Cytotoxic and Antibacterial Evaluation of Coumarins and Chromanone Acid from Calophyllum symingtonianum.

Calophyllum symingtonianum is a rare species from the Calophyllum genus that belongs to the Guttiferae family. Calophyllum has been recognized as a potential medicinal plant due to its many bioactive phytochemicals especially coumarins and chromanone acids. In this study, the cytotoxic activities against MCF-7 and A-549 and antibacterial activities towards S. aureus, B. subtilis, P. aeruginosa and E. Coli of three coumarins known as inophyllum D, inophyllum H and calanone as well as chromanone acid identified as isocordato-oblongic acid isolated from this plant were evaluated. Inophyllum H exhibited the highest IC50 values against MCF-7 at 25.56 μg/mL and A-549 at 26.41μg/mL. Isocordato-oblongic acid showed moderate antibacterial activity against S. aureus and B. subtilis at 125μg/mL and 62.5μg/mL, respectively. This study suggests C. symingtonianum as a potential plant for cytotoxic and antibacterial phytochemicals.

Antibacterial properties of Persicaria minor (Huds.) ethanolic and aqueous-ethanolic leaf extracts.

Persicaria minor known as small water-pepper is used traditionally for the treatment of dandruffs and stomach indigestion. Therefore, this study was designed to evaluate the antibacterial activity of plant leaf material. 30% aqueous-ethanol and 100% aqueous were used for solvent extraction. Both extracts were evaluated for total protein and polysaccharide contents and results were compared. The extracts were then tested against four strains of bacteria; Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 11229, Staphylococcus aureus ATCC 6538and Pseudomonas aeruginosa ATCC 1544,at different concentrations using disc-diffusion and microplate dilution assays with penicillin being used as a positive control standard. Both extracts showed antibacterial activity against S. aureus, E. faecalis, and E. coli, respectively with aqueous-ethanolic extract being more potent. However, none of the extracts were active against P. aeruginosa. Results from this study truly illustrated high potential of P. minor leaves to be used topically as antibacterial agent for controlling of tested colony.

Antioxidant and tyrosinase inhibition activities of α- mangostin and Garcinia mangostana Linn. pericarp extracts.

The methanol, ethyl acetate and petroleum ether crude extracts of mangosteen pericarp and α- mangostin were evaluated for the antioxidant capacity and tyrosinase inhibition properties. The ferric reducing antioxidant power (FRAP) assay was used to investigate their antioxidant capacity. Tyrosinase inhibition effect was evaluated using mushroom tyrosinase inhibition assay. Methanol extract has higher antioxidant reducing capacity (m= 1.621), compared to the rest of the extracts. Meanwhile, ethyl acetate extract and α- mangostin showed potent tyrosinase inhibition activities as compared to Kojic acid, a well- known tyrosinase inhibitor. It is observed that tyrosinase inhibition effect is antioxidant independent as ethyl acetate extract possessed low antioxidant capacity. This study suggests direct tyrosinase inhibition by ethyl acetate extract of Garcinia mangostana.

Antioxidant and tyrosinase inhibition activities of Eurycoma longifolia and Swietenia macrophylla.

Extract from plants have been reported to contain valuable bioactive compounds that have potential in promoting antioxidant activity. The present study was aimed to investigate the extracts of two plants available in Southeast Asia, Eurycoma longifolia and Swietenia macrophylla for their primary metabolite contents, phenolic contents, antioxidant and anti- tyrosinase activity. Two types of solvents were utilised in the extraction process of both plants. Ethyl acetate found to be a better solvent for isolation of primary metabolite compound compared to methanol. For Folin-Ciocalteu assay, methanol extract of Swietenia macrophylla possed higher phenolic content while for Eurycoma longifolia, ethyl acetate extract had higher phenolic content. In DPPH assay, the radical scavenging activity of extracts were strongly correlated to the total phenolic content based on the percentage of DPPH radical scavenging of each extracts (p<0.05). In tyrosinase inhibition assay, the activity of each extracts were very low compared to standard Kojic acid. It was assumed that, the ability of plant extracts to inhibit tyrosinase are partly contributed by antioxidant potential of the extracts (p<0.01).

Chemical constituents from Piper caninum and antibacterial activity.

Six flavonoids and two amides, characterized as 5,7-dimethoxyflavanone (1), 5,7-dimethoxyflavone (2), 4’,5,7- trimethoxyflavone (3), 4’-hydroxy-5,7-dimethoxyflavone (4), 5-hydroxy-7-methoxyflavone (5), 2’-hydroxy- 4’,6’-dimethoxychalcone (6), N-isobutyl-(2E,4E,14Z)-eicosatrienamide (7) and N-isobutyl-15-(3’,4’- methylenedioxyphenyl)-2E,4E,12E-pentadecatrienamide (8) have been isolated and identified from the stem of Piper caninum. The identification of all compounds was achieved by physical properties and spectroscopically. These data were also confirmed by comparison with previously reported spectral data. Antibacterial activity of the extracts and isolated compounds was determined by disc diffusion method and minimum inhibitory concentration (MIC). All of the extracts displayed weak antibacterial activity against the tested bacteria. Compound (7) showed good activity towards Bacillis subtilis with MIC value of 125 μg/mL. Flavonoid compounds with high content in P. caninum can probably be used as a chemical marker for this Piper species.

