Journal of Chemistry

Research Article

UPLC-ESI-MS/MS Profile and Antioxidant, Cytotoxic, Antidiabetic, and Antiobesity Activities of the Aqueous Extracts of Three Different Hibiscus Species

Table 1

Metabolites identified in the aqueous extracts of Hibiscus deflersii (HdA), H. micranthus (HmA), and H. calyphyllus (HcA) using UPLC−ESI−MS in negative and positive ionization modes.


Comp. no.	Compound name	R_t (min)	[M − H]⁻ (m/z)	[M + H]⁺ (m/z)	MS² fragments (m/z)	HdA	HcA	HmA	References

1	L-ascorbic acid	0.30		177	133, 129, 127, 113, 103, 101, 57	√	√	√	1
2	Oleuropein	0.82	539		377, 341, 307, 215, 179	√		√	2
3	Succinic acid	0.86		119	101	√			—
4	Tyrosol	0.93		121	103, 97, 93, 89, 79, 77, 73, 65, 45	√			3
5	Sucrose	0.95	341		179 (M − H-162)⁻, 161. 131, 119, 117, 113, 103, 101, 89, 87, 71, 59			√	4
6	Hydroxycitric acid derivative	1.36		593	209		√		1
7	Butein	1.43		273	163, 143, 137	√			5
8	Apigenin C-hexoside-C-pentoside	1.53	563		545 (M − H-18)⁻, 443 (M − H-120)⁻, 431 (M − H-132)⁻, 353 (M − H-120-90)⁻, 341 (M − H-132-90)⁻, 311 (M − H-132-120)⁻		√		6
9	L-ascorbic acid isomer	1.81		177	133, 129, 127, 113, 103, 101, 57			√	1
10	N-feruloyltyramine	3.32		314	235, 181, 177, 145, 121, 103, 93, 45			√	1
11	Cyanidin 3-O-galactoside	3.57		449	287, 137		√		7, 8
12	L-ascorbic acid isomer	4.52		177	133, 129, 127, 113, 103, 101, 57	√			1
13	Patuletin (6-methoxyquercetin)	4.97		333	318, 301, 169, 155	√			9
14	Succinic acid isomer	6.05	117		99 (M − H-18)⁻	√			10
15	Diosmetin-7-O-glucuronide-3′-O-pentoside	6.31	607		475 (M − H-132)⁻, 299 (M − H-132-176)⁻, 179			√	11
16	L-ascorbic acid isomer	6.32		177	133, 129, 127, 113, 103, 101, 57		√		1
17	Succinic acid isomer	6.49	117		117, 99			√	10
18	Cyanidin 3-O-sambubioside	6.76	579		339, 285		√		12
19	Apigenin C-hexoside-C-pentoside isomer	7.02	563		545 (M − H-18)⁻, 443 (M − H-120)⁻, 431 (M − H-132)⁻, 341 (M − H-132-90)⁻, 311 (M − H-132-120)⁻	√			13
20	Vicenin (apigenin 6,8-di-C-glucoside)	7.10	593		473 (M − H-120)⁻, 383 (M − H-120-90)⁻, 285	√			14, 15
21	Kaempferol-3-O-rutinoside/luteolin-7-O-rutinoside	7.25	593		285 (M − H-Rut.)⁻	√			16/17
22	Apiin (apigenin-7-apiosylglucoside)	7.29	563		443, 413, 269 (M − H-132-162)⁻		√		5, 18
23	Apiin isomer	7.31		565	433 (M + H-132)⁺, 413, 271(M + H-162- 132)⁺	√			5
24	Cyanidin 3-O-glucoside	7.37		494	287 (M + H-162)⁺, 137	√			3
25	Diosmetin C-glucoside C-pentoside	7.37	593		413 (M − H-90-90)⁻, 383 (M − H-90-120)⁻		√		—
26	Tyrosol isomer	7.46		121	93, 77		√		3
27	Orientin (luteolin 8-C-glucoside)	7.46	447		357 (M − H-90)⁻, 327 (M − H-120)⁻, 297 (M − H-150)⁻, 285(M − H-162)⁻	√			13, 15, 19, 20
28	Delphinidin malonyl glucuronide	7.59		565	303 (M + H-176-86)⁺		√		—
29	Methyl apigenin derivative	7.81		799	285	√			—
30	Luteolin C-hexoside-C-pentoside	7.82	579		489 (M − H-90⁻), 459 (M − H-120)⁻, 429 (M − H-150)⁻, 411, 399, 369 (M − H-120-90)⁻, 365, 353, 339 (M − H -120-120)⁻, 299			√	13
31	Luteolin derivative	7.98	737		285		√		18, 21
