ACCESSION: MSBNK-IPB_Halle-PB011801
RECORD_TITLE: (20S)-14-oxapentacyclo[20.2.2.210,13.115,19.02,7]nonacosa-1(24),2(7),3,5,10(29),11,13(28),15,17,19(27),22,25-dodecaene-5,16,20,24-tetrol; LC-ESI-QTOF; MS2; CE: 30.58772; [M+H]+
DATE: 2019.06.20
AUTHORS: Stefanie Doell, Kristian Peters, Hendrik Treutler, Dept. Biochemistry of Plant Interactions, Leibniz Institute of Plant Biochemistry, Germany
LICENSE: CC BY
COPYRIGHT: Copyright (C) Stefanie Doell, Kristian Peters, Hendrik Treutler, Dept. Biochemistry of Plant Interactions, Leibniz Institute of Plant Biochemistry, Germany
COMMENT: CONFIDENCE Predicted
CH$NAME: (20S)-14-oxapentacyclo[20.2.2.210,13.115,19.02,7]nonacosa-1(24),2(7),3,5,10(29),11,13(28),15,17,19(27),22,25-dodecaene-5,16,20,24-tetrol
CH$NAME: Maruchantin E
CH$COMPOUND_CLASS: Lignane
CH$FORMULA: C28H24O5
CH$EXACT_MASS: 440.162
CH$SMILES: C1CC2=C(C=CC(=C2)O)C3=C(C=C(C[C@@H](C4=CC(=C(C=C4)O)OC5=CC=C1C=C5)O)C=C3)O
CH$IUPAC: InChI=1S/C28H24O5/c29-21-7-11-23-19(15-21)5-1-17-2-8-22(9-3-17)33-28-16-20(6-12-25(28)30)26(31)13-18-4-10-24(23)27(32)14-18/h2-4,6-12,14-16,26,29-32H,1,5,13H2/t26-/m0/s1
CH$LINK: PUBCHEM
CID:101549217
CH$LINK: INCHIKEY
BTGPMKAMOFOWKF-SANMLTNESA-N
SP$SAMPLE: Marchantia polymorpha
AC$INSTRUMENT: Bruker MicrOTOF-Q
AC$INSTRUMENT_TYPE: LC-ESI-QTOF
AC$MASS_SPECTROMETRY: MS_TYPE MS2
AC$MASS_SPECTROMETRY: ION_MODE POSITIVE
AC$MASS_SPECTROMETRY: IONIZATION ESI
AC$MASS_SPECTROMETRY: CAPILLARY_TEMPERATURE 190 C
AC$MASS_SPECTROMETRY: CAPILLARY_VOLTAGE 5000V
AC$MASS_SPECTROMETRY: COLLISION_ENERGY 30.58772
AC$MASS_SPECTROMETRY: FRAGMENTATION_MODE CID
AC$MASS_SPECTROMETRY: FUNNEL1_RF 200Vpp
AC$MASS_SPECTROMETRY: FUNNEL2_RF 300VPP
AC$MASS_SPECTROMETRY: HEXAPOLE RF 100VPP
AC$MASS_SPECTROMETRY: COLLISION_CELL_RF 400VPP
AC$MASS_SPECTROMETRY: TRANSFER_TIME 70µs
AC$MASS_SPECTROMETRY: PREPULSE_STORAGE_TIME 5µs
AC$CHROMATOGRAPHY: COLUMN_NAME ACQUITY UPLC HSS T3 Column
AC$CHROMATOGRAPHY: RETENTION_TIME 10.517 min
AC$CHROMATOGRAPHY: FLOW_GRADIENT 0 to 1 min, isocratic 95% A , 5% B; 1 to 18 min, linear from 5% to 95% B, delay 18 to 20 min, 95% A isocratic
AC$CHROMATOGRAPHY: FLOW_RATE 0.15 ml/min
AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B acetonitrile with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 441.1697
MS$FOCUSED_ION: PRECURSOR_M/Z 441.1697
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$DATA_PROCESSING: REANALYZE Peaks with additional N2/O included
MS$DATA_PROCESSING: WHOLE RMassBank 2.9.1
