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1 Toshihiro HKURA, Minako MCHIZUKI, Michiyo HNISHI, Yuzou KA, Mitsunori DI An analytical method using liquid chromatography tandem mass spectrometry (LC/MS/MS) and liquid chromatography Time-of-Flight mass spectrometry (LC/TF-MS) equipped with electrospray ionization (ESI) was demonstrated for the determination of amount of polyphenols, such as anthocyanins (5 compounds), flavanones (5 compounds), flavones (10 compounds), flavonols (6 compounds), isoflavones (6 compounds) and anthraquinones (3 compounds), catechins(4 compounds), and furanocoumarins (4 compounds) in so-called health-promoting food. The HPLC eluted analytes within 32 min, and analytical cycle was 50 min by a sample. The sample was crushed, powdered with mortar, extracted with methanol and subjected to LC/MS/MS and LC/TF-MS without hydrolysis. The limit of quantification of developed method was μg/g(S/N=10) in samples. Amount of individual compound of polyphenols and furanocoumarins (43 compounds) was determined by analyzing each of 39 health-promoting food items which sell in the high-ranking of all obtained in Japan and the daily intake of individual compounds was estimated by the amount of compound and the daily intake of individual item. A Study on the daily intake of polyphenols and furanocoumarins through foods obtained in Ehime Prefecture was carried out by the total diet-market basket method on the basis of food classification and the data of food consumption in the Shikoku region obtained from the Japan Nutrition Survey. In several health-promoting food items, isoflavones were detected and the highest daily intake of isoflavone aglycone was estimated to be 21 mg/day. This highest daily intake of isoflavone was lower than the upper limit for safe daily extra dietary intake of soy isoflavone as a food for specified health use (30 mg/day). The dietary intake of isoflavone aglycone was estimated to be 15 mg/day. polyphenols, furanocoumarins, health-promoting food, liquid chromatography mass spectrometry, LC/MS/MS, LC/TF-MS, daily intake, food, total diet-market basket

2 1) 2) 3) 4) 5) 303 4LC/MS/MS 643 LC/TF-MS 1 (LC/MS(/MS)) Alliance 2695( )Agilent 1200 SL(Agilent Technologies) Quattro micro API() micrtf II(Bruker Daltonics) ChromaDex,Inc.LKT Laboratories,Inc.Alfa AesarCayman ChemicalMP Biomedicals LC/MS PTFE0.2μm Mini-UniPrep HPLC Ascentis Express RP-Amide (2.1mm i.d. 150mm, 2.7μm) (SUPELC) 秤 50100μg/mL RMilli-Q Gradient-A ) 13 16

3 17

4 H H + H Anthocyanin Cyanidin-3-glucoside H H -glucose Petunidin-3-glucoside H CH3 -glucose Pelargonidin-3-glucoside H H -glucose Peonidin-3-glucoside CH3 H -glucose Malvidin-3-glucoside CH3 CH3 -glucose H Flavanone Hesperetin H CH3 H Hesperidin H CH3 -rutinose Naringenin H H H Naringin H H -neohesperidose Neohesperidin H CH3 -neohesperidose R4 R5 R4 H Flavone R4 R5 Apigenin H H H H H Vitexin H H H H glucose Cosmetin H H H -glucose H Baicalein H H H H H Baicalin H H H -glucuronic acid 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 Isoflavone R4 Daidzein H H H H Genistein H H H H Glycitein H H CH3 H Daidzin H H H -glucose Genistin H H H -glucose Glycitin H H CH3 -glucose R5 H R5 R4 R4 H Flavonol R4 R5 Astragalin H H H -glucose H Hyperoside H H H -galactose H Kaempferol H H H H H Quercetin H H H H H Quercitrin H H H -rhamnose H Rutin H H H -rutinose H (-C9H15) Anthraquinone R4 R5 Purupurin H H H H H Emodin H CH3 H H H Rhein H CH H H H H H H H 7 6 H gallate H H Furanocoumarin Bergapten H CH3 Isopimpinellin CH3 CH3 Bergamottin H -C9H15 6,7-Dihydroxybergamottin H -C9H15(H)2 Catechin (-)-Epicatechin H H H (-)-Epigallocatechin H H H (-)-Epicatechin-3-gallate H -gallate H (-)-Epigallocatechin-3-gallate H -gallate H 18

5 5 200mg 秤 10mL flavonol 200ng/mL5.0mL PTFE0.2μm 1μLLC/MS(/MS) 2 1 MS/MS LC/MS ESI MS/MS MS/MS 2ESI(+)43MS/MS 2 ESI(+)TF-MS (HR-EIC) MS/MS TF-MS M (M+H) HR-EICm/z

6 Intens min min Time [min] min 11 LC/MS/MS Intens LC/TF-MS : MRMof 6 Channels ES > e5 % : MRMof 6 Channels ES > e5 % : MRMof 6 Channels ES > e5 % : MRMof 6 Channels ES > e5 % x min 6 0 genistein > genistein > apigenin > apigenin > apigenin genistein baicalein Time luteolin-3',7-diglucoside hesperidin min min min 14 C18 RP-Amide neohesperidin rutin Time [min] 3 LC/MS LC/MS2 HPLCRP-Amide / MS/MS 8 TF-MS LC 8mM- (CH3CN/H2=3/2) LCC18apigenin genisteinmrm(ms/ms) 3 RP-Amide MRM(MS/MS) 4TF-MSHR-EIC Intens. x LC/TF-MS HR-EIC Std.mix. 100μg/L min 21 flavonol (I.S.) min min min min min min min min min min min min min min min min min min min min min min min min min Time [min] 20

7 4 flavonol(200μg/l) (101000μg/L)flavonol 5 LC/MS/MS (r 2 )daidzein, glycitein μg/L daidzein, glycitein (r 2 )10500μg/L μg/L %(n=6) (S/N=10)0.2 20μg/L LC/TF-MSdaidzin, glycitin, daidzein, glycitein, isopimpinellin, apigenin, bergamottin, emodin (r 2 ) 21

8 LC/TF-MS LC/MS/MS 8(r 2 ) μg/L %(n=6) (S/N=10)0.5 20μg/L (100μg/L)LC/TF-MS HR-EIC5 5 2 N,N- DMFLC/MS DMF 6 0.2μg1μg 6 LC/MS/MS0.2μg %1μg % 0.2μg1.39.1%1μg % baicaleinquercetin LC/TF-MS0.2μg %1μg % 0.2μg %1μg % 0.2μg 1μgbaicalein quercetin (flavonol 200μg/L) (S/N=10) μg/g μg/ 18 2) 30mg (43 ) LC/MS/MS LC/TF-MS 1 HPLCRP-Amide / 50 2 ESI(+)flavonol 43 (S/N=10)0.2 20μg/L 3 LC/MS/MSLC/TF-MS 22

9 4 5 LC/MS/MS LC/TF-MS0.2μg 1μg baicaleinquercetin 6 (S/N=10) μg/g mg mg 23

10 24

11 25

12 1) :, ( ) 2) :, ( ) 3) :, 2007, 454 4) :, (2007), () 5) :,11,20-28(2008) 6) :, (211) 26

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