International Scholarly Research Notices

Review Article

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

Table 13

Anthocyanin derivatives identified in 4–23 months aged wines.
RT (min)Compound[M]+ (m/z) fragment ions (nm)Aged wine (months)
(m/z)48131623
21.7Dp-3-glc465303277, 342, 524 * * * * *
26.1Cy-3-glc449287279, 516 * * * * *
28.1Pt-3-glc479317277, 347, 525 * * * * *
34.1Pn-3-glc463301280, 517 * * * * *
35.5Mv-3-glc493331277, 348, 527 * * * * *
38.3Dp-3-acetylglc507303276, 346, 527 * * * * *
41.0Cy-3-acetylglc491287280, 523 * * * * *
41.6Pt-3-acetylglc521317270, 529 * * * * *
43.6Pn-3-acetylglc505301280, 522 * * * * *
44.3Mv-3-acetylglc535331278, 350, 530 * * * * *
43.1Dp-3-p-coumglc cis 611303280, 301, 534 * * * * *
44.3Dp-3-p-coumglc trans 611303282, 313, 531 * * * * *
45.1Cy-3-p-coumglc cis595287280, 301, 533 * * * * *
46.3Cy-3-p-coumglc trans 595287284, 314, 524 * * * * *
45.3Pt-3-p-coumglc cis 625317281, 301, 536 * * * * *
46.6Pt-3-p-coumglc trans 625317282, 313, 532 * * * * *
47.5Pn-3-p-coumglc cis 609301283, 300, 535 * * * * *
48.6Pn-3-p-coumglc trans 609301283, 313, 526 * * * * *
47.5Mv-3-p-coumglc cis 639331280, 301, 535 * * * * *
48.7Mv-3-p-coumglc trans 639331282, 313, 532 * * * * *
41.1Dp-3-cafglc trans 627303283, 331, 532 * n.d.n.d.n.d.n.d.
43.6Pt-3-cafglc trans 641317283, 328, 531 * * n.d.n.d.n.d.
45.6Pn-3-cafglc trans 625301283, 328, 525 * n.d.n.d.n.d.n.d.
44.8Mv-3-cafglc cis 655331  * * n.d.n.d.n.d.
45.7Mv-3-cafglc trans 655331282, 328, 534 * * * * *
16.7Dp-3,7-diglc627303279, 523 * n.d.n.d.n.d.n.d.
20.4Pt-3,5-diglc641317275, 521 * n.d.n.d.n.d.n.d.
24.6Pt-3,7-diglc641317275, 349, 522 * * * * *
28.7Pn-3,7-diglc625301  * * n.d.n.d.n.d.
23.5Mv-3,5-diglc655331275, 524 * * n.d.n.d.n.d.
30.8Mv-3,7-diglc655331278, 350, 526 * * * * *
34.7Dp-3-glc + L(+)lactic acid537   * * * * *
37.5Pt-3-glc + D(−)lactic acid551   * * * * n.d.
39.2Pt-3-glc + L(+)lactic acid551317278, 526 * * * * *
40.5Pn-3-glc + D(−)lactic acid535   * * n.d.n.d.n.d.
41.7Pn-3-glc + L(+)lactic acid535301281, 525 * * * * *
40.8Mv-3-glc + D(−)lactic acid565331278, 350, 530 * * * * *
42.1Mv-3-glc + L(+)lactic acid565331278, 348, 531 * * * * *
5.7Dp-3-glc-GC769607, 439531 * * * * *
7.1Cy-3-glc-GC753591, 453282, 524 * * * * *
7.2Pt-3-glc-GC783621, 453279, 532 * * * * *
10.8Pn-3-glc-GC767605, 437  * * * * *
10.6Mv-3-glc-GC797635, 467281, 531 * * * * *
22.3Mv-3-glc-EGC797635, 467  * * * * *
24.4Mv-3-acetylglc-GC839  n.d. * * * n.d.