PK$SPLASH: splash10-01t9-0291000000-39d565a15ebe3a39cc79
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
107.05 C7H7O+ 1 107.0491 8.02
115.06 C2H11O5+ 2 115.0601 -0.87
117.07 C9H9+ 2 117.0699 1.05
119.05 C8H7O+ 1 119.0491 7.21
120.05 C8H8O+ 1 120.057 -58.02
121.06 C8H9O+ 1 121.0648 -39.58
122.07 C8H10O+ 1 122.0726 -21.43
123.04 C7H7O2+ 1 123.0441 -32.96
124.04 C3H8O5+ 1 124.0366 27.21
125.02 C6H5O3+ 1 125.0233 -26.56
127.05 C10H7+ 1 127.0542 -33.27
128.06 C10H8+ 1 128.0621 -16.02
129.07 C10H9+ 2 129.0699 0.96
130.07 C6H10O3+ 2 130.0624 58.08
131.05 C9H7O+ 1 131.0491 6.55
133.06 C9H9O+ 1 133.0648 -36.01
135.04 C8H7O2+ 1 135.0441 -30.03
136.05 C8H8O2+ 1 136.0519 -13.82
137.06 C8H9O2+ 1 137.0597 2.15
139.04 C7H7O3+ 1 139.039 7.4
140.05 C7H8O3+ 1 140.0468 22.88
141.07 C11H9+ 2 141.0699 0.87
143.08 C11H11+ 1 143.0855 -38.63
144.06 C10H8O+ 1 144.057 21.06
145.06 C10H9O+ 1 145.0648 -33.03
146.07 C10H10O+ 1 146.0726 -17.91
147.04 C9H7O2+ 1 147.0441 -27.58
149.06 C9H9O2+ 1 149.0597 1.97
151.04 C8H7O3+ 1 151.039 6.82
152.06 C12H8+ 2 152.0621 -13.49
153.07 C12H9+ 2 153.0699 0.81
154.07 C8H10O3+ 2 154.0624 49.03
155.08 C12H11+ 1 155.0855 -35.64
157.07 C11H9O+ 1 157.0648 33.16
158.07 C11H10O+ 1 158.0726 -16.55
159.08 C11H11O+ 1 159.0804 -2.77
161.06 C10H9O2+ 1 161.0597 1.83
163.07 C10H11O2+ 1 163.0754 -32.84
164.07 C6H12O5+ 1 164.0679 12.65
165.07 C13H9+ 2 165.0699 0.75
166.08 C13H10+ 2 166.0777 13.84
167.08 C13H11+ 2 167.0855 -33.08
168.08 C9H12O3+ 1 168.0781 11.33
169.06 C12H9O+ 1 169.0648 -28.34
170.07 C12H10O+ 1 170.0726 -15.38
171.08 C12H11O+ 1 171.0804 -2.58
172.09 C12H12O+ 1 172.0883 10.07
173.06 C11H9O2+ 1 173.0597 1.7
175.07 C11H11O2+ 2 175.0754 -30.59
176.06 C14H8+ 2 176.0621 -11.65
177.07 C14H9+ 2 177.0699 0.7
178.08 C14H10+ 2 178.0777 12.91
179.09 C7H15O5+ 2 179.0914 -7.82
180.1 C7H16O5+ 2 180.0992 4.3
181.07 C13H9O+ 1 181.0648 28.77
182.07 C13H10O+ 1 182.0726 -14.37
183.08 C13H11O+ 1 183.0804 -2.41
184.08 C9H12O4+ 2 184.073 37.97
185.1 C13H13O+ 1 185.0961 21.12
186.1 C13H14O+ 1 186.1039 -21.04
187.07 C12H11O2+ 2 187.0754 -28.63
188.08 C12H12O2+ 1 188.0832 -16.91
189.08 C8H13O5+ 2 189.0757 22.48
190.08 C15H10+ 2 190.0777 12.09
191.09 C8H15O5+ 2 191.0914 -7.33
192.09 C15H12+ 2 192.0934 -17.45
193.09 C11H13O3+ 2 193.0859 21.13
194.08 C14H10O+ 1 194.0726 38.05
195.08 C14H11O+ 1 195.0804 -2.26
196.09 C14H12O+ 1 196.0883 8.84
197.06 C13H9O2+ 1 197.0597 1.49
198.07 C13H10O2+ 1 198.0675 12.47
199.08 C13H11O2+ 1 199.0754 23.33
