Identification of Glycoside Compounds from Tobacco by High Performance Liquid Chromatography/Electrospray Ionization Linear Ion-Trap Tandem Mass Spectrometry Coupled with Electrospray Ionization Orbitrap Mass Spectrometry

Jia, Chunxiao; Zhu, Yonghua; Zhang, Jinjie; Yang, Jing; Xu, Chunping; Mao, Duobin

doi:10.21577/0103-5053.20160211

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Journal of the Brazilian Chemical Society

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Articles • J. Braz. Chem. Soc. 28 (4) • Apr 2017 • https://doi.org/10.21577/0103-5053.20160211 copy

Identification of Glycoside Compounds from Tobacco by High Performance Liquid Chromatography/Electrospray Ionization Linear Ion-Trap Tandem Mass Spectrometry Coupled with Electrospray Ionization Orbitrap Mass Spectrometry

Authorship SCIMAGO INSTITUTIONS RANKINGS

In order to comprehensively screen and identify the glycoside compounds in tobacco, a simple, rapid and sensitive method of high performance liquid chromatography/electrospray ionization linear ion-trap tandem mass spectrometry (HPLC-ESI-LIT/MSⁿ) coupled with electrospray ionization orbitrap mass spectrometry (ESI-Orbitrap-MS) was developed for the first time. As a result, twenty-two glycoside compounds, including eleven alcoholic glycosides, eight phenolic glycosides, two ester glycosides and an indole glycoside, were reliably identified from tobacco with high mass accuracy (within 5 mDa). Among them, four compounds were confirmed as novel molecules and other four compounds, as far as we know, were not reported previously in tobacco. This study provided a useful tool to identify the new structures of glycoside compounds in natural products, especially when there were no reference compounds available.

