Hydroxyflavones as a New Family of Matrices for MALDI Tissue. Imaging

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Supporting Information: Hydroxyflavones as a New Family of Matrices for MALDI Tissue Imaging Xiaodong Wang, Jun Han, Albert Chou, Juncong Yang, Jingxi Pan, and Christoph H. Borchers *,, University of Victoria - Genome British Columbia Proteomics Centre, Vancouver Island Technology Park, #3101-4464 Markham St., Victoria, BC V8Z 7X8, Canada Department of Biochemistry and Microbiology, University of Victoria, Petch Building Room 207, 3800 Finnerty Rd., Victoria, BC V8P 5C2, Canada *Corresponding author: Christoph H. Borchers, Ph.D. Email: christoph@proteincentre.com Tel.: (250) 483-3221; Fax: (250) 483-3238 S-1

Supporting Information - Methods Lipid Extraction and LC-MS/MS Analysis. Total lipids from the same rat liver and brain, which have been subjected to MALDI profiling or imaging, were extracted according to a previously described protocol, 1 with slight modifications. Briefly, the tissue aliquots in an amount of ca. 20 mg were homogenized in 200 µl of water inside 1.5 ml Eppendorf tubes with a Retsch MM400 mixer mill (Haan, Germany) with the aid of two 5-mm stainless steel metal balls for 30 s x 2 at a vibration frequency of 30 Hz. Next, 800 µl of a mixed chloroform-methanol (1:3, v/v) solvent was added to each tube, followed by another 30-s homogenization step using the same mixer mill settings. The tubes were then centrifuged at 4,000 x.g. and 4 o C for 20 minutes in a Beckman Coulter Allegra X-22R centrifuge (Brea, CA). The supernatants were collected and mixed with 250 µl of chloroform and 100 µl of water. After vortex mixing for 15 s and centrifugation at 10,600 x.g. for 5 min in a microcentrifuge, the lower organic phase in each tube was carefully removed using a 200-µL gel loading pipette tip, and then dried in a Savant SPD1010 speed-vacuum concentrator (Thermo Electron Corporation, Waltham, MA). The residues were stored at -80 o C until used. LC-MS/MS. Because of the low-mass cut-off (ca. m/z 130) and the relatively low sensitivity of the 12-Tesla FTICR MS instrument for MALDI-MS/MS of many of the lipids, hydrophilic interaction liquid chromatography (HILIC)-MS/MS was performed for verification of the lipid identities. Briefly, a Waters ACQUITY UPLC system coupled to a Waters Synapt HDMS quadrupole-time-of-flight (Q-TOF) mass spectrometer (Beverly, MA) was employed. The dried lipid extract residues were reconstituted in 100 µl of chloroform, and 10-µL aliquots were injected onto a Waters Atlantis HILIC silica column (3 µm particle size, 4.6 mm i.d. x150 mm; Beverly, MA) for separation of different lipid species based on their head groups. 2-4 The mobile phase for S-2

binary gradient elution was composed of methanol-water (75:5, v/v) containing 0.2% ammonium formate (ph adjusted to 5.9 with formic acid) as solvent A and acetonitrile-methanol-water (95:2:3, v/v/v) containing 0.2% ammonium formate (ph 5.9) as solvent B. The elution gradient was as follows: 100% B, 0 to 5 min; 100% to 90% B, 5 to 6 min; 90% to 35% B, 6 to 30 min; 35% to 10% B, 30 to 32 min, and 10% solvent B, 32 to 34 min. The column was then re-equilibrated at 100% B for 6 min between injections. The flow rate was 0.6 ml/min and the HILIC column was maintained at 30 o C. LC/MS data were collected in both positive and negative ESI modes, with respective injections. The detection mass range was m/z 80 to 1,200, with a scan rate of 0.25 s. MS/MS experiments were conducted using collision-induced dissociation (CID) at three collision energies (10, 20, and 30 V), which were applied to the trapping collision cell of the Q-TOF instrument. UPLC-full-scan MS data were processed with the MarkerLynx module embedded in the Waters MassLynx software (version 4.1) suite. Lipid identities were assigned by combining mass-matched metabolome database searching against the METLIN database 5 with MS/MS spectral searching against the standard MS/MS libraries in the METLIN, HMDB 6, 7 or LIPID MAPS databases, 8, 9 or using manual mass spectral interpretation. The parameters for peak extraction and alignment within the MarkerLynx module were as follows: allowable mass window, 50 ppm; retention time shift tolerance, ±0.1 min; ion intensity threshold, 50; and LC retention time range for data extraction, 1 to 27 min. S-3

Supporting Information Figure S1. Orthogonal array testing for optimization of quercetin matrix solution compositions. (A) Three variables (% of methanol in water, quercetin concentration, and % of NH 4 OH) x three levels for each factor tested. (B) Range analysis ( N max) for nine combinations of three factors x three levels for each factor. The % of NH 4 OH was shown as a dominant factor, while the % of methanol in water was a factor with the weakest impact. (C) Coated quercetin matrix appearances on rat liver tissue sections from spray of the nine matrix solutions. Combinations 2 and 5 showed good matrix application; combinations 3, 6, 8, and 9 led to matrix over-coating; and combinations 1, 4, and 7 led to deficient matrix coating. (D-F) Mass spectra of on-tissue lipid detection with quercetin as the matrix, using three different solution compositions. The solution composing 2.6 mg/ml quercetin in 80% methanol with 0.1% NH 4 OH was the best. (G) Overlay of mass spectra of the quercetin adduct ion [2M+K] +, before and after matrix solution optimization, showing the reduction of [2M+K] + ion after optimization. Two ESIgenerated ions from the ESI tuning mix solution, i.e., m/z 622.02908 and m/z 922.0098, were used as the controls. S-4

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Supporting Information Figure S2. (A) Comparison of the matrix morphology of quercetin and 2-MBT on rat liver tissue sections, examined by scanning electron microscopy after matrix coating. (B) Comparison of MALDI-FTICR mass spectra of lipid profiles detected on two serial rat liver tissue sections with 2-MBT (upper) and quercetin (lower) as the MALDI matrices, respectively. The matrix-related signals have been labeled with triangles. (C) collision-induced dissociation mass spectra of m/z 457.20 [M-H] - and m/z 749.53[M-H] - by LC-(-)ESI MS/MS. These two phosphotidic acids (PAs) were identified as PA(20:4/0:0) and PA(18:0/22:5), respectively. These two PAs were detected as their [M+K] + ions, on the same rat liver tissue sections, with positive-ion MALDI-FTICR MS with quercetin as the matrix. S-6

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Supporting Information Figure S3. Venn diagram comparison of lipid detection on rat liver sections by MALDI-FTICR MS in the positive-ion mode using quercetin or 2-MBT as the matrices. S-9

Supporting Information Figure S4. Evaluation of the stability of quercetin as a MALDI matrix. Rat liver sections were coated with quercetin and loaded onto the FTICR ion sources operated at a ~10-7 mbar vacuum for different time periods. Mass spectra were acquired at 0 hour (A), 6 hours (B), 12 hours (C), and 24 hours (D); and re-measured by MALDI-FTICR MS after being kept at room temperature for 13 days (E) and 28 days (F). A total of 161, 159, 159, 158, 157, 158 lipid entities were detected and identified, and no change in lipid detection was found, demonstrating the low volatility of quercetin under both the high vacuum and atmospheric pressure conditions. S-10

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Supporting Information Figure S5. Optical images of a H&E-stained rat brain section before the matrix coating and after removal of the coated quercetin matrix. S-12

Supporting Information Figure S6. MALDI-FTCIR mass spectrum acquired from a 12-µm thick rat brain tissue section with quercetin as the matrix. A total of 212 lipids were identified. S-13

Supporting Information Table S1. Optimized matrix solution compositions for the ten flavonoid compounds. Compounds Final concentration (mg/ml) Methanol (%) NH 4 OH (%) Flavone 2.5 80 0.1 7,3,4 - trihydroxyflavone 2.5 80 0.1 3-hydroxyflavone Saturated (<2.5) 90 0.5 5-hydroxyflavone Saturated (<2.5) 90 0.5 3,7-dihydroxyflavone 2.5 85 0.3 Chrysin 2.5 85 0.3 Fisetin 2.5 85 0.3 Luteolin 2.5 85 0.3 Quercetin 2.6 80 0.1 Morin 2.6 80 0.1 S-

