Chemistry and Biochemistry of Microbial α‐Glucosidase Inhibitors

Wiley - Tập 20 Số 9 - Trang 744-761 - 1981
Ernst Truscheit1, Werner Frommer1, Bodo Junge1, Lutz Müller1, Delf Schmidt1, W. Wingender1
1Chemisch-wissenschaftliches Labor Pharma der Bayer AG, Postfach 10 1709, 5600 Wuppertal 1 (Germany)

Tóm tắt

Abstractα‐Glucosidases are among the most important carbohydrate‐splitting enzymes. They catalyze the hydrolysis of α‐glucosidic linkages. Their substrates are—depending on their specificity—oligo‐ and polysaccharides. Microbial inhibitors of α‐amylases and other mammalian intestinal carbohydrate‐splitting enzymes studied during the last few years have aroused medical interest in the treatment of metabolic diseases such as diabetes. Moreover, they extend the spectrum of microbial secondary metabolites which comprises an enormous variety of structures. They also contribute considerably to a better understanding of the mechanism of action of α‐glucosidases. These inhibitors belong to different classes of substances. Those studied most thoroughly are microbial α‐glucosidase inhibitors which are members of a homologous series of pseudooligosaccharides of the general formula (4). They all have a core in common which is essential for their inhibitory action, a pseudodisaccharide residue consisting of an unsaturated cyclitol unit, and a 4‐amino‐4,6‐dideoxy‐ glucose unit. The—in many respects—most interesting representative of this homologous series is acarbose (5), a pseudotetrasaccharide exhibiting a very pronounced inhibitory effect on intestinal α‐glucosidases such as sucrase, maltase and glucoamylase. The present paper will review this new field of microbial α‐glucosidase inhibitors which has been studied with particular intensity during the past ten years.

Từ khóa


Tài liệu tham khảo

Fritz H., 1971, Proceedings of the International Research Conference on Proteinase Inhibitors

Fritz H., 1974, Bayer‐Symposium V

10.1002/ange.19740860104

10.1002/anie.197400101

10.1146/annurev.bi.49.070180.003113

10.1007/BF02216836

Summary byN.Heimburger H.Haupt H. G.Schwickin [1] p. 1.

Chrzaszcz T., 1933, Biochem. Z., 260, 354

1933, Biochem. Z., 264, 193

10.1021/ja01246a512

Kneen E., 1946, Arch. Biochem., 9, 235

10.1126/science.102.2649.358

Hernandez A., 1968, Acta Cient. Venez., 19, 183

Jaffé W. G., 1973, Nutr. Rep. Int., 7, 169

Marshall J. J., 1975, J. Biol. Chem., 250, 8030, 10.1016/S0021-9258(19)40811-9

10.1111/j.1745-4514.1978.tb00183.x

10.1515/bchm2.1978.359.2.1371

10.1080/00327487908061693

Rao M. N., 1967, Indian J. Biochem., 4, 185

1970, Indian J. Biochem., 7, 241

10.1021/bk-1975-0015.ch016

10.1016/S0031-9422(00)86672-8

(c) Proc. 3. Int. Congr. Obesity Satellite Symp. No. 7 Siena (Italien) October 13–15 1980; Regulators of Intestinal Absorption in Obesity Diabetes and Nutrition;

(d)V.Buonocore E.Poerio V.Silano in [16c] Vol.1 p.87;

1980, La Clinica Dietologica, 7, 429

10.1111/j.1745-4514.1978.tb00195.x

10.1111/j.1745-4514.1978.tb00607.x

(g)M.Richardson N.Kashlanin [16c] Vol.1 p.103;

(h)C. M.O'Connor M. D.O'Donnell K. F.McGeeneyin [16c] Vol. 2 p. 119;

1980, La Clinica Dietologica, 7, 443

10.1016/0005-2744(81)90310-7

D. D.Schmidt W.Puls DOS 2003934 (1971) (German priority January 26 1970).Bayer AG.

E.Tnacheit D. D.Schmidt A.Arens H.Lange W.Wingenderin [16c]. Vol. 2 p. 157;

1980, La Clinica Dietologica, 7, 451

10.1007/BF01230687

Puls W., 1980, Habilitationsschrift

W.Frommer W.Puls D.Schäfer D. D.Schmidt DOS 2064092 (1972) (German priority December 28 1970) Bayer AG.

