Development of a One-Step Method for Producing Allobetulin from Birch Outer Bark and Study of Its Antioxidant Activity

IF 1.1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY
E. S. Skurydina, N. Yu. Vasil’eva, S. A. Kuznetsova, N. M. Titova, B. N. Kuznetsov
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Abstract

Objective: Birch bark contains extractives of lupane series, that have pharmacological activity and are of interest for obtaining new medicines. The predominant component of the birch outer bark extracts is pentacyclic triterpene alcohol, betulin. Allobetulin (19,28-epoxyoleanan-3-ol), a pentacyclic oleanane-type triterpenoid, is an isomer of betulin. Allobetulin and its derivatives are nontoxic compounds having antiviral, antimicrobial, and antitumor activities. Methods: The composition of the allobetulin sample after recrystallization from isopropanol was confirmed by elemental analysis, and its structure, by IR and 1H NMR spectroscopy. The antioxidant properties of allobetulin were tested in vivo and in vitro. Results and Discussion: In the present study, a new one-step method was developed for producing allobetulin directly from birch outer bark by combining the stages of betulin extraction with ethanol and isomerization into allobetulin in the presence of an orthophosphoric acid catalyst. The effect of the duration of the birch outer bark treatment with ethanol and of the H3PO4 content on the allobetulin yield was evaluated. The highest yield of crude allobetulin, 35% of the weight of absolutely dry bark (a.d.b.), was achieved at a process duration of 8 h in the presence of 5% H3PO4 and also at a process duration of 15 h in the presence of 3% H3PO4. Conclusions: The yield of recrystallized allobetulin was ~22% of the weight of a.d.b.

Abstract Image

桦树外皮一步法制备异白桦素及其抗氧化活性研究
目的:桦树皮中含有具有药理活性的羽扇烷系列提取物,对开发新药具有重要意义。桦树外皮提取物的主要成分是五环三萜醇,白桦素。异白桦素(19,28-环氧齐墩烷-3-醇)是一种五环齐墩烷型三萜,是白桦素的异构体。异白桦素及其衍生物是具有抗病毒、抗菌和抗肿瘤活性的无毒化合物。方法:用元素分析确定异丙醇重结晶后的异桦木林样品的组成,用红外光谱和核磁共振氢谱分析确定样品的结构。对异白桦素的体内外抗氧化性能进行了实验研究。结果与讨论:在正磷酸催化剂的作用下,将乙醇提取桦木素和异白桦素异构化两个步骤结合起来,建立了直接从桦木外树皮中提取异白桦素的一步法。考察了乙醇处理桦树外皮时间和H3PO4含量对异白桦素产量的影响。在5%的H3PO4和3%的H3PO4的作用下,分别在8 h和15 h的处理时间下,得到了最高的异白桦素粗收率,占绝对干树皮重量的35%。结论:异白桦脂重结晶得率约为a.d.b重的22%。
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来源期刊
Russian Journal of Bioorganic Chemistry
Russian Journal of Bioorganic Chemistry 生物-生化与分子生物学
CiteScore
1.80
自引率
10.00%
发文量
118
审稿时长
3 months
期刊介绍: Russian Journal of Bioorganic Chemistry publishes reviews and original experimental and theoretical studies on the structure, function, structure–activity relationships, and synthesis of biopolymers, such as proteins, nucleic acids, polysaccharides, mixed biopolymers, and their complexes, and low-molecular-weight biologically active compounds (peptides, sugars, lipids, antibiotics, etc.). The journal also covers selected aspects of neuro- and immunochemistry, biotechnology, and ecology.
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