Supporting Information Table S2. Comparison of lipid detection on rat liver sections by MALDI-FTICR MS in the positive-ion mode with ten flavone-type compounds as the MALDI matrices. Classification Glycerophospholipids Phosphatidylcholines (PCs) Flavone 3-HF 5-HF 3,7-DHF Chrysin Peak lists of lipid candidates 7, 3, 4 - THF Fisetin Luteolin Quercetin Morin Compounds - 496.33968 496.33912 496.33976 496.33920-496.33815 496.33956 496.34001 496.33953 PC(16:0/0:0) - 518.32416-518.32425 518.32412-518.32417 518.32409 518.32422 518.32406-520.33999-520.33987 520.33996-520.34034 520.33939 520.34018 520.33958 - - - - - - - - 522.35546 522.35537 PC(18:3) LysoPC(18:3) PC(18:2) LysoPC(18:2) PC(O-18:1) PC(18:1) - 524.37106 524.37133 524.37131 524.37124-524.37119 524.37106 524.37096 524.37107 PC(18:0/0:0) - 534.29564-534.29568 534.29567-534.29558 534.29588 534.29566 534.29572 PC(16:0/0:0) - 542.32171 542.32154 542.32173 542.32173-542.32172 542.323 542.32162 542.32167 PC(18:2) LysoPC(18:2) - 544.33951-544.33892 544.33910-544.33888 544.33933 544.33950 544.33959 PC(20:4/0:0) - 546.35302 546.35291 546.35301 546.35304-546.35308 546.35267 546.35360 546.35398 PC(18:0/0:0) - 558.29559 558.29566 558.29560 558.29561-558.29553 558.29538 558.29555 558.29555 PC(18:2) LysoPC(18:2) - 560.317-560.31133 560.31132-560.31126 560.315 560.31124 560.31136 PC(18:1/0:0) - 562.32696-562.32697 562.32696-562.32677 562.3269 562.32699 562.32683 PC(18:0/0:0) - 566.32167 566.32165 566.32169 566.32167-566.32155 566.328 566.32168 566.32160 PC(20:4/0:0) - - - 568.33890 568.33883-568.33876-568.33865 568.33873 PC(22:6) LysoPC(22:6) - 582.29565 582.29528 582.29565 582.29563-582.29558 582.29539 582.29565 582.29566 PC(20:4/0:0) Structur ally specific CID ions (m/z) a) 104, 184, 478, 496 104, 184, 506, 524 104, 184, 478, 496 104, 184, 526, 544 104, 184, 506, 524 104, 184, 504, 522 104, 184, 506, 524 104, 184, 526, 544 104, 184, 526, 544 S-15

Classification Flavone 3-HF 5-HF 3,7-DHF Chrysin Peak lists of lipid candidates 7, 3, 4 - THF Fisetin Luteolin Quercetin Morin - 606.29549-606.29564 606.29552-606.29539 606.29526 606.29568 606.29540 Compounds PC(22:6) LysoPC(22:6) - 608.31153-608.31201 608.31220-608.31213 608.31205 608.31183 608.31222 LysoPC(22:5) - 734.56934 734.56949 734.56932 734.56989-734.56958 734.56966 734.56951 734.56948 PC(16:0/16:0) - 756.55150 756.55075 756.55103 756.55119-756.55054 756.55069 756.55242 756.55067 PC(16:0/16:0) Structur ally specific CID ions (m/z) a) 104, 184, 478, 735 104, 184, 478, 735-758.56936 758.56951 758.56971 758.56995-758.56965 758.56981 758.57132 758.56926 PC(34:2) 184, 759-760.58560 760.58550 760.58569 760.58550-760.58565 760.58510 760.58562 760.58558 PC(16:0/18:1) - 772.52500 772.52539 772.52517 772.52531-772.52561 772.52537 772.52500 772.52542 PC(16:0/16:0) - 778.53536 778.53575 778.53518 778.53534-778.53556 778.53564 - - PC(34:3) - 780.55095 780.55110 780.55079 780.55109-780.55028 780.55079 780.55131 780.55037 PC(34:2) 86, 184, 761 104, 184, 478, 735-782.56882 782.56939 782.56894 782.56897-782.56903 782.56875 782.56805 782.56841 PC(36:4) 184, 783-784.58685 784.58654 784.58732 784.58648-784.58635 784.58612 - - PC(36:3) 184, 785-786.60052 786.60077 786.60067 786.60081-786.60058 786.60052 786.60084 786.60098 PC(36:2) 184, 787-788.61657 788.61737 788.61745 788.61753-788.61646 788.61639 788.61645 788.61652 PC(36:1) 184, 789-792.56762-792.56641 792.56713-792.56636 792.56751 792.56749 792.56749 1-hexadecanyl-2-(8-[3]- ladderane-octanyl)-snglycerophosphocholine - 794.50963 794.50933 794.50995 794.50911-794.51032 794.51026 794.50946 794.51016 PC(34:3) - 796.52605 796.52600 796.52602 796.52609-796.52605 796.52608 796.52608 796.52606 PC(34:2) 184, 758-798.542 798.54150 798.54133 798.54110-798.54128 798.54123 798.54121 798.54132 PC(16:0/18:1) - - - - - - - - 800.55731 800.55725 PC(34:0) - 804.55122 804.55160 804.55121 804.55134-804.55043 804.55162 804.55117 804.55154 PC(36:4) 184, 783-808.58268 808.58282 808.58268 808.58281-808.58252 808.58284 808.58267 808.58262 PC(36:2) 184, 787-810.60072 810.60086 810.60105 810.60134-810.60077 810.60112 810.60073 810.60078 PC(18:0/20:4) 184, 754 86, 184, 760 184, 627, 752, 811-818.50937 818.50931 818.50926 818.50928-818.50910 818.50939 818.50924 818.50913 PC(36:5) 184, 780-820.52492 820.52534 820.52507 820.52522-820.52527 820.52536 820.52527 820.52524 PC(36:4) 184, 783-822.54061 822.54031 822.54058 822.54090-822.54110 822.54041 822.54098 822.54060 PC(36:3) 184, 785 S-16

Classification Flavone 3-HF 5-HF 3,7-DHF Chrysin Peak lists of lipid candidates 7, 3, 4 - THF Fisetin Luteolin Quercetin Morin Compounds Structur ally specific CID ions (m/z) a) - 824.55639 824.55681 824.55648 824.55662-824.55664 824.55678 824.55658 824.55639 PC(36:2) 184, 787-826.57301 826.57307 826.57302 826.57302-826.57313 826.57305 826.57301 826.57311 PC(36:1) 184, 789-828.55196 828.554 828.55116 828.55182-828.55118 828.55153 828.55157 828.555 PC(38:6) 184, 807-832.58235 832.58285 832.58244 832.58266-832.58251 832.58263 832.58268 832.58236 PC(18:0/20:4) - - - - - - - - 836.61394 836.61385 PC(38:2) 184, 627, 752, 811-844.52564 844.52563 844.52501 844.52511-844.52555 844.52557 844.52558 844.52566 PC(38:6) 184, 807-846.54121 846.54056 846.54087 846.54116-846.54113 846.54089 846.54118 846.54117 PC(38:5) 184, 809-848.55616 848.55668 848.55638 848.55660-848.55653 848.55680 848.55644 848.55653 PC(18:0/20:4) - 856.58236 856.58303 856.58249 856.58273-856.58221 856.58296 856.58253 856.58263 PC(18:0/22:6) - - -- - - - - - 870.541 870.54106 PC(40:7) - 872.55616 872.55669 872.55631 872.55635-872.55616 872.55699 872.55617 872.55603 PC(18:0/22:6) 184, 627, 752, 811 86, 184, 776, 834 86, 184, 776, 834-874.57265 874.57226 874.57261 874.57284-874.57261 874.57306 874.57223 874.57243 PC(40:5) 184, 837-883.69055-883.69035 883.690 - - - 883.69037 883.69028 PC(42:4) Phosphatidylethanolamines (PEs) - 492.24859-492.24864 492.24845-492.24863 492.24833 492.24874 492.24864 PE(16:0/0:0) - 510.35586-510.35578 510.35551 510.35589 510.35598 510.35548 510.35552-516.24879-516.24901 516.24909-516.24849 516.24891 516.24869 516.24876 - - - - - - - - 518.26454 518.26446 PE(20:0) LysoPE(20:0) PE(18:2) LysoPE(18:2) PE(18:1) LysoPC(18:1) - 520.28006-520.27996 520.27997-520.28037 520.27974 520.28004 520.27996 PE(18:0/0:0) - 534.35530 534.35523 534.35512 534.35539-534.35504 534.35534 534.35540 534.35544 PE(22:2) 153, 196, 2, 255, 391, 409, 452 0, 153, 196, 2, 283, 419, 437, 480 S-17

Classification Flavone 3-HF 5-HF 3,7-DHF Chrysin Peak lists of lipid candidates 7, 3, 4 - THF Fisetin Luteolin Quercetin Morin - 538.386-538.38619 538.38655-538.38663 538.38684 538.38640 538.38627 Compounds LysoPE(22:2) PE(22:0) LysoPE(22:0) - 540.24831-540.24846 540.24893-540.24879 540.24871 540.24878 540.24874 PE(20:4/0:0) - - 544.28039 544.28019 - - 544.28009-544.28024 544.28006-548.31080-548.31122 548.31099-548.31107 548.31095 548.31098 548.31118 - - - 564.24852 564.24867-564.24894-564.24857 564.24872-568.27973 568.27963 568.27803 568.27883-568.27953 568.27873 568.28018 568.28003 PE(20:2) LysoPE(20:2) PE(20:0) LysoPE(20:0) PE(22:6) LysoPE(22:6) PE(22:4) LysoPE(22:4) - 623.43938 623.43980 623.43949 623.43943-623.43973 623.43967 623.43941 623.43915 PE(26:1) Structur ally specific CID ions (m/z) a) 153, 195, 259, 303, 500-754.47824 754.47794 754.47870 754.47851-754.47777 754.47883 754.47809 754.47813 PE(34:2) 255, 279-772.585 772.58555 772.58568 772.58585-772.58527 772.58557 772.58555 772.58505 PE(38:2) 283, 307-778.47873 778.47848 778.47838 778.47809-778.47867 778.47869 778.47805 778.47780 PE(16:0/20:4) - - - 782.50963 782.50986-782.50945 782.50996 782.50967 782.50953 PE(18:1/18:1) - 796.52465 796.52471 796.52462 796.52489-796.52465 796.52478 796.52498 796.52476 PE(P-40:7) or 1-(8-[3]-ladderane- octanoyl)-2-(8-[3]- ladderane-octanyl)snglycerophosphoethanola mine - 798.54020 798.54021 798.540 798.54015-798.54018 798.54024 798.54022 798.54036 PE(P-18:0/22:6) - - - - - - - - 800.55594 800.55586 PE(P-40:5) - 800.61633 800.61642 800.61631 800.616-800.61620 800.61639 800.61646 800.61634 PE(40:2) 195, 255, 259, 303, 434, 452, 482, 500, 738 195, 281, 460, 478, 742 283, 327, 446, 464, 774 S-18

