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. 2017 Oct 19;22(10):1756. doi: 10.3390/molecules22101756

Table 1.

Summary of chemical constituents identified in Menthae Haplocalycis herba by UHPLC-ESI-MS/MS.

Peak tR (min) Compound Formula Identification Experimental Mass m/z Theoretical Mass m/z Mass Error (× 10−6) MS2 Data(Measured)
1 PA1 1.52 C7H7O2 Benzoic acid 123.04371 123.04405 −2.81 95(100),82(2),81(16),67(3),57(2)
2 T1 4.41 C16H26O8Na b Petroside 369.15112 369.15198 −2.35 352(7),351(47),328(27),307(12),285(9),207(100),203(34),185(22),149(6)
3 T2 4.63 C10H17O3 (1R*,2S*)-1,2-dihydroxy-ρ-menth-4(8)-en-3-one 185.11687 185.11722 −1.89 168(4),167(100),157(6),149(18),139(19),125(32),121(26)
4 T3 5.21 C16H28O8Na b (2R,3R,4S,5S,6R)-2-(((1S,2R,3S)-2,3-dihydroxy-3-methyl-6-(propan-2-ylidene)cyclohexyl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 371.16702 371.16763 −1.66 355(2),353(0.2),203(100),201(6),193(4),191(2)
5 T4 5.82 C16H30O8Na b Bohenoside A 373.18250 373.18328 −2.11 357(11),356(10),355(100),346(4),211(4)
6 T5 6.71 C10H17O2 Bohecineole A a 169.12190 169.12230 −2.40 151(71),133(7),123(86),113(5),109(56),107(100),58(4) △
6.75 C10H16O2Na b 191.10388 191.10425 −1.94
7 P1 6.71 C25H32O11Na b Clemastanin A 531.18329 531.18368 −0.74 514(10),513(100),502(4),501(46),369(9),351(3)
8 PA2 7.01 C9H11O3 Phloretic acid 167.06995 167.07027 −1.92 149(100),139(23),126(42),125(57),121(40),109(10),107(49),97(10)
9 T6 7.11 C16H28O7Na b (1R,2R,4S)-trans-1,8-cineole-2-O-β-d-glucopyranoside a 355.17206 355.17272 −1.87 337(14),285(100),268(53),193(6),185(9),135(2) △
7.30 355.17209 −1.78 337(12),285(3),267(36),257(2),203(21),201(100),193(4),185(2)
10 P2 7.62 C26H32O12Na b (+)-1-Hydroxypinoresinol-1-O-β-d-glucoside 559.17682 559.17859 −3.17 541(19),536(4),515(28),437(7),398(9),397(100),396(15),395(65),337(67),309(24)
11 F1 7.95 C27H31O15 Luteolin-7-O-rutinoside 595.16522 595.16574 −0.88 577(0.3),549(0.4),449(100),287(12)
12 F2 8.19 C21H21O11 Luteolin-7-O-glucoside a 449.10611 449.10783 −3.84 287(100) △
8.16 449.10635 −3.31 431(3),416(1),287(100),269(2)
13 F3 8.45 C21H19O12 2-(2,5-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl β-d-glucopyranosiduronic acid 463.08578 463.08710 −2.85 445(0.3),427(0.2),375(0.2),287(100)
14 T7 8.75 C19H34O7Na b Linarionoside B 397.21912 397.21967 −1.39 379(100),326(28),217(26),203(88),187(30)
15 F4 9.48 C27H31O14 Apigenin-7-O-rutinoside 579.16974 579.17083 −1.88 561(1),433(100),417(1),271(9)
16 F5 10.23 C27H33O14 Naringin a 581.18488 581.18648 −2.75 563(59),545(50),527(30),509(11),435(99),419(100),417(92),401(15),383(9),315(27),273(30) △
9.58 581.18573 −1.29 563(20),545(12),527(7),419(100),273(24)
17 F6 10.19 C16H13O6 Chrysoeriol 301.07007 301.07066 −1.97 286(6),286(100),270(0.49),255(3),183(0.5),121(0.23)
18 F7 10.35 C28H33O15 Diosmin a 609.17963 609.18139 −2.90 591(1),573(0.2),463(100),447(1),301(11) △
10.50 609.17999 −2.30 591(0.1),463(100),447(1),429(0.3),301(11),286(0.1),258
19 PA3 10.64 C36H30O16Na Sodium salvianolic acid E 741.14203 741.14260 −0.77 723(1),561(100),543(28),381(3),363(4),345(2),317(2)
