Kato A, Adachi I, Miyauchi M, Ikeda K, Komae T, Kizu H, Kameda Y, Watson AA, Nash RJ, Wormald MR, Flee GWJ, Asano N Polyhydroxylated pyrrolidine and pyrrolizidine alkaloids from Hyacinthoides non-scripta and Scilla campanulata Carbohydrate Research316(1-4) (1999)
95-103
The structure was elucidated in this paper NCBI PubMed ID:10515698 Publication DOI:10.1016/S0008-6215(99)00043-9 Journal NLM ID:0043535 Publisher: Elsevier Correspondence: Asano N <naoki22po.incl.ne.jp> Institutions: Department of Hospital Pharmacy, Toyama Medical and Pharmaceutical University, Toyama 930-0194, Japan, Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa 920-1181, Japan, Institute of Grassland and Environmental Research, Aberystwyth, Cardiganshire SY23 3EB, UK, Glycobiology Institute, Oxford University, Oxford OX1 3QU, UK, Dyson Perrins Laboratory, Oxford University, Oxford OX1 3QY, UK
Aqueous ethanol extracts from the immature fruits and stalks of bluebell (Hyacinthoides non-scripta) were subjected to various ion-exchange column chromatographic steps to give 1,4-dideoxy-1,4-imino-D-arabinitol (1), 2(R),5(R)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine (DMDP) (2), 6-deoxy-6-C-(2,5-dihydroxyhexyl)-DMDP (3), 2,5-dideoxy-2,5-imino-dl-glycero-D-manno-heptitol (homoDMDP) (4), homoDMDP-7-O-apioside (5), homoDMDP-7-O-β-D-xylopyranoside (6), (1S*,2R*,3R*,5R*,7aR*)-1,2-dihydroxy-3,5-dihydroxymethylpyrrolizidine (7), and (1S*,2R*,3R*,5R*,6R*,7R*,7aR*)-3-hydroxymethyl-5-methyl-1,2,6,7-tetrah ydroxypyrrolizidine (8). Bulbs of Scilla campanulata (Hyacinthaceae) yielded (1S*,2R*,3R*,5S*,7aR*)-1,2-dihydroxy-3,5-dihydroxymethylpyrrolizidine (9) in addition to compounds 1-7. Compounds 3, 6, 7, 8, and 9 are new natural products. Compound 4 is a potent competitive inhibitor with K(i) values of 1.5 μM for Caldocellum saccharolyticum β-glucosidase and 2.2 μM for bovine liver β-galactosidase. The 7-O-β-D-xyloside 6 was a stronger competitive inhibitor than 4 of C. saccharolyticum β-glucosidase and rat intestinal lactase, with K(i) values of 0.06 and 0.07 μM, respectively, but a weaker inhibitor of bovine liver β-galactosidase. Furthermore, compound 4 is also a competitive inhibitor (K(i)=1.8 μM) of porcine kidney trehalase, but 6 was inactive against this enzyme.
Methods: 13C NMR, 1H NMR, GLC-MS, inhibition studies, HPTLC, HR-FAB-MS, trimethylsilylation, optical Biological activity: HomoDMDP-7-O-apioside at concentrations of 40 and 1.6 μM gave 50% inhibition of β-galactosidase from bovine liver and rat intestinal lactase, respectively. Comments, role: 1H and 13C NMR spectra of 5 were in accordance with published data; compound 5 was isolated from fruiting stalks of H. non-scripta and bulbs of S. campanulata
Kato A, Adachi I, Miyauchi M, Ikeda K, Komae T, Kizu H, Kameda Y, Watson AA, Nash RJ, Wormald MR, Flee GWJ, Asano N Polyhydroxylated pyrrolidine and pyrrolizidine alkaloids from Hyacinthoides non-scripta and Scilla campanulata Carbohydrate Research316(1-4) (1999)
95-103
The structure was elucidated in this paper NCBI PubMed ID:10515698 Publication DOI:10.1016/S0008-6215(99)00043-9 Journal NLM ID:0043535 Publisher: Elsevier Correspondence: Asano N <naoki22po.incl.ne.jp> Institutions: Department of Hospital Pharmacy, Toyama Medical and Pharmaceutical University, Toyama 930-0194, Japan, Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa 920-1181, Japan, Institute of Grassland and Environmental Research, Aberystwyth, Cardiganshire SY23 3EB, UK, Glycobiology Institute, Oxford University, Oxford OX1 3QU, UK, Dyson Perrins Laboratory, Oxford University, Oxford OX1 3QY, UK
Aqueous ethanol extracts from the immature fruits and stalks of bluebell (Hyacinthoides non-scripta) were subjected to various ion-exchange column chromatographic steps to give 1,4-dideoxy-1,4-imino-D-arabinitol (1), 2(R),5(R)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine (DMDP) (2), 6-deoxy-6-C-(2,5-dihydroxyhexyl)-DMDP (3), 2,5-dideoxy-2,5-imino-dl-glycero-D-manno-heptitol (homoDMDP) (4), homoDMDP-7-O-apioside (5), homoDMDP-7-O-β-D-xylopyranoside (6), (1S*,2R*,3R*,5R*,7aR*)-1,2-dihydroxy-3,5-dihydroxymethylpyrrolizidine (7), and (1S*,2R*,3R*,5R*,6R*,7R*,7aR*)-3-hydroxymethyl-5-methyl-1,2,6,7-tetrah ydroxypyrrolizidine (8). Bulbs of Scilla campanulata (Hyacinthaceae) yielded (1S*,2R*,3R*,5S*,7aR*)-1,2-dihydroxy-3,5-dihydroxymethylpyrrolizidine (9) in addition to compounds 1-7. Compounds 3, 6, 7, 8, and 9 are new natural products. Compound 4 is a potent competitive inhibitor with K(i) values of 1.5 μM for Caldocellum saccharolyticum β-glucosidase and 2.2 μM for bovine liver β-galactosidase. The 7-O-β-D-xyloside 6 was a stronger competitive inhibitor than 4 of C. saccharolyticum β-glucosidase and rat intestinal lactase, with K(i) values of 0.06 and 0.07 μM, respectively, but a weaker inhibitor of bovine liver β-galactosidase. Furthermore, compound 4 is also a competitive inhibitor (K(i)=1.8 μM) of porcine kidney trehalase, but 6 was inactive against this enzyme.
Methods: 13C NMR, 1H NMR, GLC-MS, inhibition studies, HPTLC, HR-FAB-MS, trimethylsilylation, optical Biological activity: HomoDMDP-7-O-β-D-xylopyranoside at concentrations of 4.6, 0.34, 24, 0.18, 140 and 100 μM gave 50% inhibition of β-glucosidases from almond and C. saccharolyticum, β-galactosidase from bovine liver and rat intestinal lactase, snail β-mannosidase and A. niger amyloglucosidase, respectively. Comments, role: NMR temperature was not specified; compound 6 was isolated from fruiting stalks of H. non-scripta and bulbs of S. campanulata. The published 13C NMR spectrum (referenced to TSP at 0) was shifted 1.7 ppm upfield by CSDB staff to accord to a TMS reference.
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