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2 JAPANESE BUTTERBUR EXTRACT Petasites japonicus Japanese Butterbur (P. japonicus Maxim.)P. japonicus Maxim. var. giganteus ,800 90% 40% 10 5 JA TNF- 1
3 in vivo ) fukinoside 2) 1) Shimoda H., Tanaka J., Yamada E., Morikawa T., Kasajima N., Yoshikawa M. Anti type I allergic property of Japanese butterbur extract and its mast cell degranulation inhibitory ingredients. J. Agric. Food Chem., 54, (2006). 2) Yoshikawa M., Morikawa T., Tanaka J., Shimoda H. Medicinal foodstuff XXXII. Novel sesquiterpene glycoside sulfate, fukinoside A, with antiallergic activity from Japanese butterbur (Petasites japonicus). Heterocycles, 68 (11), (2006) in press. H H C H H 1-4) H 5) CH 3 CC=CHCH ) 9) 10) 11) 12) 13) 14) DNA 15, 16 Petasites hybridus 17, 18) C 2
4 19) 1) Naya K., Takagi I. The structure of petasitin, a new sesquiterpene from Petasites japonicus Maxim. Tetrahedron Lett., 5, (1968). 2) Naya K., Nakagawa M., Hayashi M., Tsuji K., Naito M. The constituents of Petasites japonicus Maxim. Rhizomes. Tetrahedron Lett., 31, (1971). 3) Tori M., Kawahara M., Sono M. Novel epoxyeremophilanolides, eremopetasitenins A1, A2, B1, and B2, from Petasites japonicus. Tetrahedron Lett., 38, (1997). 4) Goto Y., Kojima Y., Nakayama T., Terazawa M. Allelopathic sesquiterpenoids from rhizomes of Petasites japonicus ssp. Giganteus Kitam. Phytochemistry, 57, (2001). 5) Tobinaga S., Takeuchi N., Kasama T., Yamashita J., Aida Y., Kaneko T. Anti-histaminic and anti-allergic principles of Petasites japonicus Maxim. Chem. Pharm. Bull., 31, (1983). 6) FELD, Hildegard 2004 p. 89 (2004). 7) 2004 p. 89 (2004). 8) 3, (2004). 9) 2004 p. 87 (2004). 10) Kusano A., Seyama Y., Nagai M., Shibano M., Kusano G. Effects of fukinolic acid and cimicifugic acids from Cimicifuga species on collagenolytic activity. Biol. Pharm. Bull., 24, (2001). 11) Loser B., Kruse S.., Melzig M. F., Nahrstedt A. Inhibition of neutrophil elastase activity by cinnamic acid derivatives from Cimicifuga racemosa. Planta Med., 66, (2000). 12) Kruse S.., Lohning A., Pauli G. F., Winterhoff H., Nahrstedt A. Fukilic and piscidic acid esters from the rhizome of Cimicifuga racemosa and the in vitro estrogenic activity of fukinolic acid. Planta Med., 65, (1999). 13) Noguchi M., Nagai M., Koeda M., Nakayama S., Sakurai N., Takahira M. Vasoactive effects of cimicifugic acids C and D, and fukinolic acid in cimicifuga rhizome. Biol. Pharm. Bull., 21, (1998). 