A Comprehensive Review of the Structure Elucidation of Tannins from Terminalia Linn.

Table 6

The MS spectral data of compounds 1–82 except those which have no reported MS data.

No.	Compound name	Molecular formula	Ion source	[M-H]^–	Fragments	Reference
1	Tri-O-galloylshikimic acid	C28H22O17	ESI	628.9	477 (15), 325 (1), 169 (100)	[16]
2	1,2,6-Tri-O-galloyl-β-D-glucose	C27H24O18		635	465 (100), 313 (20), 169 (10)	[92]
				635.093	465.0479, 313.0427, 169.0061	[93]
3	1,3,6-Tri-O-galloylglucose	C27H24O18		635.0895	465.06714 [C20H17O13]^−, 211.02463 [C9H7O6]^−, 169.01404 [C7H5O5]^−, 125.02427 [C6H5O3]^−	[94]
5	3,4,6-Tri-O-galloyl-D-glucose	C27H24O18	ESI	635.0882	169 (9), 235 (2), 271 (4), 295 (14), 313 (9), 405 (5), 423 (30), 465 (68), 483 (100), 617 (11)	[95]
6	1,2,3,4-Tetra-O-galloyl-β-D-glucose	C34H28O22	ESI	787	617, 393, 169	[32]
7	1,3,4,6-Tetra-O-galloyl-β-D-glucose	C34H28O22		787	635, 617	[96]
8	2,3,4,6-Tetra-O-galloyl-D-glucose	C34H28O22	ESI	787	617, 635	[97]
			ESI	787.0914	635.0902, 617.0795,465.0709	[98]
				787.0989	169.0158, 295.0297, 313.0570, 447.1352, 465.1383, 483.0638, 617.1949, 635.2112	[99]
				787.0996	617.0902 [M-H-GA]^−, 447.0732 [M-H-2GA]^−, 295.0418 [M-H-2GA-C7H4O4]^−, 169.0140 [GA-H]^−	[100]
			ESI	787.1079	617.0834, 465.0731, 313.0606, 169.0177	[101]
			ESI	787	635 [M-H-152]^−, 617 [M-H-170]^−, 483 [M-H-304]^−, 465 [M-H-322]^−, 447 [M-H-340]^−, 169 [GA-H]^−	[102]
9	1,2,3,6-Tetra-O-galloyl-β-D-glucose	C34H28O22	ESI	787.0986	295 (1), 403 (2), 421 (0.4), 429 (1), 447 (2), 465 (3), 529 (0.2), 573 (4), 617 (100), 635 (31)	[95]
11	1,2,3,4,6-Penta-O-galloyl-β-D-glucose	C41H32O26	ESI	939.1101	329 (0.4), 439 (0.4), 447 (0.2), 515 (0.2), 599 (1), 601 (0.2), 617 (3), 725 (1), 769 (100), 787 (8)	[95]
				939.111	787.1282 [M-H-C7H4O4]^−, 769.1003 [M-H-GA]^−, 617.0884 [M-H-GA-C7H4O4]^−, 447.0593 [M-H-2GA-C7H4O4]^−, 259.0248 [M-H-4GA]^−, 169.0140 [GA-H]^−	[103]
			ESI	939	769[M-H-GA]^–, 617[M-H + H2O-2GA]^–	[104]
			ESI	939.11090	769.1, 617.1, 465.1, 447.1, 295.0, 169.0	[105]
			ESI	939	769, 787, 617	[97]
			ESI	939	939[M-H]^−, 769[M-H-GA]^−, 617[M-H + H2O-2GA]^−, 447[M-H + H2O-3GA]^−, 169[GA]^−, 125[GA-CO2]^−	[50]
			ESI	939	787, 769, 617, 599, 447	[106]
				939.112	169, 617, 769	[107]
				939	469, 769, 629, 617, 465, 313, 169, 125	[108]
			ESI	939	787, 769, 635, 617	[109]
