Toshihiro OHKURA, Michiyo ONISHI, Makoto AONO, Takurou TAKECHI
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1 Toshihiro HKURA, Michiyo NISHI, Makoto AN, Takurou TAKECHI An analytical method using liquid chromathography tandem mass spectrometry (LC/MS/MS) equipped with electrospray ionization (ESI) was demonstrated for the determination of polyphenols, such as anthocyanins (5 compounds), flavanones (5 compounds), flavones (8 compounds), flavonols (6 compounds), isoflavones (6 compounds) and anthraquinones (3 compounds), and furanocoumarins (4 compounds) in so-called health-promoting food. The HPLC eluted analytes within 26 min, and analytical cycle was 35 min by a sample. The sample was crushed, powdered with mortar, extracted with methanol and subjected to LC/MS/MS without hydrolysis. The limit of quantification of developed method was.1-7.µg/g(s/n=3) in sample. The recoveries of analytes ranged from 81 to 126, and the variations in reproducibility ranged from 1.2 to 9.9 and were acceptable for quantitative analysis. polyphenols, furanocoumarins, health-promoting food, liquid chromathography tandem mass spectrometry, LC/MS/MS
2 LC/MS/MS 1 (LC/MS) Alliance 2695( )Quattro micro API( ) ChromaDex,Inc.LKT Laboratories,Inc.Alfa AesarCayman ChemicalMP Biomedicals LC/MS N,N-DMF PTFE.2µmMini-UniPrep HPLCAscentis Express C18 (2.1mm i.d. 15mm, 2.7µm) (SUPELC) DMF 5µg/mL DMF RMilli-Q Gradient-A1 4 2mg 1mL DMF5µg/mL flavonol5µl5 4.5mL 535 PTFE.2µm 2µLLC/MS/MS 2 1 MS/MS LC/MS ESI MS/MS MS/MS MS.1(w/v) / (1/1).4mL/min.1µg/mL DMF1µL3MS 3MS M column Ascentis Express C18 (2.1mm i.d. 15mm, 2.7µm) (SUPELC) mobile phase A : CH 3 CN B :.5-HCH in H 2 C : H 2 A:B:C 15:2:65 (3min.) 6:2:2 (13min.) 76:1:14 (1523min.) 15:2:65 (23min.) flow rate.2ml/min ion source temp. 12 column temp. 3 desolvation temp. 35 injection volume 2L desorvation gas flow rate 6L/hr ionization mode cone gas flow rate 5L/hr acquisition mode MRM(MS/MS) capillary voltage 3.2kV 21
3 (MH) (M-2H) (M16) 6,7-dihydroxy bergamottin(mhc) bergapten, isopimpinellin, bergamottin ESI() MRM R.T Compound cone collision precursor product function (min.) (V) (ev) ( ) ( ) cyanidin-3-glucoside petunidin-3-glucoside pelargonidin-3-glucoside peonidin-3-glucoside malvidin-3-glucoside daidzin glycitin luteolin-3',7-diglucoside vitexin rutin hyperoside genistin astragalin quercitrin naringin cosmetin rhoifolin diosmin neohesperidin hesperidin daidzein glycitein luteolin quercetin genistein naringenin apigenin kaempferol hesperetin bergapten isopimpinellin ,7-dihydroxy bergamottin rhein chrysin purpurin flavonol (I.S.) emodin bergamottin ionization mode ESI() ESI() scan range () 7 7 ion source temp. desolvation temp desolvation gs flow rate 6L/hr 6L/hr cone gas flow rate 5L/hr 5L/hr capillary voltage 3.2kV 3.kV cone voltage 25V 45V 22