14) Kusano G., Takahira M., S., Shibano M., Kusano A., kamoto Y., Tsujibo H., Numata A., Inamori Y. Studies on inhibitory activities of fukilic acid esters on germination, -amylase and carboxypeptidase A. Biol. Pharm. Bull., 21, (1998). 15) Mizushina Y., Hirota M., Murakami C., Ishidoh T., Kamisuki S., Shimazaki N., Takemura M., Perpelescu M., Suzuki M., Yoshida H., Sugawara F., Koiwai., Sakaguchi K. Some anti-chronic inflammatory compounds are DNA polymerase -specific inhibitors. Biochem. Pharmacol., 66, (2003). 16) Mizushina Y., Kamisuki S., Kasai N., Ishidoh T., Shimazaki N., Takemura M., Asahara H., Linn S., Yoshida S., Koiwai., Sugawara F., Yoshida H., Sakaguchi K. Petasiphenol: a DNA polymerase inhibitor. Biochemistry, 41, (2002). 17) Lee D. K., Carstairs I. J., Haggart K., Jacson C. M., Currie G. P., Lipworth B. J. Butterbur, a herbal remedy, attenuates adenosine monophosphate induced nasal responsiveness in seasonal allergic rhinitis. Clin. Exp. Allergy, 33, (2003). 18) Schapowal A. Randomised controlled trial of butterbur and cetirizine for treating seasonal allergic rhinitis. B. M. J., 328, 1-4 (2002). 19) Bickel D., Rder T., Bestmann H. J. Brune K. Identification and characterization of inhibitors of peptide-leukotriene-synthesis from Petasites hybridus. Plant Med., 60, (1994). 3
5 RBL-2H3 fukinoside A (potassium 2β-hydroxyfukinone-2--β- D-glucopyranoside-6'-sulfate) H K S H H H (+)-fukinone 2β-hydroxyfukinone fukinoside A H HC H chlorogenic acid H H C fukinolic acid H H caffeic acid H H H C H H 3,5-dicaffeoyl quinic acid Dotorioside II H H R 4,5-dicaffeoyl quinic acid: R=H 4,5-dicaffeoyl quinic acid methyl ester: R=CH 3 H H 2. H mussaendoside R H H C H 4
6 IgE IgE LynSyk 5- TNF- TNF- ( 3) 3. 5
7 TNF TNF- 4. 6
8 RBL-2H RBL-2H3 n= RBL-2H3 IC50 IC50g/ml RBL-2H3 mussaendoside R 6 3 7
9 RBL-2H3 n=4 3. RBL-2H3 IC50 IC50g/ml IC50g/ml (+)-Fukinone 4.2 2β-Hydroxyfukinone 4.2 Chlorogenic acid 9.5 Fukinolic acid 2.1 Caffeic acid 8.6 3,5-Dicaffeoyl quinic acid 2.9 4,5-Dicaffeoyl quinic acid 3.3 4,5-Dicaffeoyl quinic acid methyl ester 4.0 Dotorioside II 4.0 Mussaendoside R >100 IC50g/ml Potassium 2β-hydroxyfukinone-2--β-D-glucopyranoside-6'-sulfate 8.6 RBL-2H3 10%100 unit/ml 100 g/ml Minimum Essential Medium Eagle MEM Sigma 375%C2 RBL-2H l/well 1 DNP-IgE Sigma (0.45 g protein/ml) l siraganian bufferph mm NaCl, 5 mm KCl, 0.4 mm MgCl2, 25 mm PIPES l 5.6 mm glucose, 1 mm CaCl2 0.1% BSA 8