Classification Flavone 3-HF 5-HF 3,7-DHF Chrysin Peak lists of lipid candidates 7, 3, 4 - THF Fisetin Luteolin Quercetin Morin Compounds Structur ally specific CID ions (m/z) a) - 802.47787-802.47780 802.47818-802.47822 802.47894 802.47791 802.47811 PE(38:6) 279, 303 - - - - - - - - 804.49389 804.49378 PE(38:5) - 806.50961 806.50953 806.50938 806.50913-806.50959 806.50968 806.50941 806.50953 PE(38:4) - - - 824.61693 - - 824.61710 824.61698 824.61664 824.61641 PE(42:4) - 826.57155 826.576 826.576 826.572-826.57163 826.57155 826.571 826.57139 PE(P-42:6) - - - - - - 830.51028 830.51015 830.50988 830.50990 PE(40:6) - 834.54083 834.54096 834.54052 834.54102-834.54075 834.54025 834.54108 834.54129 PE(40:4) - - - - - - - - 864.55077 864.55089 PE(44:9) - - - - - - - - 880.52549 880.52538 PE(44:9) 259, 283, 303, 462, 480, 482, 500, 767 283, 327, 462, 480, 506, 524, 791 Phosphatidic acids (PAs) - 475.22239-475.22213 475.22180-475.22202 475.22173 475.22223 475.22206 PA(18:1/0:0) - - - - - - - - 477.23832 477.23800 PA(18:0/0:0) LPA(18:0/0:0) - 487.27921-487.27959 487.27948-487.27973 487.27929 487.27934 487.27977 PA(20:1/0:0) - - - - - - - - 497.20688 497.20651 PA(20:4/0:0) - 499.22224-499.22219 499.22201-499.22199 499.22174 499.22228 499.22211 PA(20:3/0:0) - - - 501.23785 501.23755-501.23725 501.23735 501.23733 501.23764 PA(20:2/0:0) - 503.25316-503.25353 503.25343-503.25340 503.25310 503.25362 503.25349 PA(20:1/0:0) - 631.46937-631.46925 - - 631.46920 631.46941 631.46930 631.46929 PA(P-32:1) - - - 633.48497 - - 633.48498-633.48490 633.48496 PA(O-32:1) or PA(P- 32:0) - 649.51607 649.51602 649.51612 649.516-649.51603 649.516 649.51607 649.51612 PA(O-18:0/15:0) - 655.46925-655.46912 - - 655.46915 655.46939 655.46925 655.46919 PA(P-34:3) or PA(O- 34:4) 79, 153, 171, 283, 437 153, 171, 259, 303, 457 S-19

Classification Flavone 3-HF 5-HF 3,7-DHF Chrysin Peak lists of lipid candidates 7, 3, 4 - THF Fisetin Luteolin Quercetin Morin - - - 659.50051 - - 659.50045 659.50043 659.50053 659.50055 Compounds PA(P-34:1) or PA(O- 34:2) - - - - - - - - 679.46916 679.46919 PA(P-16:0/20:5) - - - - - - - - 683.50052 683.50063 PA(P-36:3) or PA(O- 36:4) - 711.43669-711.43646 711.43673-711.43667 711.43693 711.43630 711.43692 PA(16:0/18:2) - 713.45169 713.45253 713.45177 713.45139-713.45136 713.45189 713.45176 713.45171 PA(16:0/18:1) - - - 735.43604 735.43590-735.43646 735.43588 735.43654 735.43637 PA(36:4) - 737.45160 737.4578 737.45172 737.45186-737.45183 737.45167 737.45169 737.45178 PA(18:1/18:2) - 739.46729 739.46788 739.46750 739.46750-739.46741 739.46750 739.46734 739.46700 PA(18:0/18:2) - 749.50916 749.50957 749.50931 749.50983-749.50973 749.50930 749.50945 749.50985 PA(38:3) - 759.43663-759.43663 759.43632-759.43648 759.43664 759.43690 759.43658 PA(16:0/22:6) - 761.45162 761.45243 761.45167 761.45181-761.45161 761.45184 761.45187 761.45178 PA(38:5) 763.46765 763.46756 PA(38:4) - 765.48307 765.48319 765.48311 765.483-765.48317 765.48316 765.48343 765.48331 PA(38:3) - - - - - - - - 767.49881 767.49872 PA(38:2) - 773.50915 773.50915 773.50923 773.50984-773.50917 773.50929 773.50911 773.50907 PA(40:5) - - - - - - - - 773.51186 773.51177 PA(42:8) - 785.45159 785.45197 785.45167 785.45183-785.45115 785.45177 785.45195 785.45189 PA(40:7) - 787.46759 787.46769 787.46864 787.46798-787.46748 787.46770 787.46760 787.46762 PA(18:0/22:6) Structur ally specific CID ions (m/z) a) 79, 153, 255, 279, 391, 409, 671 153, 255, 281, 391. 409, 417, 435, 673 279, 281, 415, 417, 433, 435 78, 153, 279, 283, 415, 419, 433, 437, 699 153, 255, 283, 391, 409, 463, 481, 719 153, 283, 327, 419, 437, 463, S-20

Classification Flavone 3-HF 5-HF 3,7-DHF Chrysin Peak lists of lipid candidates 7, 3, 4 - THF Fisetin Luteolin Quercetin Morin Compounds - 789.48301 789.48326 789.48302 789.48311-789.48306 789.48312 789.48317 789.48317 PA(18:0/22:5) - 813.48264 813.48367 813.48286 813.483-813.48310 813.48319 813.48352 813.48286 PA(42:7) Structur ally specific CID ions (m/z) a) 481, 747 153, 283, 329, 419, 437, 465, 483, 749 Phosphoglycerols (PGs) - 507.24844-507.24832 507.24834-507.24791 507.24783 507.24825 507.24806 PG(P-16:0) - - - - - - - 837.50426 837.50461 837.50475 PG(18:0/20:4) 152, 259, 283, 303, 419, 437, 438, 457, 593, 511, 513, 531, 798 Phosphatidylserine (PS) - 864.55207 - - - - - - 864.55198 864.55201 PS(O-40:4) or PS(P- 40:3) phosphatidylinositols (PIs) - - - - - - - - 849.45234 849.45225 PI(34:6) - 925.51920 - - - - 925.52094-925.52081 925.52012 PI(18:0/20:4) - - - - - - - - 949.52087 949.52072 PI(40:6) 240, 259, 283, 303, 419, 437, 439, 457, 581, 599, 601, 619, 886-963.47625 963.47687 963.47611 963.47669-963.47702 963.47665 963.47657 963.47645 Glycerophosphoglycerophosphoglycerols CL(1\'- [18:2(9Z,12Z)/0:0],3\'- [18:2(9Z,12Z)/0:0]) S-21

Classification Flavone 3-HF 5-HF 3,7-DHF Chrysin Peak lists of lipid candidates 7, 3, 4 - THF Fisetin Luteolin Quercetin Morin Compounds Structur ally specific CID ions (m/z) a) Cyclic phosphatidic acids (cpas) - - - - - - 431.19606-431.19613 431.19576 CPA(16:0) - - - - - - - - 455.19630 455.19599 CPA(18:2) - - - - - - - - 457.21203 457.21080 CPA(18:1) - - - 459.22756 - - 459.22737 459.22722 459.22746 459.22730 CPA(18:0) Sphingolipids Ceramides (Cers) - 506.36052-506.36050 - - 506.36060 506.36077 506.36044 506.36045 CerP(d18:1/8:0) - - - - - - - - 688.60038 688.59974 Cer(d18:1/24:0) - - - - - - 766.55157-766.55176 766.55151 CerP(d18:1/24:1) 264, 470, 488, 506 264, 671, 689 264, 749, 767 Sphingomyelins (SMs) - 703.57471 703.57512 703.57429 703.57556 - - 703.57475 703.57461 703.57472 SM(d18:1/16:0) 644, 520-725.55653 725.55705 725.55669 725.55655-725.55679 725.55667 725.55652 725.55709 SM(d18:1/16:0) - 741.53052 741.53082 741.53067 741.53070-741.53067 741.53054 741.53049 741.53041 SM(d18:1/16:0) - 769.56201 769.56253 769.56261 769.56250-769.56228 769.56267 769.56205 769.56205 SM(d18:1/18:0) - - - - - - - - 797.59353 797.59344 SM(d18:1/20:0) - 813.68403 813.68486 813.68518 813.68557 - - - - - SM(d18:1/24:1) - 815.69989 815.70051 815.70059 815.69952 - - 815.70104 - - SM(d18:1/24:0) - - - - - - - - 825.62454 825.62456 SM(d18:1/22:0) 7, 666, 542 184, 163, 682 184, 703, 731-837.68208 837.68274 837.68209 837.6811-837.68233 837.68239 837.68251 837.68240 SM(d18:1/24:0) 778, 654-851.64005 851.64091 851.64042 851.64065-851.64094 851.64085 851.63930 851.64060 SM(d18:1/24:1) - 853.65611 853.65622 853.65656 853.65635-853.65623 853.65663 853.65555 853.65551 SM(d18:1/24:0) S-22