			ESI	939.1104	787 [M-H-C7H4O4]^−, 769 [M-H-C7H6O5]^−, 635 [M-H-C14H8O8]^−, 617 [M-H-C14H10O9]^−, 465 [M-H-C21H14O13]^−, 447 [M-H-C21H16O14]^−, 313 [M-H-C28H18O17]^−, 295 [M-H-C28H19O18]^−, 169 [M-H-C34H26O21]^−, 125 [C35H26O23]^−	[110]
			ESI	939.3	169.0, 393.1, 769.2	[111]
13	4-O-(4″-O-Galloyl-α-L-rhamnopyranosyl) ellagic acid	C27H20O16	ESI	599	447 (23), 429 (2), 301 (100), 297 (6), 169 (3)	[16]
15	Castalin	C27H20O18		631	613 (100)	[112]
			ESI	631.1	301 [EA-H]^–, 331.0 [Galloylglu-H]^−, 481.0 [HHDP-glu-H]^−	[113]
				631	479, 317, 301	[114]
			ESI	631.0586	461.033 (71) [M-H–C7H4O4–H2O]^−, 445.0461 (17) [M-H-C7H4O5-H2O]^−, 300. 9986 (78) [ellagic acid]^−, 273.0030, 245.0092 (44), 229.0142(45), 169.0143 (100) [GA]^−, 125.0254 (30)	[115]
18	Corilagin	C27H22O18		633.0734	470.9841	[116]
				633.0762	463.0793, 300.9986, 169.0133	[117]
				633.0725	463 (7), 301 (100), 275 (30), 245 (5), 169 (7), 125 (4)	[118]
			ESI	633	476, 454	[32]
19	Sanguiin H-4	C27H22O18	ESI	633.0719	327, 343, 177	[119]
			ESI	633	481, 301, 275, 249, 635, 617, 465, 447, 353, 339, 321, 315, 303, 277, 257, 229, 211, 259, 231	[120]
22	Chebulanin	C27H24O19		651	633, 481, 463, 291, 275	[100]
				651	481 [M-galloyl]^−, 651 [M-H]^−, 1303 [2M-H]^−	[121]
				651	633 [M-H-H2O]^−, 405, 300, 275	[122]
23	Chebumeinin A	C29H30O18		669	366.9	[123]
24	Chebumeinin B	C28H28O19		669	366.8	[123]
25	4-O-(3″,4″-Di-O-galloyl-α-L-rhamnopyranosyl) ellagic acid	C34H24O20	ESI	751.1	599 (22), 581 (6), 449 (30), 411 (4), 300 (100), 297 (8), 169 (6),151 (2)	[16]
27	3′-O-Methyl-4-O-(3″,4″-di-O-galloyl-α-L-rhamnopyranosyl) ellagic acid	C35H26O20	ESI	765.2	613 (32), 595 (100), 461 (5), 449 (30), 443 (41), 425 (10), 315 (31), 169 (56)	[16]
28	Punicalin	C34H22O22		781	601, 301	[124]
			ESI	781.0531	721, 601, 271	[125]
			ESI	781.5	299.4	[126]
				781	721, 601, 557, 451, 299	[100]
				781	601, 299	[127]
30	Pedunculagin	C34H24O22		783.0673	300.9975	[116]
			ESI	783.07	1567.14 [2M-H]^−, 391.03 [M-2H]^2–	[128]
			ESI	783	481, 301, 257	[129]
			ESI	783	391 [M-2H]^2–, 783 [M-H]^−, 1567 [2M-H]^–	[121]
			ESI	783.2	783.2, 481.1, 301.0	[130]
			ESI	783.0686	481.0516, 300, 9975	[131]
				783	481, 301, 244	[114]
				783.068	481, 301, 275	[125]
			ESI	783.0692	935.0790, 613.0463, 300.9990	[132]
			ESI	783.0679	481, 301	[133]
				783.0699	481.0606, 391.0307,300.9999, 275.0191	[134]
				783	301, 481, 275	[97]
			ESI	783.06	481.06, 301.00, 275.02	[135]
31	Terflavin B	C34H24O22	ESI	783	631 (11), 451 (100), 299 (1)	[16]
33	Tellimagrandin I	C34H26O22	ESI	785.08	301.00, 275.02, 169.01	[135]
