Crataegus pentagyna willd. Fruits, leaves and roots: phytochemicals, antioxidant and antimicrobial potentials

Taleghani, Akram; Eghbali, Samira; Moghimi, Roya; Mokaber-Esfahani, Majid

doi:10.1186/s12906-024-04430-4

BMC Complementary Medicine and Therapies

Table 2 Phenolic constituents identified in the hydro-methanolic extracts of the fruit, leaf, and root of C. pentagyna using HPLC-ESI-MS/MS.

From: Crataegus pentagyna willd. Fruits, leaves and roots: phytochemicals, antioxidant and antimicrobial potentials

No.	Compound	[M-H^]−− (m/z)	MS² Fragments	R_t (min)/Intensitya (Eⁿ)/ Mass error (ppm)			Used Parts in Literature ^a	Ref.
No.	Compound	[M-H^]−− (m/z)	MS² Fragments	Fruits	Leaves	Roots	Used Parts in Literature ^a	Ref.
1	Chlorogenic acid glycoside: 4-O-(3′-O-glucopyranosyl)-caffeoyl quinic acid	515	353	0.91/7.2E⁵/ 0.22	0.93/2.7E⁵/ 0.23	0.93/4.8E⁵/ 0.23	F, L	[68]
2	Sinapic acid-O-hexoside	385	223, 208	1.1/7.3E⁴/ 1.21	-	1.3/1.2E⁵/ 1.17	F	[45]
3	Caffeoylquinic acid derivative	353	191, 179	1.3/8.2E⁵/ 0.27	-	-	F ^⁎, L ^⁎, Fl ^⁎	[18]
4	Caffeoylquinic acid derivative	353	191, 179	1.3/6.9E⁴/ 0.27	1.4/4.4E⁵ 0.25	-	F, L ^⁎, Fl ^⁎	[12, 18, 33, 79]
5	Coumaroylquinic acid derivative	337	191	1.5/9.7E⁴/ -0.87	-	-	F^⁎, Fl^⁎, L^⁎	[19, 68, 87]
6	Caffeoylquinic acid derivative	353	191, 179	-	-	1.6/6.3E⁴/ 0.24	F ^⁎, L ^⁎, Fl ^⁎	[15, 18, 45, 51]
7	Coumaroylquinic acid derivative	337	191	-	1.7/1.1E⁵/ -0.81	1.6/2.0E⁵/ -0.83	F, L	[68]
8	Coumaroylquinic acid derivative	337	191	-	1.7/2.4E⁵/ -0.82	-	F ^⁎, L	[18, 68]
9	Sinapic acid	223	208	-	1.9/1.3E⁵/ 2.54	1.8/6.7E⁴/ 2.57	F, Fl	[45]
10	Protocatechuic acid	153	109	2.5/1.5E⁵/ 0.64	-	-	F^⁎, Fl^⁎, L^⁎	[19, 77]
11	Caffeic acid	178	178, 135	2.9/2.6E⁵/ -1.9	-	-	F ^⁎, L ^⁎, Fl ^⁎	[18, 19, 45, 71]
12	Salicylic acid	137	93	4.3/1.3 E⁵/ 1.45	4.4/3.0 E⁶/ 1.39	4.3/1.3E⁵/ 1.45	F^⁎, Fl^⁎, L^⁎	[19, 56]
13	Hydroxybenzoic acid derivative	137	93	4.3/1.2E⁵ 1.35	-	-	F^⁎, Fl^⁎, L^⁎	[19, 45]
14	Hydroxybenzoic acid derivative	137	93	4.3/1.3E⁵/ 1.35	-	-	F	[45]
15	Ferulic acid	193	178, 149	4.7/1.2E⁵/ -0.31	-	-	F ^⁎, L ^⁎, Fl	[45,46,47, 57, 77]
16	Myricetin-3-O-(6″ galloyl) galactoside	631	479, 317	5.3/2.0E⁵/ -1.21	5.4/1.6E⁵/ -1.25	5.3/1.6E⁵/ -1.20	F	[56]
17	Coumaric acid	163	119	-	5.3/2.8E⁵/ 0.89	5.4/2.1E⁵/ 0.84	F ^⁎, L ^⁎, Fl ^⁎	[18, 78]
18	Quercetin-3-O-rutinoside	609	271, 301	5.5/1.0E⁵ 0.45	5.5/2.4E⁵/ 0.43	-	L	[55]