Classification Flavone 3-HF 5-HF 3,7-DHF Chrysin Peak lists of lipid candidates 7, 3, 4 - THF Fisetin Luteolin Quercetin Morin Compounds Structur ally specific CID ions (m/z) a) Neutral Lipids Glycerolipids Monoacyllglycerol (MAG) - - - 369.24007 369.24060-369.24013 369.23987 369.24022 369.24020 MG (16:0) - - - 397.27162 397.27109-397.27151 397.27155 397.27152 397.275 MG (18:0) - - - - - - - - 417.24044 417.24023 MG (20:4) 239, 257, 313, 331, 369 Diacylglycerols (DAGs) - - - - - - - - 551.50349 551.50383 DG(P-:0/18:1(9Z)) - 603.53497-603.53484 - - 603.53443 603.53419 603.53477 603.53510-621.48564 - - - - - 621.48547 621.48522 - - 631.47035-631.47025 - - 631.47020 631.47031 631.47030 631.47039 DG(34:2) - 633.48598-633.48597 - - 633.48598-633.48590 633.48589 DG(34:1) - 649.51717 649.51702 649.51712 649.517-649.51708 649.517 649.51707 649.51712 DG(16:0/19:0/0:0)[iso2] - 651.53467 651.53473 651.53463 651.53427-651.53509 651.53506 651.53468 651.53470 1-(-methyl- pentadecanoyl)-2-(8-[3]- ladderane-octanyl)-snglycerol 1-(6-[5]-ladderane- hexanoyl)-2-(8-[3]- ladderane-octanyl)-snglycerol 1-(8-[3]-ladderane- octanoyl-2-(8-[3]- ladderane-octanyl)-snglycerol - - - 655.47009 - - 655.47015 655.47019 655.47015 655.47009 DG(36:4) - - - 659.50171 - - 659.50165 659.50173 659.50183 659.50155 DG(36:2) - - - - - - - - 679.47036 679.47027 DG(38:6) - 682.45697 682.45708 682.45715 682.45727-682.45664 682.45701 682.45709 682.45726 DG(40:8) - - - - - - - - 683.50165 683.50183 DG(38:4) Sterol Lipids S-23

Classification Flavone 3-HF 5-HF 3,7-DHF Chrysin Peak lists of lipid candidates 7, 3, 4 - THF Fisetin Luteolin Quercetin Morin Compounds - - - - - - - - 431.32805 - Conicasterol B - 687.54822-687.54781 687.54787-687.54799-687.54759 687.54707-397.27097-397.27092 397.27099-397.27095 397.27096 397.27092 397.27094 18:2 Cholesteryl ester or zymosteryl oleate 3-Oxo-5β-cholan-24-oic Acid Structur ally specific CID ions (m/z) a) Fatty acyls Fatty acids (FAs) - 319.20344 319.20310 319.20337 319.20332-319.20367 319.20331 319.20347 319.20335 FA(18:2) - 321.21965 - - 321.21920 - - 321.21965 321.21906 - FA(18:1) - - - - - - - - 335.19832 335.19826 FA(18:2) - 343.20353-343.20335 343.20325-343.20326 343.20329 343.20348 343.20337 FA(20:4) - - - - - - - - 351.19360 351.19349 FA(18:2) - - - 367.20329 367.20317-367.20348 367.20325 367.20351 367.20343 FA(22:6) - 415.35461 415.35474 415.35457 415.35472-415.35447 415.35455 415.35463 415.35462 FA(26:2) - - - - - - - - 431.32901 431.32899 FA(26:2) - - - - - - - - 433.34416 433.34423 FA(26:1) 195, 277, 295 113, 167, 195, 249, 293 177, 229, 249, 283, 299, 327 Lipids numbers 0 1 77 125 113 0 125 121 161 158 a), Structurally specific CID ions of extracted lipids were detected by LC-MS/MS using CID. Red fragment ions were detected in the positive ion mode, and blue fragment ions were detected in the negative ion mode. S-24

Supporting Information Table S3A. Comparison of lipid detection on rat liver sections by MALDI-FTICR MS in the positive-ion mode using quercetin and 2-MBT as the matrices, respectively. Classification Glycerophospholipids Phosphatidylcholines (PCs) No. Measured m/z Error (ppm) Assignment Quercetin 2-MBT Calculated m/z Quercetin 2-MBT Ion form Compound Molecular formula 1 496.33958 496.33938 496.33977-0.38-0.77 [M+H] + PC(16:0/0:0) C 24 H 50 NO 7 P 10-12 2 518.32432 518.32421 518.32412 0.39 0.17 [M+H] + PC(18:3) LysoPC(18:3) 3 520.33949 520.34026 520.33977-0.54 0.94 [M+H] + PC(18:2) LysoPC(18:2) 4 522.35558 522.35563 522.35542 0.32 0.41 [M+H] + PC(O-18:1) PC(18:1) C 26 H 48 NO 7 P Ref. C 26 H 50 NO 7 P 10, 13 C 26 H 52 NO 7 P 5 524.37096 524.37117 524.37107-0.20 0.20 [M+H] + PC(18:0/0:0) C 26 H 54 NO 7 P 13 6 534.29565 534.29533 534.29565 0.00-0.60 [M+K] + PC(16:0/0:0) C 24 H 50 NO 7 P 7 542.32154 542.32164 542.32171-0.32-0.13 [M+Na] + PC(18:2) LysoPC(18:2) 8 542.32395 542.32412-0.30 [M+H] + PC(20:5) C 28 H 48 NO 7 P C 26 H 50 NO 7 P 9 544.33953 544.34011 544.33977-0.44 0.64 [M+H] + PC(20:4/0:0) C 28 H 50 NO 7 P 13 10 546.35306 546.35301 0.09 [M+Na] + PC(18:0/0:0) C 26 H 54 NO 7 P 11 546.35489 546.35542-0.96 [M+H] + PC(20:3) LysoPC(20:3) 12 558.29558 558.29559 558.29565-0.12-0.10 [M+K] + PC(18:2) LysoPC(18:2) C 28 H 52 NO 7 P C 26 H 50 NO 7 P 13 560.31125 560.31170 560.31130-0.08 0.72 [M+K] + PC(18:1/0:0) C 26 H 52 NO 7 P 562.32695 562.32702 562.32695 0.00 0.12 [M+K] + PC(18:0/0:0) C 26 H 54 NO 7 P 15 566.32169 566.32164 566.32171-0.04-0.13 [M+Na] + PC(20:4/0:0) C 28 H 50 NO 7 P 16 568.33962 568.33963 568.33977-0.25-0.24 [M+H] + PC(22:6) LysoPC(22:6) C 30 H 50 NO 7 P 17 582.29563 582.29559 582.29565-0.03-0.10 [M+K] + PC(20:4/0:0) C 28 H 50 NO 7 P 18 606.29561 606.29563 606.29565-0.07-0.03 [M+K] + PC(22:6) LysoPC(22:6) C 30 H 50 NO 7 P S-25

Classification No. Measured m/z Error (ppm) Assignment Quercetin 2-MBT Calculated m/z Quercetin 2-MBT Ion form Compound Molecular formula 19 608.31189 608.31130 0.98 [M+K] + LysoPC(22:5) C 30 H 52 NO 7 P Ref. 20 732.55357 732.55378-0.29 [M+H] + PC(32:1) C 40 H 78 NO 8 P 13 21 734.56948 734.56917 734.56943 0.07-0.35 [M+H] + PC(32:0) C 40 H 80 NO 8 P 15-17 22 756.55091 756.55111 756.55138-0.61-0.35 [M+Na] + PC(16:0/16:0) C 40 H 80 NO 8 P 16, 18-20 23 758.56963 758.56938 758.56943 0.26-0.07 [M+H] + PC(34:2) C 42 H 80 NO 8 P 13, 21 24 760.58561 760.58549 760.58508 0.70 0.54 [M+H] + PC(34:1) C 42 H 82 NO 8 P 10, 11, 13-16, 22, 23 25 762.60056 762.60073-0.22 [M+H] + PC(34:0) C 42 H 84 NO 8 P 26 772.525 772.52531-0.22 [M+K] + PC(16:0/16:0) C 40 H 80 NO 8 P, 16, 18, 24, 25 27 778.53556 778.53573-0.21 [M+Na] + PC(34:3) C 42 H 78 NO 8 P 28 780.55164 780.55138 0.34 [M+Na] + PC(34:2) C 42 H 80 NO 8 P 13, 21, 25 29 780.55394 780.55378 0.20 [M+H] + PC(36:5) C 44 H 78 NO 8 P 30 782.56992 782.57013 782.56943 0.62 0.89 [M+H] + PC(36:4) C 44 H 80 NO 8 P 10, 13, 15, 24 31 784.58250 784.58268-0.22 [M+Na] + PC(34:0) C 42 H 84 NO 8 P 32 784.58551 784.58508 0.54 [M+H] + PC(36:3) C 44 H 82 NO 8 P 10, 13 33 786.60028 786.60000 786.60073-0.57-0.93 [M+H] + PC(36:2) C 44 H 84 NO 8 P 10, 13, 34 788.61646 788.61665 788.61638 0.10 0.34 [M+H] + PC(36:1) C 44 H 86 NO 8 P 10,, 16, 22 35 792.56625 792.56678-0.68 [M+K] + ladderane-octanyl)-snglycerophosphocholine 1-hexadecanyl-2-(8-[3]- 36 794.50996 794.50956 794.50966 0.38-0.13 [M+K] + PC(34:3) C 42 H 78 NO 8 P C 44 H 84 NO 6 P 37 796.52603 796.52610 796.52531 0.90 0.99 [M+K] + PC(34:2) C 42 H 80 NO 8 P 13,, 25 38 798.54122 798.54096 0.33 [M+K] + PC(16:0/18:1) C 42 H 82 NO 8 P 13-16, 18, 20, 22, 24-26 39 800.55716 800.55721 800.55661 0.69 0.75 [M+K] + PC(34:0) C 42 H 84 NO 8 P 40 804.55124 804.55131 804.55138-0.17-0.09 [M+Na] + PC(36:4) C 44 H 80 NO 8 P 13,, 27, 28 41 808.58233 808.58268-0.43 [M+Na] + PC(36:2) C 44 H 84 NO 8 P 13, 42 808.58511 808.58508 0.03 [M+H] + PC(38:5) C 46 H 82 NO 8 P 13 43 810.60066 810.60086 810.60073-0.09 0.16 [M+H] + PC(18:0/20:4) C 46 H 84 NO 8 P 10, 13 44 818.50904 818.50966 818.50966-0.77-0.01 [M+K] + PC(36:5) C 44 H 78 NO 8 P 45 820.52510 820.52594 820.52531-0.26 0.76 [M+K] + PC(36:4) C 44 H 80 NO 8 P 10,, 20, 24-26 46 822.54021 822.54070 822.54096-0.92-0.32 [M+K] + PC(36:3) C 44 H 82 NO 8 P 13, 26 S-26