4 H H H H Anthocyanin Flavanone Cyanidin-3-glucoside H H -glucose Hesperetin H CH3 H Petunidin-3-glucoside H CH3 -glucose Hesperidin H CH3 -rutinose Pelargonidin-3-glucoside H H -glucose Naringenin H H H Peonidin-3-glucoside CH3 H -glucose Naringin H H -neohesperidose Malvidin-3-glucoside CH3 CH3 -glucose Neohesperidin H CH3 -neohesperidose R5 R4 H Flavone R4 R5 Apigenin H H H H H Vitexin H H H H glucose Cosmetin H H H -glucose H Chrysin H H H H H Diosmin H CH3 H -rutinose H Luteolin H H H H H Luteolin-3,7-diglucoside -glucose H H -glucose H Rhoifolin H H H -neohesperidose H R4 R5 R4 H Flavonol R4 R5 Isoflavone R4 Astragalin H H H -glucose H Daidzein H H H H Hyperoside H H H -galactose H Genistein H H H H Kaempferol H H H H H Glycitein H H CH3 H Quercetin H H H H H Daidzin H H H -glucose Quercitrin H H H -rhamnose H Genistin H H H -glucose Rutin H H H -rutinose H Glycitin H H CH3 -glucose R5 H (-C9H15) R4 Anthraquinone R4 R5 Furanocoumarin Purupurin H H H H H Bergapten H CH3 Emodin H CH3 H H H Isopimpinellin CH3 CH3 Rhein H CH H H H Bergamottin H -C9H15 6,7-Dihydroxybergamottin H -C9H15(H)2 23
5 MS/MS MS/MS 2 HPLC HPLC / MS/MS LC/MS ESI cyanidin-3-glu 1ppm 6,7-dihydroxy cyanidin-3-glu 6,7-dihydroxy bergamottin bergamottin 1ppm (2.392) Cm (114:13-62:83) 1: Scan ES (2.438) Cm (95:17-67:78) 2: Scan ES e5 155 M e [MH] (2.31) Cm (19:126-66:82) 2: Scan ES e5 [M-2H] [M16] (2.448) Cm (97:17-72:81) 1: Scan ES e5 113 [MHC] hesperidin 1ppm bergamottin hesperidin bergamottin 1ppm (2.377) Cm (92:-13:142) 2: Scan ES (2.498) Cm (99:17-73:8) 2: Scan ES e [MH] 1.5e6 [MH] (2.286) Cm (8:97-151:169) 1: Scan ES- 173 [M-H] 1.59e (2.47) Cm (95:12-62:69) 1: Scan ES- 1.5e astragalin astragalin 1ppm bergapten 1ppm bergapten (2.936) Cm (145:16-113:125) 1: Scan ES (2.417) Cm (95:14-(77:84117:121)) 2: Scan ES e [MH] [MH] 1.49e (2.886) Cm (141: :128) 2: Scan ES (2.347) Cm (91:-57:7) 1: Scan ES e5 [M-H] 1.49e
6 (w/v)LC/MS/MS 4 5 pelargonidin-3-glukaempferolglycitein.5.1(5-(a)) Anthocyanin Flavanone Flavone Flavonol Isoflavone Anthra quinone Furano coumarin Compound M.F. cone (V) collision (ev) ESI() precursor ( ) product ( ) cone (V) collision (ev) ESI() precursor ( ) product ( ) cyanidin-3-glucoside C 21 H petunidin-3-glucoside C 22 H pelargonidin-3-glucoside C 21 H peonidin-3-glucoside C 22 H malvidin-3-glucoside C 23 H hesperetin C 16 H hesperidin C 28 H naringenin C 15 H naringin C 27 H neohesperidin C 28 H apigenin C 15 H vitexin C 21 H cosmetin C 21 H chrysin C 15 H diosmin C 28 H luteolin C 15 H luteolin-3',7-diglucoside C 27 H rhoifolin C 27 H astragalin C 21 H hyperoside C 21 H kaempferol C 15 H quercetin C 15 H quercitrin C 21 H rutin C 27 H daidzein C 15 H genistein C 15 H glycitein C 16 H daidzin C 21 H genistin C 21 H glycitin C 22 H purpurin C 14 H emodin C 15 H rhein C 15 H bergapten C 12 H isopimpinellin C 13 H bergamottin C 21 H ,7-dihydroxy bergamottin C 21 H
