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林产化学与工业

林产化学与工业 ›› 2018, Vol. 38 ›› Issue (4): 47-51.doi: 10.3969/j.issn.0253-2417.2018.04.008

• 研究报告 • 上一篇    下一篇

桦木醇选择性氧化产物的合成及抗肿瘤活性研究

陶冉1,2, 王成章1,2, 张昌伟2, 周昊1,2, 陈虹霞2   

  1. 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;生物质化学利用国家工程实验室;国家林业局 林产化学工程重点开放性实验室; 江苏省 生物质能源与材料重点实验室, 江苏 南京 210042
  • 收稿日期:2018-01-25 出版日期:2018-08-25 发布日期:2018-08-10
  • 通讯作者: 王成章,研究员,博士,博士生导师,主要从事天然产物研究与利用;E-mail:wangczlhs@sina.com。 E-mail:wangczlhs@sina.com
  • 作者简介:陶冉(1982-),男,江苏连云港人,助理研究员,博士,主要从事天然产物化学研究;E-mail:trmoon1949@163.com
  • 基金资助:
    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）

Synthesis and Antitumor Activity of Selective Oxidation Products of Betulin

TAO Ran1,2, WANG Chengzhang1,2, ZHANG Changwei2, ZHOU Hao1,2, CHEN Hongxia2   

  1. 1. Research Institute of Forestry New Technology, CAF, Beijing 100091, China;
    2. Institute of Chemical Industry of Forestry Products, CAF;National Engineering Lab. for Biomass Chemical Utilization;Key and Open Lab. of Forest Chemical Engineering, SFA;Key Lab. of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China
  • Received:2018-01-25 Online:2018-08-25 Published:2018-08-10

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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CrO3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，CrO3和TEMPO作为混合氧化剂，C-28桦木醛产率有所提高，达36.98%；当m-CPBA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（HepG2、A549）半数抑制质量浓度（IC50），结果表明：C-28和C-29桦木酸对HepG2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HepG2和A549细胞毒性无显著差异，C-28位和C-29位桦木酸对于HepG2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HepG2和A549细胞毒性均没有显著性差异。

关键词: 桦木醇, 桦木酸, 氧化物, 合成, 抗肿瘤

Abstract: 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 CrO3 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 CrO3 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 IC50 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.

Key words: betulin, betulinic acid, oxide, synthesis, antitumor

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