20 F8 10.77 C28H35O15 Hesperidin a 611.19617 611.19704 −1.43 593(36),575(34),491(12),489(25),465(97),449(100),447(75),431(26),345(30),303(45) △
10.92 611.19635 −1.14 593(19),575(33),557(14),491(10),489(21),465(62),449(100),447(59),431(22),345(17),303(42)
21 F9 10.98 C16H15O6 Homoeriodictyol 303.08563 303.08630 −2.25 285(13),179(46),177(100),153(28),151(5),136(1)
22 PA4 11.53 C9H9O4 2,4-Dihydroxycinnamic acid 181.04900 181.04953 −2.95 163(100),153(0.4),139(3),137(0.2),135(2),121(0.1),117(0.1)
23 PA5 11.56 C18H17O8 Rosmarinic acid a 361.09134 361.09179 −1.25 347(10),343(24),333(7),328(12),293(11),263(9),191(13),164(5),163(100),145(7) △
11.84 361.09122 −1.58
24 F10 11.94 C21H19O12 Luteolin-7-O-glucuronide 463.08563 463.08710 −3.17 445(0.5),427(0.4),405(0.3),288(1),287(100)
25 PA6 12.14 C27H23O12 Cis-salvianolic acid J 539.11725 539.11840 −2.13 539(7),521(7),495(6),493(6),393(5),341(100),323(3),297(8),295(9),179(5)
26 PA7 12.28 C18H15O8 Bis(3,4-dihydroxybenzylidene)succinic acid 359.07587 359.07614 −0.76 341(100),323(3),313(34),297(4),295(10),285(7),221(15),179(1),123(16)
27 PA8 12.28 C36H30O16Na Sodium lithospermate B 741.14203 741.14260 −0.77 723(0.3),579(100),561(25),533(19),517(19),381(4),355(3)
28 PA9 12.39 C18H13O7 2,4,12-Trihydroxy-7-oxo-8,9-dihydro-7H-benzo[f]naphtho[1,8-bc]oxepine-8-carboxylic acid 341.06497 341.06557 −1.78 323(96),313(18),297(63),295(100),279(18),277(22),267(2),253(12),249(18)
29 PA10 12.61 C36H30O16Na Sodium lithospermate B 741.14233 741.14260 −0.37 579(100),561(27),533(25),517(20),399(5),355(3)
30 T8 12.65 C16H28O7Na b (1R,2S,5R)-(−)-methol β-d-Glucuronide 355.17181 355.17272 −2.57 340(7),339(3),337(11),325(5),323(13),309(4),295(6),285(13),267(100),257(16),205(6),183(3)
31 PA11 13.04 C36H30O16Na Sodium lithospermate B 741.14197 741.14260 −0.85 561(100),543(59),517(23),363(11),362(19),319(3)
32 PA12 13.06 C27H23O12 Lithospermic acid a 539.11725 539.11840 −2.13 539(31),538(28),521(100),493(19),481(15),452(18),393(23),231(21),199(21) △
13.07 C27H23O12 539.11768 −1.34 539(13),538(42),521(66),516(38),495(32),494(30),493(22),377(33),341(11),297(5),265(43),199(86),177(52)
33 PA13 13.16 C36H30O16Na b Salvianolic acid B a 741.14142 741.14260 −1.60 561(100),543(51),517(19),363(11),362(17),319(2) △
13.18 741.14099 −2.18 579(2),561(100),543(56),517(19),363(12),362(17),361(5)
34 F11 14.21 C28H33O14 Buddleoside a 593.18536 593.18648 −1.89 575(0.2),447(100),431(1),413(0.3),285(12),257,242 △
14.42 593.18439 −3.52 575(0.2),447(100),431(1),395(0.3),285(10),270,242
35 F12 14.23 C16H13O5 6,7-Dihydroxy-4’-methoxyisoflavone 285.07495 285.07575 −2.80 285(35),271(8),270(100),242(14),239(3),158(2),152(6),132(3)
36 PA14 14.42 C18H15O8 Prolithospermic acid 359.07535 359.07614 −2.21 341(100),315(1),313(1.4),249(3),187(1),181(21),179(25),163(11)
37 PA15 14.43 C9H9O4 Caffeic acid 181.04904 181.04953 −2.73 163(100),153(0.4),139(1),135(0.6),117(0.1)
38 F13 14.45 C16H13O6 Hispidulin 301.06982 301.07066 −2.80 301(19),286(100),269(1),241(1),183(1)
39 PA16 14.63 C18H13O7 Salvianolic acid G 341.06479 341.06557 −2.31 323(100),305(3),297(21),295(8),267(1),279(3),231(5),195(11),163(11)
40 F14 14.98 C28H35O14 Didymin 595.20074 595.20213 −2.33 577(16),559(25),541(12),449(39),433(100), 287(34)
