Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.
Aqueous methanol extracts from the bulbs of Hyacinthusorientalis were subjected to various ion-exchange column chromatographic steps to give 2(R),5(R)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine (DMDP) (1), 2,5-dideoxy-2,5-imino-dl-glycero-d-manno-heptitol (homoDMDP) (2), 2,5-imino-2,5,6-tride...
| Main Authors: | , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
1998
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| _version_ | 1826300747157864448 |
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| author | Asano, N Kato, A Miyauchi, M Kizu, H Kameda, Y Watson, A Nash, R Fleet, G |
| author_facet | Asano, N Kato, A Miyauchi, M Kizu, H Kameda, Y Watson, A Nash, R Fleet, G |
| author_sort | Asano, N |
| collection | OXFORD |
| description | Aqueous methanol extracts from the bulbs of Hyacinthusorientalis were subjected to various ion-exchange column chromatographic steps to give 2(R),5(R)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine (DMDP) (1), 2,5-dideoxy-2,5-imino-dl-glycero-d-manno-heptitol (homoDMDP) (2), 2,5-imino-2,5,6-trideoxy-d-manno-heptitol (6-deoxy-homoDMDP) (3), 2,5-imino-2,5,6-trideoxy-d-gulo-heptitol (4), 1-deoxynojirimycin (5), 1-deoxymannojirimycin (6), alpha-homonojirimycin (7), beta-homonojirimycin (8), alpha-homomannojirimycin (9), beta-homomannojirimycin (10), and 7-O-beta-d-glucopyranosyl-alpha-homonojirimycin (MDL 25,637) (11). The structures of the new natural products 3 and 4 were determined by spectroscopic analysis, including extensive 1D and 2D NMR studies. Compound 2 was found to be a potent inhibitor of bacterial beta-glucosidase, mammalian beta-galactosidases, and mammalian trehalases, while 3 was a potent inhibitor of rice alpha-glucosidase and rat intestinal maltase. Compound 4 was observed to be a good inhibitor of alpha-l-fucosidase. |
| first_indexed | 2024-03-07T05:21:52Z |
| format | Journal article |
| id | oxford-uuid:df2f129a-fca0-4441-9f0a-9f7d704565a7 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T05:21:52Z |
| publishDate | 1998 |
| record_format | dspace |
| spelling | oxford-uuid:df2f129a-fca0-4441-9f0a-9f7d704565a72022-03-27T09:37:41ZNitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:df2f129a-fca0-4441-9f0a-9f7d704565a7EnglishSymplectic Elements at Oxford1998Asano, NKato, AMiyauchi, MKizu, HKameda, YWatson, ANash, RFleet, GAqueous methanol extracts from the bulbs of Hyacinthusorientalis were subjected to various ion-exchange column chromatographic steps to give 2(R),5(R)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine (DMDP) (1), 2,5-dideoxy-2,5-imino-dl-glycero-d-manno-heptitol (homoDMDP) (2), 2,5-imino-2,5,6-trideoxy-d-manno-heptitol (6-deoxy-homoDMDP) (3), 2,5-imino-2,5,6-trideoxy-d-gulo-heptitol (4), 1-deoxynojirimycin (5), 1-deoxymannojirimycin (6), alpha-homonojirimycin (7), beta-homonojirimycin (8), alpha-homomannojirimycin (9), beta-homomannojirimycin (10), and 7-O-beta-d-glucopyranosyl-alpha-homonojirimycin (MDL 25,637) (11). The structures of the new natural products 3 and 4 were determined by spectroscopic analysis, including extensive 1D and 2D NMR studies. Compound 2 was found to be a potent inhibitor of bacterial beta-glucosidase, mammalian beta-galactosidases, and mammalian trehalases, while 3 was a potent inhibitor of rice alpha-glucosidase and rat intestinal maltase. Compound 4 was observed to be a good inhibitor of alpha-l-fucosidase. |
| spellingShingle | Asano, N Kato, A Miyauchi, M Kizu, H Kameda, Y Watson, A Nash, R Fleet, G Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis. |
| title | Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis. |
| title_full | Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis. |
| title_fullStr | Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis. |
| title_full_unstemmed | Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis. |
| title_short | Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis. |
| title_sort | nitrogen containing furanose and pyranose analogues from hyacinthus orientalis |
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