Cytotoxic tirucallane triterpenes from the stem of Luvunga scandens

Two tirucallane triterpenes, namely flindissol (1) and 3-oxotirucalla-7,24-dien-21-oic-acid (2), were isolated from the dichloromethane extract of the stem of Luvunga scandens (Roxb.) Buch-Ham ex Wight & Arn, Rutaceae. This is the first report of their isolation from this plant. Their structures were constructed by high resolution mass and 2D NMR spectroscopic data. The cytotoxic potential of the two pure compounds 1 and 2 were determined by MTT assay against human breast adenocarcinoma cell line (MCF-7). Compounds 1 and 2 showed potent cytotoxicity against MCF-7 cell line with IC50 values of 13.8 μM and 27.5 μM, respectively. This result suggested their potential activity as antitumor agents.

Chemical composition of Piper stylosum Miq. and Piper ribesioides Wall.essential oils, and their antioxidant, antimicrobial and tyrosinaseinhibition activities / Composición química de los aceites esenciales de Piper stylosum Miq. y Piper ribosoides Wall. y sus actividadesantioxidantes, antimicrobiana y de inhibición de la tirosinasa

Chemical compositions of P. stylosum and P. ribesioides essential oils, and their antioxidant, antimicrobial and tyrosinase inhibition activities were determined. GC and GC–MS analysis of essential oils from leaves and stems of P. stylosum resulted in the identification of 50 (89.2 percent) and 45 (88.8 percent) components, respectively. The major components were aromadendrene (leaves 26.6 percent; stems 18.8 percent), sabinene (leaves 13.8 percent; stems 6.7 percent) and beta-caryophyllene (leaves 11.5 percent; stems 17.9 percent). A total of 60 (87.0 percent) and 39 (82.9 percent) components were identified from leaves and stems of P. ribesioides, respectively. The most abundant components were beta-caryophyllene (leaves 20.0 percent; stems 14.4 percent), camphene (leaves 16.3 percent; stems 12.3 percent) and delta-cadinene (leaves 4.4 percent; stems 7.8 percent). Antioxidant activity using DPPH and total phenolic content were tested for essential oils. However, the essential oils showed low antioxidant activity and phenolic content, compared to BHT. Studies of tyrosinase inhibition showed that the essential oils of P. ribesioides leaves had the highest inhibition (30.0 percent), although were lower than the control (kojic acid 81.8 percent). The evaluation of antimicrobial activities revealed that P. ribesioides essential oils showed strong activity against Bacillus cereus and Staphylococcus aureus, both with MIC value 62.5 micrograms/mL.

Se determinaron las composiciones químicas, las actividades antioxidante y antimicrobiana, y el contenido total de fenoles de los aceites esenciales de P. stylosum y P. ribesioides. El análisis GC y GC-MS de los aceites esenciaales de hojas y tallos de P. stylosum permitió la identificación de 50 (89.2 por ciento) y 45 (88.8 por ciento) de components, respectivamente. Los principales componentes fueron aromadendreno (hojas 26.6 por ciento; tallos 18.8 por ciento), sabineno (hojas 13.8 por ciento; tallos 6.7 por ciento) y beta-cariofileno (hoja 11.5 por ciento; tallo 17.9 por ciento). Se identificaron 60 (87.0 por ciento) y 39 (82.9 por ciento) components en los aceites esenciales de hojas y tallos de P. ribesioides. Los componentes más abundantes fueron beta-cariofileno (hojas 20.0 por ciento; tallos 14.4 por ciento), canfeno (hojas 16.3 por ciento; tallos 12.3 por ciento) y delta-cadineno (hojas 4.4 por ciento; tallos 7.8 por ciento). Los aceites esenciales se ensayaron para determinar sus actividades antioxidantes con DPPH y el contenido de fenoles totales. Para los aceites esenciales obtenidos se determinaron valores bajos en la actividad antioxidante con DPPH y el contenido total de fenoles, en comparación con BHT. Sin embargo, los ensayos de inhibición de tirosinasa most raron que el aceite esencial de las hojas de P. ribesioides presento la mayor inhibición (30.0 por ciento), aunque mas baja que el compuesto control (Àcido Kójico, 81.8 por ciento). Para el aceite esencial de P. ribesioides se determinó una MIC 62.5 mg/mL contra Bacillus cereus y Staphylococcus aureus.

Antioxidant and Anti-tyrosinase Activities from Piper officinarum C.DC (Piperaceae).

The present study was carried out to evaluate antioxidant and anti-tyrosinase activities from Piper officinarum stems, as well as investigation of its chemical constituents. In a series of in vitro assays, antioxidant (DPPH radical scavenging and total phenolic content) and anti-tyrosinase (mushroom tyrosinase) activities of various extracts of stem were evaluated. The isolation and purification of the constituents were carried out on the extracts using various chromatographic methods and identified by direct comparison of their spectroscopic data with respective published data. The results showed that the methanol extracts showed the highest DPPH (80.0%) at 1 mg/ml, as well as total phenolic content (50.5%). Phytochemical analysis of the stem extracts have isolated five compounds identified as 4-allyl resorcinol (1), aristolactam AII (2) aristolactam BII (3), stigmast-4-en-3-one (4) and 6-hydroxystigmast-4-en-3-one (5). Compound (1), (2) and (3) showed significant activity towards DPPH radical scavenging (I%=17.3-28.1%), while (2), (3) and (4) demonstrated potent inhibitory effects against tyrosinase mushroom (I%=11.1-24.4%). The results showed that the stem extracts has significant antioxidant activity that may help to discover new chemical classes of natural antioxidant substances.