橙黄制霉素酮新糖苷的合成及胶原酶抑制作用：天然抗生素橙黄制霉素的苷元

Synthesis and collagenase inhibition of new glycosides of aranciamycinone: the aglycon of the naturally occurring antibiotic aranciamycin.

作者信息

Bols M, Binderup L, Hansen J, Rasmussen P

机构信息

Department of Organic Chemistry, Technical University of Denmark, Lyngby.

出版信息

Carbohydr Res. 1992 Nov 4;235:141-9. doi: 10.1016/0008-6215(92)80084-e.

DOI:10.1016/0008-6215(92)80084-e

PMID:1335359

Abstract

Glycosides of aranciamycinone were prepared by glycosylation with sugar acetates and trimethylsilyl triflate in dichloromethane. Glycosides of the following sugars were prepared: alpha-L-rhamnopyranose, beta-D-glucopyranose, beta-D-ribopyranose, beta-D-xylopyranose, alpha-L-fucopyranose, 2-azido-2,6-dideoxy-alpha-L-mannopyranose, 2,6-dideoxy-alpha-L-arabino-hexopyranose, 3,6-dideoxy-alpha-L-arabino-hexopyranose, and 4,6-dideoxy-alpha-L-lyxo-hexopyranose. The new glycosides were tested for inhibition of Clostridium histolyticum collagenase and Yoshida Sarcoma tumor cells.

摘要

通过在二氯甲烷中用糖醋酸酯和三氟甲磺酸三甲基硅酯进行糖基化反应制备了橙霉素酮糖苷。制备了以下糖类的糖苷：α-L-鼠李吡喃糖、β-D-葡萄糖吡喃糖、β-D-核糖吡喃糖、β-D-木糖吡喃糖、α-L-岩藻糖吡喃糖、2-叠氮基-2,6-二脱氧-α-L-甘露吡喃糖、2,6-二脱氧-α-L-阿拉伯己吡喃糖、3,6-二脱氧-α-L-阿拉伯己吡喃糖和4,6-二脱氧-α-L-来苏己吡喃糖。对新的糖苷进行了溶组织梭菌胶原酶和吉田肉瘤肿瘤细胞抑制试验。