Antisalmonellal Activities of Extracts, Fractions, Compounds and Semi-synthetic Flavonoid Derivatives from <i>Tristemma hirtum</i> P. Beauv (Melastomataceae)

Abstract

The development and spread of resistance to currently available antibiotics is a major drawback in the treatment of microbial infections. Salmonellosis for example remains among the most common cause of morbidity and mortality in developing countries. This study aimed to evaluate the antisalmonellal potential of extracts, fractions, isolated compounds and semi-synthetic flavonoids from Tristemma hirtum P. Beauv. Bioguided fractionation by column chromatography of the EtOAc and n-BuOH fractions led to the isolation of eleven compounds including two new esterified glucuronide flavonoids namely: luteolin-3′-O-β-D-glucuronopyranosylbutyl ester (1), a mixture of compound 1 and quercetin-3-O-β-D-glucuronopyranosylbutyl ester (2). Chemical transformation mainly based on the prenylation of 6-hydroxyapigenin-7-O-β-D-glucopyranoside (5) afforded four new semi-synthetic flavonoid derivatives namely: 6, 4'-O-diprenylapigenin-7-O-β-D-glucopyranoside (5a), 8-Cprenyl-6, 4'-O-diprenylapigenin-7-O-β-D-glucopyranoside (5b), 8-C-prenyl-4'-O-prenylapigenin-7-O-β-D-glucopyranoside (5c), 4'-O-prenylapigenin-7-O-β-D-glucopyranoside (5d). The chemical structures of these compounds were assigned using NMR techniques, mass spectrometry and by comparison of their data with reported ones. The antisalmonellal activity was assessed by determining the Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) using serial microdilution methods. The results showed that the MeOH extract and EtOAc fraction were active against all the bacteria tested with MICs ranging from 24 to 1536 µg/mL. Seven isolated compounds and three semi-synthetic compounds tested showed MIC values ranging from 16 to 256 µg/mL. Compounds 1, 3, 5a, 5c and 11 displayed the most potent antisalmonellal properties but were generally less potent than those of reference drugs. The activity of extracts and isolated compounds could be used as the starting point for the development of alternative phytodrugs against salmonellosis.

Phytochemical Analysis, Antifungal, and Antioxidant Properties of Two Herbs (Tristemma mauritianum and Crassocephalum bougheyanum) and One Tree (Lavigeria macrocarpa) Species

“…The results of this work indicate that all the studied plant extracts contain steroids and phenols such as flavonoids and tannins. In comparison to our results, bioguided fractionation of the MeOH extract of T. mauritianum aerial parts led to the identification of luteolin-3′-O- β -D-glucuronopyranosyl butyl ester, quercetin-3-O- β -D-glucuronopyranosyl butyl ester, arjunolic acid-28- β -D-glucopyranosyl ester (Arjunglucoside II), asiatic acid-28- β -D-glucopyranosyl ester (Quadranoside IV), β -sitosterol, oleanolic acid, ellagic acid, casuarinine, luteolin, pterocaryanin C, quercetin-3-O- β -D-glucopyranoside, and 6-hydroxyapigenin-7-O- β -D-glucopyranoside [ 39 ]. Other study has found that T. mauritianum extract possesses significant quantities of phenols and flavonoids [ 25 ].…”