Supporting Information
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1 1 Supporting Information Single-cell metabolite profiling of stalk and glandular cells of intact trichomes with internal electrode capillary pressure probe electrospray ionization mass spectrometry Taiken Nakashima 1, Hiroshi Wada 2, Satoshi Morita 2, Rosa Erra-Balsells 3, Kenzo Hiraoka 4, *Hiroshi Nonami Plant Biophysics/Biochemistry Research Laboratory, Faculty of Agriculture, Ehime University, Matsuyama, , Japan Kyushu Okinawa Agricultural Research Center, National Agriculture and Food Research Organization (NARO), Chikugo, , Japan CIHIDECAR CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Buenos Aires, 1428, Argentina Clean Energy Research Center, University of Yamanashi, Kofu , Japan S-1
2 TABLE OF CONTENT Figure S1. Photographs of different types of trichomes subjected to this study. Figure S2. Schematic diagram of IEC-PPESI-MS system Figure S3. Comparison of detection sensitivities for the external and internal electrode capillary PPESI-MS in negative and positive ion modes. Table S1. Comparison of limit of detection for IEC-PPESI-MS with engine oil and ionic liquid as additives in silicon oil. Figure S4. Positive and negative ion mode background mass spectra of IEC-PPESI-MS with engine oil or ionic liquid mixture Table S2. Chemical properties of three ionic liquids examined for the use in IEC-PPESI-MS. Figure S5. Signal intensity of standard analytes in positive and negative ion modes with different types of ionic liquids in Table S2. Figure S6. Effect of ionic liquid concentration in silicone oil on signal intensity of IEC-PPESI- MS in positive and negative ion modes. Table S3. List of metabolites detected in stalk and glandular cells of type I, II, IV and VI trichomes using IEC-PPESI in negative ion mode. Figure S7. Magnified peaks in mass spectra of stalk cells from different types of trichomes shown in Figure 3. Figure S8. NanoESI mass spectra of type I and II stalk cells for comparison with IEC-PPESI. Figure S9. Magnified peaks in mass spectra of glandular cells from type I, IV and VI trichomes shown in Figure 4. Figure S10. IEC-PPESI-MS/MS fragmentation patterns of flavonoids observed in stalk cells of type VI trichomes. Figure S11. IEC-PPESI-MS/MS fragmentation patterns of acyl sugars observed in glandular cells of type IV trichomes. Movies S1. Sampling of glandular cell secretion of type IV trichome on fruit. Movies S2. Dilution of the sample with pure water droplet held at the tip of micropipette. S-2
3 Figure S1. Different types of tomato trichome; type I on a stem (A), type II on a leaf (B), type IV (C) and type VI (D) on a fruit of tomato plants. Each arrow indicates the basal stalk (SC) and secretory glandular cells (GC) subjected to IEC-PPESI-MS measurement. The inset photograph in A shows a glandular cell of type I trichome at higher magnification S-3
4 Figure S2. (A) Schematic diagram of the IEC-PPESI-MS system. A pressure probe capillary filled with the ionic liquid mixture was fitted to a capillary holder filled with pure silicone oil. The titanium wire was pre-embedded in the capillary holder as an internal electrode. The capillary holder was linked to a stainless T-connector on which a pressure transducer and stainless pipe were mounted. The peek tubing connected to the capillary holder and T-connector as well as stainless pipe were airtightly filled with the pure silicone oil, so that pressure at the capillary tip can be immediately transmitted to the sensor through the silicone oil and monitored by a digital indicator. Because pure silicone oil is an insulator, electric damage to the sensor was prevented. As the volume of the silicone oil can be accurately controlled by back-and-forth motion of the metal rod inserted into the stainless pipe, pressure at the capillary tip during cell sap sampling and subsequent ionizing can be adjusted precisely by remotelycontrolled stepping motor. (B) Calculated changes in volumes of ionic liquid mixture in the pressure probe capillary while plunging the metal rod. Maximum injection of metal rod into the system induces replacement of 3.53 µl ionic liquid mixture to pure silicone oil, which is equivalent to 11 mm distance from the rear opening of capillary. This calculation indicates that importance of inserting electrode into the capillary for repetitive pressure probe operation. S-4