					784.6, 450.9, 402.6, 391.7, 214.7	[136]
			ESI	785	301, 483, 615	[137]
			ESI	785	301, 483, 633, 615, 463, 419	[97]
			ESI	785.0836	301, 483, 633	[133]
			ESI	785.0866	633, 481,301, 275, 222	[138]
			ESI	785	392 [M–2H]^2–, 785 [M–H]^−, 1571 [2M–H] ^−	[121]
			ESI	785.084	633.07, 615.06, 483.08, 300.99, 275.02	[139]
			ESI	785	615,483,301	[129]
35	1,3-Di-O-galloyl-2,4-chebuloyl-β-D-glucose	C34H28O23	ESI	802.9	337 (100), 319 (47), 293 (41), 275 (61), 169 (8)	[16]
37	Castalagin	C41H26O26	ESI	933	915, 631, 451, 301	[140]
			ESI	933.0644	915.0509, 631.0575, 479.0464, 461.0377, 300.9991	[141]
			ESI	933	915, 631, 613, 569, 493, 301	[142]
					915, 783, 631, 613, 569, 467, 493, 323, 301, 146
			ESI	933	915 (95), 631 (100), 425 (20), 301 (5)	[112]
				933	181.1, 466.0	[113]
			ESI	933.0649	466.0299, 300.9968	[134]
			ESI	933	915, 631, 613, 569	[106]
				933	915, 871, 569, 301	[114]
			ESI	933.1	783.1, 631.1, 451.1, 301.0	[130]
			ESI		466 [M-2H]^2–, 933 [M-H]^–, 933 [2M-2H]^2–, 1867 [2M-H]^–	[121]
			ESI		935, 915, 613, 301	[143]
			ESI	933	631, 451, 301	[144]
39	2-O-Galloylpunicalin	C41H26O26		933	781, 721, 601	[124]
41	Casuarinin	C41H28O26	ESI	935.0796	785.1, 633.1, 483.1, 451.0, 425.0, 301.0, 275.0, 169.0	[105]
			ESI	935	917, 633, 783, 301	[137]
			ESI	935	467 [M-2H]^2–, 935 [M-H]^–, 1871 [2M-H]^–	[121]
				935.076	633.075, 300.9999	[145]
43	Tellimagrandin II	C41H30O26	ESI	937.0953	301.0, 275.0, 249.0, 169.0	[105]
			ESI	937	767, 741, 465, 301	[97]
			ESI	937	785, 767, 635, 465, 301	[106]
			ESI	937.0945	785, 633, 483, 301, 278, 237	[138]
44	Geraniin	C41H28O27	ESI	951.0747	907.0849, 781.0537, 605.0788, 479, 425.0251, 298, 273.0042	[141]
			ESI	951.0762	933.0717 (100) [M-H-H2O]^–, 300.9991 (52), 169.0141 (2)	[115]
				951.6751	463.0505, 301.9987, 273.0040, 169.0132	[146]
			ESI	951	457 [M-2H2O-2H]^2–, 466 [M-H2O-2H]^2–, 951 [M-H]^–, 1903 [2M-H]^–	[121]
			ESI	951.0721	933.0770 [M-H-H2O]^–, 300.9990, 169.0144	[147]
			ESI	951.07	951.07 [M-H]^–, 466.03 [M-2H]^2–, 300.99 [EA-H]^–, 633.07 [M-318-H]^–	[128]
45	Granatin B	C41H27O27	ESI	951.0719	933 (7), 463 (20), 301 (100), 273 (32), 245 (17), 229 (3), 167 (3)	[118]
			ESI	951	933, 915, 301	[148]
			ESI	951.0745	933.0604, 613.2044, 300.9980	[131]
46	Praecoxin A	C41H28O27	ESI	951	783, 605, 889, 481, 301	[149]
48	Chebulagic acid	C41H30O27	ESI	953	476, 169	[32]
				953	935, 807, 633, 481, 463, 319, 301	[100]
			ESI	953	476 [M-2H]^2–, 953 [M-H]^–	[121]
