Oleanane-type saponins from Lysimachia laxa Baudo and their anti-bacterial activities.

Seven new oleanane-type triterpene saponins, lysimaponins A-G, were isolated from aerial parts of Lysimachia laxa Baudo. Their chemical structures have been elucidated by analysis of spectroscopic and chemical methods. All compounds were evaluated for their anti-bacterial effects against Microcystis aeruginosa, Vibrio parahaemolyticus, V. harveyi, V. vulinificus, V. cholerae, and V. alginolyticus. All compounds showed potent anti-bacterial activities against the cyanobacteria M. aeruginosa with IC50 values ranging from 14.4 ± 1.2 to 35.3 ± 2.2 µg/mL. Compounds 1, 2, 4-7 inhibited V. parahaemolyticus with MIC values ranging from 64 to 256 µg/mL. The results suggested that saponins from L. laxa could be potential anti-cyanobacteria agents.

Atractylodes macrocephala Rhizomes Contain Anti-inflammatory Sesquiterpenes.

Two new compounds, named eudesm-4(15),7-diene-3α,9ß,11-triol (1) and eudesm-4(15),7-diene-1ß,3α,9ß,11-tetraol (2) together with three known sesquiterpene lactones (1S,5R,7R,10R)-secoatractylolactone (3), (1S,5R,7R,10R)-secoatractylolactone-11-O-ß-D-glucopyranoside (4) atractylenolide III (5) were isolated from the rhizomes of Atractylodes macrocephala. Their structures were elucidated by using one-dimensional (1D) and 2D-NMR spectra and high resolution electrospray ionization (HR-ESI)-MS data. Compound 5 exhibited the most active anti-inflammatory activity with IC50 values of 27.5 µM in inhibiting of nitric oxide production. Compounds 1, 2, and 3 showed moderate effects while compound 4 was inactive.

Penicillium digitatum as a Model Fungus for Detecting Antifungal Activity of Botanicals: An Evaluation on Vietnamese Medicinal Plant Extracts.

Medicinal plants play important roles in traditional medicine, and numerous compounds among them have been recognized for their antimicrobial activity. However, little is known about the potential of Vietnamese medicinal plants for antifungal activity. In this study, we examined the antagonistic activity of twelve medicinal plant species collected in Northern Vietnam against Penicillium digitatum, Aspergillus flavus, Aspergillus fumigatus, and Candida albicans. The results showed that the antifungal activities of the crude extracts from Mahonia bealei, Ficus semicordata, and Gnetum montanum were clearly detected with the citrus postharvest pathogen P. digitatum. These extracts could fully inhibit the growth of P. digitatum on the agar medium, and on the infected citrus fruits at concentrations of 300-1000 µg/mL. Meanwhile, the other tested fungi were less sensitive to the antagonistic activity of the plant extracts. In particular, we found that the ethanolic extract of M. bealei displayed a broad-spectrum antifungal activity against all four pathogenic fungi. Analysis of this crude extract by enrichment coupled with high-performance liquid chromatography revealed that berberine and palmatine are major metabolites. Additional inspections indicated berberine as the key compound responsible for the antifungal activity of the M. bealei ethanolic extract. Our study provides a better understanding of the potential of Vietnamese medicinal plant resources for combating fungal pathogens. This work also highlights that the citrus pathogen P. digitatum can be employed as a model fungus for screening the antifungal activity of botanicals.

Metabolomics Approach for Discrimination and Quality Control of Natural and Commercial Fallopia multiflora Products in Vietnam.

A precise HPLC-DAD-based quantification together with the metabolomics statistical method was developed to distinguish and control the quality of Fallopia multiflora, a popular medicinal material in Vietnam. Multivariate statistical methods such as hierarchical clustering analysis and principal component analysis were utilized to compare and discriminate six natural and twelve commercial samples. 2,3,4',5-Tetrahydroxystilbene 2-O-ß-D-glucopyranoside (THSG) (1), emodin (4), and the new compound 6-hydroxymusizin 8-O-α-D-apiofuranosyl-(1⟶6)-ß-D-glucopyranoside (5) could be considered as important markers for classification of F. multiflora. Furthermore, seven phenolics were quantified that the variation in the contents of selected metabolites revealed the differences in the quality of natural and commercial samples. Recovery of the compounds from the analytes was more than 98%, while the limits of detection (LOD) and the limits of quantitation (LOQ) ranged from 0.5 to 6.6 µg/ml and 1.5 to 19.8 µg/ml, respectively. The linearity, LOD, LOQ, precision, and accuracy satisfied the criteria FDA guidance on bioanalytical methods. Overall, this method is a promising tool for discrimination and quality assurance of F. multiflora products.

4'­O­Methylalpinumisoflavone inhibits the activation of monocytes/macrophages to an immunostimulatory phenotype induced by 27­hydroxycholesterol.

The epidemiological, animal and cell effects of plant metabolites suggest versatile health benefits of flavonoids. However, whether flavonoids affect the deleterious biological activity of oxygenated cholesterol molecules remains to be elucidated. The present study investigated the effects of 4'­O­methylalpinumisoflavone (mAI) isolated from Maclura tricuspidata (Cudrania tricuspidata) on the 27­hydroxycholesterol (27OHChol)­induced activation of monocytes/macrophages using human THP­1 cells. mAI dose­dependently impaired the expression of C­C motif chemokine ligand (CCL)2 chemokine and the migration of monocytic cells enhanced by 27OHChol. mAI downregulated the surface and cellular levels of CD14 and inhibited the release of soluble CD14. This isoflavone significantly weakened the lipopolysaccharide responses that were enhanced in the presence of 27OHChol, and inhibited the transcription and secretion of the active gene product of matrix metalloproteinase­9. mAI also suppressed the expression of C­C motif chemokine receptor 5 ligands, including CL3 and CCL4, and M1­phenotype markers induced by 27OHChol. Furthermore, mAI impaired phosphorylation of the nuclear factor­κB p65 subunit without affecting the phosphorylation of Akt. These results indicate that mAI inhibits the activation of monocytes/macrophages to the immunostimulatory phenotype in a milieu rich in 27OHChol, suggesting potential benefits of the flavonoid for the treatment of diseases in which the pathogenesis is linked to 27OHChol­induced inflammatory responses.