International Scholarly Research Notices

Review Article

Recent Applications of Mass Spectrometry in the Study of Grape and Wine Polyphenols

Table 3

LC/ESI- product ions of flavan-3-ol monomers, dimers, and oligomers recorded in positive-ion mode. Neutral losses are shown in parentheses. C, EC, and GC: catechin, epicatechin, and gallocatechin, respectively. (E)C and (E)GC: (epi)catechin and (epi)gallocatechin, respectively. (E) indicates either catechin/epicatechin or gallocatechin/epigallocatechin.


Compound	[M + H]⁺	HRF_C		RDA_C		BFF_C		BFF_C/H₂O	HRF_C/H₂O

C	291	165 (126)		139 (152)		169 (122), 123		151 (140), 123	147 (144)
EC	291	165 (126)		139 (152)		169 (122), 123		151 (140), 123	147 (144)
GC	307	181 (126)		139 (168)		169 (138), 139		151 (156), 139	163 (144)

	[M + H]⁺			HRF_C	RDA_C	RDA_F	HRF_C		RDA_F/HRF_C
	[M + H]⁺						RDA_F	H₂O/BFF_F

(E)GC-(4,8)-(E)C	595	305		469 (126)	427 (168)	443 (152)	317 (152)	329 (140)	317 (126)
(E)GC-(4,6)-(E)C	595			469 (126)	427 (168)	443 (152)	317 (152)	329 (140)	317 (126)
(E)C-(4,8)-(E)C	579		291	453 (126)	427 (152)	427 (152)	301 (152)	313 (140)	301 (126)
(E)C-(4,8)-(E)C	579	289		453 (126)	427 (152)	427 (152)	301 (152)	313 (140)	301 (126)
(E)C-(4,8)-(E)C	579		291	453 (126)	427 (152)	427 (152)	301 (152)	313 (140)	301 (126)
(E)C-(4,8)-(E)C	579	289		453 (126)	427 (152)	427 (152)	301 (152)	313 (140)	301 (126)

	[M + H]⁺	/	/	/RDA_I/HRF_F	HRF_C/		HRF_C/RDA_F		HRF_C/H₂O/BFF_F

(E)C-(E)GC-(E)C	883	—/595	593/—	595 (288)/443 (152)/317 (126)	757 (126)/467 (290)		757 (126)/589 (168)		757 (126)/601 (156)
(E)GC-(E)GC-(E)C	899	—/595	609/291	595 (304)/443 (152)/317 (126)	773 (126)/483 (290)		773 (126)/605 (168)		773 (126)/617 (156)
(E)C-(E)C-(E)C	867	—/579	577/291	579 (288)/427 (152)/301 (126)	741 (126)/451 (290)		741 (126)/589 (152)		741 (126)/601 (140)
(E)C-(E)C-(E)C	867	—/579	577/—	579 (288)/427 (152)/301 (126)	741 (126)/451 (290)		741 (126)/589 (152)		741 (126)/601 (140)
(E)C-(E)C-(E)C	867	—/579	577/—	579 (288)/427 (152)/301 (126)	741 (126)/451 (290)		741 (126)/589 (152)		741 (126)/601 (140)

	[M + H]⁺	Diagnostic ions

(E)C-(E)C-(E)C-(E)C	1155	867, 865, 579
(E)C-(E)C-(E)GC-(E)C	1171	883, 881, 595
(E)C-(E)GC-(E)GC-(E)C	1187	899, 897, 595
(E)GC-(E)GC-(E)GC-(E)C	1203	913, 899, 595
(E)C-(E)C-(E)C-(E)C-(E)C	1443	1155, 1153, 867, 579
(E)C-(E)GC-(E)C-(E)C-(E)C	1459	1171, 1169, 867, 579
(E)C-(E)GC-(E)GC-(E)C-(E)C	1475	1187, 1185, 883, 579
(E)C-(E)C-(E)C-(E)C-(E)C-(E)C	1731	1441, 1143, 1155, 867, 579

RDA: retro-Diels-Alder fission; HRF: heterocyclic ring fission; BFF: benzofuran forming fission; QM: quinone methide fission; : the ion derived from the QM fission of ring-C/ring-D linkage bond by the loss of upper unit; : the ion derived from the QM fission of ring-C/ring-D linkage bond by the loss of lower unit; : the ion derived from the QM fission of ring-F/ring-G linkage bond by the loss of upper unit; : the ion derived from the QM fission of ring-F/ring-G linkage bond by the loss of lower unit [41].