W.Frommer B.Junge U.Keup L.Müller W.Puls D. D.Schmidt DOS 2347782 (1975) (German priority September 22 1973) Bayer AG.

10.1007/BF00483561

Umezawa H., 1972, Enzyme Inhibitors of Microbial Origin

10.1055/s-0028-1097207

W.Wingenderin [2] p. 548;

Aoyagi T., 1975, Proteases and Biological Control, Cold Spring Harbor Conf. Cell Proliferation, 2, 429

Umezawa H., 1978, Bioactive Peptides Produced by Microorganisms

T.Aoyagi H.Umezawain Lj. Vitale V. Simeon:Industrial and Clinical Enzymology. FEBS Symp.61 89(1980).

10.1042/bj1220609

Manners D. J., 1974, Essays Biochem., 10, 37

10.1016/S0065-2318(08)60267-X

10.1016/0014-5793(70)80573-7

10.1016/0003-9861(74)90507-4

10.1016/0005-2795(72)90273-5

10.1016/0076-6879(55)01021-5

Ruyssen R., 1978, Pharmaceutical EnzymesmdashProperties and Assay Methods, 66

10.1093/jn/104.7.930

10.1002/star.19750270808

Semenza G., 1976, Enzymes Biol. Membr., 3

10.1016/0005-2744(73)90135-6

10.1016/S0021-9258(19)41116-2

10.1016/0003-2697(77)90181-6

G.Semenza Carbohydr. Metab. Its Disord. Vol. III. Academic Press London1981 in press.

10.1159/000458348

Brodbeck U., 1980, Enzyme Inhibitors (Proc Meet., Basel, March 20–21,1980)

(b)L.Müller B.Junge W.Frommer D. D.Schmidt E.Truscheitin [43a] p. 106.

10.1007/BF00368825

10.1159/000388403

D. D.Schmidt W.Frommer B.Junge L.Müller E.Truscheit W.Wingenderin [16c] Vol. 1 p. 203;

1980, La Clinica Dietologica, 7, 449

S.Ueda Y.Koba US‐Pat. 3806421 (1974) (Jap. priority May 31 1971) Hayashibara Biochemical Laboratories;

10.1271/bbb1961.37.2025

10.1271/bbb1961.40.1167

10.1016/S0008-6215(00)84486-9

10.1271/bbb1961.43.2265

S.Murao US‐Pat. 4010258 (1977) (Jap. priority March 15 1974) Ajinomoto Co. Inc. und Eisai Co. Ltd.;

10.1271/bbb1961.39.2271

10.1271/bbb1961.41.919

10.1271/bbb1961.41.2221

10.1271/bbb1961.43.679

H.Goto T.Inukei M.Amano Japanische Offenlegungsschrift 7577594 (1975) (Jap. priority November 20 1973) Amano Pharmaceutical Co. Ltd.

W.Frommer L.Müller D. D.Schmidt W.Puls H. P.Krause U.Heber DOS 2658563 (1978) (German priority December 23 1976).

Inouye S., 1966, J. Antibiot., 19, 288

10.1002/cber.19671000314

10.1016/0040-4020(68)88115-3

10.1080/00021369.1970.10859713

10.1016/S0008-6215(00)80274-8

H.Murai K.Ohata H.Enomoto Y.Yoshikuni T.Kono M.Yagi DOS 2656602 (1977) (Jap. priority December 29. 1975) Nippon Shinyaku Co. Ltd.

S.Matsumura H.Enomoto Y.Aoyagi Y.Ezure Y.Yoshikuni M.Yagi DOS 2850467 (1979) (Jap. priority November 21 1977) Nippon Shinyaku Co. Ltd.

10.1271/bbb1961.44.219

K.Ueda S.Gochyo Japanische Offenlegungsschrift 51–54990 (1976) (Jap. priority November 5 1974) Ajinomoto Co. Ltd.

