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Unravelling the Biochemical Distribution of Secondary

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Unravelling the Biochemical Distribution of Secondary SUPPLEMENTARY MATERIAL Unravelling the Biochemical Distribution of Secondary Metabolites in Olea Europaea L.: Exhaustive Characterization of Eight Olive-Tree Derived Matrices by Complementary Platforms (LC-ESI/APCI-MS and GC-APCI-MS) Lucía Olmo-García1, Nikolas Kessler2, Heiko Neuweger2, Karin Wendt2, Alberto Fernández- Gutiérrez1, José María Olmo-Peinado3, Carsten Baessmann2, Alegría Carrasco-Pancorbo1* 1 Department of Analytical Chemistry, Faculty of Science, University of Granada, Ave. Fuentenueva s/n, 18071, Granada, Spain. 2 Bruker Daltonik GmbH, Fahrenheitstraße 4, 28359 Bremen, Germany. 3 Acer Campestres S.L., Almendro, 37 (Pol. Ind. El Cerezo), 23670, Castillo de Locubín, Jaén, Spain *Corresponding author: [email protected] Index Figure S1. Extracted Ion Chromatograms (EICs) of all the identified compounds in olive oil obtained from stoned and dehydrated fruits, when it is analyzed by means of each evaluated platform and polarity. Figure S2. MetFrag in-silico fragmentation for two tentatively annotated metabolites (A and B), and spectral library match for compound B. Figure S3. Distribution of secoiridioids in the eight matrices under study (representation of the sum of absolute areas). Table S1. List of compounds detected with LC-MS methodologies. Table S2. List of compounds detected with GC-APCI-MS. Table S3. Distribution of the determined metabolites in the eight evaluated samples (all the given values are % referred to the richest sample regarding each analyte). 1 /14 Figure S1. Extracted Ion Chromatograms (EICs) of all the identified compounds in olive oil obtained from stoned and dehydrated fruits, when it is analyzed by means of each evaluated platform and polarity. Intens. x106 LC-ESI-MS(-) 6 4 2 0 74 Intens. (+) x106 LC-ESI-MS 6 4 2 0 Intens. (-) x105 LC-APCI-MS 4 3 2 1 0 Intens. LC-APCI-MS(+) x106 6 4 2 0 4 7 0 2 4 6 8 10 12 14 Time [min] Intens. (+) x106 GC-APCI-MS 6 4 2 0 1 0 10 20 30 40 Time [min] 2 /14 Figure S2. MetFrag in-silico fragmentation for two tentatively annotated metabolites (A and B), and spectral library match for compound B. A) Gingerol 221.154 205.123 177.092 148.054 B) Dihydrokaempferol 125.026 177.055 151.003 213.056 201.055 133.029 241.048 259.063 159.044 3 /14 Figure S3. Distribution of secoiridoids in the eight matrices under study (representation of the sum of absolute peak areas). Area x108 8 6 4 2 0 Leaves Stems Skin Pulp VOO Dehydro Seed Seed Oil VOO Elenolic acid derivatives Oleuropein derivatives Ligstroside derivatives Glycosilated secoiridoids 4 /14 Table 1. List of compounds detected with LC-MS methodologies. Neutral Negative Positive Rt Compound Molecular Error Error ID (min) m/z mSigma ESI MS signal APCI MS signal m/z mSigma ESI MS signal APCI MS signal formula (mDa) (mDa) - + + + quinic acid C7H12O6 0.6 191.0555 -0.621 8.8 [M-H] - 193.0710 0.318 8.7 [M+H] , [M-H2O+H] [M+H] S - + + citric acid C6H8O7 0.7 191.0191 -0.651 3 [M-H] - 175.0238 0.052 8.4 [M-H2O+H] , [M+H] - L - - + + + 3,4-dihydroxyphenylglycol C8H10O4 0.8 151.0399 -0.342 8.9 [M-H2O-H] , [M-H] - 153.0544 -0.235 