Bioactive sulfur-containing compounds from Xanthium sibiricum, including a revision of the structure of xanthiazinone,Phytochemistry

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Bioactive sulfur-containing compounds from Xanthium sibiricum, including a revision of the structure of xanthiazinone
Phytochemistry ( IF 3.2 ) Pub Date : 2020-05-01 , DOI: 10.1016/j.phytochem.2020.112293
Zhao Xia ₁ , Tian-Qi Xu ₁ , Hai-Xin Zhang ₁ , Yi-Min Chen ₁ , Wei Xu ₁ , Guang-Xiong Zhou ₁

Affiliation

Seven previously undescribed sulfur-containing compounds, (+)- and (-)-xanthiazinone A, (+)- and (-)-xanthiazinone B, (+)- and (-)-xanthiazinone C and xanthiazinone D, and four known thiazinedione derivatives, together with three thiophene derivatives were isolated from the fruits of Xanthium sibiricum. Racemic xanthiazinones A-C were separated by chiral HPLC columns. Their chemical structures were elucidated based on extensive spectroscopic analyses, ECD calculations, and single crystal X-ray diffractions. The X-ray crystallographic analyses for xanthiazinones A-C represent the first example described for the structure elucidation of the thiazinedione with the five-membered lactone ring attached via an oxygen atom. Accordingly, the previously proposed structure for xanthiazinone was revised. The anti-inflammatory and cytotoxic activities were evaluated for all the isolated compounds. (+)-xanthiazinone B and 2-hydroxy-xanthiazone exhibited potent inhibitory effects against nitric oxide production in lipopolysaccharide-activated RAW 264.7 mouse macrophage cells with IC50 values of 8.75 and 10.90 μM, respectively. All compounds obviously were inactive for three human tumor cell lines (HepG2, MCF-7, and A549) with IC50 values more than 10 μM.

中文翻译：

来自 Xanthium sibiricum 的生物活性含硫化合物，包括对黄噻嗪酮结构的修正

七种以前未描述的含硫化合物，(+)- 和 (-)-黄噻嗪酮 A、(+)- 和 (-)- 黄噻嗪酮 B、(+)- 和 (-)- 黄噻嗪酮 C 和黄噻嗪酮 D，以及四种已知的从苍耳的果实中分离出噻嗪二酮衍生物和三种噻吩衍生物。外消旋黄噻嗪酮 AC 通过手性 HPLC 柱进行分离。基于广泛的光谱分析、ECD 计算和单晶 X 射线衍射阐明了它们的化学结构。黄噻嗪酮 AC 的 X 射线晶体学分析代表了第一个实例，用于阐明具有通过氧原子连接的五元内酯环的噻嗪二酮的结构。因此，修改了先前提出的黄噻嗪酮结构。评估了所有分离化合物的抗炎和细胞毒性活性。(+)-xanthiazinone B 和 2-羟基-xanthiazone 对脂多糖激活的 RAW 264.7 小鼠巨噬细胞中的一氧化氮产生具有强效抑制作用，IC50 值分别为 8.75 和 10.90 μM。显然，所有化合物对三种人类肿瘤细胞系（HepG2、MCF-7 和 A549）均无活性，IC50 值超过 10 μM。

更新日期：2020-05-01

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