Absolute configurations and the c-ring conformations of lycorine and related compounds evidenced by NMR and CD spectroscopies

Kotera, K.; Hamada, Y.; Tori, Kazuo; Aono, Katsutoshi; Kuriyama, Koichi

doi:10.1016/s0040-4039(00)76288-5

Cited by 27 publications

(9 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The relative configuration of alkaloid 1 was elucidated by a ROESY experiment. The ROESY correlations of H-10b/H-1 and H-4a/H-2 indicated the β-orientation of H-1 and α-orientation of H-2 and are consistent with those reported by Kotera et al[32]. Therefore, alkaloid 1 was identified as 1-O-acetyl-5,6-dehydrolycorine.…”

supporting

confidence: 90%

Isolation of Three Lycorine Type Alkaloids from Rhodolirium speciosum (Herb.) Ravenna Using pH-Zone-Refinement Centrifugal Partition Chromatography and Their Acetylcholinesterase Inhibitory Activities

et al. 2020

View full text Add to dashboard Cite

Preparative separation of three lycorine type alkaloids from Rhodolirum speciosum (Amaryllidaceae) was successfully carried out using pH-zone-refinement centrifugal partition chromatography (CPC) using the solvent system methyl-tert-butyl ether/acetonitrile/water (4:1:5, v/v/v) in descending mode. Using this system, Alkaloid 1 (165.7 mg, 88.2%, purity), 2 (60.1 mg, 97.7% purity) and 3 (12.3 mg, 84.4% purity) were obtained in one step. For structure elucidation, the pure alkaloids were subjected to spectroscopy analysis using nuclear magnetic resonance experiments (1H-NMR, 13C-NMR) and gas chromatography coupled with mass spectrometry (GC-MS). Alkaloids 1, 2, and 3 were identified as 1-O-acetyl-5,6-dehydrolycorine, 1-O-acetyl-lycorine, and 1,2-O-diacetyl-5,6-dehydrolycorine, respectively. The acetylcholinesterase inhibitory activity of these alkaloids was IC50 151.1 μg/mL, IC50 203.5 μg/mL, IC50 470.0 μg/mL, and IC50 17.1 μg/mL, respectively.

show abstract

supporting

confidence: 90%

Isolation of Three Lycorine Type Alkaloids from Rhodolirium speciosum (Herb.) Ravenna Using pH-Zone-Refinement Centrifugal Partition Chromatography and Their Acetylcholinesterase Inhibitory Activities

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Its structure was first determined by Nagakawa et al, in 1956, 14,15 and its absolute stereochemistry was first assigned by chemical correlation 16 and thereafter by applying the octant rule to circular dichroism (CD) and optical rotatory dispersion (ORD) spectra of lycorine derivatives. 17,18 Furthermore, Shiro et al 19 carried out the X-ray analysis of dihydrolycorine hydrobromide, confirming that the stereochemistry previously assigned to 1 was indeed correct. 20 The first study on the biological activity of 1, revealing its ability to inhibit ascorbic acid biosynthesis, 21 increased the interest towards 1 and as well as the demand for its availability.…”

Section: Lycorinementioning

confidence: 77%

“…Its structure was first determined by Nagakawa et al . , in 1956, and its absolute stereochemistry was first assigned by chemical correlation and thereafter by applying the octant rule to circular dichroism (CD) and optical rotatory dispersion (ORD) spectra of lycorine derivatives . Furthermore, Shiro et al .…”

Section: Lycorine Alkaloids Subgroupmentioning

confidence: 99%

Amaryllidaceae alkaloids: Absolute configuration and biological activity

et al. 2017

View full text Add to dashboard Cite

Plants belonging to the Amaryllidaceae family are well known for their ornamental and medicinal use. Plant members of this group are distributed through both tropical and subtropical regions of the world and are dominant in Andean South America, the Mediterranean basin, and southern Africa. Amaryllidaceae plants have been demonstrated to be a good source of alkaloids with a large spectrum of biological activities, the latter being strictly related to the absolute stereochemistry of the alkaloid scaffold. Among them, great importance for practical applications in medicine has galanthamine, which has already spawned an Alzheimer's prescription drug as a potent and selective inhibitor of the enzyme acetylcholinesterase. Furthermore, lycorine as well as its related isocarbostyryl analogs narciclasine and pancratistatine have shown a strong anticancer activity in vitro against different solid tumors with malignant prognosis. This review addresses the assignment of the absolute configuration of several Amaryllidaceae alkaloids and its relationship with their biological activities.

show abstract

“…This shows that the double bond is located at the end of the chain in the form of the CH-----CH--CHs grouping. The nitrogen-free substance obtained by the hydrogenation of bucharaine [I] was oxidized by Percheron's method [2,3]. Of the oxidation products, acetic and valeric acids were identified by paper chromatography.…”

mentioning

confidence: 99%