New furoquinoline alkaloid and flavanone glycoside derivatives from the leaves ofOricia suaveolens and Oricia renieri(Rutaceae)

Abstract

Fractionation of the methanol extract of the leaves of Oricia renieri and Oricia suaveolens (Rutaceae) led to the isolation of 13 compounds including the hitherto unknown furoquinoline alkaloid named 6,7-methylenedioxy-5-hydroxy-8-methoxy-dictamnine (1) and a flavanone glycoside named 5-hydroxy-4'-methoxy-7-O-[α-L-rhamnopyranosyl(1‴→5″)-β-D-apiofuranosyl]-flavanoside (2), together with 11 known compounds (3-13). The structures of the compounds were determined by comprehensive analyses of their 1D and 2D NMR, mass spectral data and comparison. All compounds isolated were examined for their activity against human carcinoma cell lines. The alkaloids 1, 5, 12, 13 and the phenolic 2, 8, 11 tested compounds exhibited non-selective moderate cytotoxic activity with IC50 8.7-15.9 μM whereas compounds 3, 4, 6, 7, 9 and 10 showed low activity.

Anin silicoperception for newly isolated flavonoids from peach fruit as privileged avenue for a countermeasure outbreak of COVID-19

“…Additionally, the 1 H-NMR spectrum exhibited a singlet at d H 3.80 (3H), indicating the presence of a methoxy group in the B ring. 42 The 13 C-NMR spectrum showed the presence of a quaternary carbon C-4 at d C 192.77, an oxymethine carbon C-2 at d C 80.00, an oxymethylene carbon C-3 at d C 46.43, and other carbons of two benzene rings, which indicated the presence of a avanone moiety. 43 Also, the 13 C-NMR spectrum showed an anomeric…”

A Novel Frameshifting Inhibitor Having Antiviral Activity against Zoonotic Coronaviruses

“…Compound KCB261770, 2-(5-acetylthiophen-2yl)furo [2,3- b ]quinoline, is a newly synthesized furo[2,3- b ]quinoline with a molecular weight of 294.3 [ 30 ]. Although furo-quinoline occurs naturally [ 31 , 32 ], diverse furo-quinoline derivatives have also been synthesized [ 30 , 33 ] owing to their pharmacological and biological properties including anti-inflammatory [ 34 , 35 ], anti-malarial [ 36 ], and antimicrobial activities [ 37 ]. The inhibitory effects, cell viabilities, IC 50 values, and chemical structures of the rest are shown in Figure S1 .…”

Synthesis of 2‐Substituted Furo[2,3‐b]‐ and Furo[3,2‐c]quinolines via Heterogeneous Palladium‐catalyzed Heteroannulation

“…1 H and 13 C NMR spectra were recorded on a JEOL JNM-AL400 Spectrometer (400 MHz for 1 H and 100 MHz for 13 C) using CDCl 3 as the solvent and TMS as internal standard. 1 H and 13 C NMR spectra were recorded on a JEOL JNM-AL400 Spectrometer (400 MHz for 1 H and 100 MHz for 13 C) using CDCl 3 as the solvent and TMS as internal standard.…”

“…Furoquinoline scaffolds are one of the important heterocycles and their analogues are found not only in nature but also in pharmacological and biological materials, whose properties include anti‐inflammatory, TLR8 (Toll‐like receptor‐8) agonistic, anti‐cancerous, a protein inhibitory, and antimicrobial activity . Owing to their diverse biological activities, there have been great efforts to extract or synthesize furoquinolines, i.e ., [3 + 2] cyclization reaction for furo[2,3‐ b ]quinolines, [4 + 2] cycloaddition of imines with enol ethers, and a three component reaction of 4‐hydroxyquinolin‐2( 1H )‐one, aromatic aldehyde and isonitrile, and so on .…”