Kazuhiro Yoshinaga, 1, Hideto Ishiba, 1 Yasushi Yoshimoto 1 and Toyohiko Katano 1

Transkript

1 (2011) Functional Research and Production Technology Development of 1,5 Anhydro D fructose 1,5 D ( ) ( ) Kazuhiro Yoshinaga, 1, Hideto Ishiba, 1 Yasushi Yoshimoto 1 and Toyohiko Katano NIHON STARCH CO., LTD Minami sakae, Kagoshima , Japan 1,5 D (1,5 AF) α 1,4 (GLase) 1,5 AF 1,5 AF 1,5 AF 1,5 AF GLase GLase α 1,4 α 1,6 1,5 AF 1,5 AF 1,5 AF 1,5 Dα 1, α 1,4 α 1,4 1) (EC , GLase) 1,5 D (1,5 AF) 2 Morchella 1) Gracilaria 2) GLase 3) 4) 5) 1,5 AF 1,5 D (1,5 AG) GLase GLase 1 5 Gracilaria chorda ( ) 5 U g 1 22 (Tel. & Fax , E mail: kyoshinaga@sunus.co.jp) Key words: 1,5 anhydro D fructose, α 1,4 glucan lyase, antioxidant, antibacterial agent

2 1,5 D 71 1 GLase (U g 1 ) Gracilaria chorda 5 Gracilaria sp. 2 Morchella hortensis 0.04 Morchella esculenta Pulcherrium caeruleum Athela rolfsii 3 1,5 D GLase 1,5 D (1,5 AF) 1,5 AF 1,5 AF 1,5 AF 6) GLase 1,5 AF GLase 1,5 AF 1,5 AF 99.2% NMR 13 C NMR DEPT C 1 C 6 2 OH C 2 1,5 AF 1,5 AF 1 4 α 1,4 GLase α 1,4 1,5 AF α 1,6 7) GLase 1,5 AF GLase GLase GLase α 1,6 Yu 7) GLase 1,5 AF GLase GLase GLase 2 6 GLase 2 Km 2.3 mm mm mm k s 1 8) Km (0.03 mm) k0 ( s 1 ) GLase GLase 3 61% 24 2 GLase km * (mm) k0 (s 1 ) k0 km (s 1 mm 1 ) 1 1,5 AF 2.3±0.1 56± ±0.1 60± ± ± ± ± ± ± ± ± ± ± ± ± ± ± km

3 (2011) 3 GLase km (mm) k0 (s 1 ) k0 km 29 ± ± ± ± α 0.7 ± ± α 2.9 ± ± ± ± Gracilaria chorda GLase 24 20% ( 2) GLase α 1,6 GLase GLase (GL LD) GL LD 1,6 GL LD GLase μmole ml 1 GL LD GLase α 1,6 1 α 1,6 GLase 2 α 1,6 6 3 k0 Km ( 3) GLase 4 1,3,4 8) GLase (productive) 6 3 α k0 km α km 2.9 mm 6 3 α 0.7 mm k s α (5.8 s 1 ) α 6 3 α α 1,6 GLase α 1,6 α 1,6 3 3 A GLase (PO) PO 2 20% 8 GLase PO PO GLase α 1,4 α 1,6

4 1,5 D 73 (L PO) PO High Performance Anion Exchange Chromatography with Pulsed Amperometric Detection (HPAEC PAD) PO Kamasaka 9) 4 L PO PO GLase 3 6 PO L PO GLase 3 (J j ) 3 L PO HPAEC PAD PO 1 1,5 AF GLase A A 4 (PO) GLase (L PO) (a) L PO (b) PO. J 3 3 K 3 4 L M 6 3 dn (1 4) α D D P C 3 or C 6 10) α 11) 3 B ( 5) 6 A GLase GLase 1 1,5 AF α 1,6 5 1,5 AF 1,5 AF 1,5 AF 12) 1,5 AF 1,5 AF 50 C 1,5 AF 13) 1,5 AF 1,5 AF 1,5 AF 6) 1,5 AF 1,5 AF 1,5 AF

