-O- [(6 sinapoyl-β-glucopyranosyl) (1→2)-β-arabinopyranoside]-7-O-β-glucopyranoside	C43H48O25	[M−H]−	963.2406	963.2443	801, 595, 463, 385	[17,20,42]
17	5.70	Quercetin3-O-[(6-feruloyl-β-glucopyranosyl) -(1→2)-β-arabinopyranoside]-7-O-β-glucopyranoside	C42H46O24	[M−H]−	933.2301	933.2311	771, 739, 301	[17,18,42]
18	5.93	1-methoxy-1H-indole-3-carbaldehyde	C10H9NO2	[M+H] +	176.0712	176.0749	161, 133, 117	[40,49]
19	6.09	4-Hydroxyglucobrassicin	C16H20N2O10S2	[M−H]−	463.0481	463.1205	463, 291, 275, 259, 241, 195	[48,53]
20	6.46	9(methylsulfonyl)hydroxy nonyl glucosinolate	C17H33NO12S3	[M−H]−	538.1087	538.8553	259, 275, 291	[37]
21	6.46	Kaempferol-3 rutinoside	C27H30O15	[M−H]−	593.1506	593.1503	285, 447	[19,42]
22	6.66	Syringaldehyde	C9H10O4	[M−H]−	181.0501	181.0511	181, 151	[54]
23	6.84	Quercetin-4’-glucoside	C21H20O12	[M+H]+	465.1033	465.1028	465, 303	[55]
24	6.91	Luteolin-7-O-glucoside	C21H20O11	[M−H]−	447.0927	447.09366	447, 285	[56]
25	6.94	Kaempferol-3,7-O-bis-α-L-rhamnoside	C27H30O14	[M−H]−	577.1557	577.1576	431, 285	[57]
26	6.95	Quercetin 3-O-galactoside	C21H20O12	[M+H]+	465.1033	465.1049	465, 303	[58]
27	6.97	Quercetin-3-D-xyloside	C20H18O11	[M−H]−	433.0771	433.0772	301, 300, 271, 151	[52]
28	6.99 *	Cyanidin-3-glucoside	C21H21O11	[M]+	449.1084	449.1075	449, 287	[59,60,61]
29	7.00 *	Kaempferol-3-O glucoside	C21H20O1	[M+H]+	449.1084	449.1085	449, 287	[58,62]
30	7.09	Quercetin 3-O-[(6-sinapoyl-β-glucopyranosyl)-(1→2)-β arabinopyranoside	C37H38O20	[M−H]−	801.1878	801.1855	801, 595, 300	[17]
31	7.23	Petunidin-3-O-β-glucopyranoside	C22H23O12	[M]+	479.1190	479.116	317, 302	[63]
32	7.75	Vitexin	C21H20O10	[M−H]−	431.0978	431.0989	431, 311, 283,	[64]
33	7.77	Cosmosiin	C21H20O10	[M+H]+	433.1135	433.1154	433, 271	[65]
34	7.79	Syringetin-3-O-glucoside	C23H24O13	[M−H]−	507.1139	507.1134	507, 345, 179	[66]
35	7.97	Peonidine-3-O-glucoside	C22H23O11	[M]+	463.1240	463.1223	463, 301, 286	[59,60]
36	8.14	Malvidin-3-galactoside	C23H25O12	[M]+	493.1346	493.1358	493, 331	[59,60]
37	8.31	Caffeic acid	C9H8O4	[M−H]−	179.0344	179.0343	179, 151, 136, 133	[67]
38	8.69	Hesperetin	C16H14O6	[M−H]−	301.0712	301.0711	301, 283, 271, 258	[68]
39	8.72	Quercetin	C15H10O7	[M+H]+	303.0505	303.0457	303, 153	[69]
40	9.13	Isorhamnetin	C16H12O7	[M−H]−	315.0505	315.0513	315, 300, 151	[20,70]
41	9.39	Luteolin	C15H10O6	[M−H]−	285.0399	285.0402	285, 267, 257, 241, 223, 197,175	[64,71]
42	9.40	Kaempferol	C15H10O6	[M−H]−	285.0399	285.0392	285, 257, 241, 223, 197, 151	[64,71]
43	9.60	P -coumaric acid	C9H8O3	[M−H]−	163.0395	163.0389	163, 119	[72]
44	9.88	Sinapic acid	C11H12O5	[M−H]−	223.0606	223.0964	223, 208, 179, 164	[42]
45	10.23	Ferulic acid	C10H10O4	[M−H]−	193.0501	193.0503	193, 178, 149	[42]
46	10.68	Apigenin	C15H10O5	[M−H]−	269.0450	269.0458	269, 241, 225, 181, 169	[64]
47	11.23	Kaempferide	C16H12O6	[M+H]+	301.0712	301.0712	301, 286	[73]
48	24.77	δ- tocotrienol	C27H40O2	[M+H]+	397.3107	397.3115	397, 201, 187	[74]
49	26.89	β- tocotrienol	C28H42O2	[M+H]+	411.3263	411.3271	411, 205, 191, 151	[74]

* Interchangeable values.