高圣草素-7-O-β-D-葡萄糖苷及其非对映异构体的合成
收稿日期: 2016-12-05
修回日期: 2017-01-03
网络出版日期: 2017-01-20
基金资助
上海市生物医药领域科技支撑计划（No.15431902700）资助项目.
Synthesis of Homoeriodictyol-7-O-β-D-glycoside and Its Diastereoisomer
Received date: 2016-12-05
Revised date: 2017-01-03
Online published: 2017-01-20
Supported by
Project supported by the Shanghai Biomedical Science and Technology Support Project (No. 15431902700).
高圣草素-7-O-β-D-葡萄糖苷作为传统中药槲寄生的有效成分已被广泛研究，以间苯三酚、D-葡萄糖为原料，经傅克酰基化、选择性羟基保护、羟醛缩合、相转移催化下的糖苷化等反应步骤首次实现高圣草素-7-O-β-D-葡萄糖苷及其非对映异构体的合成，有效解决提取困难的问题，为其进行相关药理研究奠定物质基础.所合成化合物结构经核磁共振氢谱、碳谱和高分辨质谱确证.
关键词： 槲寄生; 高圣草素-7-O-β-D-葡萄糖苷; 非对映异构体; 合成
康满满 , 马志龙 , 刘彪 , 潘登 , 李建其 . 高圣草素-7-O-β-D-葡萄糖苷及其非对映异构体的合成[J]. 有机化学, 2017 , 37(6) : 1516 -1522 . DOI: 10.6023/cjoc201612012
As the active component in visci herba of traditional Chinese medicine, homoeriodictyol-7-O-β-D-glycoside has been widely studied for years. In this paper, the first synthesis of homoeriodictyol-7-O-β-D-glycoside and its diastereoisomer has been achieved, which was carried out using phloroglucinol and D-glucose as the starting materials through Friedel-Crafts acylation, selective hydroxy protecting, aldol condensation, glycosylation under phase transfer catalytic condition and other reactions. Our work laid the foundation for large scale preparation of homoeriodictyol-7-O-β-D-glycoside instead of inefficient extration, and provided material baisis for furthur pharmaceutical investigation. The structures of synthetic compounds were confirmed by 1H NMR, 13C NMR and HRMS spectra.
Key words： visci herba; homoeriodictyol-7-O-β-D-glycoside; diastereoisomer; synthesis
[1] Cao, D.; Weng, Z.-J.; Li, J.-Q.; Yang, P.-M.; He, Q.-Q.; Cheng, L.; Kong, D.-Y. Chin. Tradit. Herb. Drugs 2015, 46, 1562 (in Chinese). (曹朵, 翁志洁, 李建其, 杨培明, 何泉泉, 成亮, 孔德云, 中草药, 2015, 46, 1562.)
[2] Shanghai Viscum Group. Chin. J. Pharm. 1977, 3, 39 (in Chinese). (上海槲寄生研究协作组, 中国医药工业杂志, 1977, 3, 39.)
[3] Kong, D.-Y.; Luo, S.-Q.; Li, H.-T.; Lei, X.-H. Acta Pharm. Sin. 1988, 23, 593 (in Chinese).(孔德云, 罗思齐, 李惠庭, 雷兴翰, 药学学报, 1988, 23, 593.)
[4] Yang, L.-Y.; Lin, J.; Zhou, B.; Liu, Y.-G.; Zhu, B.-Q. Nat. Prod. Res. 2016, 25, 1.
[5] Zhao, Y.-L.; Ma, M.-Y.; Gao, X.-X.; Liu, T.; Yu, Z.-G.; Bi, K.-S. Chin. J. Chromatogr. 2006, 24, 479 (in Chinese).(赵云丽, 马铭研, 高晓霞, 刘涛, 于志国, 毕开顺, 色谱, 2006, 24, 479.)
[6] Wu, L.; Luo, J.; Zhang, Y.-L.; Zhu, M.-D.; Wang, X.-B.; Luo, J.-G.; Yang, M.-H.; Yu, B.-Y.; Yao, H.-Q.; Dai, Y.; Guo, Q.-L.; Chen, Y.-J.; Sun, H.-B.; Kong, L.-Y. Tetrahedron Lett. 2015, 56, 229.
[7] Zhang, B.-X.; Duan, D.-Z.; Ge, C.-P.; Yao, J.; Liu, Y.-P.; Li, X.-M.; Fang, J.-G. J. Med. Chem. 2015, 58, 1795.
[8] Van, S. N.; Dong, L.-P.; Wang, S.-C.; Wang, Q.-A. Eur. J. Org. Chem. 2015, 10, 2297
[9] Chao, S.-W.; Su, M.-Y.; Chiou, L.-C.; Chen, L.-C.; Chang, C.-I; Huang, W.-J. J. Nat. Prod. 2015, 78, 1969.
[10] Yang, J.-H.; Zuo, W.-B.; Guo, D.-D.; Luo, J.-S.; Huang, W.-Q. Chin. Chem. Lett. 2012, 23, 1375.
[11] Zalihe, H.; Benjamin, C.; Allison, M. H.; Jason, Q. D. G.; Ian, E. W.; Spencer, J. W. Carbohydr. Res. 2010, 345, 2079.
[12] Cai, S.-L.; Wu, Z.; Wu, J.; Wang, Q.-A.; Shan, Y. Chin. J. Org. Chem. 2012, 32, 560 (in Chinese).(蔡双莲, 吴峥, 吴进, 汪秋安, 单杨, 有机化学, 2012, 32, 560.)
[13] Wang, Q.-A.; Wu, Z.; Liu, L.; Zou, L.-H.; Luo, M. Chin. J. Org. Chem. 2010, 30, 1682 (in Chinese). (汪秋安, 吴峥, 刘莉, 邹亮华, 罗茗, 有机化学, 2010, 30, 1682.)
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