5 Figure S3. Signal intensity of sucrose and malate in positive and negative ion mode, respectively, measured with previously used external wire electrode capillary (EEC) and newly developed internal electrode capillary (IEC) holder. Engine oil mixture was used in both measurements. Means±SE (n=5). Means followed by different letters are significantly different at P< 0.01 by Tukey s range test S-5
6 Table S1. The detectable lowest amount of standard metabolites obtained using IEC-PPESI- MS with engine oil (EO) or ionic liquid (IL) mixtures. The values are in fmol S-6
7 Figure S4. Background IEC-PPESI mass spectra obtained using a capillary filled with 10% engine oil supplement/ silicone oil mixture (EO/SO) (A, C) and 0.01% ionic liquid/ silicone oil mixture (IL/SO) (B, D) in negative (A, B) and positive ion mode (C, D). 100 pl of ultra-pure water was loaded as blank S-7
8 Table S2. Chemical properties and miscibility in silicone oil of the three ionic liquid candidates tested for IEC-PPESI-MS application *Ref. The product catalogue provided by the chemical supplier S-8
9 Figure S5. Effect of different types of ionic liquids, namely trihexyltetradecyl phosphonium bis trifluoromethylsulfonyl amide (I), 1-ethyl-3-methylimidazolium bis trifluoromethylsulfonyl imide (II) and 1-ethyl-3-methyllimidazolium dicyanamide (III) on signal intensity of sucrose in positive ion mode (A) and malate in negative ion mode (B). 0.01% (v/v) ionic liquid mixtures were used. 0.5 pmol sucrose or malate were injected as standard solutions. Means±SE (n=5). Means followed by different letters are significantly different at P< 0.01 by Tukey s range test S-9
10 Figure S6. Effect of IL-I concentration on signal intensity of sucrose in positive ion mode (A) and malate in negative ion mode (B). 5 pmol of malate or sucrose were injected as standard analytes, and the trihexyltetradecyl phosphonuim bis (trifluoromethylsulfnyl) amide was used for the measurement. Means±SE (n=5) S-10
11 Table S3. List of metabolites detected in stalk (SC) and glandular cells (GC) of type I, II, IV and VI trichomes using IEC-PPESI in negative ion mode. Frequency of detection b MS/MS Reference Metabolites Molecular formulae Ion type detected Observed Theoretical a m Type I Type II Type IV Type VI shown in m/z m/z ppm SC GC SC SC GC SC GC Amino acid Serine C3H7NO3 [M-H] Proline C5H9NO2 [M-H] Valine C5H11NO2 [M-H] Threonine C4H9NO3 [M-H] Oxoproline C5H7NO3 [M-H] Hydroxyproline C5H9NO3 [M-H] Asparagine C4H8N2O3 [M-H] Aspartic acid C4H7NO4 [M-H] Oxoglutaric acid C5H6O5 [M-H] Glutamine C5H10N2O3 [M-H] Lysine C6H14N2O2 [M-H] Glutamate C5H9NO4 [M-H] Histidine C6H9N3O2 [M-H] Phenylalanine C9H11NO2 [M-H] Glutathione C10H17N3O6S [M-H] Organic acid Fumaric acid C4H4O4 [M-H] Succinic acid C4H6O4 [M-H] Malic acid C4H6O5 [M-H] , 26 Dehydroascorbic acid C6H6O6 [M-H] Ascorbic acid C6H8O6 [M-H] Citric acid C6H8O7 [M-H] Galacturonic acid C6H10O7 [M-H] Gluconate C6H12O7 [M-H] Homoisocitrate C7H10O7 [M-H] Citric acid monohydrate C6H10O8 [M-H] Carbohydrate Deoxyhexose C6H12O5 [M-H] Hexose C6H12O6 [M-H] , 26 Hexose C6H12O6 [M+Cl] Hex 6-phosphate C6H13O9P [M-H] L-Ascorbic acid-2-glucoside C12H18O11 [M-H] , 26 Hex2 C12H22O11 [M-H] Hex2 C12H22O11 [M+Cl] , 26 Hex3 C18H32O16 [M-H] Hex3 C18H32O16 [M+Cl] Hex4 C24H42O21 [M-H] Hex4 C24H42O21 [M+Cl] Hex5 C24H42O21 [M-H] Hex5 C24H42O21 [M+Cl] Flavonoid precursors p-coumaric acid C9H8O3 [M-H] Shikimic acid C7H10O5 [M-H] Caffeic acid C9H8O4 [M-H] Quinic acid C7H12O6 [M-H] , 26 Ferulic acid C10H10O4 [M-H] Chlorogenic Acid C16H18O9 [M-H] Flavonoids Naringenin or naringenin chalcone C15H12O5 [M-H] Figure S10-1 Quercetin aglycone C15H10O7 [M-H] Quercetagetin-methyl ether C16H12O8 [M-H] Naringenin-hexoside C21H22O10 [M-H] Figure S10-2 Tetrahydroxyflavanone-hexoside C21H22O11 [M-H] Figure S10-3 Quercetin-hexoside C21H20O12 [M-H] Figure S10-4 Naringenin-hexoside C21H22O10 [M+Cl] Kaempferol-hexosyl-hexoside C27H30O15 [M-H] Figure S Naringenin-dihexosides C27H32O15 [M-H] Figure S10-6 Quercetin-hexosyl-hexoside C27H30O16 [M-H] Figure S , 26, 27 Rhamnetin-hexosyl-hexoside C28H32O16 [M-H] Figure S10-8 Quercetin-dihexosides