41 F15 15.11 C17H15O7 Jaceosidin 331.08057 331.08122 −1.99 316(100),303(1),288(0.3),285(1),183(0.2)
42 F16 16.64 C17H15O7 5,6,4’-Trihydroxyl-7,8-dimethoxy flavone 331.08026 331.08122 −2.92 316(75),301(34),298(100),213(2),121(0.4)
43 F17 17.92 C18H17O8 Sideritiflavone 361.09082 361.09179 −2.69 347(8),346(84),331(39),328(100),300(1),213(3)
44 PA17 18.14 C27H23O12 trans-salvianolic acid J 539.11700 539.11840 −2.60 521(100),493(5),479(4),411(5),360(5),341(22),181(9),163(5)
45 PA18 18.14 C36H30O16Na Sodium lithospermate B 741.14111 741.14260 −2.01 561(100),543(52),515(2),383(19),363(3),319(2)
46 F18 18.35 C16H13O6 Diosmetin 301.07025 301.07066 −1.37 287(3),286(100),258(1)
47 T9 18.69 C10H15O2 (S)-(−)-Perillic acid 167.10649 167.10665 −0.99 149(67),139(72),125(16),121(100),95(18),93(13)
48 F19 18.98 C16H15O6 Hesperetin 303.08572 303.08630 −1.96 285(13),179(35),177(100),153(20),151(3),137(1),117(1)
49 PA19 19.22 C36H30O16Na Sodium lithospermate B 741.14081 741.14260 −2.42 579(37),561(14),533(100),517(7),399(3),353(4)
50 PA20 19.23 C36H31O16 Salvianolic acid E 719.15924 719.16066 −1.97 701(47),700(56),673(34),655(30),621(14),609(74),539(100),493(26),297(28)
51 F20 20.44 C18H17O7 Xanthomicrol 345.09613 345.09687 −2.17 345(15),330(100),329(85),315(1),301(14),300(3)
52 F21 21.51 C18H17O8 Thymonin 361.09085 361.09179 −2.61 346(100),331(75),328(53),313(33),300(13),299(4),227(1)
53 F22 22.49 C19H19O8 5,6-Dihydroxy-7,8,3’,4’-tetramethoxyflavone 375.10632 375.10744 −2.99 360(70),359(8),345(47),343(12),342(100),314(1),270(2),213(3),165(1)
54 T10 22.78 C10H15O2 (4S*)-4-hydroxy-ρ-mentha-1,8-dien-3-one 167.10641 167.10665 −1.47 149(100),139(100),131(13),126(35),125(47),121(84),95(26),93(14)
55 T11 24.27 C42H73O15 Floralquinquenoside C 817.49176 817.49439 −3.22 817(53),816(93),801(16),799(33),771(100),728(28),656(28),582(20),563(28),256(15)
56 F23 24.43 C18H17O7 Nevadensin 345.09686 345.09687 −0.05 330(100),315(69),312(50),301(1),297(28),284(12)
57 F24 24.72 C19H19O8 5,7-Dihydroxy-6,8,3’,4’-tetramethoxyflavone 375.10712 375.10744 −0.86 360(100),345(78),342(46),331(2),213
58 F25 24.78 C16H13O5 Acacetin 285.07047 285.07575 −0.98 285(35),271(9),270(100),243(3),242(15),152(5)
59 F26 24.99 C18H17O7 5,6-Dihydroxy-7,3’,4’-trimethoxy flavone 345.09662 345.09687 −0.75 330(64),315(40),312(100),284(1),240(1),213(3)
60 F27 25.08 C16H13O5 Genkwanin 285.07538 285.07575 −1.29 285(100),270(97),243(6),242(34),167(24),145(4)
61 F28 25.58 C19H19O7 5-Dydroxy-6,7,3’,4’-tetramethoxy flavones 359.11194 359.11252 −1.64 345(9),344(82),327(11),326(100),315(2),298(5),165(0.15)
62 F29 26.43 C20H21O8 5-Hydroxy-6,7,8,3’,4’-pentamethoxyflavone 389.12198 389.12309 −2.86 374(100),360(14),359(99),356(45),341(42),328(16),327(4),227(1.39),165(0.34)
63 F30 27.21 C19H19O7 Gardenin B 359.11182 359.11252 −1.97 344(100),329(92),326(53),311(37),298(15),297(5),227(1),135(1)
64 T12 28.55 C30H49O3 Ursolic acid 457.36615 457.36762 −3.21 439(67),411(100),393(4),356(3),227(3),191(6)

Flavonoids (F); Phenolic acids (PA); Terpenoids (T); Phenylpropanoids (P); a Identified by comparison with standards; △ ESI-MS2 spectra of standards; b [M + Na]+ ions.