19	Quercetin-3-O-(6″ galloyl) glucoside	615	463, 301	6.7/2.5E⁵/ -0.23	6.5/8.2E⁴/ -0.24	6.6/1.9E⁵/ -0.23	L	[56]
20	Quercetin-7,4′-dimethyl ether-3-O-rutinoside	637	491, 329	7.5/1.2E⁵/ 3.69	7.8/1.0E⁵/ 3.52	7.6/1.6E⁵/ 3.63	F	[56]
21	Quercetin-3-O-rhamnoside	447	301	8.4/7.2E⁴/ -2.71	8.2/3.0E⁵/ -2.63	-	L ^⁎, Fl ^⁎	[18]
22	Orientin or isoorientin glycoside (Orientin-2″-O-rhamnoside)	593	447	8.4/1.0E⁵/ 1.45	8.4/1.5E⁵/ 1.40	-	L ^⁎, Fl ^⁎	[12, 17]
23	Orientin or isoorientin glycoside (Isoorientin-2″-O-rhamnoside)	593	447	9.3/4.6E⁴ 1.44	-	-	Fl ^⁎
24	Vitexin-O-rhamnoside derivative	577	457, 431, 413, 311, 293	-	10.9/1.5E⁵/ 1.87	10.7/8.2E⁴/ 1.81	F, L ^⁎, Fl ^⁎	[48, 58,59,60,61,62,63,64,65]
25	Vitexin-O-rhamnoside derivative	577	457, 431, 413, 311, 293	-	10.7/1.3E⁵/ 1.87	10.9/5.7E⁵/ 1.86	-	[68]
26	Vitexin-O-glucoside derivative	593	473, 431, 413, 311, 293	10.6/1.2E⁵/ -2.41	-	-	F, L	[58, 60]
27	Naringenin-7-O-neohesperidoside	579	271	-	11.6/3.7E⁵/ 2.51	11.8/6.8E⁵/ 2.49	L	[67]
28	Vitexin-O-rhamnoside derivative	577	457, 431, 413, 311, 293	-	12.1/1.7E⁵/ 1.88	-	L, Fl	[42, 50, 64, 65]
29	Vitexin-O-glucoside derivative	593	473, 431, 413, 311, 293	12.8/5.3E⁴/ -2.44	-	-	L	[51, 64,65,66]
30	Myricetin-3-O-galactose	479	317	13.9/4.0E⁴/ -3.15	-	13.8/1.1E⁵/ -3.18	F	[56]
31	Quercetin-O-glycoside derivative	463	301	14.6/8.8E⁴/ 1.25	-	14.8/1.5E⁵/ 1.19	F, L ^⁎, Fl	[12, 15, 18, 43, 46]
32	Quercetin-O-glycoside derivative	463	301	14.6/8.9E⁴/ 1.26	-	-	F ^⁎, L ^⁎, Fl ^⁎, S	[15, 18, 42, 43, 50,51,52,53,54]
33	Quercetin-O-glycoside derivative	463	301	14.7/8.3E⁴/ 1.26	-	-	F, Fl	[1, 47,48,49]
34	Epigallocatechin gallate	457	305	15.4/9.5E⁴/ -0.86	15.2/1.4E⁵/ -0.81	-	F	[74]
35	Epicatechin gallate	441	289	15.9/9.3E⁴/ 0.56	15.8/1.1E⁵/ 0.52	-	F, L	[17, 49, 65]
36	Orientin or isoorientin	447	357, 327	16.9/8.5E⁴/ 1.23	-	-	L ^⁎, Fl ^⁎	[12, 17]
37	Orientin or isoorientin	447	357, 327	16.9/1.1E⁵/ 1.24	-	-	Fl ^⁎	[17]
38	8-methoxykaempferol	315	300	17.1/2.0E⁵/ -1.45	-	-	Fl	[17, 51]
39	Eriodictyol-7-glucuronide	463	287	-	17.5/7.1E⁴/ 2.13	-	L, Fl	[17, 43]
40	Luteolin 7-O-glucoside	447	285	17.8/7.1E⁴ 0.93	17.6/2.1E⁵/ 0.91	-	F ^⁎, L ^⁎, Fl ^⁎	[12, 17, 18, 42]
41	Luteolin-7-O-glucuronide	461	267	17.8/1.5E⁵/ 3.02	17.5/1.6E⁵/ 3.10	-	L	[43]
42	Apigenin-8-C-glucoside	431	341, 311	19.8/6.8E⁴/ 1.95	19.7/9.0E⁴/ 1.91	19.9/1.1E⁵/ 1.81	F^⁎, L^⁎, Fl^⁎, S	[12, 15, 17, 42, 43, 51, 57]
