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[摘要]
目的 设计合成齐墩果酸和熊果酸C3、C28 衍生物.方法 先将葡萄糖和半乳糖通过Schmidit 法制备三氯乙酰亚胺酯糖给体;然后分别以齐墩果酸和熊果酸为起始原料,经苄基保护,再进行糖苷化、苄基脱保护、酰胺化、苯甲酰基脱保护,得到10 个酰胺衍生物F1~F10.其中F1、F3 通过四甲基哌啶氧化物(TEMPO)及NaClO/NaClO2 氧化体系得到糖醛酸化合物F11、F12.结果 合成了5 个熊果酸C3 位葡萄糖苷C28 位酰胺衍生物、5 个齐墩果酸C3 位半乳糖苷C28 位酰胺衍生物及2个熊果酸C3 位葡萄糖醛酸苷C28 位酰胺衍生物,并分别通过1H-NMR、13C-NMR 和MS 确认结构.结论 12 个化合物均未见报道,为三萜皂苷的构效关系及生物活性研究奠定基础.
[Key word]
[Abstract]
Objective To design and synthesize the derivatives of oleanolic acid and ursolic acids C3 and C28. Methods First, glucose and galactose trichloroacetimidates donors were prepared with glucose and galactose by Schmidit method. Then oleanolic acid and ursolic acid were used as starting material to synthesize 10 target compounds F1-F10 by the benzyl protection, glycosylation, benzyl deprotection, amidation, and benzoyl deprotection. Iduronate compounds F11 and F12 were obtained from compounds F1 and F3 correspondingly via the TEMPO and NaClO/NaClO2 oxidation system. Results Five 3-glucoside-28-amid triterpenoid saponins derivatives, five 3-galactoside- 28-amid triterpenoid saponins derivatives, and two 28-amid-3-O-glucuronic acid ursolic derivatives were obtained. All compounds were confirmed by the application of 1H-NMR, 13C-NMR, and MS. Conclusion Twelve compounds are synthesized for the first time, which lays the foundation for the structure-function relationship and bioactivity studies of triterpenoid saponins.
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[基金项目]
北京市自然科学基金资助项目(7144225)