根茎
立体化学
化学
圆二色性
药效团
对映体
生物
植物
作者
Dongdong Wang,Rui Zhang,Lixuan Tang,Guo-Qing Long,Hui Yan,Yong-Cheng Yang,Zifeng Guo,Yingying Zheng,Yong Wang,Jing‐Ming Jia,An-Hua Wang
标识
DOI:10.1021/acs.joc.3c01664
摘要
(±)-Salvicatone A (1), a C27-meroterpenoid featuring a unique 6/6/6/6/6-pentacyclic carbon skeleton with a 7,8,8a,9,10,10a-hexahydropyren-1 (6H)-one motif, was isolated from the roots and rhizomes of Salvia castanea Diels f. tomentosa Stib. Its structure was characterized by comprehensive spectroscopic analyses along with computer-assisted structure elucidation, including ACD/structure elucidator and quantum chemical calculations with 1H/13C NMR and electronic circular dichroism. Biogenetically, compound 1 was constructed from decarboxylation following [4 + 2] Diels–Alder cycloaddition reaction between caffeic acid and miltirone analogue. Bioassays showed that (−)-1 and (+)-1 inhibited nitric oxide production in lipopolysaccharide-induced RAW264.7 macrophage cells with an IC50 value of 6.48 ± 1.25 and 15.76 ± 5.55 μM, respectively. The structure-based virtual screening based on the pharmacophores in ePharmaLib, as well as the molecular docking and molecular dynamics simulations study, implied that (−)-1 and (+)-1 may potentially bind to retinoic acid receptor-related orphan receptor C to exert anti-inflammatory activities.
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