5 (2011) 1,5 AF 14) 1,5 AF 1,5 AF 1,5 AF 1,5 AF 1% 1,5 AF 15) Streptococcus mutanse 1,5 AF S. mutanse 1,5 AF GLase 1,5 AF 1,5 AF 16) 17) 18) 19) 6 1,5 D 1,5 AF 1,5 AF 1,5 AF 1,5 AF 90 AMES 1,5 AF 20,21) () 90 1,5 AF TLO 1,5 AF () () () 1 ) M.A. Baute, R. Baute and G. Deffieux: Fungal enzymatic activity degrading 1,4 α D glucans to 1,5 D anhydrofructose. Phytochemistry, 27, (1988). 2 ) S. Yu, L. Kenne and M. Pedersént: α 1,4 Glucan lyase, a new class of starch glycogen degrading enzyme. I. Efficient purification and characterization from red seaweeds. Biochim. Biophys. Acta, 1156, (1993). 3 ) M. Sakuma and S. Kubota: Mouse AKR 1 E 1 is an ortholog of pig liver NADPH dependent 1,5 anhydro D fructose reductase. Biosci. Biotechnol. Biochem., 72, (2008). 4 ) Y. Shiga, S. Kametani, T. Kadokura and H. Akanuma: 1,5 Anhydroglucitol promotes glycogenolysis in Escherichia coli. J. Biochem. 125, (1999). 5 ) Y. Konishi, K. Hashima and K. Kishida: Increases in 1,5 anhydroglucitol level in germinating amaranth and ripening banana. Biosci. Biotechnol. Biochem., 64, (2000). 6 ) M. Fujisue, K. Yoshinaga, K. Muroya, J. Abe and S. Hizukuri: Preparation and antioxidative activity of 1,5 anhydrofructose. J.

6 1,5 D 75 Appl. Glycosci., 46, (1999). 7 ) S. Yu, T. Ahmad, L. Kenne and M. Pedersént: α 1,4 Glucan lyase, a new class of starch glycogen degrading enzyme. III. Substrate specificity, mode of action, and cleavage mechanism. Biochim. Biophys. Acta, 1244, 1 9 (1995). 8 ) K. Yoshinaga, M. Fujisue, J. Abe, I. Hanashiro, Y. Takeda, K. Muroya and S. Hizukuri: Characterization of exo (1,4) alpha glucan lyase from red alga gracilaria chorda. Activation, inactivation and the kinetic properties of the enzyme. Biochim. Biophys. Acta, 1472, (1999). 9 ) H. Kamasaka, M. Uchida, K. Kusaka, K. Yoshikawa, K. Yamamoto, S. Okada and T. Ichikawa: Inhibitory effect of phosphorylated oligosaccharides prepared from potato starch on the formation of calcium phosphate. Biosci. Biotechnol. Biochem., 59, (1995). 10) J. Abe, Y. Takeda and S. Hizukuri: Action of glucoamylase from Aspergillus niger on phosphorylated substrate. Biochim. Biophys. Acta, 703, (1982). 11) Y. Takeda and S. Hizukuri: Actions of Aspergillus oryzae alpha amylase, potato phosphorylase, and rabbit muscle phosphorylase a and b on phosphorylated (1 4) α D glucan. Carbohydr. Res., 153, (1986). 12) 1,5 D α 1, ) K. Yoshinaga, M. Fujisue, J. Abe, Y. Takeda and S. Hizukuri: 1,5 Anhydro D fructose, a new material for modification of amino groups as demonstrated using amino acid and proteins. J. Appl. Glycosci., 49, (2002). 14) G. Deffieux, R. Baute, M A. Baute, M. Atfani and A. Carpy: 1,5 D Anhydrofructose, the precursor of the pyrone microthecin in Morchella vulgaris. Phytochemistr., 26, (1987). 15) 1,5 D ) ) ) ) ) J. Mei, S. Yu and B. Ahrén: Basic toxicology and metabolism studies of 1,5 anhydro D fructose using bacteria, cultured mammalian cells, and rodents. Food Chem Toxicol., 42, (2004). 21) J. Mei, S. Yu and B. Ahrén: A 90 day toxicological evaluation of 1,5 anhydro D fructose in Sprague Dawley rats. Drug Chem Toxicol., 28, (2005).