ver5.1 HS 1. ALPHA LIPOIC ACID () S S COOH HS 1. α - SH COOH - ( 1) CoA -( 2)- - --P80 (--WSP8-L1-WSPC8 -LC1) - 1
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1 ORYZA OIL & FAT CHEMICAL CO., LTD. ALPHA LIPOIC ACID --P () --P80 () --WSP8 () --L1 () --PC () --PC80 () --WSPC8 () --LC1 () ver. 5.1HS
2 ver5.1 HS 1. ALPHA LIPOIC ACID () S S COOH HS 1. α - SH COOH - ( 1) CoA -( 2)- - --P80 (--WSP8-L1-WSPC8 -LC1) - 1
3 ver5.1 HS [] [] CO 2 [] [] - CoA [] [-] - CO 2 H 2 O e - [] ATP e - Q10 [] H 2 O e - ATP* *
4 ver5.1 HS 2. () - 1) () - 2) 2004 Nature Medicine- ( ) 3) - 4) 1) Saengsirisuwan V., Perez F. R., Sloniger J. A. Maier T., Henriksen E. J. Interaction of exercise training and α-lipoic acid on insulin signaling in skeletal muscle of obese Zucker rats. Am. J. Physiol. Endocrinol. Metab., 287, E (2004). 2) Burke D. G., Chilibeck P. D., Parise G., Tarnopolsky M. A., Candow D. G. Effect of α-lipoic acid combined with creatine monohydrate on human skeletal muscle creatine and phosphagen concentration. Int. J. Spot. Nutr. Exerc. Metab., 13, (2003). 3) Kim M. S., Park J. Y., Namkoong C., Jang P. G., Ryu J. W., Song H. S., Yun J. Y., Namgoong I. S., Ha J., Park I. S., Lee I. K., Viollet B., Youn J. H., Lee H. K., Lee K. U. Anti-obesity effects of α-lipoic acid mediated by suppression of hypothalamic AMP-activated protein kinase. Nat. Med., 10, (2004). 4) Dicter N., Madar Z., Tirosh O. α-lipoic acid inhibits glycogen synthesis in rat soleus muscle via its oxidative activity and the uncoupling of mitochondria. J. Nutr., 132, (2002). 3
5 ver5.1 HS (1) (in vitro) L ( 3) 3. α- (L6) (±S.E., n=6) L MTT (2) (in vivo) - 24 in vivo ( 4) 4. - (±S.E., n=6) (ddy5 ) - ( %) (MF, ) 24 4
6 ver5.1 HS (3) (in vitro) - (3T3-L1) ( ) 5) ( 5) - 3- (GPDH) 3T3-L1 GPDH - ( 6) - 5) Cho K. J., Moon H. E., Moini H., Packer L., Yoon D. Y., Chung A. S. α-lipoic acid inhibits adipocyte differentiation by regulating pro-adipogenic transcription factors via mitogen-activated protein kinase pathway. J. Biol. Chem., 278, (2003). Control 1 µg/ml 3 µg/ml 10 µg/ml 5. α GPDH (n=2-3) 5
7 ver5.1 HS 3T3-L1 2 (1 µg/ml) (0.25 µm) (0.5 mm) (1 µg/ml) 1 7 3T3-L1 GPDH [ () ] (4) (in vivo) (0.1%) 7. - (n=5) (ddy5 ) - (0.1%) (MF, ) 13 (MK-770M) 10 (5 rpm) 1 1 (5) (in vitro) (HepG2) (L6) 1 -CPTACOX AMPK PPAR ( 9) 6
8 ver5.1 HS 8. CPT CoA ACOX camp AMPK PPAR - CPT - CPT - -ACOX ACOX - AMPK PPARα PPARγ β-actin - CPTACOX AMPK PPAR ( 9) 7
9 ver5.1 HS CPT ACOX PPAR AMPK β-actin α-µg/ml α-µg/ml α-β-actin 10- S.E., n=6 ( 10) Triglyceride (% of control) Triglyceride (% of control) α-lipoic acid (µg/ml) α-lipoic acid (µg/ml) (HepG2) 12 - DMSO 24 (L6) DMSO 24 RNA (RNeasy micro QIAGEN ) RNA (SuperScript IIIInvitrogen ) DNA (PCR) 2. (HepG2) (L6) 96 1 () 8
10 ver5.1 HS (6) mg mg 4 - (100 mg/) 4 (p<0.01) (p<0.05) ( 2 ) - (200 mg/) BMI (p<0.05) ( 3 ) - ( mg/) (100 mg) / (kg) / 7 (%) / 7 BMI (kg/m 2 ) / 7 Ω / 7 (%) / 7 (%) / 7 (cm) / 7 (cm) / 7 / / 7 (mm) / 7 (mg/dl) p< / 7 (mg/dl) / 7 HDL- (mg/dl) / 7 (mg/dl) / 7 (mg/dl) / 7 (mg/dl) p< / 7 (g/dl) / 7 7 (1 ) 9