200.08 C13H12O2+ 1 200.0832 -15.9
201.09 C13H13O2+ 1 201.091 -5
202.09 C9H14O5+ 2 202.0836 31.79
203.08 C16H11+ 3 203.0855 -27.21
204.09 C16H12+ 3 204.0934 -16.42
205.07 C15H9O+ 1 205.0648 25.4
206.07 C15H10O+ 1 206.0726 -12.7
207.08 C15H11O+ 1 207.0804 -2.13
208.09 C15H12O+ 1 208.0883 8.33
209.09 C15H13O+ 2 209.0961 -29.13
210.07 C14H10O2+ 1 210.0675 11.75
211.08 C14H11O2+ 1 211.0754 22
212.08 C14H12O2+ 2 212.0832 -15
212.98 C11HO5+ 1 212.9818 -8.68
213.09 C14H13O2+ 1 213.091 -4.72
214.09 C10H14O5+ 2 214.0836 30.01
215.07 C13H11O3+ 1 215.0703 -1.26
216.07 C13H12O3+ 1 216.0781 -37.47
217.08 C13H13O3+ 1 217.0859 -27.27
219.08 C16H11O+ 1 219.0804 -2.01
220.09 C16H12O+ 1 220.0883 7.88
221.1 C16H13O+ 1 221.0961 17.68
222.1 C16H14O+ 2 222.1039 -17.63
223.08 C15H11O2+ 1 223.0754 20.82
224.08 C15H12O2+ 2 224.0832 -14.2
225.09 C15H13O2+ 1 225.091 -4.47
226.07 C14H10O3+ 2 226.0624 33.42
227.07 C14H11O3+ 1 227.0703 -1.19
228.08 C14H12O3+ 2 228.0781 8.35
229.09 C14H13O3+ 2 229.0859 17.81
230.09 C14H14O3+ 1 230.0937 -16.28
231.09 C17H11O+ 2 231.0804 41.36
233.09 C17H13O+ 2 233.0961 -26.13
235.08 C16H11O2+ 1 235.0754 19.76
236.08 C16H12O2+ 2 236.0832 -13.47
237.09 C16H13O2+ 1 237.091 -4.24
238.1 C16H14O2+ 1 238.0988 4.91
239.11 C16H15O2+ 1 239.1067 13.98
240.09 C19H12+ 3 240.0934 -13.96
241.09 C15H13O3+ 2 241.0859 16.92
242.09 C15H14O3+ 1 242.0937 -15.47
243.07 C14H11O4+ 2 243.0652 19.81
244.07 C14H12O4+ 1 244.073 -12.33
245.08 C14H13O4+ 1 245.0808 -3.41
246.08 C14H14O4+ 2 246.0887 -35.19
246.11 C18H14O+ 1 246.1039 24.72
247.1 C14H15O4+ 2 247.0965 14.22
248.19 C16H24O2+ 1 248.1771 52.05
249.09 C17H13O2+ 2 249.091 -4.04
250.1 C17H14O2+ 1 250.0988 4.67
251.09 C13H15O5+ 2 251.0914 -5.58
252.08 C16H12O3+ 2 252.0781 7.55
252.09 C20H12+ 3 252.0934 -13.3
253.09 C16H13O3+ 2 253.0859 16.12
254.09 C16H14O3+ 1 254.0937 -14.74
255.1 C16H15O3+ 1 255.1016 -6.16
256.11 C16H16O3+ 2 256.1094 2.36
257.1 C19H13O+ 1 257.0961 15.2
258.1 C19H14O+ 2 258.1039 -15.17
259.11 C19H15O+ 2 259.1117 -6.72
261.1 C18H13O2+ 2 261.091 34.45
262.1 C18H14O2+ 1 262.0988 4.46
263.1 C18H15O2+ 2 263.1067 -25.3
265.1 C21H13+ 3 265.1012 -4.44
267.1 C17H15O3+ 1 267.1016 -5.88
268.09 C20H12O+ 1 268.0883 6.47
269.1 C20H13O+ 1 269.0961 14.52
271.11 C20H15O+ 2 271.1117 -6.42
272.12 C20H16O+ 2 272.1196 1.59
273.12 C20H17O+ 2 273.1274 -27.06
274.12 C16H18O4+ 2 274.12 0.14
275.11 C19H15O2+ 1 275.1067 12.15
276.12 C19H16O2+ 2 276.1145 19.99
277.12 C19H17O2+ 2 277.1223 -8.32
281.1 C21H13O+ 1 281.0961 13.9
