Valiolamine, a new .ALPHA.-glucosidase inhibiting aminocyclitol produced by Streptomyces hygroscopicus.

Kameda, Yukihiko; Asano, Naoki; Yoshikawa, Michiyo; Takeuchi, Masayoshi; Yamaguchi, Takuji; Matsui, Kunihiko; Horii, Satoshi; Fukase, Hiroshi

doi:10.7164/antibiotics.37.1301

Cited by 163 publications

(95 citation statements)

References 7 publications

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“…1 -Deoxynojirimycin (1,5-dideoxy-l,5-imino-D-glucitol), fagomine, 1 -deoxymannojirimycin (1,5-dideoxy-1,5-imino-~-mannito~), and 1,4-dideoxy-1,4-imino-D-arabinitol were purified according to published procedures (Asano et al, 1994). Validoxylamine A (Horii et al, 1972), Dgluco-dihydrovalidoxylamine A (Kameda et al, 1987) and validamine (Kameda et al, 1984) are known from the literature.…”

Section: Methodsmentioning

confidence: 99%

“…However, a drawback of these B-D-glycosylamines is their instability in solution due to anomerization and hydrolysis. Validamine, a pseudo-a-D-glucosylamine, is a very stable compound and a good inhibitor of mammalian intestinal sucrases (Kameda et al, 1984;Horii et al, 1986;Takeuchi et al, 1990), but a weak competitive inhibitor of rat intestinal and pig kidney trehalases, with K, values of 270 pM ) and 140 pM, respectively. However, 1-epivalidamine, a pseudo-P-D-glucosylamine, was a potent competitive inhibitor of pig kidney trehalase, with a K, of 1.2 pM.…”

Section: Inhibition Of Pig Kidney Trehalase By Sugar Analogsmentioning

confidence: 99%

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Two Subsites on the Active Center of Pig Kidney Trehalase

Asano

Kato

Matsui

1996

European Journal of Biochemistry

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A kinetic analysis of the active site of pig kidney trehalase was made by examining two types of inhibitors that are monosaccharide analogs and cause a Competitive inhibition of the trehalase. Trehalase hydrolyzes trehalose (a-D-glyCopyranoSyl a-D-glucopyranoside) to give an equimolar mixture of a-Dglucose and, by inversion of configuration, P-D-glUCOse. 1,4-Dideoxy-l,4-imino-D-arabinito1 is considered to be a transition state (glucosyl cation) analog, while methyl P-D-glucoside, 1,5-dideoxy-1,5-iminO-Dglucitol (1 -deoxynojirimycin), fagomine, and 1-epivalidamine are considered to be analogs of the p-Dglucose that is derived by hydrolysis of trehalose. These glucosyl cation inhibitor and P-D-glucose analog inhibitors competed with each other at the same site on the active center of pig kidney trehalase and were therefore put together in one group (group A). Methyl a-D-mannoside and 1-deoxymannojirimycin were also competitive inhibitors of trehalase and competed with each other for the same site. However, an inhibitor i n group A did not compete with the methyl a-D-mannoside or 1,5-dideoxy-l ,.%imino-D-mannito1 (I -deoxymannojirimycin). Thus these latter two inhibitors were placed in group B. These results support the hypothesis that the active center of trehalase may comprise two subsites, one for catalysis and one for recognition, that act separately on each of the glucoses of the trehalose. The catalysis site requires the correct D-glucose configuration at carbons 2, 3, 4, and 5 or a good superimposition onto the glucosyl cation intermediate. The C2 equatorial OH group of a glucopyranosyl residue appears to be important for binding at the catalytic site since I-deoxynojiriniycin is more tightly bound by two orders of magnitude over its 2-deoxy derivative, fagomine. The P-D-glUCOSe and glucosyl cation analogs best fit

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Section: Methodsmentioning

confidence: 99%

Section: Inhibition Of Pig Kidney Trehalase By Sugar Analogsmentioning

confidence: 99%

Two Subsites on the Active Center of Pig Kidney Trehalase

Asano

Kato

Matsui

1996

European Journal of Biochemistry

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“…Attempts in developing antidiabetic drug using α-glucosidase inhibitor started since the end of last century. Valiolamine, produced by Streptomyces hygroscopicus var linoneus was reported as a potent inhibitor of pig intestinal maltase and sucrase 19 . Acarbose, produced by Actinoplanes sp.…”

Section: Discussionmentioning

confidence: 99%

Characterization of nimbidiol as a potent intestinal disaccharidase and glucoamylase inhibitor present inAzadirachta indica(neem) useful for the treatment of diabetes

Mukherjee¹,

Sengupta²

2012

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…有效霉烯胺不仅是有效霉素(4)的组成片段, 在抑淀粉酶素(amylostatins) (5) [10] 、阿卡波糖(acarbose) (6) [11] 等天然产物的结构中同样作为核心片段存在(图 2). [12,13] , 此外, 有效霉烯胺还对枯草芽孢杆菌、蜡状芽孢杆菌等杆菌具有抑菌作用 [12] . 有效霉烯胺还能作为原料合成有效霉醇胺 [14,15] 、伏格列波糖 [8] 等具有更高 α-糖苷酶抑制活性的分子 [16,17] .…”

unclassified

“…有效霉烯胺还能作为原料合成有效霉醇胺 [14,15] 、伏格列波糖 [8] 等具有更高 α-糖苷酶抑制活性的分子 [16,17] . 有效霉烯胺的主要生物制备方法包括经有效霉素微生物降解 [5] 、吸水链霉菌发酵液中直接提取 [13] 、经有效霉素氢解制备 [18] 等. 虽然医药化工等领域得到有效霉烯胺的常用方法是借助发酵法获取有效霉素, 再利用生物降解法分离得到各种有效组分, 但生物法存在诸如产量相对较小、分离工艺复杂、产生大量发酵废水等不可避免的缺点.…”

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