C27H30O17 [M-H] Figure S10-9 Naringenin-dihexosides C27H32O15 [M+Cl] Figure S10-10 Quercetin-hexosyl-hexoside C27H30O16 [M+Cl] Quercetin-rhamnosyl-hexoside C33H40O21 [M-H] Figure S10-11 Acyl sugars Diacylsucrose S 2:10 C22 H38 O13 [M-H] Figure S11-1 Triacylsucrose S 3:12 C24H40O14 [M-H] Figure S Triacylsucrose S 3:14 C26H44O14 [M-H] Figure S Diacylsucrose S 2:15 C27H48O13 [M-H] Figure S TriacylsucroseS 3:15 C27H46O14 [M-H] Figure S , 27 Tetraacylsucrose S 4:16 C28H46O15 [M-H] Figure S , 26, 27 Triacylsucrose S 3:17 C29H50O14 [M-H] Figure S Tetraacylsucrose S 4:17 C29H48O15 [M-H] Figure S , 26, 27 Triacylsucrose S 3:19 C31H54O14 [M-H] Figure S Triacylsucrose S 3:20 C32H56O14 [M-H] Figure S , 27 Triacylsucrose S 3:21 C33H58O14 [M-H] Figure S , 27 Tetraacylsucrose S 4:17 C29H48O15 [M+formate] Figure S , 28 Triacylsucrose S 3:22 C34H60O14 [M-H] Figure S , 27 Tetraacylsucrose S 4:18 C30H50O15 [M+formate] Figure S , 28 Tetraacylsucrose S 4:22 C34H58O15 [M-H] Figure S , 26, 27 Triacylsucrose S 3:20 C32H56O14 [M+formate] Figure S , 28 Tetraacylsucrose S 4:24 C36H62O15 [M-H] Figure S , 27 Tetraacylsucrose S 4:22 C34H58O15 [M+formate] Figure S , 28 Tetraacylsucrose S 4:23 C35H60O15 [M+formate] Figure S , a All the theoretical values are quoted from Metlin ( b Signal detected (+); Signal not detected (-). Frequencies of detection (x) in 9-12 individual measurements are indicated as: ++++; 75%< x < 100%, +++; 50%< x < 75%, ++; 25%< x < 50%, +; 0%< x <25%. References: Gholipour et al , Li et al , Schilmiller et al , McDowell et al , Kim et al in the main manuscript. S-11
12 Figure S7-1. The range of m/z in IEC-PPESI-MS spectra obtained from stalk cells of type I (A), type II (B), type IV (C) and type VI trichomes (D). The full mass spectra are shown in Figure S-12
13 Figure S7-2. The range of m/z in IEC-PPESI-MS spectra obtained from stalk cells of type I (A), type II (B), type IV (C) and type VI trichomes (D). The full mass spectra are shown in Figure S-13
14 Figure S7-3. The range of m/z in IEC-PPESI-MS spectra obtained from stalk cells of type I (A), type II (B), type IV (C) and type VI trichomes (D). The full mass spectra are shown in Figure S-14
15 Figure S7-4. The range of m/z in IEC-PPESI-MS spectra obtained from stalk cells of type I (A), type II (B), type IV (C) and type VI trichomes (D). The full mass spectra are shown in Figure S-15
16 Figure S7-5. The range of m/z in IEC-PPESI-MS spectra obtained from stalk cells of type I (A), type II (B), type IV (C) and type VI trichomes (D). The full mass spectra are shown in Figure S-16
17 Figure S7-6. The range of m/z in IEC-PPESI-MS spectra obtained from stalk cells of type I (A), type II (B), type IV (C) and type VI trichomes (D). The full mass spectra are shown in Figure S-17
18 Figure S7-7. The range of m/z in IEC-PPESI-MS spectra obtained from stalk cells of type I (A), type II (B), type IV (C) and type VI trichomes (D). The full mass spectra are shown in Figure S-18
19 Figure S7-8. The range of m/z in IEC-PPESI-MS spectra obtained from stalk cells of type I (A), type II (B), type IV (C) and type VI trichomes (D). The full mass spectra are shown in Figure S-19
20 Figure S7-9. The range of m/z in IEC-PPESI-MS spectra obtained from stalk cells of type I (A), type II (B), type IV (C)and type VI trichomes (D). The full mass spectra are shown in Figure S-20
21 Figure S7-10. The range of m/z in IEC-PPESI-MS spectra obtained from stalk cells of type I (A), type II (B), type IV (C) and type VI trichomes (D). The full mass spectra are shown in Figure S-21
22 Figure S8. Mass spectra of type I (A) and II (B) stalk cell sap obtained by using nano ESI-MS with diluted cell sap samples in 50% acetonitrile solution S-22
23 Figure S9-1. The range of m/z in IEC-PPESI-MS spectra obtained from glandular cells of type I (A), type IV (B) and type VI trichomes (C). The full mass spectra are shown in Figure 4 and detected acyl sugars are listed in Table S S-23
24 Figure S9-2. The range of m/z in IEC-PPESI-MS spectra obtained from glandular cells of type I (A), type IV (B) and type VI trichomes (C). The full mass spectra are shown in Figure 4 and detected acyl sugars are listed in Table S S-24