Classification No. Measured m/z Error (ppm) Assignment Quercetin 2-MBT Calculated m/z Quercetin 2-MBT Ion form Compound Molecular formula 47 824.55659 824.55649 824.55661-0.03-0.15 [M+K] + PC(36:2) C 44 H 84 NO 8 P 13, 26 48 826.57301 826.57312 826.57226 0.91 0.80 [M+K] + PC(36:1) C 44 H 86 NO 8 P, 15, 23, 25, 29, 30 49 828.55197 828.55138 0.71 [M+Na] + PC(38:6) C 46 H 80 NO 8 P 10,, 18, 31 50 828.55393 828.55378 0.18 [M+H] + PC(40:9) C 48 H 78 NO 8 P 51 832.58254 832.58268-0.17 [M+Na] + PC(38:4) C 46 H 84 NO 8 P 13,, 28 52 832.58517 832.58508 0.10 [M+H] + PC(40:7) C 48 H 82 NO 8 P 53 834.60107 834.60073 0.40 [M+H] + PC(40:6) C 48 H 84 NO 8 P 10,, 23 54 836.61380 836.61398-0.21 [M+Na] + PC(38:2) C 46 H 88 NO 8 P 13 55 836.61582 836.61638-0.67 [M+H] + PC(40:5) C 48 H 86 NO 8 P 13 56 842.50939 842.50966-0.33 [M+K] + PC(38:7) C 46 H 78 NO 8 P 57 844.52564 844.52560 844.52531 0.38 0.34 [M+K] + PC(38:6) C 46 H 80 NO 8 P 10,, 18, 24, 25, 32 58 846.54092 846.54023 846.54096-0.05-0.87 [M+K] + PC(38:5) C 46 H 82 NO 8 P, 25 59 848.55650 848.55717 848.55661-0.13 0.65 [M+K] + PC(18:0/20:4) C 46 H 84 NO 8 P 13, 20, 24, 25 60 856.58284 856.58213 856.58268 0.19-0.64 [M+Na] + PC(18:0/22:6) C 48 H 84 NO 8 P 10,, 18 61 870.54121 870.546 870.54096 0.29 0.57 [M+K] + PC(40:7) C 48 H 82 NO 8 P 25 62 872.55641 872.55631 872.55661-0.24-0.35 [M+K] + PC(18:0/22:6) C 48 H 84 NO 8 P 18, 25 63 874.57269 874.57268 874.57226 0.49 0.48 [M+K] + PC(40:5) C 48 H 86 NO 8 P 64 883.69000 883.68988 0. [M+NH 4] + PC(42:4) C 50 H 92 NO 8 P Ref. Phosphatidylethanolamines (PEs) 1 492.24868 492.24870-0.03 [M+K] + PE(16:0) C 21 H 44 NO 7 P 2 510.35523 510.35545 510.35542-0.37 0.07 [M+H] + PE(20:0) LysoPE(20:0) 3 516.24874 516.24870 0.08 [M+K] + PE(18:2) LysoPE(18:2) 4 518.26454 518.26447 518.26435 0.37 0.23 [M+K] + PE(18:1) LysoPC(18:1) C 25 H 52 NO 7 P C 23 H 44 NO 7 P C 23 H 46 NO 7 P 5 520.28004 520.28000 0.08 [M+K] + PE(18:0/0:0) C 23 H 48 NO 7 P 6 534.35532 534.35542-0.19 [M+H] + PE(22:2) LysoPE(22:2) 7 538.38673 538.38631 538.38672 0.02-0.75 [M+H] + PE(22:0) LysoPE(22:0) C 27 H 52 NO 7 P C 27 H 56 NO 7 P S-27

Classification No. Measured m/z Error (ppm) Assignment Quercetin 2-MBT Calculated m/z Quercetin 2-MBT Ion form Compound Molecular formula 8 540.24871 540.24870 0.02 [M+K] + PE(20:4/0:0) C 25 H 44 NO 7 P 9 544.28035 544.28000 0.65 [M+K] + PE(20:2) LysoPE(20:2) 10 548.317 548.31130 0.32 [M+K] + PE(20:0) LysoPE(20:0) 11 564.24885 564.24870 0.26 [M+K] + PE(22:6) LysoPE(22:6) 12 568.28025 568.28000 0.44 [M+K] + PE(22:4) LysoPE(22:4) C 25 H 48 NO 7 P C 25 H 52 NO 7 P C 27 H 44 NO 7 P C 27 H 48 NO 7 P 13 623.43912 623.43948-0.59 [M+NH 4] + PE(26:1) C 31 H 60 NO 8 P 754.47803 754.47836-0.45 [M+K] + PE(34:2) C 39 H 74 NO 8 P 15 772.58572 772.58554 772.58508 0.82 0.59 [M+H] + PE(38:2) C 43 H 82 NO 8 P 13, 16 778.47856 778.47836 0.26 [M+K] + PE(16:0/20:4) C 41 H 74 NO 8 P 17 782.50951 782.50966-0.20 [M+K] + PE(18:1/18:1) C 41 H 78 NO 8 P 18 796.52460 796.52484 796.52516-0.70-0.40 [M+Na] + PE(P-40:7) C 45 H 76 NO 7 P 19 798.54022 798.54081-0.74 [M+Na] + PE(P-18:0/22:6) C 45 H 78 NO 7 P 20 800.55594 800.55587 800.55646-0.65-0.74 [M+Na] + PE(P-40:5) C 45 H 80 NO 7 P 21 800.61693 800.61716 800.61638 0.68 0.97 [M+H] + PE(40:2) C 45 H 86 NO 8 P 22 802.47838 802.47836 0.02 [M+K] + PE(38:6) C 43 H 74 NO 8 P 23 804.49321 804.49401-0.99 [M+K] + PE(38:5) C 43 H 76 NO 8 P 24 806.50956 806.50966-0.13 [M+K] + PE(38:4) C 43 H 78 NO 8 P 25 824.61668 824.61671 824.61638 0.36 0.39 [M+H] + PE(42:4) C 47 H 86 NO 8 P 26 826.57197 826.57190 826.57211-0.17-0.25 [M+Na] + PE(P-42:6) C 47 H 82 NO 7 P 27 830.50964 830.51020 830.50966-0.02 0.65 [M+K] + PE(40:6) C 45 H 78 NO 8 P 28 834.54072 834.54102 834.54096-0.30 0.06 [M+K] + PE(40:4) C 45 H 82 NO 8 P 29 842.56966 842.56943 0.26 [M+H] + PE(44:9) C 49 H 80 NO 8 P 30 864.55078 864.55079 864.55138-0.69-0.68 [M+Na] + PE(44:9) C 49 H 80 NO 8 P 31 880.52569 880.52571 880.52531 0.42 0.45 [M+K] + PE(44:9) C 49 H 80 NO 8 P Ref. Phosphatidic acids (PAs) 1 475.22220 475.22215 0.10 [M+K] + PA(18:1/0:0) C 21 H 41 O 7 P S-28