20.1 [M-H2O+H] , [M+H] [M+H] L - - + + oxydized hydroxytyrosol C8H8O3 1.0 151.0398 -0.808 15.6 [M-H] [M-H] 153.0536 0.092 8.9 [M+H] , [M-H2O+H] - L - - + + + + hydroxytyrosol glucoside C14H20O8 1.7 315.1085 -0.065 3.8 [M-H] [M-H] 317.1235 0.357 5.7 [M+H] , [M-H2O+H] [M+H] , [M-H2O+H] L + + hydroxydecarboxymethylelenolic - - [M-H2O+H] , [M+H] , C9H12O5 1.7, 2.1 199.0607 -0.473 8.5 [M-H] [M-H] 183.0654 0.230 9 - L acid isomers I and II [M+Na]+ - gallic acid C7H6O5 1.8 169.0140 -0.793 26.6 [M-H] - - - - - - S - - [M+H]+, [M-H2O+H]+, + acyclodihydroelenolic acid hexoside C17H28O11 1.8 407.1560 0.105 11.1 [M-H] [M-H] 409.1701 -0.476 6.3 [M+H] L [M+Na]+ + + decarboxylated form of - - - [M-H2O+H] , [M+H] , + + C10H14O5 1.9, 2.2 213.0768 -0.044 9.2 [M-H] , [M-H2O-H] [M-H]-, [M-H-H2O] 197.0813 0.614 15.2 [M-H2O+H] , [M+H] L hydroxyelenolic acid isomers I and II [M+Na]+ - - + + hydroxytyrosol C8H10O3 1.9 153.0551 -0.594 0.2 [M-H] [M-H] 155.0700 -0.276 7.7 [M+H] [M+H] S - - + + protocatechuic acid C7H6O4 1.9 153.0190 -0.309 8.2 [M-H] [M-H] 155.0338 -0.644 12.5 [M+H] , [M-H2O+H] - S - - + tyrosol glucoside C14H20O7 2.0 299.1139 0.191 1.6 [M-H] [M-H] 301.1292 0.870 19.2 [M+H] - L - + + aesculin C15H16O9 2.0 339.0720 0.026 17.2 [M-H] - 341.0877 1.033 0.4 [M+H] [M+H] L - - - dihydrooleuropein C25H36O13 2, 2.9 543.2082 -1.109 28.6 [M-H] , [M-H2O-H] [M-H]-, [M-H-H2O] - - - - - L - - + oleoside/secologanoside C16H22O11 2.1 389.1091 0.014 4.7 [M-H] [M-H] 391.1165 0.163 7.6 [M+H] - L - - + eudesmic acid C10H12O5 2.2 211.0607 0.236 28.9 [M-H] [M-H] 231.0766 0.092 3.5 [M+H] - L + + - - [M-H2O+H] , [M+H] , tyrosol C8H10O2 2.3 137.0608 -0.006 6.2 [M-H] [M-H] 121.0642 -0.628 4.6 - S [M+Na]+ - + gentisic acid C7H6O4 2.3 153.0119 -0.309 8.2 [M-H] - 155.0338 -0.644 20.1 [M+H] - S - + luteolin diglucoside C27H30O16 2.3 609.1461 1.746 30.1 [M-H] - 611.1608 -0.409 20.1 [M+H] - L - - + cyanidin 3-O-glucoside C21H22O11 2.3 449.1095 0.530 3.4 [M-H] [M-H] 451.1217 -0.755 17.3 [M+H] - L - + + 4-hydroxybenzoic acid C7H6O3 2.4 137.0246 0.339 8.2 [M-H] - 139.0384 -0.512 5.5 [M+H] [M+H] S - - + + + elenolic acid glucoside C17H24O11 2.4 403.1246 0.093 9.3 [M-H] [M-H] 405.1396 -0.383 21.2 [M+H] , [M-H2O+H] [M+H] L - - + 4-hydroxyphenylacetic acid C8H8O3 2.4 151.0397 -0.279 5.6 [M-H] [M-H] 153.0542 -0.133 7.2 [M+H] - S - - + unknown 1 C16H26O10 2.4 377.1453 0.000 5.7 [M-H] [M-H] 379.1604 0.500 23.3 [M+H] - - - - + + aesculetin C9H6O4 2.5 177.0188 -0.923 3.3 [M-H] [M-H] 179.0340 -0.163 27.6 [M+H] [M+H] L - - + vanillic acid C8H8O4 2.5 167.0345 -0.459 7.1 [M-H] [M-H] 169.0497 -0.868 30.6 [M+H] - S - + + + caffeic acid C9H8O4 2.5 179.0347 -0.310 8.3 [M-H] - 181.0495 -0.036 29.1 [M+H] , [M-H2O+H] [M+H] S - gallocatechin C15H14O7 2.6 305.0702 3.507 27.6 [M-H] - - - - - - L + + - [M+H] , [M-H2O+H] , + + unknown 2 C9H14O3 2.6 169.0869 0.135 17.1 [M-H] - 171.1016 0.012 6.2 [M+H] , [M-H2O+H] - [M+Na]+ - - + + + decarboxymethylelenolic acid C9H12O4 2.6 183.0658 -0.526 8 [M-H] [M-H]-, [M-H-H2O] 185.0812 0.348 7.8 [M+H] , [M-H2O+H] [M+H] L 5 /14 Neutral Negative Positive Rt Compound Molecular Error Error ID (min) m/z mSigma ESI MS signal APCI MS signal m/z mSigma ESI MS signal APCI MS signal formula (mDa) (mDa) - - + + 2-phenethyl β-primeveroside C19H28O10 2.6 415.1612 0.102 3.8 [M-H] [M-H] 417.1749 -2.830 41.3 [M+H] [M+H] L - - + unknown 3 C18H34O14 2.6 473.1863 1.278 40.3 [M-H] [M-H] 475.2054 0.976 30.2 [M+H] - - - - + syringic acid C9H10O5 2.6 197.0452 -0.004 12.4 [M-H] [M-H] 199.0601 -0.402 8.9 [M+H] - S - - + + homovanillic acid C9H10O4 2.7 181.0502 -0.778 13.6 [M-H] [M-H] 183.0655 0.051 36.9 [M+H] [M+H] S - - + rutin C27H30O16 2.7 609.1464 0.278 5 [M-H] [M-H] 611.1615 0.290 25.9 [M+H] - S - - + luteolin rutinoside C27H30O15 2.7 593.1516 0.047 27.3 [M-H] [M-H] 595.1671 0.805 26.2 [M+H] - L - - hydroxyoleuropein C25H32O14 2.7 555.1717 -0.391 4.7 [M-H] [M-H]-, [M-H-H2O] - - - - - L + + - - [M+H] , [M-H2O+H] , + p-coumaric acid C9H8O3 2.8 163.0397 -0.107 11.8 [M-H] [M-H] 165.0545 -0.084 7.3 [M+H] S [M+Na]+ - - + + quercetin 4-O-glucoside C21H20O12 2.8 463.0882 -0.010 29.3 [M-H] [M-H] 465.1007 -2.035 30.8 [M+H] [M+H] S - - + + luteolin 7-O-glucoside C21H20O11 2.8 447.0933 0.009 11 [M-H] [M-H] 449.1078 -0.586 17.2 [M+H] [M+H] S - + verbascoside C29H36O15 2.8 623.1981 -0.003 14.6 [M-H] - 625.2139 -0.840 31.7 [M+H] - L - - oleuropein glucoside C31H42O18 2.9 701.2303 0.503 7.7 [M-H] [M-H] - - - - - L - + + apigenin 7-O-rutinoside C27H30O14 2.9 577.1568 1.094 29.5 [M-H] - 579.1701 -0.732 18.6 [M+H] [M+H] SL hydroxyelenolic acid isomers I, 2.9, 3.1, - - - + + + C11H14O7 257.0669 0.187 12.4 [M-H] , [M-H2O-H] [M-H-H2O]-, [M-H] 259.0816 1.412 12.9 [M+H] , [M-H2O+H] [M+H] L II and III 3.3 - - + nuzhenide C31H42O17 2.9 685.2346 -0.005 5.8 [M-H] [M-H] 507.1867 0.600 12.9 [M-C6H12O6+H] - L - - + + + sinapic acid C11H12O5 2.9 223.0615 -0.045 9.9 [M-H] [M-H] 225.0765 0.482 11.8 [M+H] [M+H] , [M-H2O+H] S - - cafselogoside C25H28O14 2.9 551.1409 0.307 8 [M-H] , [M-H2O-H] - - - - - - L + + - - [M+H] , [M+Na] , + + unknown 4 C11H16O6 3.0 243.0876 0.141 11.1 [M-H] [M-H] 245.1025 0.486 13.7 [M-H2O+H] , [M+H] - [M+K]+ - - + + vanillin C8H8O3 3.0 151.0396 -1.103 9.8 [M-H] [M-H] 153.0543 0.567 14.1 [M+H] [M+H] S - - + + + + ferulic acid C10H10O4 3.1 193.0503 -0.570 7.6 [M-H] [M-H] 195.0658 0.597 9.6 [M+H] , [M-H2O+H] [M-H2O+H] , [M+H] S - - + + luteolin 4'-O-glucoside C21H20O11 3.1 447.0934 0.075 13.4 [M-H] [M-H] 449.1057 -0.638 16.2 [M+H] [M+H] SL - - + + + taxifolin C15H12O7 3.1 303.0509 0.079 18.3 [M-H] [M-H]-, [M-H-H2O] 305.0661 0.206 27 [M+H] , [M-H2O+H] [M+H] L - - + + apigenin 7-O-glucoside C21H20O10 3.1 431.0990 0.667 26.9 [M-H] [M-H] 433.1124 -0.506 5.5 [M+H] [M+H] S - + quercetin glucoside isomer C21H20O12 3.1 463.0884 -0.068 6.1 [M-H] - 465.1001 -2.035 30.8 [M+H] - L - - + + desoxyelenolic acid C11H14O5 3.1, 3.6 225.0771 -0.292 7 [M-H] [M-H] 227.0913 -0.415 21.3 [M+H] [M+H]+, [M-H2O+H] L - - + luteolin glucoside isomer C21H20O11 3.2 447.0914 -0.259 11 [M-H] [M-H] 449.1056 -0.749 9.4 [M+H]+ [M+H] L - - + + chrysoeriol 7-O-glucoside C22H22O11 3.2 461.1078 -0.885 31.8 [M-H] [M-H] 463.1235 -0.537 20.3 [M+H] [M+H] SL - - + + comselogoside isomers I and II C25H28O13 3.2, 3.6 535.1457 0.014 37.5 [M-H] [M-H]-, [M-H-H2O] 537.1527 -3.132 39.1 [M+H] [M+H] L 10-hydroxyoleuropein aglycone - - + C19H22O9 3.3, 4.1 393.1197 -0.871 35.9 [M-H] [M-H] 395.1331 1.180 20.6 [M+H] - L isomers I and II hydroxytyrosol - - + + C19H26O8 3.3 381.1560 0.482 22.1 [M-H] , [M-H2O-H] [M-H]-, [M-H-H2O]-
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