布鲁诺尼A-C,C20-二烯酸类化物与来自Delphinium brunonianum Royle的蓝色组
Qing Li1, Zhi-Wei Wang1, Mu-Xuan Wang1
1. Department of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering and Jiangsu Province Hi-Tech Key Laboratory for Biomedical Research, Southeast University, Nanjing, 211189, China.
Phytochemistry
|January 13, 2024
概括
从Delphinium brunonianum中分离出了三种含有蓝的新二类化物,其中一种化合物通过诱导亡和细胞循环停止而显示出强大的抗瘤活性.
科学领域:
- 自然产品化学 自然产品化学
- 药用化学 医学化学
- 药理学 药理学是指药理学的学科.
背景情况:
- 色功能组在天然产品中很少见,特别是在C20-diterpene类化合物中.
- Delphinium brunonianum是新型化物结构的潜在来源.
研究的目的:
- 从Delphinium brunonianum中分离和描述新的化物.
- 评估分离的化合物的抗瘤活性.
主要方法:
- 使用HR-ESI-MS,1D/2D NMR,ECD计算和X射线衍射进行隔离和结构阐明.
- 在体外对A549,Caco-2,H460和Skov-3细胞系进行抗瘤活性查.
- 机理学研究包括细胞循环分析,迁移/入侵测定和西部斑点.
主要成果:
- 确定了三种前所未有的C20-diterpenoid类化合物,brunonianines A-C (1-3),具有蓝色组和atisine骨干.
- 化合物1-3代表了第一个具有蓝色部分的自然存在的阿提辛类型二类化物.
- 化合物2对Skov-3细胞表现出显著的抑制活性 (IC50 2.20 ± 0.21 μM),超过了基托丁.
- 化合物2通过Bax/Bcl-2/Caspase-3通路诱导了G2/M细胞周期停止,抑制了细胞运动,并触发了细胞亡.
结论:
- 布鲁诺尼A-C是一种具有独特结构特征的新型天然产品.
- 化合物2显示出有前途的抗瘤潜力,需要进一步调查.
- 这项研究扩大了二类化物及其生物活动的结构多样性.
相关概念视频
01:32Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
2.8K
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
2.8K
01:26Physical Properties of Amines
3.2K
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
3.2K
01:07Amines: Introduction
4.4K
Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
4.4K
01:10Nomenclature of Aryl and Heterocyclic Amines
2.4K
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
2.4K
01:19Diazonium Group Substitution: –OH and –H
2.8K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.8K
01:12Nomenclature of Secondary and Tertiary Amines
3.9K
The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for...
3.9K