Antibacterial property of isoflavonoids isolated from Erythrina variegata against cariogenic oral bacteria.

The antibacterial property of 7 compounds, isolated from Erythrina variegata (Leguminosae) by repeated silica gel column chromatography, against cariogenic oral bacteria was investigated. Extensive spectroscopic study revealed that all were isoflavonoids. Among them, 3,9-dihydroxy-2,10-di(gamma,gamma-dimethylallyl)-6a,11a-dehydropterocarpan (erycristagallin) showed the highest antibacterial activity against mutans streptococci, other oral streptococci, Actinomyces and Lactobacillus species with a minimum inhibitory concentration (MIC) range of 1.56-6.25 microg/ml, followed by 3,6a-dihydroxy-9-methoxy-2,10-di(gamma,gamma-dimethylallyl)pterocarpan (erystagallinA) and 9-hydroxy-3-methoxy-2-gamma,gamma-dimethylallylpterocarpan (orientanol B) (MIC range: 3.13-12.5 microg/ml). The antibacterial effect of erycristagallin to mutans streptococci was based on a bactericidal action. Erycristagallin (6.25 microg/ml: MIC) completely inhibited incorporation of radio-labelled thymidine into Streptococcus mutans cells. Incorporation of radio-labelled glucose into bacterial cells was also strongly inhibited at MIC, and 1/2 MIC of the compound reduced the incorporation approximately by half. The findings indicate that erycristagallin has a potential as potent phytochemical agent for prevention of dental caries by inhibiting the growth of cariogenic bacteria and by interfering with incorporation of glucose responsible for production of organic acids.     

Erythrina poeppigiana-derived phytochemical exhibiting antimicrobial activity against Candida albicans and methicillin-resistant Staphylococcus aureus

AIMS: To screen five phytochemicals isolated from Erythrina poeppigiana (Leguminosae) for antimicrobial activity against both Candida albicans and methicillin-resistant Staphylococcus aureus (MRSA). METHODS AND RESULTS: Roots of E. poeppigiana were macerated with acetone and the chloroform-soluble fraction of the residue was subjected to repeated silica gel column chromatography using various eluting solvents. Structures of the isolated compounds were determined by extensive spectroscopic studies. Each compound was dissolved in dimethyl sulphoxide and added to agar plates (final concentration: 1.56-100 microg ml(-1)) and minimum inhibitory concentrations (MICs) against C. albicans and MRSA were determined. Spectral data indicated the presence of three different types of phytochemicals; isoflavonoids (erypoegin A, demethylmedicarpin and sandwicensin), alpha-methyldeoxybenzoin (angolensin) and cinnamylphenol (erypostyrene). While all compounds showed anti-MRSA activity in this concentration range, isoflavonoids and alpha-methyldeoxybenzoin failed to inhibit the growth of C. albicans. Erypostyrene (E-1-[2-hydroxy-4-methoxy-5-(gamma,gamma-dimethylallyl)benzyl]-2-(4-hydroxyphenyl)ethylene) exhibited not only the highest anti-MRSA activity (MIC value of 6.25 microg ml(-1)) but also anti-candidal potency (MIC value of 50 microg ml(-1)). The compound reduced viable cell numbers of C. albicans and MRSA by approximately 1 of 2000 and 1 of 1000 after 1 h incubation at each MIC, respectively. CONCLUSIONS: A new cinnamylphenol, erypostyrene, possessed anti-candidal and anti-MRSA activity. SIGNIFICANCE AND IMPACT OF THE STUDY: Erypostyrene could be a leading candidate for development of antimicrobial agents with anti-candidal and anti-MRSA activity.     

Different antibacterial actions of isoflavones isolated from Erythrina poeppigiana against methicillin-resistant Staphylococcus aureus

AIMS: To screen six isoflavones isolated from Erythrina poeppigiana (Leguminosae) for their antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). METHODS AND RESULTS: Stem bark of E. poeppigiana was macerated with acetone and the methylene chloride-soluble fraction of the residue was applied to repeated silica gel column chromatography and eluted. Minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) were determined by a broth dilution method. Inactive compounds that failed inhibiting bacterial growth at 25 microg ml(-1) were further investigated for their combination effects with methicillin and oxacillin. Of the isolated isoflavones, 5,7,4'-trihydroxy-8,3'-di(gamma,gamma-dimethylallyl)isoflavone (isolupalbigenin) exhibited the highest anti-MRSA activity (MICs: 1.56-3.13 microg ml(-1); MBCs: 6.25-12.5 microg ml(-1)), followed by 5,7,4'-trihydroxy-6-gamma,gamma-dimethylallylisoflavone (erythrinin B). Inactive compounds were combined with methicillin or oxacillin, 5,4'-dihydroxy-(3',4'-dihydro-3'-hydroxy)-2',2'-dimethylpyrano[5',6':6,7]isoflavone (M-Wi-2) intensifying the susceptibility of MRSA strains to these antibiotics. In all but one strain, the MIC values of methicillin were reduced from > or =100 to 6.25-12.5 microg ml(-1) in the presence of M-Wi-2 (25 microg ml(-1)). CONCLUSIONS: Isoflavones from E. poeppigiana showed two different antibacterial activities against MRSA: direct growth inhibition and intensification of methicillin sensitivity. SIGNIFICANCE AND IMPACT OF THE STUDY: Isolupalbigenin and M-Wi-2 could lead to the development of compounds for new approaches against MRSA infection.     