32	Schaftoside (apigenin 6-C-glucoside 8-C-riboside)	7.99		565	529, 511, 475, 457, 445, 427, 415(M + H-150)⁺, 409, 391, 379, 361, 349, 337, 325, 307, 295, 273			√	1, 22
33	4-Hydroxybenzoic acid	7.99		139	121, 111, 105, 97, 93, 79		√		1
34	Peonidin-3-(p-coumaroyl-glucoside)	8.27		609	301(M + H-146-162)⁺		√		23
35	Kaempferol-3-(p-coumaryl-glucoside)	8.27	593		593, 447(M − H-146)⁻, 327, 285(M − H-146-162)⁻			√	24
36	Apigenin C-hexoside-C-pentoside isomer	8.32	563		545 (M − H-18)⁻, 473 (M − H-90)⁻, 443 (M − H-120)⁻, 431 (M − H-132)⁻, 353 (M − H-120-90)⁻, 341 (M − H-132-90)⁻, 311 (M − H-132-120)⁻	√		√	13
37	Kaempferol-3-O-glucoside	8.41	447		285		√		6, 8
38	Gamma-eudesmol rhamnoside derivative	8.47	577		439, 397, 379, 367, 349, 322, 293, 249, 197, 127		√		1
39	L-ascorbic acid isomer	8.55		177	133, 129, 127, 113, 103, 101, 57	√			1
40	Peonidin-3-(p-coumaroyl-glucoside) isomer	8.69		609	301(M + H-146-162)⁺	√	√		23
41	Vicenin isomer	8.89	593		473 (M − H-120)⁻, 395, 383 (M-120-90)⁻, 338, 327, 298			√	15, 25
42	Apiin isomer	8.98		565	433 (M + H-132)⁺, 413, 271(M + H-162-132)⁺	√		√	5
43	Apigenin C-hexoside-C-pentoside isomer	8.98	563		545 (M − H-18)⁻, 443 (M − H-120)⁻, 431 (M − H-132)⁻, 353 (M − H-120-90)⁻, 341 (M − H-132-90)⁻, 311 (M − H-132-120)⁻	√			6, 13
44	Unknown	9.04	319		239, 204, 195, 97			√	—
45	Kaempferol-3-(p-coumaryl-glucoside) isomer	9.12	593		447 (M − H-146)⁻, 327, 285(M − H-146-162)⁻	√			24
46	Peonidin-3-(p-coumaroyl-glucoside) isomer	9.37		609	609, 579, 463 (M + H-146)⁺, 301 (peonidin) (M + H-146-162)⁺	√	√	√	23
47	Methyl apigenin-C-rhamnoside-O-glucoside	9.38		593	327 (M + H-162-104)⁺, 297 (M + H-162-134)⁺, 285		√		—
48	Diosmetin-7-O-rutinoside	9.50	607		607, 577, 461 (M − H-146)⁻, 299 (M − H-146-162)⁻	√		√	26
49	Luteolin hexoside	9.55		449	287 (M + H-162)⁺	√			5
50	Luteolin C-hexoside-C-pentoside isomer	9.63	579		369 (M − H-120-90)⁻, 339 (M − H-120-120)⁻, 322, 281, 259, 124		√		13
51	Schaftoside isomer	9.94		565	529, 511, 475, 457, 445, 427, 415(M + H-150)⁺, 409, 391, 379, 361, 349, 337, 325, 307, 295, 273		√		1, 22
52	Succinic acid isomer	10.01	117		99		√		10
53	L-ascorbic acid isomer	10.36		177	133, 129, 127, 113, 103, 101, 57		√		1
54	Peonidin dirhamnoside	10.37		593	301 (M + H-146-146)⁺	√			—
55	3-Hydroxybenzoic acid	10.49		139	105, 97, 93, 79		√		1
56	Acacetin-rhamnoglucoside	10.61	591		283 (M − H-Rut.)⁻, 103, 58	√		√	18
57	Kaempferol dimethyl ether dipentoside	10.68		579	579, 315 (M + H-132-132)⁺			√	—
58	Peonidin glucoside feruloyl glucuronide	10.82		815	463 (M + H-352 feruloyl glucuronide)⁺	√			7
59	3-Hydroxybenzoic acid isomer	10.94		139	105, 97, 93, 79		√		1
60	N-feruloyltyramine isomer	10.96		314	235, 218, 181, 177, 145, 121, 103, 93, 45			√	1
61	Unknown	11.07	877		877, 813, 783, 557		√		—
62	Apigenin-O-dihexoside	11.38	593		269 (M − H-162-162)⁻		√		9
63	Isorhamnetin-3-O-rutinoside	11.59	623		315 (M − H-Rut.)⁻, 300, 271	√			27
64	Peonidin dirhamnoside isomer	11.69		593	447 (M + H-146)⁺, 301 (M + H-146-146)⁺	√	√		—
65	Acacetin-rhamnoglucoside isomer	11.69	591		283 (M − H-Rut.)⁻	√		√	18
