. 2018 Jun 5;9:566. doi: 10.3389/fphar.2018.00566

Table 1.

Secondary metabolites from a methanol extract of S. aqueum leaves by HR-LC-MS/MS.

No.	t_R(min)	[M-H]^-	MS/MS fragment	Tentatively identified compounds
1	1.63	191	127	Quinic acid^a
2	2.23	341	179	Caffeoyl hexoside
3	2.87	343	191	Galloylquinic acid^a
4	3.02	331	169	Galloyl hexose^a
5	3.26	609	305, 423, 441, 591	(epi)-Gallocatechin-(epi)-gallocatechin
6	3.88	483	169, 331	Digalloyl hexose
7	4.43	933	301, 301, 631, 915	Castalagin/Vescalagin^∗,a
8	6.13	477	169, 313, 331	Gallic acid coumaroyl-hexose
9	6.28	633	301, 463, 615	Galloyl-hexahydroxydiphenoyl (HHDP)-hexoside
10	6.36	609	305, 423, 441	(epi)-Gallocatechin-(epi)-gallocatechin^a
11	6.51	343	125, 169	Galloylquinic acid
12	6.76	1583	765, 935, 1537, 1565	Eugeniflorin D2^a
13	7.85	305	125, 179	(epi)-Gallocatechin^∗,a
14	9.14	179	161	Caffeic acid
15	9.27	315	153	p-Coumaric acid hexoside
16	10.29	441	179, 271, 423	(epi)-Catechin gallate
17	12.23	301	229, 257, 301	Ellagic acid^b
18	12.87	593	289, 425, 557	(epi)-Catechin-(epi)-gallocatechin
19	16.12	761	305, 423, 593, 609	(epi)-Gallocatechin-(epi)-gallocatechin gallate^a
20	17.11	897	305, 559, 609, 771	(epi)-Gallocatechin-(epi)-gallocatechin-(epi)-catechin
21	17.81	783	301, 615, 765	Pedunculagin^∗
22	18.21	273	187, 229	(epi)-Afzelechin
23	19.90	633	301, 481, 615	Galloyl-hexahydroxydiphenoyl (HHDP)-hexoside
24	21.20	745	289, 577, 593, 727	(epi)-Catechin-(epi)-gallocatechin gallate^a
25	22.61	285	153	p-Coumaric acid pentoside
26	22.72	483	169, 331	Digalloyl hexose
27	23.41	759	229, 301, 633	Samarangenin A^∗
28	24.79	577	289, 407, 425, 559	(epi)-Catechin-(epi)-catechin^a
29	25.74	745	305, 423, 457, 593	(epi)-Gallocatechin-(epi)-catechin gallate^a
30	25.94	575	287, 423	(epi)-Catechin-A-(epi)-catechin
31	28.25	761	305, 423, 609	(epi)-Gallocatechin-(epi)-gallocatechin gallate
32	28.91	785	301, 483, 633, 765	Digalloyl- HHDP-hexoside
33	29.89	457	305, 331	(epi)-Gallocatechin gallate^∗,a,¥
34	33.48	745	289, 441, 593, 619	(epi)-Gallocatechin-(epi)-catechin gallate^a
35	33.7	1217	423, 761, 1047, 1065	(epi)-Gallocatechin-(epi)-gallocatechin-(epi)-gallocatechin-(epi)-gallocatechin^a
36	34.92	1049	423, 745, 761	(epi)-Catechin-(epi)-gallocatechin -(epi)-gallocatechin gallate^a
37	35.94	785	301, 483, 615, 633, 765	Digalloyl-HHDP-hexoside
38	37.00	1201	423, 475, 1049	(epi)-Catechin-(epi)-gallocatechin-(epi)-gallocatechin-(epi)-gallocatechin
39	37.27	367	191	Feruloylquinic acid
40	37.5	337	191	p-Coumaroylquinic acid^a
41	38.82	881	423, 591, 729	(epi)-catechin gallate-(epi)-catechin gallate
42	40.71	1217	423, 761, 913, 1030	(epi)-Gallocatechin-(epi)-gallocatechin-(epi)-gallocatechin-(epi)-gallocatechin^a
43	41.09	441	169, 289	(epi)-Catechin gallate^∗,a
44	42.18	1017	407, 575, 729	(epi)-Catechin-(epi)-catechin-(epi)-catechin gallate^a
45	42.23	913	423, 591, 761	Prodelphinidin B2 3,3′-digallate^∗
46	43.13	451	169, 289	(epi)catechin glycoside
47	45.41	911	285, 423, 571, 759	Samarangenin B^∗
48	49.03	625	317, 463	Myricetin rhamnosyl-hexoside^a
49	49.53	479	317	Myricetin hexoside^a
50	50.27	449	179, 317	Myricetin pentoside^a
51	51.72	595	179, 271, 301, 463	Quercetin pentosyl-hexoside
52	52.08	623	285, 447	Myrigalone-G glucuronide-hexoside
53	53.15	463	179, 317	Myricetin3-O- rhamnoside^∗,a,¥
54	54.43	375	361	Methyligstroside aglycone
55	54.83	631	317, 479	Myricetin galloly-hexoside
56	56.85	729	289, 407, 559	Procyanidin dimer monogallate^a
57	57.15	593	285, 447	Myrigalone-G rhamnosyl-hexoside
58	57.22	601	317, 449	Myricetin galloyl-pentoside
59	57.9	881	289, 407, 559, 729	(epi)-Catechin gallate-(epi)-catechin gallate^a
60	58.08	493	331	Europetin hexoside
61	58.18	609	301	Quercetin rutinoside^a
62	58.33	645	331, 493	Europetin galloly-hexoside
63	58.51	737	300, 433	Quercetin pentosyl digallate
64	58.58	749	301, 447, 595, 597	Quercetin rhamnosyl-digallate
65	62.17	433	301	Quercetin pentoside
66	63.36	477	331	Europetin rhamnoside^∗
67	63.84	447	301	Quercetin rhamnoside
68	64.04	615	317, 463	Myricetin galloyl-rhamnoside^a,c
69	64.13	615	301, 463	Quercetin galloyl-hexoside^a
70	64.8	447	315	Isorhamnetin pentoside
71	64.98	417	285	Myrigalone-G pentoside
72	65.28	461	315	Isorhamnetin rhamnoside
73	65.3	585	301, 433	Quercetin galloyl-pentoside^a
74	66.34	601	179, 317, 449	Myricetin galloyl-pentoside
75	66.43	935	301, 463, 633, 783	Quercetin hexoside trigallate
76	67.01	599	301, 447	Quercetin galloyl-rhamnoside
77	67.36	615	317, 463	Myricetin galloyl-rhamnoside^a
78	68.06	417	285	Myrigalone-G pentoside
79	68.15	523	361	Ligstroside
80	68.26	431	285	Myrigalone-G rhamnoside
81	68.27	329	285	Acetylemyrigalone-G^∗
82	69.09	461	329	Tricin pentoside
83	69.35	585	179, 301, 433	Quercetin galloly-pentoside
84	71.56	629	179, 301, 463, 477	Quercetin methyl galloyl-hexoside
85	72.11	299	151, 243, 271	Myrigalone-B^∗
86	73.36	285	163, 241, 271	Myrigalone-G^∗
87	74.20	269	121, 255, 271	Cryptostrobin^a

^∗Previously isolated from the plant (Nonaka et al., 1992) and (Manaharan et al., 2012). ^¥Identification was confirmed using authentic standard compounds. ^aIdentification was based on Sobeh et al. (2018b). ^bIdentification was based on Sobeh et al. (2018a).