Lupeol acetate as a potent antifungal compound against opportunistic human and phytopathogenic mold Macrophomina phaseolina

Abstract

Antifungal activity of Monothecabuxifolia methanolic extract and its various fractions were assessed against Macrophominaphaseolina, a soil-borne fungal pathogen of more than 500 vegetal species as well as rare and emerging opportunistic human pathogen. Different concentrations of methanolic extract (3.125 to 200 mg mL−1) inhibited fungal biomass by 39–45%. Isolated n-hexane, chloroform and ethyl acetate fractions suppressed fungal biomass by 32–52%, 29–50% and 29–35%, respectively. Triterpenes lupeol and lupeol acetate (1, 2) were isolated from n-hexane while betulin, β-sitosterol, β-amyrin, oleanolic acid (3–6) were isolated from chloroform fraction. Vanillic acid, protocatechuic acid, kaempferol and quercetin (7–10) were isolated from the ethyl acetate fraction and identified using various spectroscopic techniques namely mass spectroscopy and NMR. Antifungal activity of different concentrations (0.0312 to 2 mg mL−1) of the isolated compounds was evaluated and compared with the activity of a broad spectrum fungicide mancozeb. Different concentrations of mencozeb reduced fungal biomass by 83–85%. Among the isolated compounds lupeol acetate (2) was found the highest antifungal against M.phaseolina followed by betulin (3), vanillic acid (7), protocatechuic acid (8), β-amyrin (5) and oleanolic acid (6) resulting in 79–81%, 77–79%, 74–79%, 67–72%, 68–71% and 68–71%, respectively. Rest of the compounds also showed considerable antifungal activity and reduced M.phaseolina biomass by 41–64%.

Chemical Composition of Reichardia tingitana Methanolic Extract and Its Potential Antioxidant, Antimicrobial, Cytotoxic and Larvicidal Activity

“…Recent studies have focused on the identification of active chemical components, as well as the biological applications of extracted plants [ 11 , 12 ]. Tumors, hepatic illnesses, poor digestion, constipation, calculi, heart issues, pains, spleen disorders, and hiccough are just a few of the afflictions that the whole plant can help with [ 13 , 14 ].…”

Characterization of a Pentacyclic Triterpene Acetyltransferase Involved in the Biosynthesis of Taraxasterol and ψ-Taraxasterol Acetates in Lettuce

“…GC/MS analysis of leaf extracts of four lettuce cultivars revealed the accumulation of various types of pentacyclic triterpene acetates in leaves and these triterpene acetates as major constituents. Triterpene acetates showed higher antifungal and antibacterial activities than free triterpenes (do Nascimento et al, 2014;Javed et al, 2021). Thus, triterpene acetylation from free-triterpenes in plants may be an important biological defense mechanism against microorganisms.…”

“…Acylated triterpenes esterified by acetic acid and fatty acids are very common in many plant species (Warnaar, 1987;Catharina et al, 2013;Hill and Connolly, 2017;Choi et al, 2020). Triterpene acetates showed higher antifungal and antibacterial activities than free triterpenes (do Nascimento et al, 2014;Javed et al, 2021). Triterpene acetates are found in the soil of plant vegetation and can be used as potential chemotaxonomic markers of Asteraceae to track past vegetation changes (Lavrieux et al, 2011;Nakamura, 2019).…”

<em></em><em>Artocarpus Camansi</em> Blanco: A Review on Its Traditional Use, Nutritional Value, Phytochemistry, and Pharmacology

“…Additionally, this plant constituent reported several pharmacologic activity: antibacterial, anxiolytic, anticonvulsant, anti-inflammatory, anti-angiogenic, and immune-modulating activity [41,42] Lupeol acetate is a pentacyclic triterpene or a lupeol molecule having the oxygen at carbon-3 acetylated. This compound offers various pharmacologic activities: antifungal, antifertility, anti-inflammatory, enzyme inhibition activities (𝛂𝛂-amylase and tyrosine phosphatase 1B), and antimalarial activities [43][44][45][46][47].…”