Production of beta-maltooligosaccharides of alpha- and delta-tocopherols by Klebsiella pneumoniae and cyclodextrin glucanotransferase as anti-allergic agents.
The glycosylation of alpha- and delta-tocopherols using Klebsiella pneumoniae and cyclodextrin glucanotransferase (CGTase) was investigated. K. pneumoniae converted alpha- and delta-tocopherols into the corresponding beta-glucosides in 10 and 8% yield, respectively. CGTase glycosylated alpha-tocopheryl beta-glucoside to alpha-tocopheryl beta-maltoside (51%) and alpha-tocopheryl beta-maltotrioside (35%). On the other hand, delta-tocopheryl beta-glucoside was converted into the corresponding beta-maltoside (45%) and beta-maltotrioside (29%) by CGTase. The beta-glucoside of alpha-tocopherol, and beta-glucoside and beta-maltoside of delta-tocopherol showed inhibitory effects on IgE antibody production and on histamine release from rat peritoneal mast cells.
Shimoda
Kei
K
Department of Chemistry, Faculty of Medicine, Oita University, 1-1 Hasama-machi, Oita 879-5593, Japan. shimoda@med.oita-u.ac.jp
Akagi
Masaaki
M
Hamada
Hiroki
H
D000818:Animals; D018926:Anti-Allergic Agents / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D002460:Cell Line; D005964:Glucosyltransferases / Q000378:metabolism*; D006031:Glycosylation; D006636:Histamine Release / Q000187:drug effects; D007711:Klebsiella pneumoniae / Q000378:metabolism*; D008407:Mast Cells / Q000187:drug effects / Q000378:metabolism; D009844:Oligosaccharides / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D010529:Peritoneal Cavity / Q000166:cytology; D051381:Rats; D024505:Tocopherols / Q000737:chemistry / Q000378:metabolism*; D024502:alpha-Tocopherol / Q000737:chemistry / Q000378:metabolism*
D018926:Anti-Allergic Agents; D009844:Oligosaccharides; C021705:maltooligosaccharides; D005964:Glucosyltransferases; C019963:cyclomaltodextrin glucanotransferase; D024502:alpha-Tocopherol; C479072:delta-tocopherol; D024505:Tocopherols
Appl Biochem Biotechnol. 2009 May;156(1-3):45-58
19130306
Mol Vis. 2009;15:855-60
19390643
FASEB J. 1999 Jul;13(10):1145-55
10385606
N Engl J Med. 1993 May 20;328(20):1450-6
8479464
Lipids. 1996 Jul;31(7):671-701
8827691
Adv Carbohydr Chem Biochem. 1979;36:265-313
380276
Cancer Prev Res (Phila). 2009 Feb;2(2):143-52
19155443
Chem Pharm Bull (Tokyo). 2001 Aug;49(8):948-53
11515583
Science. 1922 Dec 8;56(1458):650-1
17838496
J Am Coll Nutr. 2008 Aug;27(4):505-11
18978171
N Engl J Med. 1993 May 20;328(20):1444-9
8479463
J Ind Microbiol Biotechnol. 2003 Nov;30(11):661-8
14618406
Int Arch Allergy Appl Immunol. 1990;92(3):209-16
1703513
J Biol Chem. 1992 Aug 25;267(24):16767-70
1512217
Carbohydr Res. 2000 Mar 24;325(1):72-80
10741829
Carbohydr Res. 1997 Mar 26;299(1-2):23-31
9129294
Biol Pharm Bull. 1994 May;17(5):732-4
7522732
J Control Release. 2004 Nov 24;100(2):221-31
15544870