10 siraganian buffer l 10 DNP-BSA10 g/ml l M bufferph mm p-nitrophenyl-n-acetyl--glucosaminide (PNAG) 50 l l 0.1M NaHC3/Na2C3, ph: nm 7 7. RBL-2H3 n=6 30 ELIZA Leukotriene C4/D4/E4 enzyme immunoassay system 9
11 TNF- TNF g/ml RBL-2H3 TNF-n=4 4 TNF- ELIZA Tumor Necrosis Factor Alpha [()TNF]RatBiotrak ELIZA system in vivo I PCA
12 9. PCA n=6 Wistar, 7 PBS (-) DNP-IgE (100 l/site) %2 DNP-BSA (1.5 mg/ml) 1%PBS (-) (0.5 ml) 30 D4 500 mg/kg 10. D4 n=4 11
13 20 5% 2 1%PBS (-) (0.5 ml) 30 D 4 1 g/ml PBS (-) L/site) mm KCl 10 M % % g/ml 1 M g/ml 10 nm D % % g/ml g/ml 11. n=3-6*: p<0.05**: p<0.01: 12
14 KCl D4 KCl g/ml D4 KCl 4 D KCl n (%) 1 (g/ml) ** ** **: p< His n (%) (g/ml) His 1 (M) * *: p< D4LT n (%) (g/ml) LT 10 (nm)
15 KCl Wistar gkrebs-henseleit NaCl: 118 mm, KCl: 2.7 mm, KH 2 P 4 : 1.2 mm, MgS 4 : 1.2 mm, CaCl 2 : 2.5 mm, NaHC 3 : 25 mm, Glucose: 10 mm 15 mm : 6 ml5% 2, 95%N 2 1 g MacLab 8e AD Instruments, Chart v M KCl 100 L 50 mm M KCl100 L DMS 3 L 30 EDTA37.2 mg/l Krebs-Henseleit 1 mm DMS 6 L 10 1 mm 6 L mm DMS 6 L10 DMS 6 L10 1 nm10 M Hartley g1 M Krebs-Henseleit 34 mm 1 g 10 mm 6 L 10 M mm 6 L10 3 DMS 6 L mm D 4 10 M D 4 6 L 10 nm M D 4 6 L 10 3 DMS 6 L M D 4 6 L 14
16 [10 3 ] 250 mg mg/ /cm 2 12 /cm I ECP 15
17 13. 16
18
19 -P P 100% -P ph 1 -P ph 16-P ph 100% 18
20 -WSP 0.5pH ph g/100g 6.2 g/100g g/100g 20.9 g/100g 68.5 g/100g kcal/100g 0.3 g/ mg/100g (+++) ; 9; 4;
21 ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm ppm
22 2000 mg/kg ICR 5 14 LD mg/kg -P 250 mg 1) 2) -WSP -P,-WSP 5kg -PC-WSPC 5kg -LC 5kg 21
23 -P -WSP INCI Petasites Japonicus Powder -PC / INCI DextrinPetasites Japonicus Leaf/Stem Extract -WSPC / INCI DextrinPetasites Japonicus Leaf/Stem Extract -LC BG/ INCI Butylene GlycolWaterPetasites Japonicus Leaf/Stem Extract 22
24 -P Petasites japonicus (1) 250 mg HPLC10 HPLC 10 ml 0.45 m PTFE HPLC 0.1 mg/ml 5 l HPLC capcellpak C18 () 4.6 mm 250 mm Solvent A = 2.1 g 1L Solvent B = [min] %A 100%A 80%A 20%B 80%A 20%B 60%A 40%B 60%A 40%B 100%B 100%B 1 ml/minuv 324 nm 30 (2) 2.0 g 10 ml 1 10 ml rpm % 3 ml Sep-Pak C1870 % 7 ml 5 ml 10 ml 0.45 m PTFE 0.1 mg/ml 10 l (HPLC) Shim-pack CLC-DS6.0 mm 150 mm 82 1 ml/minuv 254 nm30 23
25 1.0 % Folin-Denis [] 300 l/100 g (-P 60 l/100 g ) 10.0 % 1g ppm 2 1 ppm /g /g BGLG 80% 20% 100% 24