25 Figure S9-3. The range of m/z in IEC-PPESI-MS spectra obtained from glandular cells of type I (A), type IV (B) and type VI trichomes (C). The full mass spectra are shown in Figure 4 and detected acyl sugars are listed in Table S S-25
26 Figure S10-1. IEC-PPESI-MS/MS spectra of putative flavonoid peak at m/z from a single stalk cell of type VI trichome performed using a Thermo Scientific Velos Pro linear ion trap-orbitrap mass spectrometer. A selected peak of precursor ion without addition of CID energy (A) and fragmentation patterns of the precursor ion induced with He at 23% collision energy (B). According to the MS/MS spectra, the precursor ion was identified as [Naringenin- H] - or [Naringenin chalcone-h] S-26
27 Figure S10-2. IEC-PPESI-MS/MS spectra of putative flavonoid peak at m/z from a single stalk cell of type VI trichome performed using a Thermo Scientific Velos Pro linear ion trap-orbitrap mass spectrometer. A selected peak of precursor ion without addition of CID energy (A) and fragmentation patterns of the precursor ion induced with He at 23% collision energy (B). According to the MS/MS spectra, the precursor ion was identified as [Naringenin hexoside-h] -, tentatively [Naringenin-O-glucoside-H] S-27
28 Figure S10-3. IEC-PPESI-MS/MS spectra of putative flavonoid peak at m/z from a single stalk cell of type VI trichome performed using a Thermo Scientific Velos Pro linear ion trap-orbitrap mass spectrometer. A selected peak of precursor ion without addition of CID energy (A) and fragmentation patterns of the precursor ion induced with He at 23% collision energy (B). According to the MS/MS spectra, the precursor ion was identified as [Tetrahydroxyflavone-hexoside-H] S-28
29 Figure S10-4. IEC-PPESI-MS/MS spectra of putative flavonoid peak at m/z from a single stalk cell of type VI trichome performed using a Thermo Scientific Velos Pro linear ion trap-orbitrap mass spectrometer. A selected peak of precursor ion without addition of CID energy (A) and fragmentation patterns of the precursor ion induced with He at 23% collision energy (B). According to the MS/MS spectra, the precursor ion was identified as [Quercetinhexoside-H] -, tentatively [Quercetin-O-glucoside-H] S-29
30 Figure S10-5. IEC-PPESI-MS/MS spectra of putative flavonoid peak at m/z from a single stalk cell of type VI trichome performed using a Thermo Scientific Velos Pro linear ion trap-orbitrap mass spectrometer. A selected peak of precursor ion without addition of CID energy (A) and fragmentation patterns of the precursor ion induced with He at 23% collision energy (B). According to the MS/MS spectra, the precursor ion was identified as [Kaempferolhexosyl-hexoside-H] -, tentatively [Kaempferol-O-rutinoside-H] S-30
31 Figure S10-6. IEC-PPESI-MS/MS spectra of putative flavonoid peak at m/z from a single stalk cell of type VI trichome performed using a Thermo Scientific Velos Pro linear ion trap-orbitrap mass spectrometer. A selected peak of precursor ion without addition of CID energy (A) and fragmentation patterns of the precursor ion induced with He at 23% collision energy (B). According to the MS/MS spectra, the precursor ion was identified as [Naringenindihexoside-H] -, tentatively [Naringenin-5,7-O-di-diglucoside-H] S-31
32 Figure S10-7. IEC-PPESI-MS/MS spectra of putative flavonoid peak at m/z from a single stalk cell of type VI trichome performed using a Thermo Scientific Velos Pro linear ion trap-orbitrap mass spectrometer. A selected peak of precursor ion without addition of CID energy (A) and fragmentation patterns of the precursor ion induced with He at 23% collision energy (B). According to the MS/MS spectra, the precursor ion was identified as [Quercetinhexosyl-hexoside-H] -, tentatively [Quercetin-O-rutinoside-H] S-32
33 Figure S10-8. IEC-PPESI-MS/MS spectra of putative flavonoid peak at m/z from a single stalk cell of type VI trichome performed using a Thermo Scientific Velos Pro linear ion trap-orbitrap mass spectrometer. A selected peak of precursor ion without addition of CID energy (A) and fragmentation patterns of the precursor ion induced with He at 23% collision energy (B). According to the MS/MS spectra, the precursor ion was identified as [Rhamnetinhexosyl-hexoside-H] -, tentatively [Rhamentin-O-rutinoside-H] S-33