43	Naringenin-6-C-glucoside	433	343, 313	20.5/3.9E⁵/ 2.34	20.6/5.3E⁵/ 2.30	20.4/9.0E⁴/ 2.35	L	[68]
44	Naringenin-7-O-glucoside	433	271	21.4/2.7E⁵/ 1.98	21.7/1.4 E⁵/ 1.93	21.5/1.4E⁵/ 1.95	L	[68]
45	Procyanidin B3 7-glucoside	739	721, 450, 435	-	22.9/1.6E⁵/ 2/54	-	F	[75]
46	Myricetin	317	300, 179, 151	23.5/1.5E⁵/ 1.31	23.5/8.8E⁴/ 1.19	-	F	[56]
47	5-O-methylmyricetin	331	315	23.7/1.3E⁵/ -0.32	23.9/1.3E⁵/ -0.37	23.7/1.2E⁵/ -0.33	-	[56]
48	Quercetin	301	151, 158	23.9/5.9E⁴/ 3.34	23.8/1.3E⁵/ 3.31	23.9/1.5E⁵/ 3.29	F^⁎, L^⁎, Fl	[18, 19, 42, 44, 45]
49	Catechin or epicatechin monomers	289	271, 245, 137	24.2/1.5E⁵/ 2.23	24.3/2.6E⁵/ 2.23	24.3/1.4E⁵/ 2.30	F^⁎, L^⁎, Fl	[19, 66, 71]
50	Kaempferol-3-O-rutinoside	593	285	24.4/9.0E⁴/ 0.45	-	-	F ^⁎, L ^⁎	[18]
51	Catechin or epicatechin monomers	289	271, 245, 137	24.4/7.6E⁴/ 1.69	24.4/1.0E⁵/ 1.61	24.6/1.6E⁵/ 1.58	F ^⁎, L ^⁎, Fl ^⁎	[1, 18, 72, 73]
52	Luteolin	285	269	24.6/1.3E⁵/ 3.01	24.9/6.7E⁴/ 3.04	24.7/1.0E⁵/ 3.10	L	[42]
53	Kaempferol	285	-	24.6/2.9E⁵/ -0.82	24.9/7.7E⁴/ -0.73	-	F ^⁎, Fl ^⁎	[18, 44]
54	Eriodictyol	287	153, 163 179	24.6/2.7E⁵/ -2,41	24.5/1.7E⁵/ -2.39	24.4/1.0E⁵/ -2.20	Fl	[42]
55	Hesperetin	301	153, 163, 179	24.8/6.5E⁴/ 0.103	24.7/1.2 E⁵/ 0.101	24.8/3.9E⁴/ 0.10	Fl	[42]
56	Apigenin	269	-	24.9/8.4E⁵/ 2.92	24.8/1.1E⁵/ 2.84	24.9/1.5E⁵/ 2.92	L	[42]
57	Naringenin	271	152	-	26.5/2.0E⁵/ -0.39	26.4/1.0E⁵ -0.38	L	[42, 66]
58	Procyanidin tetramer-hexoside	1315	-	-	-	26.9/1.0E⁵/ 1.36	F	[75]
59	Procyanidin C2	865	713, 576, 425, 289	26.9/5.1E⁴/ 2.78	26.8/1.0E⁵ 2.72	26.8/1.4E⁵ 2.70	F, L, Fl	[75, 76]
60	Procyanidin pentamer-hexoside	1605	-	-	28.8/7.1E⁴/ 1.83	28.8/1.0E⁵/ 1.80	F	[75]
61	Procyanidin tetramers	1154	-	28.8/1.6E⁵/ -0.32	28.9/4.4E⁴/ -0.38	28.8/1.2E⁵/ -0.32	F, L, Fl	[75, 76]
62	B-type procyanidin pentamers	1442	1156	29.1/8.5E⁴ 3.24	29.3/4.0E⁴ 3.19	29.0/9.9E⁴ 3.19	F, L, Fl	[75, 76]
63	B-type procyanidin hexamers	1731	1154, 1156, 1444	29.4/1.2E⁵/ 1.42	29.8/3.3E⁴ 1.45	29.5/3.9E⁵/ 1.45	F, L, Fl	[75, 76]

- The MZmine analysis software program, version 2.3, was used to process the data. ^a Reported parts from other hawthorn species (Crataegus spp.) based on the previous literature sources; fruit (F), leaf (L), flower (Fl), seed (S), and root (R). ^⁎ Identified phenolic compounds in different parts of C. pentagyna in previous works

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