66	Succinic acid isomer	11.78	117		99		√		10
67	Tyrosol isomer	12.05		121	93, 77		√		3
68	Diosmetin rhamnoside feruloyl glucuronide	12.46	797		445 (M − H-176-176)⁻, 299 (M − H-176-176-146)⁻, 237, 205	√			—
69	Apiin isomer	12.87	563		269	√			18
70	Succinic acid isomer	12.90	117		99		√		10
71	Peonidin dipentoside	13.13		565	565, 301(M + H-132-132)⁺, 336 265, 195, 135, 91, 45	√			—
72	Methyl gallate	13.25		185	168, 124		√		5
73	Succinic acid isomer	13.65	117		99	√			10
74	Delphinidin-3-arabinoside derivative	15.40		799	435, 303 (M + H-364-132)⁺	√			7, 23
75	Hydroxy-octadecadienoic acid derivative	15.57	593		295 (M − H-298)⁻, 277 (M − H-298- 18)⁻, 251(M − H-298-18-CO₂)⁻, 195, 171	√			28
76	Syringic acid derivative	15.83	377		197		√		21
77	22-Dehydrocholesterol	16.00		393	393, 273, 173, 171, 130, 125			√	1
78	Malvidin derivative	16.72		565	331, 147	√			—
79	Kaempferide derivative isomer	17.40	623		299 (M − H-2 Glc.)⁻, 163	√			29
80	Unknown	17.42		274	274, 256 (M + H-18)⁺, 210 (M + H-18 -46)⁺, 111, 105, 102, 88, 71		√	√	—
81	Unknown	17.54		399	267, 253, 227	√			—
82	L-ascorbic acid isomer	17.82		177	133, 129, 127, 113, 103, 101, 57		√		1
83	Succinic acid isomer	21.49	117		117, 99		√		10
84	Apiin isomer	21.89		565	433 (M + H-132)⁺, 413, 271 (M + H-162-132)⁺			√	5
85	Methyl gallate derivative	23.06	325		183 (M − H-142)⁻	√			29
86	Gallocatechin derivative	24.48	561		305	√			21
87	Succinic acid isomer	24.96	117		99		√		10
88	Unknown	25.01		515	515, 353. 331, 313, 239			√	—
89	4-Hydroxybenzoic acid isomer	25.28		139	121, 111, 105, 97, 93, 79	√	√		1
90	Succinic acid isomer	26.11	117		117, 101, 99	√	√		10
91	Unknown	26.66		805	615, 606, 598, 413, 391, 279, 167, 149, 113	√			—
92	Luteolin-7-glucuronide-3´/4′-pentoside	26.77	593		461 (M − H-132)⁻, 285 (M − H-132-176)⁻, 169			√	11
93	Peonidin dipentoside isomer	27.45		565	547, 301 (M + H-132-132)⁺, 259, 219, 133, 113, 85, 45	√		√	—
94	Tyrosol isomer	27.55		121	93, 77		√		3
95	L-ascorbic acid isomer	27.61		177	133, 129, 127, 113, 103, 101, 57			√	1
96	Delphinidin-3-(p-coumaroyl-glucoside) derivative	28.36		799	611, 303 (M + H-188-308)⁺		√		23
97	Epicatechin derivative	28.91		678	289		√		6
98	Kaempferol-8C-glucoside	29.40		449	329 (M + H-120)⁺, 299 (M + H-150)⁺		√		—
99	Malvidin 3-O-glucoside derivative	29.83		871	493, 331	√			8
100	Unknown	30.00		871	593, 552, 369, 260, 105			√	—
101	L-ascorbic acid isomer	30.41		177	133, 129, 127, 113, 103, 101, 57	√	√		1
102	Peonidin derivative	30.65		799	648 (M + H-galloyl)⁺, 301 (peonidin)		√		—
103	Succinic acid isomer	31.52	117		117, 99	√			10

1: [13]; 2: [14]; 3: [15]; 4: [16]; 5: [17]; 6: [18]; 7: [19]; 8: [20]; 9: [21]; 10: [22]; 11: [23]; 12: [24]; 13: [25]; 14: [26]; 15: [27]; 16: [28]; 17: [29]; 18: [30]; 19: [31]; 20: [32]; 21: [33]; 22: [34]; 23: [35]; 24: [28]; 25: [26]; 26: [36]; 27: [37]; 28: [38]; 29: [39]. Tentative identified; R_t: retention time; Rut.: rutinose; Glc.: glucose; HdA: Hibiscus deflersii; HcA: H. calyphyllus; HmA: H. micranthus.