11 ver5.1 HS 3. - (200 mg) (kg) / 10 (%) / 10 BMI (kg/m 2 ) / 10 Ω / 10 (%) / 7 (%) / 10 (cm) / 10 (cm) / 10 / / 10 (mm) / 10 (mg/dl) / 10 (mg/dl) / 10 HDL- (mg/dl) / 10 (mg/dl) / 10 (mg/dl) / 10 (mg/dl) p< / 10 (g/dl) /
12 ver5.1 HS 11- (100 mg) 11
13 ver5.1 HS 3. (1) (in vitro) - B16 ( 12) (B16) (±S.E., n=6) B16 2 mmmem (10%100 units/ml100 µg/ml) ( /ml) µl - (55 µl) 3 PBS (300 µl) 96 (415 nm 700 nm) (in vivo) (- 0 mg/kg) (0 ) - (25 50 mg/kg) ( 14 ) - in vitro in vivo 12
14 (L ) mg/kg 1 mg/kg 25 mg/kg 50 mg/kg ver5.1 HS 13. (±SD, n=3) 1 mg/kg 25 mg/kg 50 mg/kg (4 ) (0 ) 2 (2 ) [ () ] (UVB2000 mj/cm 2 ) (0 ) 8 10 (L*) () 13
15 ver5.1 HS (2) (in vitro) - NB1RGB Control NB1RGB (±S.E., n=6) NB1RGB 96-2 MTT (in vitro) Control - (1 µg/ml) ( 16) - () [TESTSKIN () ]
16 ver5.1 HS Control - (1g/mL) ( 400 ) 4. SOD SOD DPPH 15
17 ver5.1 HS 5. - (--WSP8 WSPC8) - (WSP8 WSPC8) WSP8 WSPC8 6. α --WSP8 (- 8)- -P (- 100) - 30 mg/kg (SD 7 ) - (n=3)- -WSP8 --P 3 (AUC) --WSP8 --P 3 --WSP8 --WSP WSP ( ) 16
18 ver5.1 HS 7. (1) --P (2) ph pH ph ph 17
19 ver5.1 HS 8. α 0.2 g/100g 0.0 g/100g g/100g 0.0 g/100g 0.0 g/100g kcal/100g g/100 1 mg/100g 1) ) ( ) 100 (+++) 3) ( ) 4; 9; 4; α (1) (LD 50 ) ddy-ld mg/kg 277 mg/kg60 kg g (2) / OECD No.404 ( ) Commission Directive 2004/73/EC 3 () /- 0.5 g Draize p.i.i. (primary irritation index) 3 1 () 24 p.i.i / Safepharm Laboratories Limited /007 (3) 3 () L Draize C-I168 18
20 ver5.1 HS (4) OECD No Commission Directive 2004/73/EC 3 () - 70mg Kay ( 18 5) Safepharm Laboratories Limited /008 (5) OECD No Commission Directive 2004/73/EC 1 4 (CBA/Ca ) (LLNA Assay) Safepharm Laboratories Limited /009 (6) (Ames ) OECD No.471 Commission Directive 2000/32/EC (Ames ) Salminella typhimurium (TA1535TA1537TA98TA100) Escherichia coli (WP2uvrA) 10 S9-Mix g/- Safepharm Laboratories Limited /010 (7) 1 5 ppm ppm - 3 -tert- 5 ppm ppm ppm ppm ppm
21 ver5.1 HS 10. α (1) - -- () 2 - A () - B ( ) 23 - A B R 1 S S : A R 1 = R 2 = H or R 2 n COOH B : R 1 = R 2 = H or COOR 3 R 3 = H or Et (2) - () - B () 500 mg/kg - B IB05039 in press. 11.α mg mg 20
22 ver5.1 HS 12.α --P --P80 --WSP8 --L1 --PC --PC80 --WSPC () --LC P, P80, WSP8 () --PC, PC80, WSPC8 () 5 kg --L1 () --LC1 () 5 kg 14. (15) (- -L1-LC1) 5 21
23 ver5.1 HS P --P80 --WSP8 --L1 --PC --WSPC8 --LC1 INCI Thioctic acid INCIMaltosilcyclodextrin (and) Thioctic acid INCI Polyglyceryl-10 Myristate (and) Propylene Glycol Caprylate (and) Glycerin (and) Thioctic acid (and) Alcohol -10 PG ( ) 100g (g)
24 ver5.1 HS P α- (1,2-dithiolane-6-pentanoic acid) 98.0 % nm nm α % (HPLC) () 0.5 % (1 g40, 4 ) 0.1 % (1 g) (1) 6,8-Epitrithiooctanoic acid 0.1 % (HPLC) (2) 2.0 % () (3) Pb 10 ppm () (4) As 2 O 3 1 ppm () /g () /g ( ) (BGLB ) (1) 0.1 % (GC) (2) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) 100 % 23
25 ver5.1 HS P80 α- (1,2-dithiolane-6-pentanoic acid) 80.0 % nm nm α % (HPLC) 0.5 % (1 g40, 4 ) 0.1 % ( 1 g) (1) 6,8-Epitrithiooctanoic acid 0.1 % (HPLC) (2) 10 ppm () (3) 1 ppm () /g () /g ( ) (BGLB ) (1) 0.1 % (GC) (2) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) 80 % 20 % 100 % 24