26 -WSP Petasites japonicus 250 mg HPLC10 HPLC 10 ml 0.45 m PTFE HPLC 0.1 mg/ml 5 l HPLC capcellpak C18 () 4.6 mm 250 mm Solvent A = 2.1 g 1L Solvent B = [min] %A 100%A 80%A 20%B 80%A 20%B 60%A 40%B 60%A 40%B 100%B 100%B 1 ml/minuv 324 nm % Folin-Denis 10.0 % 1g ppm 2 1 ppm 25
27 310 3 /g /g BGLG 80% 20% 100% 26
28 Petasites japonicus (1) 1.5 g 70%15 ml 70270% 15 ml 70 HPLC10 HPLC 25 ml 0.45 m PTFE HPLC 0.1 mg/ml 5 l HPLC capcellpak C18 () 4.6 mm 250 mm Solvent A = 2.1 g 1L Solvent B = [min] %A 100%A 80%A 20%B 80%A 20%B 60%A 40%B 60%A 40%B 100%B 100%B 1 ml/minuv 324 nm30 (2) 5.0 g 70%50 ml 70270% 30 ml ml 1 10 ml rpm % 3 ml Sep-Pak C1870 % 7 ml 5 ml 10 ml 0.45 m PTFE 0.1 mg/ml 10 l 27
29 (HPLC) Shim-pack CLC-DS6.0 mm 150 mm 82 1 ml/minuv 254 nm % 1g ppm 2 1 ppm /g /g BGLG 100% 28
30 -PC Petasites japonicus (1) 250 mg HPLC10 HPLC 10 ml 0.45 m PTFE HPLC 0.1 mg/ml 5 l HPLC capcellpak C18 () 4.6 mm 250 mm Solvent A = 2.1 g 1L Solvent B = [min] %A 100%A 80%A 20%B 80%A 20%B 60%A 40%B 60%A 40%B 100%B 100%B 1 ml/minuv 324 nm 30 (2) 2.0 g 10 ml 1 10 ml rpm % 3 ml Sep-Pak C1870 % 7 ml 5 ml 10 ml 0.45 m PTFE 0.1 mg/ml 10 l (HPLC) Shim-pack CLC-DS6.0 mm 150 mm 82 1 ml/minuv 254 nm30 29
31 1.0 % Folin-Denis [] 300 l/100 g (-PC 60 l/100 g ) 10.0 % 1g ppm ppm /g /g BGLG 80% / 20% 100% 30
32 -WSPC Petasites japonicus 250 mg HPLC10 HPLC 10 ml 0.45 m PTFE HPLC 0.1 mg/ml 5 l HPLC capcellpak C18 () 4.6 mm 250 mm Solvent A = 2.1 g 1L Solvent B = [min] %A 100%A 80%A 20%B 80%A 20%B 60%A 40%B 60%A 40%B 100%B 100%B 1 ml/minuv 324 nm % Folin-Denis 10.0 % 1g ppm ppm 3 31
33 110 2 /g /g BGLG 80% / 20% 100% 32
34 -LC Petasites japonicus 1,3-BG 30 l 3.5 ml 0.2 ml 0.4 ml 1 10 ppm ( 2 ) 2 1 ppm ( 3 ) /g /g BGLG BG 69% 30% / 1% 100% 33
35 TEL(0586) () FAX(0586) URL/ F TEL (03) FAX (03) * * * *
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RYZA IL & FAT CHEMICAL C., LTD. SAKURA EXTRACT Ver.1.4MK Ver. 1.4MK 1) 1300 1929 1 Ver. 1.4MK Sakura 1-caffeoyl---D-glucopyranoside quercetin 3---D-glucopyranoside 1) :, 4, 11-22 (1995). 2 Ver. 1.4MK 3
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ORYZA CERAMIDE -PTPCDP8TP20CD -WSPWSP8 -LL0.8 -PCPC8PC20 -WSPCWSPC8 -LCLC0.8 Ver.13.0HS ORYZA CERAMIDE Ver.13.0HS 1. 2. 20 NMR 4 ( 1) 1 Ver.13.0HS HO CH 2 OH O O OH OH OH C CH CH H 2 NH C O R C H C H (CH
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ver. 4.3 HS 14 1,620-6- 1) 2) 1 24% p- 45 1) Schwab D. et al., Hepatic uptake of synthetic chlorogenic acid derivatives by the organic anion transport proteins. J. Pharmacol. Exp. Ther. 296, 91-8 (2001).