49	Rugosin B	C41H30O27	ESI	953.0902	909.1, 785.1, 766.1, 597.0, 301.0, 275.0, 249.0, 169.0	[105]
				953.2	909 (100), 883 (1), 785 (5)	[150]
50	Chebulinic acid	C41H32O27		955	477 [M-2H]^2–, 169	[32]
				955	937, 803, 785, 641, 607, 465, 337, 275, 131	[100]
				955	477 [M-2H]^2–, 955 [M-H]^–	[121]
				955.1018	785, 169	[151]
52	Neochebulagic acid	C41H32O28		971	953 [M-H-H2O]^–, 935 [M-H-H2O-H2O]^–, 467 [M-2H-H2O-H2O]^2–, 301	[122]
56	Methyl neochebulinate	C42H36O28	ESI	987.2	635 (100), 465 (1), 351 (3), 169 (1)	[16]
60	Grandinin	C46H34O30	ESI	1065	1047 (50), 1029 (50), 975 (100),	[112]
62	α-Punicalagin	C48H27O30	ESI	1083.056	781 (40), 601 (35), 575 (20), 301 (100), 275 (7), 249 (5)	[118]
				1083	781 (60), 601 (100), 575 (22)	[152]
				1083.059	781.6071, 601.3680, 301.4796	[131]
			ESI	1083	781, 541, 301	[153]
63	β-Punicalagin	C48H27O30	ESI	1083.054	1083 (43), 781 (55), 719 (29), 601 (86), 575 (29), 301 (100), 275 (43), 249 (15)	[118]
				1083	781 (35), 601 (100), 575 (15)	[152]
				1083.059	781.6071, 601.3680, 301.4796	[131]
			ESI	1083	781, 541, 301	[153]
67	Eucalbanin A	C48H30O30	ESI	1085	765, 633, 473	[137]
			ESI	1085	933, 783, 765, 739, 633, 597, 469, 407	[97]
			ESI	1085.074	783.07, 633.07, 450.99, 300.99	[139]
68	Rugosin A	C48H34O31	ESI	1105.101	530.0, 891.1, 301.0, 169.0	[105]
			ESI	1105.3	1061 (100), 937 (5), 935 (10), 917 (3)	[150]
75	Procyanidin B1	C30H26O12		577.1344	577, 451, 425, 407, 289, 245, 161, 125	[154]
				577.16	287, 289, 425, 451	[155]
			ESI	577.1351	425.0875 (100), 451.1030 (90), 289.0713 (60), 407.0767 (60), 299.0556 (30), 287.0557 (10)	[156]
76	Procyanidin B2	C30H26O12		577.152	287, 289, 425, 451	[155]
			ESI	577	451 (23.7), 425 (100), 407 (69.6), 289 (29.0), 408 (17.7), 407 (100), 289 (100), 281 (85.7), 256	[157]
77	Procyanidin B3	C30H26O12	ESI	577.1331	407 (75), 289 (81), 245 (67)	[158]
			ESI	577.1375	425, 407, 289, 287	[159]
78	3′-O-Galloyl procyanidin B2	C37H30O16		729.1458	407.0766, 289.0716	[160]
				729.1471	303.05055, 364.58214, 441.08203	[161]
79	Procyanidin C1	C45H38O18	ESI	865.1964	739.1640, 575.1171	[162]
			ESI	865.195	865 (37), 695 (100), 577 (1), 407 (64), 289 (42)	[158]
			MALDI	865.191	287, 289, 575, 577, 713, 425, 739, 451, 413	[155]
			ESI	865	675.3, 528.6	[163]
			ESI	865.1984	739, 713, 577, 289	[119]
			ESI	865.1985	739.1722, 577.1378, 451.1054, 407.0793, 287.0575, 245.0460	[164]
81	Acutissimin A	C56H38O31	ESI	1205	1205, 915, 613, 602, 301	[143]