Classification No. Measured m/z Error (ppm) Assignment Quercetin 2-MBT Calculated m/z Quercetin 2-MBT Ion form Compound 2 477.23776 477.23780-0.09 [M+K] + PA(18:0) LPA(18:0) Molecular formula C 21 H 43 O 7 P 3 487.27958 487.27951 0.13 [M+Na] + PA(20:1) C 23 H 45 O 7 P 4 497.20644 497.20650-0.11 [M+K] + PA(20:4/0:0) C 23 H 39 O 7 P 5 499.22217 499.22215 0.03 [M+K] + PA(20:3) C 23 H 41 O 7 P 6 501.23777 501.23780-0.06 [M+K] + PA(20:2) C 23 H 43 O 7 P 7 503.25346 503.25345 0.02 [M+K] + PA(20:1) C 23 H 45 O 7 P 8 631.46923 631.46972-0.78 [M+H] + PA(P-32:1) C 35 H 67 O 7 P 9 633.48495 633.48537-0.66 [M+H] + PA(O-32:1) or PA(P-32:0) C 35 H 69 O 7 P 10 649.51610 649.51667-0.88 [M+H] + PA(O-18:0/15:0) C 36 H 73 O 7 P 11 655.46921 655.46972-0.78 [M+H] + PA(P-34:3) C 37 H 67 O 7 P 12 659.50057 659.50102-0.68 [M+H] + PA(P-34:1) or PA(O-34:2) C 37 H 71 O 7 P 13 679.46920 679.46972-0.77 [M+H] + PA(P-16:0/20:5) C 39 H 67 O 7 P 683.50052 683.50102-0.73 [M+H] + PA(P-36:3) or PA(O-36:4) C 39 H 71 O 7 P Ref. 15 711.43612 711.43616-0.07 [M+K] + PA(16:0/18:2) C 37 H 69 O 8 P 16 713.45168 713.45181-0.18 [M+K] + PA(16:0/18:1) C 37 H 71 O 8 P 17 735.43627 735.43616 0.15 [M+K] + PA(36:4) C 39 H 69 O 8 P 18 737.45179 737.45181-0.03 [M+K] + PA(18:1/18:2) C 39 H 71 O 8 P 19 739.46819 739.46746 0.98 [M+K] + PA(18:0/18:2) C 39 H 73 O 8 P 20 749.50957 749.50918 0.52 [M+Na] + PA(38:3) C 41 H 75 O 8 P 21 759.43613 759.43616-0.04 [M+K] + PA(16:0/22:6) C 41 H 69 O 8 P 22 761.45184 761.45181 0.03 [M+K] + PA(38:5) C 41 H 71 O 8 P 23 763.46782 763.46746 0.47 [M+K] + PA(38:4) C 41 H 73 O 8 P 24 765.48344 765.48311 0.42 [M+K] + PA(38:3) C 41 H 75 O 8 P S-29

Classification No. Measured m/z Error (ppm) Assignment Quercetin 2-MBT Calculated m/z Quercetin 2-MBT Ion form Compound Molecular formula 25 767.49891 767.49876 0.18 [M+K] + PA(38:2) C 41 H 77 O 8 P 26 773.50927 773.50918 0.12 [M+Na] + PA(40:5) C 43 H 75 O 8 P 27 773.51197 773.51158 0.50 [M+H] + PA(42:8) C 45 H 73 O 8 P 28 785.45157 785.45181-0.31 [M+K] + PA(40:7) C 43 H 71 O 8 P 29 787.46733 787.46746-0.17 [M+K] + PA(18:0/22:6) C 43 H 73 O 8 P 30 789.48310 789.48311-0.02 [M+K] + PA(18:0/22:5) C 43 H 75 O 8 P 31 813.48305 813.48311-0.07 [M+K] + PA(42:7) C 45 H 75 O 8 P Ref. Phosphoglycerols (PGs) 1 507.24813 507.24863 507.24836-0.45 0.53 [M+K] + PG(P-16:0) C 22 H 45 O 8 P 2 837.50438 837.50424 0.16 [M+K] + PG(18:0/20:4) C 44 H 79 O 10 P Phosphatidylserine (PS) 1 864.55208 864.55199 864.55153 0.64 0.53 [M+K] + PS(O-40:4) or PS(P-40:3) C 46 H 84 NO 9 P Phosphatidylinositols (PIs) 1 849.45218 849.45245-0.32 [M+Na] + PI(34:6) C 43 H 71 O 13 P 2 925.52054 925.52029 0.28 [M+K] + PI(18:0/20:4) C 47 H 83 O 13 P 3 949.52102 949.52029 0.77 [M+K] + PI(40:6) C 49 H 83 O 13 P Glycerophosphoglycerophosphoglycerols 1 963.47647 963.47605 0.43 [M+K] + CL(1\'-[18:2(9Z,12Z)/0:0],3\'- [18:2(9Z,12Z)/0:0]) C 45 H 82 O 15 P 2 Cyclic phosphatidic acids (cpas) 1 431.19599 431.19593 0. [M+K] + CPA(16:0) C 19 H 37 O 6 P 2 455.19603 455.19593 0.21 [M+K] + CPA(18:2) C 21 H 37 O 6 P 3 457.21163 457.21158 0.10 [M+K] + CPA(18:1) C 21 H 39 O 6 P 4 459.22733 459.22723 0.20 [M+K] + CPA(18:0) C 21 H 41 O 6 P S-30

Classification No. Measured m/z Error (ppm) Assignment Quercetin 2-MBT Calculated m/z Quercetin 2-MBT Ion form Compound Molecular formula Ref. Sphingolipids Ceramides (Cers) 1 506.36052 506.36011 506.36050 0.03-0.77 [M+H] + CerP(d18:1/8:0) C 26 H 52 NO 6 P 2 688.60044 688.60045-0.02 [M+K] + Cer(d18:1/24:0) C 42 H 83 NO 3 3 766.55160 766.55113 0.61 [M+K] + CerP(d18:1/24:1) C 42 H 82 NO 6 P Sphingomyelins (SMs) 1 703.57476 703.57418 703.57485-0.13-0.95 [M+H] + SM(d18:1/16:0) C 39 H 79 N 2 O 6 P 10, 2 725.55619 725.556 725.55680-0.83-0.90 [M+Na] + SM(d18:1/16:0) C 39 H 79 N 2 O 6 P, 15, 20, 27 3 741.53061 741.53028 741.53073-0.17-0.61 [M+K] + SM(d18:1/16:0) C 39 H 79 N 2 O 6 P 33 4 769.56210 769.56203 0.09 [M+K] + SM(d18:1/18:0) C 41 H 83 N 2 O 6 P, 16 5 787.66862 787.66875-0.17 [M+H] + SM(d18:1/22:0) C 45 H 91 N 2 O 6 P 6 797.59364 797.59353 797.59333 0.38 0.24 [M+K] + SM(d18:1/20:0) C 43 H 87 N 2 O 6 P, 26 7 813.68492 813.68440 0.64 [M+H] + SM(d18:1/24:1) C 47 H 93 N 2 O 6 P 8 815.70035 815.70005 0.37 [M+H] + SM(d18:1/24:0) C 47 H 95 N 2 O 6 P 9 825.62447 825.62462 825.62463-0.20-0.01 [M+K] + SM(d18:1/22:0) C 45 H 91 N 2 O 6 P 10 837.68227 837.68211 837.68200 0.32 0. [M+Na] + SM(d18:1/24:0) C 47 H 95 N 2 O 6 P, 20 11 851.64015 851.64112 851.64028-0.15 0.99 [M+K] + SM(d18:1/24:1) C 47 H 93 N 2 O 6 P 12 853.65618 853.65543 853.65593 0.28-0.59 [M+K] + SM(d18:1/24:0) C 47 H 95 N 2 O 6 P Neutral Lipids Glycerolipids Monoacylglycerols (MAGs) 1 369.24019 369.24023 369.24017 0.05 0.17 [M+K] + MG (16:0) C 19 H 38 O 4 2 397.27150 397.277 0.07 [M+K] + MG (18:0) C 21 H 42 O 4 3 417.24024 417.24017 0.17 [M+K] + MG (20:4) C 23 H 38 O 4 Diacylglycerols (DAGs) 1 551.50347 551.50339 0.15 [M+H] + DG(P-:0/18:1(9Z)) C 35 H 66 O 4 S-31

Classification No. Measured m/z Error (ppm) Assignment Quercetin 2-MBT Calculated m/z Quercetin 2-MBT Ion form Compound 2 603.53465 603.53438 603.53469-0.07-0.51 [M+H] + 2-(8-[3]- 1-(-methyl-pentadecanoyl)- ladderane-octanyl)-sn-glycerol 3 621.48543 621.48492 621.48537 0.10-0.72 [M+H] + 2-(8-[3]-ladderane-octanyl)- 1-(6-[5]-ladderane-hexanoyl)- sn-glycerol Molecular formula C 39 H 70 O 4 4 631.47033 631.46983 0.79 [M+K] + DG(34:2) C 37 H 68 O 5 5 633.48591 633.48548 0.68 [M+K] + DG(34:1) C 37 H 70 O 5 6 649.51715 649.51713 649.51678 0.57 0.54 [M+K] + DG(16:0/19:0/0:0)[iso2] C 38 H 74 O 5 7 651.53467 651.53446 651.53469-0.03-0.35 [M+H] + (8-[3]-ladderane-octanyl)-snglycerol 1-(8-[3]-ladderane-octanoyl-2- Ref. C 34 H 69 O 7 P C 43 H 70 O 4 8 655.47011 655.46983 0.43 [M+K] + DG(36:4) C 39 H 68 O 5 9 659.50157 659.50113 0.66 [M+K] + DG(36:2) C 39 H 72 O 5 10 679.47021 679.46983 0.56 [M+K] + DG(38:6) C 41 H 68 O 5 11 682.45715 682.45677 0.56 [M+Na] + DG(40:8) C 43 H 63 D 5 O 5 12 683.50172 683.50113 0.86 [M+K] + DG(38:4) C 41 H 72 O 5 Sterol Lipids 1 431.32808 431.32844-0.83 [M+Na] + Conicasterol B C 29 H 44 O 2 687.54793 687.54769 0.34 [M+K] + 18:2 Cholesteryl ester or zymosteryl oleate C 45 H 76 O 2 3 397.27098 397.27132 0.86 [M+Na] + 3-Oxo-5β-cholan-24-oic Acid C 24 H 38 O 3 Fatty acyls Fatty acids (FAs) 1 319.20345 319.20339 0.20 [M+K] + FA(18:2) C 18 H 32 O 2 2 321.21911 321.21904 0.21 [M+K] + FA(18:1) C 18 H 34 O 2 3 335.19836 335.19830 0.16 [M+K] + FA(18:2) C 18 H 32 O 3 4 343.20343 343.20339 0.13 [M+K] + FA(20:4) C 20 H 32 O 2 5 351.19328 351.19322 0.18 [M+K] + FA(18:2) C 18 H 32 O 4 6 367.20342 367.20339 0.08 [M+K] + FA(22:6) C 22 H 32 O 2 S-32

