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莫雷酰胺A:一种来自海洋蓝藻莫雷阿·布永氏藻的类大麻素脂质。

Mooreamide A: a cannabinomimetic lipid from the marine cyanobacterium Moorea bouillonii.

作者信息

Mevers Emily, Matainaho Teatulohi, Allara' Marco, Di Marzo Vincenzo, Gerwick William H

机构信息

Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego, La Jolla, CA, 92093, USA.

出版信息

Lipids. 2014 Nov;49(11):1127-32. doi: 10.1007/s11745-014-3949-9. Epub 2014 Sep 10.

Abstract

Bioassay-guided fractionation of a collection of Moorea bouillonii from Papua New Guinea led to the isolation of a new alkyl amide, mooreamide A (1), along with the cytotoxic apratoxins A-C and E. The planar structure of 1 was elucidated by NMR spectroscopy and mass spectrometry analysis. Structural homology between mooreamide A and the endogenous cannabinoid ligands, anandamide, and 2-arachidonoyl glycerol inspired its evaluation against the neuroreceptors CB(1) and CB(2). Mooreamide A was found to possess relatively potent and selective ligand binding activity to CB(1) (K(1) = 0.47 µM) versus CB(2) (K(1) > 25 µM). This represents the most potent marine-derived CB(1) ligand described to date and adds to the growing family of marine metabolites that exhibit cannabinomimetic activity.

摘要

对来自巴布亚新几内亚的莫雷阿岛布氏海绵(Moorea bouillonii)样本进行生物测定导向的分级分离,得到了一种新的烷基酰胺——莫雷酰胺A(1),以及具有细胞毒性的阿普拉毒素A - C和E。通过核磁共振光谱和质谱分析阐明了1的平面结构。莫雷酰胺A与内源性大麻素配体花生四烯乙醇胺和2 - 花生四烯酸甘油之间的结构同源性促使对其针对神经受体CB(1)和CB(2)进行评估。发现莫雷酰胺A对CB(1)(K(1) = 0.47 µM)相对于CB(2)(K(1) > 25 µM)具有相对较强且选择性的配体结合活性。这代表了迄今为止所描述的最强效的海洋来源CB(1)配体,并为不断增加的具有大麻素模拟活性的海洋代谢产物家族增添了一员。

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