283.11 C21H15O+ 2 283.1117 -6.15
284.1 C17H16O4+ 2 284.1043 -15.17
285.1 C20H13O2+ 2 285.091 31.55
286.1 C20H14O2+ 2 286.0988 4.09
287.11 C20H15O2+ 1 287.1067 11.65
288.11 C20H16O2+ 2 288.1145 -15.55
289.12 C20H17O2+ 2 289.1223 -7.98
290.13 C20H18O2+ 2 290.1301 -0.45
291.12 C16H19O5+ 2 291.1227 -9.27
291.14 C16H19O5+ 2 291.1227 59.42
293.11 C19H17O3+ 2 293.1172 -24.63
295.11 C22H15O+ 2 295.1117 -5.9
296.12 C22H16O+ 2 296.1196 1.46
297.09 C21H13O2+ 2 297.091 -3.39
299.11 C21H15O2+ 2 299.1067 11.18
300.1 C17H16O5+ 3 300.0992 2.58
301.12 C21H17O2+ 2 301.1223 -7.66
302.12 C17H18O5+ 2 302.1149 16.96
303.13 C17H19O5+ 2 303.1227 24.08
304.13 C17H20O5+ 3 304.1305 -1.73
305.12 C20H17O3+ 2 305.1172 9.11
306.12 C20H18O3+ 2 306.125 -16.48
307.13 C20H19O3+ 3 307.1329 -9.35
308.14 C20H20O3+ 2 308.1407 -2.26
311.11 C22H15O2+ 3 311.1067 10.75
312.11 C22H16O2+ 2 312.1145 -14.36
313.12 C22H17O2+ 2 313.1223 -7.37
314.1 C21H14O3+ 3 314.0937 19.91
315.11 C25H15+ 3 315.1168 -21.66
316.14 C22H20O2+ 2 316.1458 -18.29
317.12 C21H17O3+ 3 317.1172 8.76
318.12 C21H18O3+ 2 318.125 -15.86
319.13 C21H19O3+ 3 319.1329 -9
320.13 C24H16O+ 2 320.1196 32.59
321.12 C24H17O+ 2 321.1274 -23.02
322.12 C20H18O4+ 2 322.12 0.12
327.09 C25H11O+ 2 327.0804 29.22
327.1 C22H15O3+ 3 327.1016 -4.8
328.11 C22H16O3+ 2 328.1094 1.84
329.12 C22H17O3+ 3 329.1172 8.44
330.12 C22H18O3+ 2 330.125 -15.28
331.13 C22H19O3+ 3 331.1329 -8.67
332.14 C22H20O3+ 2 332.1407 -2.1
333.11 C21H17O4+ 3 333.1121 -6.41
334.12 C21H18O4+ 2 334.12 0.12
335.13 C21H19O4+ 2 335.1278 6.61
336.13 C21H20O4+ 2 336.1356 -16.69
337.13 C24H17O2+ 2 337.1223 22.82
345.11 C22H17O4+ 3 345.1121 -6.19
346.12 C22H18O4+ 2 346.12 0.11
347.13 C22H19O4+ 2 347.1278 6.38
348.13 C22H20O4+ 3 348.1356 -16.12
349.14 C22H21O4+ 3 349.1434 -9.84
350.14 C25H18O2+ 2 350.1301 28.19
363.13 C22H19O5+ 2 363.1227 20.1
377.16 C27H21O2+ 3 377.1536 16.95
381.15 C26H21O3+ 2 381.1485 3.88
393.15 C27H21O3+ 2 393.1485 3.76
395.16 C27H23O3+ 1 395.1642 -10.56
396.18 C27H24O3+ 1 396.172 20.2
397.16 C26H21O4+ 2 397.1434 41.71
405.15 C28H21O3+ 2 405.1485 3.65
406.15 C28H22O3+ 1 406.1563 -15.62
411.16 C27H23O4+ 1 411.1591 2.22
413.17 C27H25O4+ 1 413.1747 -11.46
414.17 C26H22O5+ 1 414.1462 57.53
423.16 C28H23O4+ 1 423.1591 2.16
424.16 C28H24O4+ 1 424.1669 -16.29
425.16 C28H25O4+ 2 425.1747 -34.66
439.16 C28H23O5+ 1 439.154 13.66
440.16 C28H24O5+ 1 440.1618 -4.15
441.17 C28H25O5+ 1 441.1697 0.79
PK$NUM_PEAK: 220
PK$PEAK: m/z int. rel.int.
