文献类型：期刊文献

中文题名：桦木醇选择性氧化产物的合成及抗肿瘤活性研究

英文题名：Synthesis and Antitumor Activity of Selective Oxidation Products of Betulin

作者：陶冉[1,2] 王成章[1,2] 张昌伟[2] 周昊[1,2] 陈虹霞[2]

第一作者：陶冉

机构：[1]中国林业科学研究院林业新技术研究所,北京100091;[2]中国林业科学研究院林产化学工业研究所;[3]生物质化学利用国家工程实验室;[4]国家林业局林产化学工程重点开放性实验室;[5]江苏省生物质能源与材料重点实验室,江苏南京210042

年份：2018

卷号：38

期号：4

起止页码：47-51

中文期刊名：林产化学与工业

外文期刊名：Chemistry and Industry of Forest Products

收录：CSTPCD;;Scopus;北大核心:【北大核心2017】；CSCD:【CSCD2017_2018】；

基金：中央级公益性科研院所基本科研业务费专项资金(CAFYBB2016SY030,CAFYBB2018GA001);中国林科院林产化学工业研究所研究团队建设创新工程项目(LHSXKQ5)

语种：中文

中文关键词：桦木醇;桦木酸;氧化物;合成;抗肿瘤

外文关键词：betulin;betulinic acid;oxide;synthesis;antitumor

分类号：TQ35

摘要：以桦木醇为先导结构,对桦木醇的C-28、C-29位进行结构修饰,分别在CrO 3和2,2,6,6-四甲基哌啶氮氧化物(TEMPO)混合物以及氧化剂间氯过氧苯甲酸(m-CPBA)氧化剂的作用下,在C-28位和C-29位选择性的引入醛基,并进一步氧化为C-28位和C-29位桦木酸,共得到4个氧化衍生物。用氢谱分别表征,结果表明:相对于单一氧化剂,CrO 3和TEMPO作为混合氧化剂,C-28桦木醛产率有所提高,达36.98%;当mCPBA作为氧化剂、丙酮作为溶剂时,C-29桦木醛产率达39.06%。利用改性噻唑蓝(MTT)法测定桦木醇及其氧化衍生物对两株细胞(HepG 2、A549)半数抑制质量浓度(IC50),结果表明:C-28和C-29桦木酸对HepG 2细胞的IC50值较其它组低,分别达到3.80和3.84 mg/L。桦木醇与C-28位和C-29位桦木醛对于HepG 2和A549细胞毒性无显著差异,C-28位和C-29位桦木酸对于HepG 2和A549细胞毒性则显著强于同位的桦木醛,桦木醇在C-28位和C-29位两个位置的氧化对于HepG 2和A549细胞毒性均没有显著性差异。
Based on the betulin with terpenoid as lead structure, the C-28 and C-29 of betulin were modified by the oxidants including the mixture of CrO 3 and TEMPO and the m -CPBA, and aldehyde groups were selectively introduced into C-28 and C-29 sites, respectively. The compounds were further oxidized to betulinic acid at C-28 and C-29 sites, respectively. Finally, four oxidized derivatives were obtained and characterized by 1H NMR. The results showed that the yield of C-28 betulinaldehyde oxidized by the mixed oxidant of CrO 3 and TEMPO was increased to 36.98% compared with that oxidized by single oxidant. When m -CPBA was used as oxidant and acetone was used as solvent, the yield of C-29 betulinaldehyde was 39.06%,which was the highest compared with others. The inhibitory rate and IC 50 of betulin and its oxidized derivatives on the proliferation of two cell lines （HepG2 and A549） were measured by modified MTT method. The results showed that there was no significant difference in the antitumor activity between betulin and betulinaldehyde at the C-28 and C-29 sites. The antitumor activity of betulinic acid at C-28 and C-29 sites was significantly higher than that of betulin and betulinaldehyde at the same site. There was no significant difference in the toxicity of HepG2 and A549 cells between the oxide of betulin C-28 and C-29 sites.