30.9Dp-3-p-coumglc-GC915607, 439 n.d. * * * n.d.
35.1Cy-3-p-coumglc-GC899  n.d. * * n.d.n.d.
35.4Pt-3-p-coumglc-GC929  n.d. * * * n.d.
38.5Pn-3-p-coumglc-GC913605, 437 n.d. * * * *
38.3Mv-3-p-coumglc-GC943635, 467 n.d. * * * *
41.1Mv-3-p-coumglc-EGC943  n.d. * * * *
10.8Dp-3-glc-C753591, 439282, 534 * * * * *
14.8Dp-3-glc-EC753591, 439  * * * * *
14.9Cy-3-glc-C737575, 423286, 526 * * * * *
18,0Cy-3-glc-EC737575, 423  * * * * *
16.2Pt-3-glc-C767605, 453279, 532 * * * * *
21.6Pt-3-glc-EC767605, 453  * * * * *
20.3Pn-3-glc-C751589, 437283, 524 * * * * *
24.3Pn-3-glc-EC751589, 437  * * * * *
21.0Mv-3-glc-C781619, 467280, 532 * * * * *
29.9Mv-3-glc-EC781619, 467279, 533 * * * * *
35.9Mv-3-acetylglc-C823619, 467 n.d. * * * *
39.0Dp-3-p-coumglc-C899591, 439 n.d. * * * *
40.5Dp-3-p-coumglc-EC899  n.d. * n.d.n.d.n.d.
39.5Cy-3-p-coumglc-C883n.d. * * * n.d.
41.4Cy-3-p-coumglc-EC883  n.d. * n.d.n.d.n.d.
41.0Pt-3-p-coumglc-C913605, 453 n.d. * * * *
42.6Pt-3-p-coumglc-EC913  n.d. * n.d.n.d.n.d.
41.8Pn-3-p-coumglc-C897589, 437 n.d. * * * *
43.8Pn-3-p-coumglc-EC897  n.d. * n.d.n.d.n.d.
43.4Mv-3-p-coumglc-C927619, 467290, 538 * * * * *
46.0Mv-3-p-coumglc-EC927  n.d. * n.d.n.d.n.d.
35.8Dp-3-glc-ethyl-C781329, 329  * n.d.n.d. * n.d.
36.7Dp-3-glc-ethyl-EC781   * n.d.n.d. * n.d.
39.5Cy-3-glc-ethyl-C765   * n.d.n.d.n.d.n.d.
39.6Pt-3-glc-ethyl-C795343  * n.d.n.d. * *
42.0Pn-3-glc-ethyl-C779327  * * n.d. * *
43.1Pn-3-glc-ethyl-EC779   * n.d.n.d. * *
41.1Mv-3-glc-ethyl-C809357  * * * * *
42.2Mv-3-glc-ethyl-C809357282, 539 * * * * *
43.1Mv-3-glc-ethyl-C809357276, 537 * * * * *
45.8Mv-3-acetylglc-ethyl-C851357  * * n.d.n.d.n.d.
47.4Mv-3-p-coumglc-ethyl-C955357  * * * * n.d.
34.7Dp-3-glc-ethyl-GC797329  * n.d.n.d.n.d. *
38.6Cy-3-glc-ethyl-GC781   * n.d.n.d.n.d.n.d.
38.7Pt-3-glc-ethyl-GC811343  * n.d.n.d. * *
40.9Pn-3-glc-ethyl-GC795   * n.d.n.d.n.d.n.d.
40.6Mv-3-glc-ethyl-GC825357  * n.d. * * *
41.1Mv-3-glc-ethyl-GC825357539 * * * * *
41.8Mv-3-glc-ethyl-GC825357  * n.d. * * *
45.0Mv-3-acetylglc-ethyl-GC867   * n.d.n.d.n.d.n.d.
