半胱氨酸-多巴胺三聚物及其绝对构型来自蝉蜕。
Enantiomeric N-acetyldopamine trimers from Cicadae Periostracum and their absolute configurations.
机构信息
School of Pharmacy, Zunyi Medical University, Zunyi, 563006, People's Republic of China; Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan, 528400, People's Republic of China.
Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan, 528400, People's Republic of China; School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, People's Republic of China.
出版信息
Phytochemistry. 2023 Sep;213:113780. doi: 10.1016/j.phytochem.2023.113780. Epub 2023 Jun 26.
Six previously undescribed N-acetyldopamine (NADA) trimmer racemates, percicamides A-F (1-6), were isolated from a 70% ethanol extract of Cicadae Periostracum. Subsequent chiral-phase separation afforded six pairs of enantiomers, (+)- and (-)-percicamides A-F (1a/1b-6a/6b). Their structures including absolute configurations were elucidated by combined extensive spectroscopic data and quantum chemical calculations. Compounds 1-6 represent the first examples of NADA trimmers with a cis-relationship of H-7'/H-8' or H-7''/H-8''. Bioassays verified that all isolated compounds showed weak inhibitory effects on nitric oxide production in RAW 264.7 cells.
从蝉蜕的 70%乙醇提取物中分离得到了 6 种以前未描述的 N-乙酰多巴胺（NADA）修剪型外消旋体，分别为 percicamides A-F（1-6）。随后的手性相分离得到了 6 对非对映异构体，（+）-和（-）-percicamides A-F（1a/1b-6a/6b）。通过综合广泛的光谱数据和量子化学计算确定了它们的结构包括绝对构型。化合物 1-6 代表了具有 H-7'/H-8' 或 H-7''/H-8'' 顺式关系的 NADA 修剪型的首例。生物测定证实，所有分离得到的化合物对 RAW 264.7 细胞中一氧化氮的产生均表现出较弱的抑制作用。
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