Classification No. Measured m/z Error (ppm) Assignment Quercetin 2-MBT Calculated m/z Quercetin 2-MBT Ion form Compound Molecular formula Ref. 7 371.31580 371.31559 0.59 [M+H] + FA(22:0) C 22 H 42 O 4 8 393.29740 393.29753-0.34 [M+Na] + FA(22:0) C 22 H 42 O 4 9 415.35484 415.35432 415.35465 0.46-0.79 [M+Na] + FA(26:2) C 26 H 48 O 2 10 431.32900 431.32859 0.95 [M+K] + FA(26:2) C 26 H 48 O 2 11 433.34424 433.34424 0.00 [M+K] + FA(26:1) C 26 H 50 O 2 S-33

Supporting Information Table S3B. Classification of lipid entities shown in Supporting Information Table S3A. Lipid classification Number of Lipidsquercetin (LN Q ) Number of Lipids-Main Class (LN MC ) LN MC /LN Total Number of Lipids-2-MBT (LN 2-MBT ) Number of Lipids-Main Class (LN MC) LN MC /LN Total LN Q /LN 2- MBT Glycerophospholipids LN MC- LN MC- Glycerophospholipids Glycerophospholipids Phosphatidylcholines (PCs) 50 31.1% 53 60.0% 0.9 Phosphatidylethanolamines (PEs) 30 18.6% 15.7% 2.1 Phosphatidic acids (PAs) 31 18.3% 0 0 Phosphoglycerols (PGs) 2 1.2% 1 1.1% 2.0 Phosphatidylserine (PS) 1 122 0.6% 75.8% 1 69 1.1% 77.5% 1.0 phosphatidylinositols (PIs) 3 1.9% 0 0 Glycerophosphoglycerophosphoglycerols 1 0.6% 0 0 Cyclic phosphatidic acids (cpas) 4 2.5% 0 0 Sphingolipids LN MC-Sphingolipids LN MC-Sphingolipids Ceramides (Cers) 3 1.9% 1 1.1% 3.0 Sphingomyelins (SMs) 9 12 5.6% 7.5% 11 12 12.4% 13.5% 0.8 Neutral Lipids LN MC-NL LN MC-NL Glycerolipids LN MC-NL: Glycerolipids LN MC-NL: Glycerolipids Monoacylglycerols (MAGs) 3 1.9% 1 1.1% 3.0 15 9.3% 5 5.6% Diacylglycerols (DAGs) 12 7.5% 4 4.5% 3.0 Sterol Lipids LN MC-NL: Sterol lipids LN MC-NL: Sterol lipids 3 3 1.9% 1.9% 0 0 0 0 Fatty acyls LN MC-Fatty acyls LN MC-Fatty acyls Fatty acids (FAs) 9 9 5.6% 5.6% 3 3 3.4% 3.4% 3.0 S-34

Lipid classification Number of Lipidsquercetin (LN Q ) Number of Lipids-Main Class (LN MC ) LN MC /LN Total Number of Lipids-2-MBT (LN 2-MBT ) Number of Lipids-Main Class (LN MC) LN MC /LN Total LN Q /LN 2- MBT LN Total 161 161 89 89 1.81 S-35

Supporting Information Table S4A. Imaged and identified lipids detected on transversally-cut rat brain tissue sections by MALDI- FTICR MS in the positive-ion mode using quercetin as a matrix. Classification No. Measured m/z Calculated m/z Error (ppm) Glycerophospholipids Phosphatidylcholines (PCs) Ion form Assignment Compound Molecular formula 1 478.32916 478.32920-0.08 [M+H] + PC(O-16:2) C 24 H 48 NO 6 P 2 506.36051 506.36050 0.02 [M+H] + PC(P-18:1) C 26 H 52 NO 6 P 3 516.28494 516.28508-0.27 [M+K] + PC(O-16:2) C 24 H 48 NO 6 P 4 518.30062 518.30073-0.21 [M+K] + PC(O-16:1) or LysoPC(P-16:0) LysoPC(18:0) 5 524.37151 524.37107 0.84 [M+H] + PC(18:0) PC(O-18:0) C 24 H 50 NO 6 P 6 528.34229 528.34245-0.30 [M+Na] + PC(O-18:2) or PC(P-18:1) C 26 H 52 NO 6 P 7 534.29554 534.29565-0.21 [M+K] + LysoPC(16:0) PC(16:0) PC(O-16:0) 8 544.31635 544.31638-0.06 [M+K] + PC(O-18:2) or PC(P-18:1) C 26 H 52 NO 6 P 9 560.31119 560.31130-0.20 [M+K] + PC(18:1) PC(O-18:1) LysoPC(18:1) 10 562.32673 562.32695-0.39 [M+K] + LysoPC(18:0) PC(18:0) PC(O-18:0) 11 602.32220 602.32186 0.56 [M+K] + PC(20:1) C 28 H 54 NO 8 P 12 606.29525 606.29565-0.66 [M+K] + PC(22:6) LysoPC(22:6) Ref. C 26 H 54 NO 7 P 13 C 24 H 50 NO 7 P C 26 H 52 NO 7 P C 26 H 54 NO 7 P C 30 H 50 NO 7 P 13 734.56962 734.56943 0.26 [M+H] + PC(32:0) C 40 H 80 NO 8 P 15-17 756.55072 756.55138-0.87 [M+Na] + PC(32:0) C 40 H 80 NO 8 P 16, 18-20 15 760.58444 760.58508-0.84 [M+H] + PC(34:1) C 42 H 82 NO 8 P 10, 11, 13-16, 22, 23 16 770.50891 770.50966-0.97 [M+K] + PC(32:1) C 40 H 78 NO 8 P S-36

Assignment Classification No. Measured m/z Calculated m/z Error (ppm) Ion form Compound Molecular formula Ref. 17 772.52494 772.52531-0.48 [M+K] + PC(32:0) C 40 H 80 NO 8 P, 16, 18, 24, 25 18 782.56650 782.56703-0.68 [M+Na] + PC(34:1) C 42 H 82 NO 8 P 19 786.54388 786.54322 0.84 [M+H] + (8-[3]-ladderane-octanyl)-snglycerophosphocholine 1-(6-[5]-ladderane-hexanoyl)-2-20 792.56623 792.56678-0.69 [M+K] + ladderane-octanyl)-snglycerophosphocholine 1-hexadecanyl-2-(8-[3]- C 46 H 76 NO 7 P C 44 H 84 NO 6 P 21 798.54126 798.54096 0.38 [M+K] + PC(34:1) C 42 H 82 NO 8 P 13-16, 18, 20, 22, 24-26 22 808.58257 808.58268-0. [M+Na] + PC(36:2) C 44 H 84 NO 8 P 13, 23 810.54098 810.54081 0.21 [M+Na] + (8-[3]-ladderane-octanyl)-snglycerophosphocholine 1-(6-[3]-ladderane-hexanoyl)-2- C 46 H 78 NO 7 P 24 810.60060 810.60073-0.16 [M+H] + PC(38:4) C 46 H 84 NO 8 P 10, 13 25 812.55687 812.55646 0.50 [M+Na] + PC(P-38:6) C 46 H 80 NO 7 P 26 820.52480 820.52531-0.62 [M+K] + PC(36:4) C 44 H 80 NO 8 P 10,, 20, 24-26 27 824.55635 824.55661-0.32 [M+K] + PC(36:2) C 44 H 84 NO 8 P 13, 26 28 826.57207 826.57226-0.23 [M+K] + PC(36:1) C 44 H 86 NO 8 P, 15, 23, 25, 29, 30 29 832.58271 832.58268 0.04 [M+Na] + PC(38:4) C 46 H 84 NO 8 P 13,, 28 30 836.61385 836.61398-0.16 [M+Na] + PC(38:2) C 46 H 88 NO 8 P 13 31 844.52521 844.52531-0.12 [M+K] + PC(38:6) C 46 H 80 NO 8 P 10,, 18, 24, 25, 32 32 846.541 846.54096 0.53 [M+K] + PC(38:5) C 46 H 82 NO 8 P, 25 33 848.55654 848.55661-0.08 [M+K] + PC(38:4) C 46 H 84 NO 8 P 13, 20, 24, 25 34 854.60317 854.60356-0.46 [M+K] + PC(38:1) C 46 H 90 NO 8 P 35 856.58199 856.58268-0.81 [M+Na] + PC(40:6) C 48 H 84 NO 8 P 10,, 18 36 872.55684 872.55661 0.26 [M+K] + PC(40:6) C 48 H 84 NO 8 P 18, 25 37 874.57159 874.57226-0.77 [M+K] + PC(40:5) C 48 H 86 NO 8 P 38 876.58764 876.58791-0.31 [M+K] + PC(40:4) C 48 H 88 NO 8 P 39 882.63433 882.63486-0.60 [M+K] + PC(40:1) C 48 H 94 NO 8 P 40 892.52530 892.52531-0.01 [M+K] + PC(42:10) C 50 H 80 NO 8 P 41 908.64993 908.65051-0.64 [M+K] + PC(42:2) C 50 H 96 NO 8 P 42 910.66577 910.66616-0.43 [M+K] + PC(42:1) C 50 H 98 NO 8 P S-37