Keywords:
glycoside; tobacco; HPLC-ESI-LIT/MSⁿ; ESI-Orbitrap-MS

Compound	MS protonated molecule (m/z)	MS² fragments (m/z)	MS³ and MS⁴ fragments (m/z)	Molecular formula	Calculated m/z	Error / mDa	Identification
1	343.1374^a a Acquired by HRMS; [M + H]⁺	325, 260, 181, 163	268, 242, 216, 177, 163, 106	C₁₆H₂₂O₈	343.1387	–1.34	coniferin
2	293.11 [M + Na]⁺ 271.1179^a a Acquired by HRMS; [M + H]⁺	275, 247, 185, 151	257, 247, 229, 167, 127	C₁₃H₁₈O₆	271.1176	0.29	benzyl β-D-glucopyranoside
3	307.1160^a a Acquired by HRMS; [M + Na]⁺	289, 279, 247, 217, 185, 179, 163	271, 259, 243, 206, 163, 132	C₁₄H₂₀O₆	307.1152	0.79	2-phenylethyl β-D-glucopyranoside
4	311.0529^a a Acquired by HRMS; [M + K]⁺	293, 279, 251, 192, 163, 133	275, 265, 227, 161	C₁₂H₁₆O₇	311.0528	0.14	arbutin
5	471.2194^a a Acquired by HRMS; [M + Na]⁺	453, 414, 309, 177, 163	435, 396, 370, 163	C²¹H³⁶O¹⁰	471.2201	–0.67	linalyl β-primeveroside
6	302.1014^a a Acquired by HRMS; [M + Na]⁺	284, 270, 245, 163, 139	266, 256, 162	C¹⁴H¹⁷O⁵N	302.0999	1.51	3-indoxyl-β-D-glucopyranoside
7	409.1842^a a Acquired by HRMS; [M + Na]⁺	394, 391, 352, 247, 179, 163, 134	373, 247, 209, 217, 175, 163, 134	C¹⁹H₃₀O₈	409.1833	0.91	vomifoliol β-D-glucopyranoside
8	633.1404^a a Acquired by HRMS; [M + Na]⁺	615, 487, 459, 368, 331, 185	325, 313, 307, 285, 269, 255, 193, 165	C₂₇H₃₀O₁₆	633.1426	–2.18	rutin
9	393.20 [M + Na]⁺ 371.2057^a a Acquired by HRMS; [M + H]⁺	375, 303, 273, 231, 203, 185, 163	357, 331, 317, 285, 273, 203	C₁₉H₃₀O₇	371.2064	–0.73	3-oxo-α-ionyl β-D-glucopyranoside
10	617.08 [M + Na]⁺ 595.1661^a a Acquired by HRMS; [M + H]⁺	593, 562, 512, 471, 308, 331, 253, 179	313, 243, 187, 185, 132	C₂₇H₃₀O₁₅	595.1657	0.35	kaempferol-3-O-rutinoside
11 ^b b novel compounds;	453.2841^a a Acquired by HRMS; [M + H]⁺	435, 421, 417, 291, 257, 273, 179, 163	291, 273, 255, 193, 175	C₂₅H₄₀O₇	453.2847	–0.58	5-androstene-3,17- diol 17-O-β-D-glucopyranoside
12	373.2217^a a Acquired by HRMS; [M + H]⁺	355, 316, 290, 257, 179, 163	337, 272, 211, 192, 179, 163, 132	C₁₉H₃₂O₇	373.2221	–0.38	7,8-dihydro-3- oxo-α-ionol β-D-glucopyranoside
13 ^c c compounds reported for the first time in this plant; MS: mass spectrometry.	535.2152^a a Acquired by HRMS; [M + H]⁺	517, 504, 478, 452, 355, 179, 163	460, 418, 348, 284, 193, 179	C₂₇H₃₄O₁₁	535.2174	–2.19	phillyrin
14 ^c c compounds reported for the first time in this plant; MS: mass spectrometry.	319.1165^a a Acquired by HRMS; [M + Na]⁺	301, 287, 262, 229, 179, 163, 157	273, 244, 218, 179, 163, 149	C₁₅H₂₀O₆	319.1152	1.29	trans-4-(1-propenyl)- phenyl β-D-glucopyranoside
15 ^b b novel compounds;	489.2259^a a Acquired by HRMS; [M + K]⁺	471, 458, 432, 327, 319, 203, 179, 163	453, 401, 327, 309, 281, 179,163	C₂₅H₃₈O₇	489.2249	0.99	17-hydroxy-17-methyl-4- estrene-3-one 17-O-β-D-glucopyranoside
16	389.2174^a a Acquired by HRMS; [M + H]⁺	371, 357, 332, 274, 227, 179, 163, 133	353, 314, 311, 288, 209, 163, 132	C₁₉H₃₂O₈	389.2170	0.41	3-hydroxy-5,6- epoxy-β-ionyl β-D-glucopyranoside
17	711.23 [2M + Na]⁺ 359.1741^a a Acquired by HRMS; [M + H]⁺	693, 679, 651, 549, 341	675, 597, 531, 211	C₁₇H₂₆O₈	359.1700	4.06	lolidide-β-D-glucopyranoside
18	437.1080^a a Acquired by HRMS; [M + H]⁺	419, 405, 363, 359, 275, 257, 179, 163	401, 383, 275, 257, 231, 215, 167, 123	C₂₀H₂₀O₁₁	437.1078	0.16	bellidifolin-8-O-β-D-glucopyranoside
19 ^c c compounds reported for the first time in this plant; MS: mass spectrometry.	625.2077^a a Acquired by HRMS; [M + H]⁺	607, 568, 479, 471, 463, 325, 179, 163	589, 463, 179, 163	C₂₉H₃₆O₁₅	625.2127	–5.00	verbascoside
20 ^c c compounds reported for the first time in this plant; MS: mass spectrometry.	517.14 [M + K]⁺ 479.1573^a a Acquired by HRMS; [M + H]⁺	499, 471, 460, 343, 179, 163	453, 428, 414, 179, 163	C₂₃H₂₆O₁₁	479.1548	2.51	3,4-dihydoxy-phenethylalcohol- 3-O-caffeoyl-β-D-glucopyranoside
21 ^b b novel compounds;	391.1733^a a Acquired by HRMS; [M + Na]⁺	373, 359, 321, 229, 163	355, 345, 186, 147, 133	C₁₉H₂₈O₇	391.1727	0.58	9-hydroxy-megastigma- 3,5,8-trien-7-one 9-O-β- D-glucopyranoside
22 ^b b novel compounds;	623.2865^a a Acquired by HRMS; [M + K]⁺	605, 591, 579, 540, 477, 347, 419, 217	587, 569, 315, 297, 201, 163	C₃₀H₄₈O₁₁	623.2828	3.68	17-hydroxy-estran-3-one rutinoside

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