A New Chalcone and Antimicrobial Chemical Constituents of Dracaena stedneuri

Abstract

Microbial infections are leading causes of death and morbidity all over the world due to the development of the resistance to antibiotics by certain microorganisms. In this study, the chemical exploration of the ethanol (EtOH) extract of the aerial part of Dracaena stedneuri (Dracaenaceae) led to the isolation of one previously unreported chalcone derivative, i.e., 2′,4′-dihydroxy-2,3′-dimethoxychalcone (1), together with 12 known compounds: 8-(C)-methylquercetagetin-3,6,3′-trimethyl ether (2), methylgalangine (3), quercetin (4), kaempferol (5), 6,8-dimethylchrysin (6), ombuine-3-O-rutinoside (4ʹ,7-dimethylquercetin-3-O-α-L-rhamnopyranosyl-(1 → 6) -β-D-glucopyranoside) (7), alliospiroside A (8), β-sitosterol 3-O-glucopyranoside (9), ishigoside (10), betulinic acid (11), oleanolic acid (12), and lupeol (13). The structures were determined by spectroscopic and spectrometric analysis including 1- and 2-Dimensional Nuclear Magnetic Resonance (1D- and 2D-NMR), High-Resolution Electrospray Ionization Mass Spectrometry (HRESIMS), and comparison with literature data. The isolated secondary metabolites and crude extract displayed antibacterial activity against some multidrug-resistant strains with minimal inhibitory concentration (MIC) values ranging from 32 to 256 μg/mL. The antibacterial activity of compound 13 against Enterobacter aerogenes ATCC13048 (MIC value: 32 μg/mL) was higher than that of chloramphenicol used as the reference drug (MIC = 64 μg/mL).

Medicinal Properties of Anchusa strigosa and Its Active Compounds

“…We demonstrated that several flavonoids of Anchusa strigosa were effective against drug-resistant microorganisms ( Figure 2 ). The antibacterial activity of kaempferol against drug-resistant Staphylococcus aureus was reported [ 34 ], but no information is available on the antibacterial activity of kaempferol 3- O -β-rhamnopyranosyl(1→6)-β-glucopyranoside and kaempferol 3- O -α-rhamnopyranosyl(1→6)-β-galactopyranoside. Although the mode of action of some antibacterial flavonoids was partially revealed [ 35 ], the mechanism of action of kaempferol and its glycoside derivatives should be investigated in the future.…”

Chemical Constituents of Macaranga occidentalis, Antimicrobial and Chemophenetic Studies

“…We herein present the first isolation of ishigoside (17) in the Euphorbiaceae. This compound, which was isolated for the first time from the brown alga Ishige okamurae (Ishigeaceae) [25], was recently isolated from the terrestrial plant Dracaena stedneuri (Dracaenaceae) [41], thus, its presence in M. occidentalis is not surprising. Being cognizant of the fact that prenylated flavonoids and stilbenes constitute the chemotaxonomic markers of the Macaranga genus [5], these chemical findings confirm the botanical identification of M. occidentalis and further indicate a close relationship with other species of this genus.…”

Chalcone: A Promising Bioactive Scaffold in Medicinal Chemistry

“…Pathogens becoming more resistant to antibiotics have caused the effectiveness of current antibiotics to decline. Both natural and artificial chalcones have demonstrated activity against some Gram-positive and Gram-negative strains [ 137 , 138 ]. Biofouling is one of the significant problems in marine-based product development.…”