A new phenolic glycoside from the leaves of Flacourtia flavescens Willd

• Published in: Natural product research 2024-08, Vol.38 (16), p.2737-2747
• Main Authors: Ngnokam Jouogo, Darille Claudia, Eckhardt, Paul, Tamokou, Jean-De-Dieu, Matsuete Takongmo, Germaine, Voutquenne-Nazabadioko, Laurence, Opatz, Till, Tapondjou, Léon Azefack, Ngnokam, David, Teponno, Rémy Bertrand
• Format: Article
• Language: English
• Subjects: Acetic acid; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; Antibacterial activity; Caffeic acid; E coli; Flacourtia; Flacourtia flavescens; Flacourtiaceae; Glucosides - chemistry; Glucosides - isolation & purification; Glucosides - pharmacology; Glycosides; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - pharmacology; Kaempferol; L-Rhamnopyranoside; Magnetic Resonance Spectroscopy; Mass spectrometry; Mass spectroscopy; Metabolites; Microbial Sensitivity Tests; Minimum inhibitory concentration; Molecular Structure; NMR; Nuclear magnetic resonance; phenolic glucoside; Phenols; Phenols - chemistry; Phenols - isolation & purification; Phenols - pharmacology; Plant Extracts - chemistry; Plant Extracts - pharmacology; Plant Leaves - chemistry; Quercetin; Secondary metabolites; Two dimensional analysis
• ISSN: 1478-6419; 1478-6427; 1478-6427
• DOI: 10.1080/14786419.2023.2232078

Chemical study of the methanol extract from the leaves of Flacourtia flavescens led to the isolation of a new phenolic glucoside (1) along with fifteen known secondary metabolites namely shanzhiside methyl ester (2), aurantiamide acetate (3), caffeic acid methyl ester (4), caffeic acid (5), apigenin (6), luteolin (7), kaempferol (8), quercetin (9), gyrophoric acid (10), luteolin-7-O-β-D-glucopyranoside (11), luteolin-4'-O-β-D-glucopyranoside (12), kaempferol-7-O-α-L-rhamnopyranoside (13), kaempferol-3-O-β-D-glucopyranosyl-(1 → 6)-O-α-L-rhamnopyranoside (14), kaempferol-3,7-O-α-L-dirhamnopyranoside (15) and (2S,3S,4R,8E)-2-((2′R)-2′-hydroxy-octadecanoylamino)-lignocerane-1,3,4-triol-8-ene (16). Their structures were elucidated by 1D and 2D NMR analysis and mass spectrometry. The extracts and the isolated compounds were evaluated for their antibacterial activities. The EtOAc extract was highly active (MIC = 32 and 64 µg/mL) against E. coli and E. faecalis, respectively. Compounds 1, 2, 2b, 5, 8, 9, and 12 (MIC = 16-32 µg/mL) were moderately active against some tested bacteria.