Antimicrobial activity of hydrophobic xanthones from Cudrania cochinchinensis against Bacillus subtilis and methicillin-resistant Staphylococcus aureus

Ten xanthones with one or two isoprenoid groups and a prenylated benzophenone isolated from roots of Cudrania cochinchinensis (Moraceae) were tested for their antimicrobial activities against Bacillus subtilis and methicillin-resistant Staphylococcus aureus (MRSA). Among these compounds, gerontoxanthone H exhibited considerable antibacterial activity against B. subtilis (MIC = 1.56 microg/ml). Four xanthones, gerontoxanthone I, toxyloxanthone C, cudraxanthone S, and 1,3,7-trihydroxy-2-prenylxanthone, showed weak antibacterial activity against the bacterium (MICs = 3.13-6.25 microg/ml). These compounds also exhibited similar MIC values against methicillin-sensitive S. aureus, MRSAs, and Micrococcus luteus.     

Antibacterial activity of plant extracts from northwestern Argentina

AIMS: To determine the antibacterial and cytotoxic activities of aqueous and ethanolic extracts of northwestern Argentinian plants used in folk medicine. To compare the mentioned activities with those of five commercial antibiotics. To identify the compounds responsible for the antibacterial activity. METHODS AND RESULTS: Plant extracts were prepared according to traditional uses in northwestern Argentina. Antibacterial activity was assayed by agar dilution in Petri dishes and broth dilution in 96-well plates. Lethal dose 50 (LD(50)) was determined by the Artemia salina assay. Phytochemical analysis was performed by sample adsorption on silica gel, thin-layer chromatography (TLC), bioautography and UV-visible spectra. The results showed that Tripodanthus acutifolius aqueous extracts have lower minimal inhibitory concentrations (MIC) (502 and 506 microg of extracted material (EM) per ml for infusion and decoction, respectively) than cefotaxim MIC (640 microg ml(-1)) against Acinetobacterfreundii (303). These data were lower than their LD(50). Tripodanthus acutifolius tincture showed lower MIC (110 microg of EM per ml) and minimal bactericidal concentration (MBC) (220 microg of EM per ml) than cefotaxim (MIC and MBC of 320 microg ml(-1)) for Pseudomonasaeruginosa. This extract also showed a MIC/MBC of 110/220 microg of EM per ml, lower than oxacillin (MIC/MBC of 160/220 microg ml(-1)) for Staphylococcus aureus (ATCC 25923). The cytotoxicity of all extracts were compared with that of commercial antibiotics. Rutin (3,3',4',5,7-pentahydroxyflavone 3-beta-rhamnosilglucoside), iso-quercitrin (3,3',4',5,7-pentahydroxyflavone 3-beta-glucoside) and a terpene would be partially responsible for the antibacterial activity of T. acutifolius infusion. CONCLUSIONS: Tripodanthus acutifolius extracts had the ability to inhibit bacterial growth. The antibacterial activity differs with the applied extractive method, and it could be partially attributed to glycoflavonoids. This paper contributes to the knowledge of antibacterial capacity of plants from northwestern Argentina. SIGNIFICANCE AND IMPACT OF THE STUDY: These antibacterial activities support further studies to discover new chemical structures that can contribute to alleviate or cure some illnesses.     

Three new constituents from the roots of Erythrina variegata and their antibacterial activity against methicillin-resistant Staphylococcus aureus

Two new isoflavonoids, eryvarins V and W (1 and 2, resp.), and a new chromen-4-one derivative, eryvarin X (3), along with three known isoflavonoids, 4-6, were isolated from the roots of Erythrina variegata. Their structures were established by spectroscopic analyses. Compound 1 is a rare naturally occurring isoflavanone which possesses a OH group at C(3). Among the new compounds 1-3, 2 exhibited a potent antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) strains.     