Classification No. Measured m/z Calculated m/z Error (ppm) Phosphatidylethanolamines (PEs) Ion form Assignment Compound Molecular formula 1 476.25382 476.25378 0.08 [M+K] + PE(P-16:0) C 21 H 44 NO 6 P 2 492.24875 492.24870 0.10 [M+K] + PE(16:0) C 21 H 44 NO 7 P 3 504.28524 504.28508 0.32 [M+K] + PE(O-18:1) or PE(P-18:0) C 23 H 48 NO 6 P 4 516.24869 516.24870-0.02 [M+K] + PE(18:2) LysoPE(18:2) 5 518.26451 518.26435 0.31 [M+K] + PE(18:1) LysoPE(18:1) C 23 H 44 NO 7 P C 23 H 46 NO 7 P 6 520.28038 520.28000 0.73 [M+K] + PE(18:0) or LysoPE(18:0) C 23 H 48 NO 7 P + PE(20:1) or 7 546.29524 546.29565-0.75 [M+K] LysoPE(20:1) PE(22:6) 8 564.24870 564.24870 0.00 [M+K] + LysoPE(22:6) 9 568.28038 568.28000 0.67 [M+K] + PE(22:4) LysoPE(22:4) C 25 H 50 NO 7 P C 27 H 44 NO 7 P C 27 H 48 NO 7 P 10 748.58468 748.58508-0.53 [M+H] + PE(36:0) or PE-NMe2(17:0/17:0) C 41 H 82 NO 8 P 11 756.49366 756.49401-0.46 [M+K] + PE(34:1) C 39 H 76 NO 8 P 12 758.51034 758.50966 0.90 [M+K] + PE(34:0) or PE-NMe2(16:0/16:0) C 39 H 78 NO 8 P 13 768.53064 768.53040 0.31 [M+K] + PE(P-36:1) or PE(O-36:2) C 41 H 80 NO 7 P 772.58534 772.58508 0.34 [M+H] + PE(38:2) C 43 H 82 NO 8 P 13, 15 774.60040 774.60073-0.43 [M+H] + PE(38:1) C 43 H 84 NO 8 P 16 784.52606 784.52531 0.96 [M+K] + PE(36:1) or PE-NMe2(34:1) C 41 H 80 NO 8 P 17 786.48358 786.48345 0.17 [M+K] + PE(P-38:6) C 43 H 74 NO 7 P 18 788.49873 788.49910-0.47 [M+K] + PE(P-38:5) or PE(O-38:6) C 43 H 76 NO 7 P 19 790.51525 790.575 0.63 [M+K] + PE(P-38:4) or PE(O-38:5) C 43 H 78 NO 7 P 20 800.61693 800.61638 0.68 [M+H] + PE(40:2) C 45 H 86 NO 8 P 21 802.47788 802.47836-0.60 [M+K] + PE(38:6) or PE(P-38:6) C 43 H 74 NO 8 P 22 802.63219 802.63203 0.20 [M+H] + PE(40:1) C 45 H 88 NO 8 P 23 804.49421 804.49401 0.25 [M+K] + PE(38:5) C 43 H 76 NO 8 P 24 806.50940 806.50966-0.32 [M+K] + PE(38:4) or PE- C 43 H 78 NO 8 P Ref. S-38

Classification No. Measured m/z Calculated m/z Error (ppm) Ion form Assignment Compound NMe2(16:0/20:4(5Z,8Z,11Z,Z) )[S] or PE(P-38:4) Molecular formula 25 812.49888 812.49910-0.27 [M+K] + PE(P-40:7) C 45 H 76 NO 7 P 26 8.51517 8.575 0.52 [M+K] + PE(P-40:6) C 45 H 78 NO 7 P 27 816.53089 816.53040 0.60 [M+K] + PE(P-40:5) or PE(O-40:6) C 45 H 80 NO 7 P 28 818.54669 818.54605 0.78 [M+K] + PE(P-40:4) or PE(O-40:5) C 45 H 82 NO 7 P 29 819.65890 819.65858 0.39 [M+NH 4] + PE(40:1) C 45 H 88 NO 8 P 30 822.60139 822.60073 0.80 [M+H] + PE(42:5) C 47 H 84 NO 8 P 31 830.50939 830.50966-0.33 [M+K] + PE(40:6) C 45 H 78 NO 8 P 32 834.54096 834.54096 0.00 [M+K] + PE(40:4) C 45 H 82 NO 8 P 33 845.67384 845.67423-0.46 [M+NH 4] + PE(42:2) C 47 H 90 NO 8 P 34 850.60874 850.60865 0.11 [M+K] + PE(P-42:2) C 47 H 90 NO 7 P 35 852.49476 852.49401 0.88 [M+K] + PE(42:9) C 47 H 76 NO 8 P 36 873.70580 873.70553 0.31 [M+NH 4] + PE(44:2) C 49 H 94 NO 8 P Ref. Phosphatidic acids (PAs) 1 395.25571 395.25570 0.03 [M+H] + PA(P-16:0/0:0) C 19 H 39 O 6 P 2 475.22219 475.22215 0.08 [M+K] + PA(18:1) C 21 H 41 O 7 P 3 477.23783 477.23780 0.06 [M+K] + PA(18:0) LPA(18:0) C 21 H 43 O 7 P 4 487.27948 487.27951-0.06 [M+Na] + PA(20:1) C 23 H 45 O 7 P 5 497.20652 497.20650 0.04 [M+K] + PA(20:4/0:0) C 23 H 39 O 7 P 6 499.22224 499.22215 0.18 [M+K] + PA(20:3) C 23 H 41 O 7 P 7 501.23785 501.23780 0.10 [M+K] + PA(20:2) C 23 H 43 O 7 P 8 503.25378 503.25345 0.66 [M+K] + PA(20:1) C 23 H 45 O 7 P 9 631.46954 631.46972-0.29 [M+H] + PA(P-32:1) C 35 H 67 O 7 P 10 659.50058 659.50102-0.67 [M+H] + PA(P-34:1) or PA(O-34:2) C 37 H 71 O 7 P 11 679.46922 679.46972-0.74 [M+H] + PA(P-36:5) C 39 H 67 O 7 P 12 681.48484 681.48537-0.78 [M+H] + PA(O-16:0/20:5) or PA(P-36:4) C 39 H 69 O 7 P 13 683.50062 683.50102-0.59 [M+H] + PA(P-36:3) C 39 H 71 O 7 P S-39

Classification No. Measured m/z Calculated m/z Error (ppm) Ion form Assignment Compound Molecular formula 685.42104 685.42051 0.77 [M+K] + PA(32:1) C 35 H 67 O 8 P 15 687.43636 687.43616 0.29 [M+K] + PA(32:0) C 35 H 69 O 8 P 16 687.53171 687.53232-0.89 [M+H] + PA(P-36:1) or PA(O-36:2) C 39 H 75 O 7 P 17 689.54743 689.54797-0.78 [M+H] + PA(P-36:0) or PA(O-36:1) C 39 H 77 O 7 P 18 697.47783 697.47788-0.07 [M+Na] + PA(34:1) C 37 H 71 O 8 P 19 701.45154 701.45166-0.17 [M+Na] + PA(P-36:5) C 39 H 67 O 7 P 20 707.50052 707.50102-0.71 [M+H] + PA(P-38:5) or PA(O-38:6) C 41 H 71 O 7 P 21 711.43657 711.43616 0.58 [M+K] + PA(34:2) C 37 H 69 O 8 P 22 713.45182 713.45181 0.01 [M+K] + PA(34:1) C 37 H 71 O 8 P 23 723.49347 723.49353-0.08 [M+Na] + PA(36:2) C 39 H 73 O 8 P 24 725.514 725.51158-0.19 [M+H] + PA(38:4) C 41 H 73 O 8 P 25 727.46783 727.46731 0.71 [M+Na] + PA(P-38:6) C 41 H 69 O 7 P 26 737.45238 737.45181 0.77 [M+K] + PA(36:3) C 39 H 71 O 8 P 27 739.46757 739.46746 0.15 [M+K] + PA(36:2) C 39 H 73 O 8 P 28 748.58468 748.58508-0.53 [M+NH 4] + PA(38:1) C 41 H 79 O 8 P 29 751.52475 751.52483-0.11 [M+Na] + PA(38:2) C 41 H 77 O 8 P 30 761.45156 761.45181-0.33 [M+K] + PA(38:5) C 41 H 71 O 8 P 31 763.46817 763.46746 0.93 [M+K] + PA(38:4) C 41 H 73 O 8 P 32 765.48378 765.48311 0.88 [M+K] + PA(38:3) C 41 H 75 O 8 P 33 767.49936 767.49876 0.78 [M+K] + PA(38:2) C 41 H 77 O 8 P 34 774.60040 774.60073-0.43 [M+NH 4] + PA(40:2) C 43 H 81 O 8 P 35 785.45153 785.45181-0.36 [M+K] + PA(40:7) C 43 H 71 O 8 P 36 789.48311 789.48311 0.00 [M+K] + PA(40:5) C 43 H 75 O 8 P 37 802.63219 802.63203 0.20 [M+NH 4] + PA(42:2) C 45 H 85 O 8 P Ref. Phosphoglycerols (PGs) 1 773.50911 773.50933-0.28 [M+K] + PG(O-34:1) or PG(P-34:0) C 40 H 79 O 9 P 2 793.49861 793.49901-0.50 [M+Na] + PG(36:4) C 42 H 75 O 10 P 3 837.50428 837.50424 0.05 [M+K] + PG(18:0/20:4) C 44 H 79 O 10 P S-40

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