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ORYZA POLYAMINE ORYZA POLYAMINE -P -PC -LC 1. Ver.1.0 MM ver. 1.0MM 1) Roseeuw D.I. et al., Epidermal keratinocytes actively maintain their intracellular polyamine levels. Cell Tissue Kinet. 16, 493-504
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ver. 3.3JT EVENING PRIMROSE EXTRACT 1 - PMS 1 2 1 4 Oenothera laciniata Oenothera striata Oenothera biennis Oenothera erythrosepala - 2 80 60 40 20 0 1. 2 3 PGGPAC 2. 3 4 ESR3.5 10 5 /g 4 3 1 Helicobacter
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ORYZA OIL & FAT CHEMICAL CO., LTD. ALPHA LIPOIC ACID --P () --P80 () --WSP8 () --L1 () --PC () --PC80 () --WSPC8 () --LC1 () ver. 5.1HS ver5.1 HS 1. ALPHA LIPOIC ACID 16 3 31 0331009 - () 19 5 24 0524001
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3--2-3-Iodo-2-propynyl butylcarbamate (IPBC) Carbamic acid, butyl-, 3-iodo-2-propynyl ester Iodocarb CAS 55406-53-6 C 8 H 12 NO 2 I C (g/cm 3 ) (mmhg) log P ow 281.09 (280.9910) 64 68 1.51 1.57 (20 C)
研究成果報告書
Arterioscler Thromb Vasc Biol., 27, 2400 2406 (2007) J. Agri. Food Chem., 59, 4544 4552 (2011) Bioorg. Med. Chem. Lett., 21, 1786 1791 (2011) Advanced glycation end products (AGEs) AGEs AGEs AGEs HbA1c
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CH 2 H H H CH 2 n-1 H CH 2 n H Potato α-glucan phosphorylase H n soluble starch P i n-1 H P() 2 glucose-1-phosphate Pi H CBPase H glucose P i glucose-1-phospate cellobiose H cellooligosaccharide n+1 CDPase
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er. 3.0SJ ver.3.0 SJ 3 2 1 ver.3.0 SJ 900 1200 () 400 2 ver.3.0 SJ OH OMe OMe O O O MeO O MeO OMe O O OMe O OMe OMe O O MeO O O H O O MeO OMe O H O OH OMe O CH 2 HO O O O O CH 3 OH HO OH OH HO OH O 1 3
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Fig. 1. Structure of [methyl-14c]zonisamide
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Key words : Zonisamide, Metabolism, Plasma, Erythrocytes, Preputial gland, Urine, Bile, Rat, Dog, Monkey Metabolism of ["Clzonisamide in rats, dogs and monkeys Katashi MATSUMOTO, Koji YOSHIDA, Toshihiko
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本文／ＹＡ９２５５Ｃ
pp. E- -SH X in vitro in vivo -SH Structure-based drug development and medical biological application of cathepsin specific inhibitors Nobuhiko Katunuma Institute for Health Sciences, Tokushima Bunri University,Nishihamabouji,
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参考資料５ 農薬評価書 メタアルデヒド（食品安全委員会資料）
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J. Jpn. Soc. Colour Mater., 79 [3], 113-119 (2006) Anthocyanins : Structural Diversity, Color, and in Vivo Behavior Yuko NAKAGAWA, Takashi ICHIYANAGI, Tetsuya KONISHI and Seiichi MATSUGO J. Jpn. Soc. Colour
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E-mail: khatano@fms.saitama-u.ac.jp Tel & Fax: 048-858-3535 Toxin Virus Bacterium Glycolipid Glycoprotein Vero toxin (Stx1 and Stx2) Side view Bottom view H H H H N H Grobotriaosyl Ceramide (Gb 3 : Galα1-4Galβ1-4Glcβ-Cer)
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ORYZA OIL & FAT CHEMICAL CO., LTD. WHITE JELLY FUNGUS EXTRACT -P () Ver. 1.3SJ Ver. 1.3SJ 1. 3000 ph 1 Ver. 1.3SJ 1. 1 2. 3 2-1. 2-2. 2-3. 2-4. SOD 3. 7 3-1. in vitro 3-2. in vivo 3-3. in vivo 3-4. in
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3240 14 8 8 50mg 75mg 13 6 25 1-(1) H 3 C O OH HO H O O H OH SO H 3 Na H H N H 2 N NH OH H N O O H H O OH H 3 C H O O N H H H HO H NH CH 3 HN HO H OH O H OH H NH O N O C 56 H 70 N 9 NaO 23 S 1292.26 5-[(1S,2S)-2-
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Vol. 1 (2005) pp. 91-103 * ( 17 1 27 ) Approach from Bioelectronics to Bio-Interface Masashi YAOITA * Our studies for approach to bio-interface were fabrication of a needle type glucose sensor for continuous
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