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Bioassay-Guided Fractionation with Antimalarial and Antimicrobial Activities of Paeonia officinalis.

ABSTRACT: Bioassay-guided fractionation technique of roots of Paeonia officinalis led to isolation and structure elucidation of seven known compounds, including four monoterpene glycosides: lactiflorin (1), paeoniflorin (4), galloyl paeoniflorin (5), and (Z)-(1S,5R)-β-pinen-10-yl β-vicianoside (7); two phenolics: benzoic acid (2) and methyl gallate (3); and one sterol glycoside: β-sitosterol 3-O-β-D-glucopyranoside (6). The different fractions and the isolated compounds were evaluated for their antimicrobial and antimalarial activities. Fraction II and III showed antifungal activity against Candida neoformans with IC₅₀ values of 28.11 and 74.37 µg/mL, respectively, compared with the standard fluconazole (IC₅₀ = 4.68 µg/mL), and antibacterial potential against Pseudomonas aeruginosa (IC₅₀ = 20.27 and 24.82 µg/mL, respectively) and Klebsiella pneumoniae (IC₅₀ = 43.21 and 94.4 µg/mL, respectively), compared with the standard meropenem (IC₅₀ = 28.67 and 43.94 µg/mL, respectively). Compounds 3 and 5 showed antimalarial activity against Plasmodium falciparum D6 with IC₅₀ values of 1.57 and 4.72 µg/mL and P. falciparum W2 with IC₅₀ values of 0.61 and 2.91 µg/mL, respectively, compared with the standard chloroquine (IC₅₀ = 0.026 and 0.14 µg/mL, respectively).

SUBMITTER: Samy MN

PROVIDER: S-EPMC9739537 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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Bioassay-Guided Fractionation with Antimalarial and Antimicrobial Activities of Paeonia officinalis.

Samy Mamdouh Nabil MN Mahmoud Basma Khalaf BK Shady Nourhan Hisham NH Abdelmohsen Usama Ramadan UR Ross Samir Anis SA

Molecules (Basel, Switzerland) 20221201 23

Bioassay-guided fractionation technique of roots of Paeonia officinalis led to isolation and structure elucidation of seven known compounds, including four monoterpene glycosides: lactiflorin (1), paeoniflorin (4), galloyl paeoniflorin (5), and (Z)-(1S,5R)-β-pinen-10-yl β-vicianoside (7); two phenolics: benzoic acid (2) and methyl gallate (3); and one sterol glycoside: β-sitosterol 3-O-β-D-gl ...[more]

PMID: 36500473

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Project description:Natural products have been a primary source of medicines throughout the history of human existence. It is estimated that close to 70 % of small molecule pharmaceuticals on the market are derived from natural products. With increasing antibiotic resistance, natural products remain an important source for the discovery of novel antimicrobial compounds. The plant rosemary (Rosmarinus officinalis), has been widely and commonly used as a food preservative due to its antimicrobial potential. To evaluate the antimicrobial profile of this plant, we used bioassay-guided fractionation and bioinformatics approaches. Through bioassay-guided fractionation, we tested in vitro activities of a R. officinalis extract and fractions thereof, as well as pure compounds micromeric acid (1), oleanolic acid (2), and ursolic acid (3) against methicillin-resistant Staphylococcus aureus (MRSA). Compounds 1 and 3 showed complete inhibition of MRSA (with MIC values of 32 μg/mL and 8 μg/mL, respectively) while compound 2 displayed only partial inhibition (MIC > 64 μg/mL). In addition, we utilized orthogonal partial least square-discriminant analysis (OPLS-DA) and selectivity ratio (SR) analysis to correlate the isolated compounds 1-3 with the observed antimicrobial activity, as well as to identify antimicrobials present in trace quantities. For mass spectrometry (MS) data collected in the negative ionization mode, compound 1 was the most positively correlated with activity, while for MS data collected in the positive ion mode, compounds 2-3 had the highest positive correlation. Using the bioinformatics approaches, we highlighted additional antimicrobials associated with the antimicrobial activity of R. officinalis, including genkwanin (4), rosmadial (5a) and/or 16-hydroxyrosmadial (5b), rosmanol (6), and hesperetin (7). Compounds 1-3 resulting from the bioassay-guided fractionation were identified by MS-MS fragmentation patterns and 1H NMR spectra. Among the compounds highlighted by the biochemical analysis, compound 6 was identified by comparison with its commercial standard by employed ultra-performance liquid chromatography-high resolution mass spectrometry (UHPLC-HRMS), while 4, 5a-b and 7 were putatively identified based on MS data and in comparison with the literature. This is the first reported antimicrobial activity of micromeric acid (1) against MRSA.

Dataset Information

Bioassay-Guided Fractionation with Antimalarial and Antimicrobial Activities of Paeonia officinalis.

Publications

Bioassay-Guided Fractionation with Antimalarial and Antimicrobial Activities of <i>Paeonia officinalis</i>.

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