Gigantelline, gigantellinine and gigancrinine, cherylline- and crinine-type alkaloids isolated from Crinum jagus with anti-acetylcholinesterase activity. (July 2020)

• Record Type: Journal Article
• Authors: Ka, Seydou; Masi, Marco; Merindol, Natacha; Di Lecce, Roberta; Plourde, Mélodie B.; Seck, Matar; Górecki, Marcin; Pescitelli, Gennaro; Desgagne-Penix, Isabel; Evidente, Antonio
• Is Part Of: Phytochemistry. Volume 175(2020)
• Publication Date: 2020-07
• Subjects: Crinum jagus -- Amaryllidaceae -- Alkaloids -- Tetrahydroisoquinoline-type -- Acetylcholinesterase -- Cytotoxicity -- Alzeihmer's disease; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2020.112390
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Three undescribed Amarylidaceae alkaloids, named gigantelline, gigantellinine and gigancrinine, were isolated from Crinum jagus (syn. = Crinum giganteum ) collected in Senegal, together with the already known sanguinine, cherylline, lycorine, crinine, flexinine and the isoquinolinone derivative hippadine. Gigantelline, gigantellinine and gigancrinine were characterized as 4-(6, 7-dimethoxy-2-methyl-1, 2, 3, 4-tetrahydro-isoquinolin-4-yl)-phenol, its 7- O -demethyl-5ꞌ-hydroxy-4ꞌ-methoxy derivative and 5, 6a, 7, 7a, 8a, 9-hexahydro-6, 9a-ethano[1, 3]dioxolo[4, 5- j ]oxireno[2, 3- b ]phenanthridin-9-ol, respectively, by using spectroscopic (1D and 2D 1 H and 13 C NMR and HRESIMS) and chemical methods. Their relative configuration was assigned by NOESY NMR spectra and NMR calculations, while the absolute configuration was assigned using electronic circular dichroism (ECD) experiments and calculations. Sanguinine, cherylline, crinine, flexinine, and the isoquinolinone hippadine, were isolated for the first time from C. jagus . Cherylline, gigantellinine, crinine, flexinine and sanguinine inhibited the activity of AChE in a dose-dependent manner, and inhibition by sanguinine was remarkably effective (IC50 = 1.83 ± 0.01 μM). Cherylline and hippadine showed weak cytotoxicity at 100 μM. Graphical abstract: Three new alkaloids, named gigantelline, gigantellinine and gigancrinine, together with five already known alkaloids and one isoquinolinone, were isolated from Crinum jagus (syn. = Crinum giganteum ) collected in Senegal. Their anti-acetylcholinesterase and cytotoxic activities were evaluated . Image 1 Highlights: Three new alkaloids were isolated from Crinum jagus collected in Senegal. The previously undescribed gigantelline and gigantellinine belong to the rare tetrahydroisoquinoline-type alkaloids. Gigancrinine, an undescribed crinine-type alkaloid, was isolated together with five known alkaloids and one isoquinoline. Acetylcholinesterase AChE inhibitory potential and cytotoxic activity were evaluated. Cherylline, gigantellinine, crinine, flexinine and sanguinine inhibited AChE.