β-Sitosterol from Piper crocatum: A Dual-Action Antifungal and Antibacterial Agent for Oral Infections
DOI:
https://doi.org/10.48048/tis.2025.10420Keywords:
β-sitosterol, Phytosterol, Piper crocatum, Bioactivity-guided, Antimicrobial, β-sitosterol, Phytosterol, Piper crocatum, Bioactivity-guided, Antibacterial, AntifungalAbstract
The high prevalence of antibiotic resistance and oral health problems has sparked research into the development of new antimicrobial medications. The habit of chewing Piper crocatum leaves among Asians has driven this research, leading to the isolation of a bioactive compound. From the methanol extract, the compound -sitosterol, a phytosterol, was isolated for the 1st time from this leaf, this compound has broad medicinal properties, including antifungal and antibacterial effects. The structure of the -sitosterol compound was validated by 1H-NMR, 13C-NMR, IR and MS spectroscopy. Using the broth dilution method, we determined the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of β-sitosterol against the oral pathogens Streptococcus mutans, Streptococcus sanguinis, and Candida albicans. The MIC values were 312.5 ± 0.16 µg/mL for S. mutans, 625 ± 0.11 µg/mL for S. sanguinis, and 625 ± 0.15 µg/mL for C. albicans, respectively. To support these data, we also predicted the potential of the compounds as specific enzyme inhibitors and their absorption, distribution, metabolism, excretion and toxicity (ADMET) properties of the compound and their derivatives by in silico. This study revealed that the derivative β-sitosterol-3-O- -d-glucoside is the most potent as inhibitor of GbpC and SrtC, as antibacterial properties, and is an antifungal agent against Sap5 and CYP51. By preventing the formation of harmful oral bacteria and fungi, the -sitosterol found in P. crocatum leaves and their derivatives can therefore potentially function as an antibacterial agent.The high prevalence of antibiotic resistance and oral health problems has sparked research into the development of new antimicrobial medications. The habit of chewing Piper crocatum leaves among Asians has driven this research, leading to the isolation of a bioactive compound. From the methanol extract, the compound -sitosterol, a phytosterol, was isolated for the 1st time from this leaf, this compound has broad medicinal properties, including antifungal and antibacterial effects. The structure of the -sitosterol compound was validated by 1H-NMR, 13C-NMR, IR and MS spectroscopy. Using the broth dilution method, we determined the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of β-sitosterol against the oral pathogens Streptococcus mutans, Streptococcus sanguinis, and Candida albicans. The MIC values were 312.5 ± 0.16 µg/mL for S. mutans, 625 ± 0.11 µg/mL for S. sanguinis, and 625 ± 0.15 µg/mL for C. albicans, respectively. To support these data, we also predicted the potential of the compounds as specific enzyme inhibitors and their absorption, distribution, metabolism, excretion and toxicity (ADMET) properties of the compound and their derivatives by in silico. This study revealed that the derivative β-sitosterol-3-O- -d-glucoside is the most potent as inhibitor of GbpC and SrtC, as antibacterial properties, and is an antifungal agent against Sap5 and CYP51. By preventing the formation of harmful oral bacteria and fungi, the -sitosterol found in P. crocatum leaves and their derivatives can therefore potentially function as an antibacterial agent.
HIGHLIGHTS
- β-sitosterol, a bioactive phytosterol with therapeutic potential, was successfully isolated from the methanol extract of P. crocatum leaves for the 1st time.
- β-sitosterol has significant activity against Streptococcus mutans, Streptococcus sanguinis, and Candida albicans, with low MIC values indicating strong inhibitory potential.
- Molecular docking revealed that β-sitosterol targets key bacterial and fungal enzymes (GbpC, SrtC, Sap5, and CYP51), supporting its role as a dual-action antimicrobial agent.
- β-Sitosterol-3-O-β-D-glucoside exhibits strong and stable binding to CYP51, as evidenced by consistently low RMSD values, favorable MM/GBSA binding energies, and minimal structural fluctuations observed via molecular dynamics (MD) simulations.
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