26 ver5.1 HS WSP8 α- (1,2-dithiolane-6-pentanoic acid) 8.0 % nm nm α- 8.0 % (HPLC) 9.0 % (1 g40, 4 ) 0.10 % ( 1 g) (1) 10 ppm () (2) 1 ppm () /g () /g ( ) (BGLB ) (1) 0.1 % (GC) (2) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) 8 % 92 % 100 % 25
27 ver5.1 HS L1 α- (1,2-dithiolane-6-pentanoic acid) α % α % (HPLC) (1) 10 ppm () (2) 1 ppm () /g () /g ( ) (BGLB ) (0.1 ppm ) (GCMS) 10 % 2 % 50 % 23 % 15 % 100 % 26
28 ver5.1 HS PC α- (1,2-dithiolane-6-pentanoic acid) 98.0 % nm nm α % (HPLC) () 0.5 % (1 g40, 4 ) 0.1 % (1 g) (1) 6,8-Epitrithiooctanoic acid 0.1 % (HPLC) (2) 2.0 % () (3) Pb 10 ppm ( 2 ) (4) As 2 O 3 1 ppm ( 3 ) /g () /g ( ) (BGLB ) (1) 0.1 % (GC) (2) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) 100 %, 27
29 ver5.1 HS PC80 α- (1,2-dithiolane-6-pentanoic acid) 80.0 % nm nm α % (HPLC) 0.5 % (1 g40, 4 ) 0.1 % (1 g) (1) 6,8-Epitrithiooctanoic acid 0.1 % (HPLC) (2) Pb 10 ppm ( 2 ) (3) As 2 O 3 1 ppm ( 3 ) /g () /g ( ) (BGLB ) (1) 0.1 % (GC) (2) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) 80 % 20 % 100 %, 28
30 ver5.1 HS WSPC8 α- (1,2-dithiolane-6-pentanoic acid) 8.0 % nm nm α- 8.0 % (HPLC) 9.0 % (1 g40, 4 ) 0.10 % (1 g) (1) Pb 10 ppm ( 2 ) (2) As 2 O 3 1 ppm ( 3 ) /g () /g ( ) (BGLB ) (1) 0.1 % (GC) (2) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) (1 ppm ) (GCMS) 92 % 8 % 100 %, 29
31 ver5.1 HS LC1 - (1,2-dithiolane-6-pentanoic acid) % % (HPLC) (1) 10 ppm ( 2 ) Pb (2) 1 ppm ( 3 ) As 2 O /g () /g ( ) (BGLB ) (0.1 ppm ) (GCMS) % 23 % 15 % 10 % 2 % 100 %, 30
32 TEL(0586) () FAX(0586) URL/ F TEL(03) FAX(03) * * * * Ver. 5.1 (pp.25-32)
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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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Isobutyl alcohol IUPAC 2-methylpropan-1-ol 2--1-2-Methyl-1-Propanol, Isobutanol CH 3 H 3 C OH CAS 78-83-1 C 4 H 10 O log P ow ( C) ( C) (kpa) (g/l) 74.12 74.14 1) -108 2) 108 2) 1.2 2) 87 2) 0.8 2) (74.1214)
ESL ()-methyl 3-{4-[2-hydroxy-3-(isopropylamino)pro poxy]phenyl} propanoate monohydrochloride H 3 C O O JAN( ) JAN( )esmolol hydrochloride r-inn( )esm
![ESL ()-methyl 3-{4-[2-hydroxy-3-(isopropylamino)pro poxy]phenyl} propanoate monohydrochloride H 3 C O O JAN( ) JAN( )esmolol hydrochloride r-inn( )esm](/thumbs/85/92935308.jpg "ESL ()-methyl 3-{4-[2-hydroxy-3-(isopropylamino)pro poxy]phenyl} propanoate monohydrochloride H 3 C O O JAN( ) JAN( )esmolol hydrochloride r-inn( )esm")
1 186 186 (1) - 192 (2) (ISAintrinsic sympathomimetic activity) 199 (3) ( MSAmembrane stabilizing activity) 2 (4) 21 (5) 212 (6) 216 (7) 219 (8) 224 (9) (ASL-8123) - 229 (1) d-esl l-esl - 231 2 235 235
2010 1 1 7 2 16 2 2 06in 3 3 錆 錆 06in 4 4 0.1 5 5 HCl Cl NaOH H Cl O 2 H H 2 O NaCl Na OH H 2 O NaCl 2010 6 6 ph3.0 30 mg/l 30 1 O-157 H7 2010 7 7 100 Cl 80 60 40 20 HClO ClO CL ph 10 100,000ppm 12 01