21.0A-type vitisin of Dp-3-glc533371297, 368, 507n.d. * * * *
27.0A-type vitisin of Cy-3-glc517  n.d.n.d.n.d. * n.d.
28.7A-type vitisin of Pt-3-glc547385299, 371, 508n.d. * * * *
35.0A-type vitisin of Pn-3-glc531369503n.d.n.d.n.d. * *
36.0Vitisin A561399299, 372, 510n.d. * * * *
40.7A-type vitisin of Pt-3-p-coumglc693  n.d.n.d. * * n.d.
43.8A-type vitisin of Pn-3-p-coumglc677369284, 508n.d. * * * *
44.1A-type vitisin of Mv-3-p-coumglc707399271, 514n.d. * * * *
24.4B-type vitisin of Dp-3-glc489327 n.d. * * * *
33.5B-type vitisin of Pt-3-glc503341492n.d. * * * *
38.5B-type vitisin of Pn-3-glc487325  * * * * n.d.
39.5Vitisin B517355294, 358, 490 * * * * *
41.4B-type vitisin of Pn-3-acetylglc529325  * * n.d.n.d.n.d.
42.4B-type vitisin of Mv-3-acetylglc559355298, 361, 494 * * * * n.d.
41.1Acetone derivative of Pn-3-glc501339475n.d. * * * n.d.
42.1Acetone derivative of Mv-3-glc531369480n.d. * * * *
45.5Dp-3-glc 4-vinylphenol adduct581419264, 412, 503 * * * * *
47.5Cy-3-glc 4-vinylphenol adduct565  n.d. * * * *
48.3Pt-3-glc 4-vinylphenol adduct595433264, 413, 502 * * * * *
50.5Pn-3-glc 4-vinylphenol adduct579417278, 406, 500 * * * * *
51.0Mv-3-glc 4-vinylphenol adduct609447263, 412, 504 * * * * *
53.2Mv-3-acetylglc 4-vinylphenol adduct651447298, 416, 505 * * * * *
49.9Dp-3-p-coumglc 4-vinylphenol adduct727419 n.d.n.d.n.d. * *
52.4Pt-3-p-coumglc 4-vinylphenol adduct741433314, 504n.d.n.d.n.d. * *
54.6Pn-3-p-coumglc 4-vinylphenol adduct725417314, 501n.d.n.d.n.d. * *
55.2Mv-3-p-coumglc 4-vinylphenol adduct755447264, 313, 416, 505n.d. * * * *
43.5Dp-3-glc 4-vinylcatechol adduct597435509 * * * * *
46.5Pt-3-glc 4-vinylcatechol adduct611449510 * * * * *
48.6Pn-3-glc 4-vinylcatechol adduct595433506 * * * * *
49.2Mv-3-glc 4-vinylcatechol adduct625463510 * * * * *
50.9Mv-3-acetylglc 4-vinylcatechol adduct667463513n.d.n.d. * * *
47.6Dp-3-p-coumglc 4-vinylcatechol adduct743435  * * * * *
50.5Pt-3-p-coumglc 4-vinylcatechol adduct757449 n.d. * * * *
53.2Mv-3-p-coumglc 4-vinylcatechol adduct771463312, 511 * * * * *
52.0Mv-3-glc 4-vinylguaiacol adduct639477511 * * * * *
54.0Mv-3-acetylglc 4-vinylguaiacol adduct681477514n.d. * * * *
55.7Mv-3-p-coumglc 4-vinylguaiacol adduct785477514n.d. * * * *
49.0Mv-3-glc 4-vinylepicatechin adduct805   * * * * *
Dp: delphinidin; Cy: cyanidin; Pt: petunidin; Pn: peonidin; Mv: malvidin; glc: glucose; p-coumglc: p-coumaroylglucoside; cafglc: caffeoylglucoside; acetylglc: acetylglucoside; catechin; GC: gallocatechin; EC: epicatechin; ECG: epigallocatechin; *detected; n.d.: not detected [30].