Homonojirimycin isomers and glycosides from Aglaonema treubii

被引：65

作者：

Asano, N ^{[1
]}

Nishida, M ^{[1
]}

Kizu, H ^{[1
]}

Matsui, K ^{[1
]}

Watson, AA ^{[1
]}

Nash, RJ ^{[1
]}

机构：

[1] AFRC,INST GRASSLAND & ENVIRONM RES,ABERYSTWYTH SY23 3EB,DYFED,WALES

来源：

JOURNAL OF NATURAL PRODUCTS | 1997年 / 60卷 / 02期

关键词：

D O I：

10.1021/np960577n

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

A 50% aqueous EtOH extract of Aglaonema treubii found to potently inhibit alpha-glucosidase was subjected to various ion-exchange column chromatographic steps to give 2(R),5(R)-bis-(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine (1), alpha-homonojirimycin (2), beta-homonojirimycin (3), alpha-homomannojirimycin (4), beta-homomannojirimycin (5), alpha-3,4-di-epi-homonojirimycin (6), 7-O-beta-D-glucopyranosyl-alpha-homonojirimycin (7), and 5-O-alpha-D-galactopyranosyl-alpha-homonojirimycin (8). Compounds 1 and 2 are known inhibitors of various alpha-glucosidases. Compounds 6 and 8 are new natural products. Compounds 3-5 and 7 have been chemically synthesized previously, but this is the first report of their natural occurrence.

引用

页码：98 / 101

页数：4

共 30 条

[1] A FACILE, PRACTICAL SYNTHESIS OF 2,6-DIDEOXY-2,6-IMINO-7-O-BETA-D-GLUCOPYRANOSYL-D-GLYCERO-L-GULO-HEPTITOL (MDL 25,637)
ANZEVENO, PB
CREEMER, LJ
DANIEL, JK
KING, CHR
LIU, PS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) : 2539 - 2542
[2] SUGARS WITH NITROGEN IN THE RING ISOLATED FROM THE LEAVES OF MORUS-BOMBYCIS
ASANO, N
TOMIOKA, E
KIZU, H
MATSUI, K
[J]. CARBOHYDRATE RESEARCH, 1994, 253 : 235 - 245
[3] NITROGEN-IN-THE-RING PYRANOSES AND FURANOSES - STRUCTURAL BASIS OF INHIBITION OF MAMMALIAN GLYCOSIDASES
ASANO, N
OSEKI, K
KIZU, H
MATSUI, K
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (22) : 3701 - 3706
[4] IMINOHEPTITOLS AS GLYCOSIDASE INHIBITORS - SYNTHESIS OF ALPHA-HOMOMANNOJIRIMYCIN, 6-EPI-ALPHA-HOMOMANNOJIRIMYCIN AND OF A HIGHLY SUBSTITUTED PIPECOLIC ACID
BRUCE, I
FLEET, GWJ
DIBELLO, IC
WINCHESTER, B
[J]. TETRAHEDRON, 1992, 48 (46) : 10191 - 10200
[5] ELBEIN AD, 1984, J BIOL CHEM, V259, P2409
[6] THE EFFECT OF DEOXYMANNOJIRIMYCIN ON THE PROCESSING OF THE INFLUENZA VIRAL GLYCOPROTEINS
ELBEIN, AD
LEGLER, G
TLUSTY, A
MCDOWELL, W
SCHWARZ, R
[J]. ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1984, 235 (02) : 579 - 588
[7] GLYCOSIDASE INHIBITION BY PLANT ALKALOIDS WHICH ARE STRUCTURAL ANALOGS OF MONOSACCHARIDES
EVANS, SV
FELLOWS, LE
SHING, TKM
FLEET, GWJ
[J]. PHYTOCHEMISTRY, 1985, 24 (09) : 1953 - 1955
[8] THE ALPHA-GLUCOSIDASE INHIBITOR N-BUTYLDEOXYNOJIRIMYCIN INHIBITS HUMAN-IMMUNODEFICIENCY-VIRUS ENTRY AT THE LEVEL OF POST-CD4-BINDING
FISCHER, P
COLLIN, M
KARLSSON, GB
JAMES, W
BUTTERS, TD
DAVIS, SJ
GORDON, S
DWEK, RA
PLATT, FM
[J]. JOURNAL OF VIROLOGY, 1995, 69 (09) : 5791 - 5797
[9] NOVEL MANNOSIDASE INHIBITOR BLOCKING CONVERSION OF HIGH MANNOSE TO COMPLEX OLIGOSACCHARIDES
FUHRMANN, U
BAUSE, E
LEGLER, G
PLOEGH, H
[J]. NATURE, 1984, 307 (5953) : 755 - 758
[10] SYNTHESIS OF BETA-1-HOMONOJIRIMYCIN AND BETA-1-HOMOMANNOJIRIMYCIN USING THE ENZYME ALDOLASE
HOLT, KE
LEEPER, FJ
HANDA, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (03): : 231 - 234

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