Facile synthesis of oleanolic acid monoglycosides and diglycosides.
Facile synthesis of oleanolic acid monoglycosides and diglycosides.
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DOI：
10.3390/molecules13071472
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发表时间：
2008-07-22
期刊：
影响因子：
--
通讯作者：
Cheng MS
中科院分区：
文献类型：
--
作者：
Sha Y;Yan MC;Liu J;Liu Y;Cheng MS
齐墩果酸及其苷类是重要的天然产物，具有抗肿瘤、抗病毒、抗炎等多种生物活性。本工作高产率地合成了15个含糖量不同的齐墩果酸皂苷，包括3-单糖苷、28-单糖苷和3，28-二糖苷。COOH(28)基团的保护基选择了苄基，而不是常用的甲基和烯丙基，以避免最终脱保护的困难。碱促进的羧酸与溴代糖苷的缩合反应更有效地合成了28-糖苷。对3，28-二苷类化合物的两种制备方法进行了研究，证明这两种方法是可行的。该方法适合于制备具有结构多样性的齐墩果酸糖苷，用于广泛的生物活性评价和构效关系研究，也为其他三萜类化合物的相应合成方法提供了新的思路。
Oleanolic acid and its glycosides are important natural products, possessing various attractive biological activities such as antitumor, antivirus and anti-inflammatory properties. In the present work, fifteen oleanolic acid saponins bearing various saccharide moieties, including 3-monoglycoside, 28-monoglycoside and 3,28-diglycoside, were easily synthesized in high yields. Benzyl was chosen as the protective group for the COOH(28) group, instead of commonly used methyl and allyl, to avoid difficulties in the final deprotection. Alkali-promoted condensation of the carboxylic acid with bromo-glycosides was found to be more efficient in the synthesis of 28-glycosides. Two approaches were investigated and proved practicable in the preparation of 3,28-diglycosides. This method is suitable for preparing oleanolic acid glycosides with structural diversity for extensive biological evaluation and structure-activity relationship study, and it also apply new idea for the corresponding synthetic methods to the glycoside derivatives of other triterpenoid.
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5.4
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