34 Figure S10-9. IEC-PPESI-MS/MS spectra of putative flavonoid peak at m/z from a single stalk cell of type VI trichome performed using a Thermo Scientific Velos Pro linear ion trap-orbitrap mass spectrometer. A selected peak of precursor ion without addition of CID energy (A) and fragmentation patterns of the precursor ion induced with He at 28% collision energy (B). According to the MS/MS spectra, the precursor ion was identified as [Quercetindihexoside-H] -, tentatively [Quercetin-O-di-glucoside-H] S-34
35 Figure S IEC-PPESI-MS/MS spectra of putative flavonoid peak at m/z from a single stalk cell of type VI trichome performed using a Thermo Scientific Velos Pro linear ion trap-orbitrap mass spectrometer. A selected peak of precursor ion without addition of CID energy (A) and fragmentation patterns of the precursor ion induced with He at 23% collision energy (B). According to the MS/MS spectra, the precursor ion was identified as [Naringenindihexoside+Cl] -, tentatively [Naringenin-O-di-glucoside+Cl] S-35
36 Figure S IEC-PPESI-MS/MS spectra of putative flavonoid peak at m/z from a single stalk cell of type VI trichome acquired with a Thermo Scientific Velos Pro linear ion trap-orbitrap mass spectrometer. A selected peak of precursor ion without addition of CID energy (A) and fragmentation patterns of the precursor ion induced with He at 23% collision energy (B). According to the MS/MS spectra, the precursor ion was identified as [Quercetinrhamnosyl-hexoside-H] -, tentatively [Quercetin-O-rutinosyl-glucoside-H] S-36
37 Figure S11-1. IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S2:10) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-37
38 Figure S11-2. IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S3:12) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-38
39 Figure S11-3. IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S3:14) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-39
40 Figure S11-4. IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S2:15) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-40
41 Figure S11-5. IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S3:15) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-41
42 Figure S11-6. IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S4:16) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-42
43 Figure S11-7. IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S3:17) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-43
44 Figure S11-8. IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S4:17) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-44
45 Figure S11-9. IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S3:19) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-45
46 Figure S IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S3:20) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-46
47 Figure S IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S3:21) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-47
48 Figure S IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S4:17) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap-orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-48
49 Figure S IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S3:22) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-49
50 Figure S IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S3:15) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-50
51 Figure S IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S4:22) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-51
52 Figure S IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S4:24) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-52
53 Figure S IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S4:24) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-53
54 Figure S IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S4:22) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-54
55 Figure S IEC-PPESI-MS/MS spectra of an acylsugar peak at m/z (S4:23) from a single type IV trichome gland performed using a Thermo Scientific Velos Pro linear ion trap- Orbitrap mass spectrometer. A selected peak of precursor ion without addition of collision energy (A) and fragmentation patterns of the precursor ion by CID (B) S-55
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