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首页> 外文学位 >Studies of the triterpenoids from the outer bark of three birch species: Betula lenta, Betula alleghaniensis and Betula nigra.
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Studies of the triterpenoids from the outer bark of three birch species: Betula lenta, Betula alleghaniensis and Betula nigra.

机译：对三种桦树种的外皮中的三萜类化合物进行研究：桦木，桦木和黑桦。

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摘要

Triterpenoid constituents in the outer bark of three Betula species were investigated. Ten triterpenoids were isolated from the outer bark of B. lenta by chromatography. Spectroscopic evidence and chemical derivatization showed that these triterpenoids were lupeol, betulin, lupenone, betulone, betulinic acid, betulin 3{dollar}beta{dollar}-caffeate, lup-20(29)-ene-3{dollar}beta{dollar}, 30-diol, lup-20(29)-ene-3{dollar}beta{dollar}-ol-30-al, lup-20(29)-ene-3{dollar}beta{dollar},28-diol-30-al and lupan-3{dollar}beta{dollar},20-diol. Betulone and lup-20(29)-ene-3{dollar}beta{dollar},28-diol-30-al, previously prepared synthetically, are new natural products. Lupeol was the most abundant triterpene, and betulin was second in abundance.; From the outer bark of B. alleghaniensis, seventeen triterpenoids were isolated and identified by the same methods. Four of them, including lup-20(29)-ene-3-one-28-ol-30-al, 29-norlupan-3{dollar}beta{dollar},20-dione, 29-norlupan-28-ol-3{dollar}beta{dollar},20-dione and lupan-3-one-20,28-diol, are new natural compounds. Other triterpenes were previously isolated either from the bark of Betula species or from other natural sources. In B. alleghaniensis, lupeol was still the predominant component, but the second most abundant component in B. alleghaniensis was lupenone, which was different from B. lenta. Betulone and lupan-3-one-20-ol were also present at the high level in B. alleghaniensis. Lup-20(29)-ene-3{dollar}beta{dollar}-ol-30-al was tested for insect antifeedant activity against Colorado potato beetle (Leptinotarsa decemlineata) and showed no activity.; From the outer bark of Betula nigra, twelve triterpenoids were isolated and identified. Among them, acetyl methyl betulinate, acetyl betulinic acid and 3{dollar}beta{dollar}-acetoxy-olean-11-oxo-12-ene-28-oic acid were isolated for the first time from a Betula species. Oleanolic acid 3{dollar}beta{dollar}-caffeate was spectrally characterized for the first time. Other triterpenes were previously isolated either from the bark of European birch species or from two dark-barked North American birches. The composition of the triterpenoids in B. nigra was quite different from the previously studied birch species. Instead of lupenone, lupeol and betulin being the major components, acetyl oleanolic acid and betulinic acid were the predominant components in B. nigra. Acetyl oleanolic acid and 3{dollar}beta{dollar}-olean-11-oxo-12-ene-28-oic acid demonstrated activity as antifeedants for the Colorado potato beetle. Oleanolic acid showed lower activity in the same bioassay.; Both the {dollar}beta{dollar}-D- and {dollar}beta{dollar}-L-glucosides of 19{dollar}beta{dollar},28-epoxy-2-hydroxy-18{dollar}alpha{dollar}-olean-1-ene-3-one were synthesized in order to find out the mechanism of action of the betulin-derived active compound. Also, a model compound was synthesized for structure-activity evaluation. These synthetically prepared compounds will be assessed for antifeedant activity.
机译：研究了三种桦树皮外皮中的三萜类成分。通过色谱法从B. lenta的外皮中分离出十个三萜。光谱证据和化学衍生化表明，这些三萜类化合物是羽扇豆酚，桦木酚，羽扇豆酮，贝托隆，桦木酸，桦木酚3 {dollar}β{dollar} -caffeate，lup-20（29）-ene-3 {dollar} beta {dollar} ，30-二醇，lup-20（29）-ene-3 {美元}β{美元} -ol-30-al，lup-20（29）-ene-3 {美元} beta {美元}，28-二醇-30-al和lupan-3 {dollar} beta {dollar}，20-diol。以前合成制备的贝妥隆和lup-20（29）-ene-3 {dollar} beta {dollar}，28-diol-30-al是新的天然产物。羽扇豆酚是最丰富的三萜烯，而白藜芦醇含量第二高。从B. alleghaniensis的外皮中，分离出十七种三萜类化合物，并用相同的方法鉴定。其中四个包括lup-20（29）-ene-3-one-28-ol-30-al，29-norlupan-3 {dolal} beta {dollar}，20-dione，29-norlupan-28-ol -3 {dollar} beta {dollar}，20-dione和lupan-3-one-20,28-diol是新的天然化合物。先前从桦属物种的树皮或其他自然资源中分离出了其他三萜。在Alleghaniensis中，羽扇豆仍是主要成分，但在Alleghaniensis中第二丰富的成分是Lupenone，这与Lenta有所不同。 Betulone和lupan-3-one-20-ol也以高水平存在于Alleghaniensis中。测试了Lup-20（29）-ene-3 {dollar} beta {dollar} -ol-30-al对科罗拉多马铃薯甲虫（Leptinotarsa decemlineata）的昆虫拒食活性，但未显示活性。从黑桦的外皮中分离并鉴定出十二种三萜。其中，从桦树属物种中首次分离出乙酰基桦木酸甲酯，乙酰基桦木酸和3 {dollar}β{dollar}-乙酰氧基-油氧基-11-氧代-12-烯-12-烯-28-oic酸。齐墩果酸3 {dollar}β{dollar}-咖啡酸盐是首次光谱表征。其他三萜类化合物以前是从欧洲桦树种的树皮中或从两个深色树皮的北美桦树中分离出来的。黑芥中的三萜类成分与先前研究的桦树种完全不同。紫杉醇和桦木酸不是主要成分，而是羽扇豆酚和桦木素，而是黑麦芽孢杆菌中的主要成分。乙酰齐墩果酸和3 {dollar} beta {dollar} -olean-11-oxo-12-ene-28-oic acid表现出作为科罗拉多马铃薯甲虫的拒食剂的活性。齐墩果酸在相同的生物测定中显示出较低的活性。 19 {dollar} beta {dollar}，28-epoxy-2-hydroxy-18 {dollar} alpha {dollar}的{dollarbeta {dollar} -D-和{dollarbetabeta {dollar} -L-glucosides）合成了-olean-1-ene-3-one，目的是寻找甜菜碱衍生的活性化合物的作用机理。另外，合成了模型化合物用于结构活性评估。将评估这些合成制备的化合物的拒食活性。

著录项

  • 作者

    Hua, Yun.;

  • 作者单位

    The University of Maine.;

  • 授予单位 The University of Maine.;
  • 学科 Chemistry Organic.
  • 学位 Ph.D.
  • 年度 1991
  • 页码 184 p.
  • 总页数 184
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 有机化学;
  • 关键词

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