2. Academic Validation
  3. Gigantelline, gigantellinine and gigancrinine, cherylline- and crinine-type alkaloids isolated from Crinum jagus with anti-acetylcholinesterase activity

Gigantelline, gigantellinine and gigancrinine, cherylline- and crinine-type alkaloids isolated from Crinum jagus with anti-acetylcholinesterase activity

  • Phytochemistry. 2020 Jul;175:112390. doi: 10.1016/j.phytochem.2020.112390.
Seydou Ka 1,  Marco Masi 2,  Natacha Merindol 3,  Roberta Di Lecce 2,  Mélodie B Plourde 3,  Matar Seck 4,  Marcin Górecki 5,  Gennaro Pescitelli 6,  Isabel Desgagne-Penix 7,  Antonio Evidente 8
Affiliations

Affiliations

  • 1 Département de Chimie, Biochimie et Physique, Université du Québec à Trois-Rivières, 3351, Boul. des Forges, C.P. 500, Trois-Rivières, Québec, G8Z 4M3, Canada; Laboratoire de Chimie Organique et Chimie Thérapeutique, Faculté de Médecine, de Pharmacie et d'Odontologie de Dakar, Dakar, Sénégal.
  • 2 Dipartimento di Scienze Chimiche, Universita' di Napoli Federico II, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, 80126 Napoli, Italy.
  • 3 Département de Chimie, Biochimie et Physique, Université du Québec à Trois-Rivières, 3351, Boul. des Forges, C.P. 500, Trois-Rivières, Québec, G8Z 4M3, Canada.
  • 4 Laboratoire de Chimie Organique et Chimie Thérapeutique, Faculté de Médecine, de Pharmacie et d'Odontologie de Dakar, Dakar, Sénégal.
  • 5 Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Giuseppe Moruzzi, 13, 56124, Pisa, Italy; Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, Warsaw, 01-224, Poland.
  • 6 Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Giuseppe Moruzzi, 13, 56124, Pisa, Italy.
  • 7 Département de Chimie, Biochimie et Physique, Université du Québec à Trois-Rivières, 3351, Boul. des Forges, C.P. 500, Trois-Rivières, Québec, G8Z 4M3, Canada. Electronic address: [email protected].
  • 8 Dipartimento di Scienze Chimiche, Universita' di Napoli Federico II, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, 80126 Napoli, Italy. Electronic address: [email protected].
PMID: 32335411 DOI: 10.1016/j.phytochem.2020.112390
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 1H and 13C 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.

Keywords

Acetylcholinesterase; Alkaloids; Alzeihmer's disease; Amaryllidaceae; Crinum jagus; Cytotoxicity; Tetrahydroisoquinoline-type.

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