7 poly_mix4 5ppb IS 1-Aug-2917:4: : MRMof 5 Channels ES > e : MRMof 5 Channels ES > e : MRMof 5 Channels ES > e : MRMof 5 Channels ES > e : MRMof 5 Channels ES > e : MRMof 5 Channels ES > e Time (a) pelargonidin-3-glu (b) kaempferol (c) glycitein.5 poly_mix4 5ppb IS 1-Aug-2917:4: : MRMof 6 Channels ES > : MRMof 6 Channels ES > : MRMof 6 Channels ES > : MRMof 6 Channels ES > : MRMof 6 Channels ES > : MRMof 6 Channels ES > Time poly_mix4 5ppb IS 1-Aug-2917:4: : MRMof 5 Channels ES > : MRMof 5 Channels ES > : MRMof 5 Channels ES > : MRMof 5 Channels ES > : MRMof 5 Channels ES > : MRMof 5 Channels ES > Time hesperetin, narigenin, luteolin astragalinbergamottin (5-(b)) (5-(c)).1(w/v) 3 LC/MS/MS MS/MSHPLC LC/MS/MS 2 MS/MS 8 flavonol(3-hydroxyflavon) flavonol flavonol 2ppm (18.6) Cm (872: :866) [MH] 2: Scan ES H e HPLCflavonol flavonol 6flavonolMS 4 flavonol(5µg/l) (1µg/L)flavonol 5 (r 2 ) quercetin, daidzein, glycitein, rhein1µg/l quercetinrhein (S/N=3)25µg/Lµg/L (r 2 )
8 daidzein, glycitein2µg/l 1µg/L(r 2 ).978 2µg/L.36.5(n=4) (S/N=3) 2 25µg/L (µg/l)lc/ms/ms Anthocyanin Flavanone Flavone Flavonol Isoflavone Anthra quinone Furano coumarin Compound conc. (µg/l) r 2 RSD() (2µg/L) (n=4) limit of quant. (µg/l) (S/N:3) cyanidin-3-glucoside petunidin-3-glucoside pelargonidin-3-glucoside peonidin-3-glucoside malvidin-3-glucoside hesperetin hesperidin naringenin naringin neohesperidin apigenin vitexin cosmetin chrysin diosmin luteolin luteolin-3',7-diglucoside rhoifolin astragalin hyperoside kaempferol quercetin quercitrin rutin daidzein genistein glycitein daidzin genistin glycitin purpurin emodin rhein bergapten isopimpinellin bergamottin ,7-dihydroxy bergamottin DMF 6.2µg1µg 6LC/MS/MS 8.2µg µg µg µg Intensity Intensity poly_mix4 ppb IS 25-Jul-291:6: : MRMof 1 Channel ES > e5 Sa6 HF24 2ngIS 25-Jul-292:53: : MRMof 1 Channel ES > e5 Std.Soln. µg/l Time Sample admixed with std..2µg I.S. I.S Time
9 naringinvitexinkaempferol quercetin.2µg 1µg (S/N=3).1.µg/g (37)LC/MS/MS Anthocyanin Flavanone Flavone Flavonol Isoflavone Anthra quinone Furano coumarin Compound.2µg (n=6) Rec. () RSD () Sample:2mg 1µg (n=6) limit of quant. Rec. RSD (µg/g) () () (S/N:3) cyanidin-3-glucoside petunidin-3-glucoside pelargonidin-3-glucoside peonidin-3-glucoside malvidin-3-glucoside hesperetin hesperidin naringenin naringin neohesperidin apigenin vitexin cosmetin chrysin diosmin luteolin luteolin-3',7-diglucoside rhoifolin astragalin hyperoside kaempferol quercetin quercitrin rutin daizdein genistein glycitein daidzin genistin glycitin purpurin emodin rhein bergapten isopimpinellin bergamottin ,7-dihydroxybergamottin MS/MS 2 HPLC DS.1(w/v)/ 3 -LC/MS/MSflavonol 37 (S/N=3) 225µg/L (S/N=3).17.µg/g 1) :, ( ) 2) :, 27, 454 3) :, (27), () 4) Merken H. M. et al: J. Agric. Food Chem., 48, (2) 5) Dugo P. et al: J. Agric. Food Chem., 49, (21) 6) Sakakibara H. et al: J. Agric. Food Chem., 51, (23) 7) Wu Q. et al: J. Agric. Food Chem., 52, (24) 8) Klejdus B. et al: J. Agric. Food Chem., 53, (25) 9) Harnly J. M. et al: J. Agric. Food Chem., 54, (26) 1) Schmiedlin-Ren P. et al: Drug Metab. Dispos., 25, (1997) 11) Paine M.F. et al: Am. J. Clin. Nutr., 83, (26) 28
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