[来自Corydalis Rhizoma的两个新的α-碳胺]
Yue-Lin Jia1, Ling-Yan Wang2, Xiao-Hong Wei2
1Key Laboratory of Chinese Internal Medicine of Ministry of Education and Beijing, Dongzhimen Hospital,Beijing University of Chinese Medicine Beijing 100700, China Wuya Innovation College, Shenyang Pharmaceutical University Shenyang 110016, China.
概括
这项研究从加工的Corydalis Rhizoma中分离出24种化合物,包括两种新的罕见类化合物,yanhuoxamide A和B. 他们的潜在的乙胆化酶 (AChE) 抑制活性也被评估.
科学领域:
- 药理学和天然产品化学 药理学和天然产品化学
- 传统中国医学 (TCM) 研究研究
- 神经科学和酶抑制研究研究
背景情况:
- 科里达利斯树根是一种至关重要的TCM草药,用于缓解疼痛和调节智力.
- 它的活性化合物的全谱及其机制仍然不完全理解.
- 研究新型化合物及其生物活性对于了解TCM疗效至关重要.
研究的目的:
- 为了隔离和识别加工的Corydalis Rhizoma的化学成分.
- 来自该来源的新型类化合物和以前未报告的化合物的特征.
- 评估新发现的化合物的乙胆酶 (AChE) 抑制潜力.
主要方法:
- 使用水的方法提取Corydalis Rhizoma的提取.
- 隔离和净化使用巨孔吸附树脂,Sephadex LH-20染色学和半准备型HPLC.
- 使用紫外线,红外线,HR-MS,1D NMR和2D NMR光谱技术进行结构阐明.
主要成果:
- 二十四种化合物被分离和鉴定出来.
- 发现了两种罕见的天然α-碳胺类化合物,即yanhuoxamide A (1) 和yanhuoxamide B (2).
- 从Corydalis Rhizoma中首次报告了15种化合物 (3-15),并从Corydalis Rhizoma中新分离了9种化合物 (16-24).
结论:
- 这项研究成功地确定了加工的Corydalis Rhizoma中的24种化合物,扩大了已知的草药化学特征.
- 扬胡胺A和B的发现为天然产品化学贡献了新的结构.
- 初步评估表明,化合物1和2具有对乙胆化酶 (AChE) 的抑制活性,表明潜在的神经药理学相关性.
相关概念视频
01:19Amines to Amides: Acylation of Amines
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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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01:16Adrenergic Agonists: Chemistry and Structure-Activity Relationship
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Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
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01:29Preparation of Amides
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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
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Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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01:26Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
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The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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