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7-脱氧-6-表-栗精胺,一种来自澳大利亚栗豆树的三羟基吲哚里西啶生物碱糖苷酶抑制剂。

7-deoxy-6-epi-castanospermine, a trihydroxyindolizidine alkaloid glycosidase inhibitor from Castanospermum australe.

作者信息

Molyneux R J, Tropea J E, Elbein A D

机构信息

Western Regional Research Center, USDA, Albany, California 94710.

出版信息

J Nat Prod. 1990 May-Jun;53(3):609-14. doi: 10.1021/np50069a011.

DOI:10.1021/np50069a011
PMID:2213032
Abstract

A new indolizidine alkaloid has been isolated from the seeds of Castanospermum [1] australe and identified as 7-deoxy-6-epi-castanospermine by ms and 1H- and 13C-nmr spectroscopy. The alkaloid is the first trihydroxylated indolizidine to be isolated from this plant and may represent an intermediate in the biosynthetic pathway to the tetrahydroxy-indolizidines and -pyrrolizidines. It inhibits amyloglucosidase and yeast alpha-glucosidase but is significantly less active as a glycosidase inhibitor than its isomer swainsonine [2] and the tetrahydroxylated alkaloids castanospermine [3], 6-epi-castanospermine [4], and australine [5].

摘要

从澳洲栗豆树种子中分离出一种新的吲哚里西啶生物碱,通过质谱以及1H-和13C-核磁共振光谱鉴定为7-脱氧-6-表栗豆胺。该生物碱是首次从该植物中分离得到的三羟基化吲哚里西啶,可能是四羟基化吲哚里西啶和吡咯里西啶生物合成途径中的一个中间体。它能抑制淀粉葡萄糖苷酶和酵母α-葡萄糖苷酶,但作为糖苷酶抑制剂,其活性明显低于其异构体苦马豆素以及四羟基化生物碱栗豆胺、6-表栗豆胺和澳洲栗精胺。

相似文献

1
7-deoxy-6-epi-castanospermine, a trihydroxyindolizidine alkaloid glycosidase inhibitor from Castanospermum australe.7-脱氧-6-表-栗精胺,一种来自澳大利亚栗豆树的三羟基吲哚里西啶生物碱糖苷酶抑制剂。
J Nat Prod. 1990 May-Jun;53(3):609-14. doi: 10.1021/np50069a011.
2
Isolation and SAR studies of bicyclic iminosugars from Castanospermum australe as glycosidase inhibitors.从澳洲栗豆树中分离双环亚氨基糖并作为糖苷酶抑制剂进行构效关系研究。
Phytochemistry. 2015 Mar;111:124-31. doi: 10.1016/j.phytochem.2014.12.011. Epub 2015 Jan 9.
3
6-Epicastanospermine, a novel indolizidine alkaloid that inhibits alpha-glucosidase.6-表卡斯塔诺精胺,一种新型的抑制α-葡萄糖苷酶的吲哚里西啶生物碱。
Arch Biochem Biophys. 1986 Dec;251(2):450-7. doi: 10.1016/0003-9861(86)90351-6.
4
Australine, a pyrrolizidine alkaloid that inhibits amyloglucosidase and glycoprotein processing.
Biochemistry. 1989 Mar 7;28(5):2027-34. doi: 10.1021/bi00431a010.
5
Studies on the mechanism of castanospermine inhibition of alpha- and beta-glucosidases.栗精胺对α-和β-葡萄糖苷酶抑制机制的研究。
Arch Biochem Biophys. 1984 May 1;230(2):668-75. doi: 10.1016/0003-9861(84)90448-x.
6
6,7-Diepicastanospermine, a tetrahydroxyindolizidine alkaloid inhibitor of amyloglucosidase.
Biochemistry. 1991 Oct 15;30(41):9981-7. doi: 10.1021/bi00105a024.
7
Thermospray liquid chromatographic-mass spectrometric analysis of castanospermine-related alkaloids in Castanospermum australe.
J Nat Prod. 1990 Mar-Apr;53(2):359-65. doi: 10.1021/np50068a014.
8
Calystegins, a novel class of alkaloid glycosidase inhibitors.旋花茄苷,一类新型生物碱糖苷酶抑制剂。
Arch Biochem Biophys. 1993 Jul;304(1):81-8. doi: 10.1006/abbi.1993.1324.
9
The effects of castanospermine and swainsonine on the activity and synthesis of intestinal sucrase.栗精胺和苦马豆素对肠道蔗糖酶活性及合成的影响。
Arch Biochem Biophys. 1993 May 15;303(1):134-44. doi: 10.1006/abbi.1993.1264.
10
Castanospermine, a tetrahydroxylated alkaloid that inhibits beta-glucosidase and beta-glucocerebrosidase.澳洲栗精胺,一种抑制β-葡萄糖苷酶和β-葡萄糖脑苷脂酶的四羟基化生物碱。
Arch Biochem Biophys. 1983 Mar;221(2):593-7. doi: 10.1016/0003-9861(83)90181-9.

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