A.Belloc J.Florent J.Lunel D.Mancy J.‐C.Palla DOS 2702417 (1977) (French priority January 22 1976) Rhône‐Poulenc Industries.

V.Oeding W.Pfaff L.Vénesy H.‐L.Weidemüller DOS 2701890 (1978) (German priority January 19 1977) Hoechst AG.

(a)L.Vénesy V.Oeding R.Bender G.Nesemann D.Sukatsch K.Zepfin [16c] Vol. 2 p. 269;

1980, La Clinica Dietologica, 7, 452

Aschauer H., 1981, Z. Physiol. Chem., 362, 465

M.Otani T.Saito S.Satoi J.Mizoguchi N.Muto DOS 2855409 (1979) (Jap. priority December 28. 1977) Toyo Jozo Co. Ltd.

K.Kangouri S.Namiki T.Nagate K.Sugita S.Omura US‐Pat. 4197292 (1980) (Jap. priority February 10 1978) Taisho Pharmaceutical Co.

Y.Suhara K.Yokose K.Watanabe K.Ogawa DOS 2905649 (1979) (Brit priority February 14 1978) Hoffmann‐La Roche und Co. AG.

10.1271/bbb1961.44.1679

10.1271/bbb1961.44.1683

(b)S.Omoto J.Itoh T.Niwa T.Shomura S.Niizato S.Inouye DOS 3035193 A1 (1981) (Jap. priority September 19 1979) Meiji Seika Kaisha Ltd.

(a)B.Junge H.Böshagen J.Stoltefuß L.Müllerin [43a] p. 123;

Junge B., 1981, Lecture, Fall Meet

W.Puls U.Keup H. P.Krause G.Thomasin [16c] Vol. 1 p. 231:

1980, La Clinica Dietologica, 7, 458

10.1159/000388404

P.Berchtold I.Hillebrand K.Boehme R.Aubell L.Nagel H.Schulzin [16c] Vol. 1 p. 261;

1980, La Clinica Dietologica, 7, 426

W.Puls U.Keup H. P.Krause K.O'Dea R.Sittin [16c] Vol. 1 p. 153;

1980, La Clinica Dietologica, 7, 458

P.Berchtold N. H.Kiesselbachin [16c] Vol. 1 p. 181;

1980, La Clinica Dietologica, 7, 426

W.Frommer B.Junge U.Keup L.Müller W.Puls D. D.Schmidt DOS 2347798 (1975) (German priority September 22 1973) Bayer AG.

W.Frommer W.Puls D. D.Schmidt DOS 2209832 (1973) (German priority March 1 1972) Bayer AG.

10.7164/antibiotics.24.59

10.7164/antibiotics.33.98

Horii S., J. Chem. Soc. Chem. Commun., 1972, 747

Kameda Y., J. Chem. Soc. Chem. Commun., 1972, 746

10.7164/antibiotics.33.1575

W.Frommer W.Puls D. D.Schmidt DOS 2209833 (1973) (German priority March 1 1972) Bayer AG.

W.Frommer W.Puls D. D.Schmidt DOS 2209834 (1973) (German priority March 1 1972) Bayer AG.

10.5458/jag1972.27.114

10.1016/S0021-9258(19)69512-8

10.1016/0005-2736(75)90022-X

Caspary W. F., Lancet, 1978, 1231

10.1007/BF01851228

10.1016/S0021-9258(19)40886-7

10.1111/j.1432-1033.1974.tb03255.x

10.1111/j.1432-1033.1975.tb04016.x

10.1016/S0021-9258(19)42174-1

Nach Untersuchungen vonW.Gau Bayer AG Wuppertal persönliche Mitteilung.

10.1016/0005-2744(77)90359-X

10.1111/j.1432-1033.1979.tb04219.x

Ernährungsbericht 1976 Deutsche Gesellschaft för Ernährung Frankfurt 1976.

10.1007/BF00483562

I.Hillebrand P.Berchtoldin (43a) p. 153.

Mörmann J. E., 1981, Lebensmittelwiss. Technol., 14, 166