Alkaloids from Crinum erubescens Aiton

Abstract

Eight alkaloids have been identified from fresh leaves of Crinum erubescens (Amaryllidaceae) collected in Costa Rica. The alkaloid 1-epidemethylbowdensine, detected by means of GC-MS as part of a global Amaryllidaceae Phytochemical Program, is reported for the first time and completely characterized by physical and spectroscopic methods. The absolute configuration of this compound is also reported. ª 2015 Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

Alkaloids of Amaryllidaceae as Inhibitors of Cholinesterases (AChEs and BChEs): An Integrated Bioguided Study

“…An alternative identification of the alkaloids was performed by comparing their GC-MS spectra with a private library database. This library has been regularly updated with alkaloids isolated and unequivocally identified via physical and spectroscopic means (Guerrieri et al, 2016). Mass spectra were deconvoluted using AMDIS 2.64 software (NIST).…”

Amaryllidaceae alkaloids: Absolute configuration and biological activity

“…The absolute configuration of 30 was determined by its CD spectrum. It showed a positive and a negative Cotton effect at ~250 and 290 nm, respectively, which, on the basis of the CD data collected for crinine 5,10b‐ethano bridge orientation, allowed assigning 30 to the β‐crinane series …”

“…1‐Epidemethylbowdensine ( 30 , Figure ) was isolated from fresh leaves of Crinum erburescens , an Amaryllidaceae plant collected in Costa Rica, together with bowdensine ( 33 ), 1‐epidemethoxybowdensine, crinamine, 11,12‐dehydroanhyrolycorine, macronine, ismine, and trisphaerdine. All the known alkaloids were identified by gas chromatography mass spectroscopy (GC‐MS) analysis with macronine being the main constituent . The structure of 30 was determined by comparison of its spectroscopic data with those of 1‐epibowdensine .…”

“…All the known alkaloids were identified by gas chromatography mass spectroscopy (GC-MS) analysis with macronine being the main constituent. 82 The structure of 30 was determined by comparison of its spectroscopic data with those of 1-epibowdensine. 83 The absolute configuration of 30 was determined by its CD spectrum.…”

“…It showed a positive and a negative Cotton effect at~250 and 290 nm, respectively, which, on the basis of the CD data collected for crinine 5,10b-ethano bridge orientation, 50,65 allowed assigning 30 to the β-crinane series. 82 Among all the Amaryllidaceae alkaloids and the related isocarbostyryls, those belonging to the crinine type, characterized by the presence of the 5,10b-ethanophenanthridine ring system, have recently been shown to be effective at inhibiting proliferation of cancer cells resistant to various proapoptotic stimuli of tumors with dismal prognoses refractory to current chemotherapy, such as glioma, melanoma, nonsmall-cell lung, esophageal, head and neck cancers, among others. 84 These results prompted developing a straightforward biomimetic route for compounds with a crinine skeleton.…”