107.05 7 7
115.06 3 3
117.07 6 6
119.05 16 16
120.05 12 12
121.06 100 100
122.07 10 10
123.04 34 34
124.04 3 3
125.02 7 7
127.05 2 2
128.06 3 3
129.07 6 6
130.07 3 3
131.05 12 12
133.06 19 19
135.04 53 53
136.05 19 19
137.06 19 19
139.04 4 4
140.05 2 2
141.07 5 5
143.08 5 5
144.06 2 2
145.06 22 22
146.07 3 3
147.04 5 5
149.06 10 10
151.04 9 9
152.06 9 9
153.07 12 12
154.07 4 4
155.08 7 7
157.07 15 15
158.07 2 2
159.08 3 3
161.06 6 6
163.07 2 2
164.07 20 20
165.07 53 53
166.08 19 19
167.08 80 80
168.08 10 10
169.06 38 38
170.07 13 13
171.08 37 37
172.09 7 7
173.06 4 4
175.07 1 1
176.06 3 3
177.07 21 21
178.08 27 27
179.09 34 34
180.1 7 7
181.07 169 169
182.07 39 39
183.08 182 182
184.08 36 36
185.1 65 65
186.1 10 10
187.07 26 26
188.08 2 2
189.08 1 1
190.08 1 1
191.09 16 16
192.09 6 6
193.09 35 35
194.08 33 33
195.08 231 231
196.09 245 245
197.06 209 209
198.07 109 109
199.08 440 440
200.08 82 82
201.09 28 28
202.09 8 8
203.08 14 14
204.09 3 3
205.07 3 3
206.07 5 5
207.08 60 60
208.09 26 26
209.09 187 187
210.07 153 153
211.08 571 571
212.08 228 228
212.98 2 2
213.09 999 999
214.09 153 153
215.07 698 698
216.07 88 88
217.08 9 9
219.08 9 9
220.09 7 7
221.1 61 61
222.1 23 23
223.08 100 100
224.08 251 251
225.09 625 625
226.07 155 155
227.07 612 612
228.08 481 481
229.09 738 738
230.09 110 110
231.09 10 10
233.09 2 2
235.08 6 6
236.08 6 6
237.09 76 76
238.1 26 26
239.11 868 868
240.09 207 207
241.09 925 925
242.09 158 158
243.07 29 29
244.07 48 48
245.08 8 8
246.08 1 1
246.11 1 1
247.1 2 2
248.19 1 1
249.09 6 6
250.1 2 2
251.09 2 2
252.08 1 1
252.09 2 2
253.09 17 17
254.09 10 10
255.1 549 549
256.11 85 85
257.1 19 19
258.1 4 4
259.11 8 8
261.1 2 2
262.1 2 2
263.1 4 4
265.1 6 6
267.1 3 3
268.09 2 2
269.1 6 6
271.11 6 6
272.12 2 2
273.12 6 6
274.12 2 2
275.11 7 7
276.12 3 3
277.12 5 5
281.1 3 3
283.11 17 17
284.1 6 6
285.1 7 7
286.1 10 10
287.11 26 26
288.11 9 9
289.12 12 12
290.13 5 5
291.12 6 6
291.14 3 3
293.11 2 2
295.11 3 3
296.12 2 2
297.09 7 7
299.11 15 15
300.1 6 6
301.12 61 61
302.12 19 19
303.13 46 46
304.13 10 10
305.12 13 13
306.12 11 11
307.13 6 6
308.14 2 2
311.11 13 13
312.11 7 7
313.12 12 12
314.1 14 14
315.11 44 44
316.14 147 147
317.12 114 114
318.12 32 32
319.13 331 331
320.13 80 80
321.12 10 10
322.12 11 11
327.09 2 2
327.1 2 2
328.11 2 2
329.12 50 50
330.12 26 26
331.13 34 34
332.14 43 43
333.11 185 185
334.12 41 41
335.13 105 105
336.13 23 23
337.13 3 3
345.11 16 16
346.12 6 6
347.13 57 57
348.13 69 69
349.14 17 17
350.14 3 3
363.13 2 2
377.16 3 3
381.15 3 3
393.15 3 3
395.16 19 19
396.18 3 3
397.16 2 2
405.15 6 6
406.15 2 2
411.16 3 3
413.17 9 9
414.17 4 4
423.16 98 98
424.16 30 30
425.16 6 6
439.16 33 33
440.16 8 8
441.17 186 186
//
