Department of BioMolecular Sciences, Division of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, United States.
National Center for Natural Product Research (NCNPR), The University of Mississippi, University, Mississippi 38677, United States.
J Nat Prod. 2021 Apr 23;84(4):1392-1396. doi: 10.1021/acs.jnatprod.0c00939. Epub 2021 Mar 18.
is an acclaimed hallucinogen consumed traditionally by the Hopi Indians to induce diagnostic visions. Its root extract afforded a new () and four known (, , , and ) 12a-hydroxyrotenoids, a known rotenoid (), and two known secondary metabolites ( and ). The structures of the compounds were elucidated based on spectroscopic and spectrometric data analysis. Electronic circular dichroism data were used to define the (6a,12a) absolute configuration of the 12a-hydroxyrotenoids. Compounds - were screened for their radioligand binding affinities toward the opioid (δ, κ, and μ) and cannabinoid (CB1 and CB2) receptor subtypes. The 6-methoxy-substituted rotenoids , , and showed the highest receptor binding affinity with moderate selectivity toward the δ-opioid receptor subtype, with negligible binding affinities for CB1 and CB2. Their binding affinities toward the δ-opioid receptor were 64.5% (), 58.7% (), and 55.3% () at 10 μM, respectively.
是一种备受赞誉的迷幻剂，传统上由霍皮印第安人食用，以引起诊断性幻觉。它的根提取物提供了一种新的（）和四种已知的（、、、和）12a-羟基罗替诺德，一种已知的罗替诺德（）和两种已知的次生代谢物（和）。基于光谱和光谱数据解析，确定了化合物的结构。电子圆二色性数据用于定义 12a-羟基罗替诺德的（6a,12a）绝对构型。对化合物-进行了放射性配体结合亲和力筛选，以评估其对阿片（δ、κ 和 μ）和大麻素（CB1 和 CB2）受体亚型的作用。6-甲氧基取代的罗替诺德、和显示出对δ-阿片受体亚型的最高受体结合亲和力，对 CB1 和 CB2 具有中等选择性，结合亲和力可忽略不计。它们对 δ-阿片受体的亲和力在 10 μM 时分别为 64.5%（）、58.7%（）和 55.3%（）。