Antimicrobial and cytotoxic activities of neolignans from Magnolia officinalis

In the light of the steady increase of infections related to vancomycin-resistant enterococci (VRE) and methicillin-resistant Staphylococcus aureus (MRSA), the medicinal plant Magnolia officinalis was subjected to bioassay-directed fractionation, which led to the isolation of the known neolignans piperitylmagnolol (1), magnolol (2), and honokiol (3) from the MeOH extract. In broth-microdilution assays, 1-3 exhibited antibacterial activities against VRE and MRSA at minimum-inhibitory concentrations (MIC) in the range of 6.25-25 microg/ml, compound 1 being the most-potent antibiotic. The ratio of MBC/MIC (MBC = minimum bactericidal concentration) was < or = 2 for all compounds. The kinetics of the antibacterial action of 1 and 3 were studied by means of time-kill assays; both compounds were bactericidal against VRE and MRSA, their actions being time dependent, or both time and concentration dependent. Magnolol (2) was acetylated to magnolol monoacetate (4) and magnolol diacetate (5) (partial or full masking of the phenolic OH functions). The cytotoxic properties of 1-5 against human OVCAR-3 (ovarian adenocarcinoma), HepG2 (hepatocellular carcinoma), and HeLa (cervical epitheloid carcinoma) cell lines were evaluated. The CD50 values for compounds 1-3 were in the range of 3.3-13.3 microg/ml, derivatives 4 and 5 being much less potent. This study indicates that piperitylmagnolol (= 3-[(1S,6S)-6-isopropyl-3-methylcyclohex-2-enyl]-5,5'-di(prop-2-enyl)[1,1'-biphenyl]-2,2'-diol; 1) possesses both significant anti-VRE activity and moderate cytotoxicity against the above cancer cell lines.     

Antibacterial properties of a new isoflavonoid from Erythrina poeppigiana against methicillin-resistant Staphylococcus aureus.

A new isoflavonoid, together with four known isoflavonoids, was isolated from the roots of Erythrina poeppigiana. The chemical structure was determined by extensive spectroscopic studies, and then its antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) was investigated. The new isoflavonoid was identified as 3,9-dihyroxy-10-gamma,gamma-dimethylallyl-6a,11a-dehydropterocarpan (compound 1). Compound 1 inhibited bacterial growth most potently of the five isolates, and had a minimum inhibitory concentration (MIC) of 125 microg/ml against thirteen MRSA strains. Inhibitory activity was based on bactericidal action and viable cell number reduced by approximately 1/10,000 after 4 h incubation with compound 1. Despite intense bactericidal action against MRSA, compound 1 never resulted in leakage of 260 nm-absorbing substances from bacterial cells. Compound 1 (12.5 microg/ml) completely inhibited incorporation of radio-labeled thymidine, uridine and leucine into MRSA cells. Although glucose incorporation was also markedly inhibited by the compound, the amount of glucose incorporated by bacterial cells increased gradually with incubation time. These findings suggest that compound 1 exhibits anti-MRSA activity by interfering with incorporation of metabolites and nutrients into bacterial cells or by affecting the nucleic acids of MRSA cells. Furthermore, this new compound could be a potent phytotherapeutic agent for treating MRSA infections.     

Antimicrobial constituents of Scrophularia deserti

A study of the chemistry and antibacterial activity of Scrophularia deserti led to the isolation of eight compounds, including the metabolite 3(zeta)-hydroxy-octadeca-4(E),6(Z)-dienoic acid (1). The known compounds ajugoside (2), scropolioside B (3), 6-O-alpha-L-rhamnopyranosylcatalpol (4), buddlejoside A(8) (5), scrospioside A (6), laterioside (7) and 3R-1-octan-3-yl-3-O-beta-D-glucopyranoside (8) were also isolated. Compounds 1-3 exhibited moderate antibacterial activity against strains of multidrug and methicillin-resistant Staphylococcus aureus (MRSA) and a panel of rapidly growing mycobacteria with minimum inhibitory concentration (MIC) values ranging from 32 to 128 microg/ml.     

Antimicrobial activity of isoprenoid-substituted xanthones from Cudrania cochinchinensis against vancomycin-resistant enterococci.

Ten xanthones with one or two isoprenoid groups and a prenylated benzophenone isolated from roots of Cudrania cochinchinensis (Moraceae) were tested for their antimicrobial activities against vancomycin-resistant enterococci (VRE). Among these compounds, gerontoxanthone H exhibited considerable antibacterial activity against five VRE strains (VanA, VanB and VanC) (MICs = 1.56 microg/ml). Four xanthones, 1,3,7-trihydroxy-2-prenylxanthone, gerontoxanthone I, alvaxanthone and isoalvaxanthone, showed weaker antibacterial activity against these VREs (MICs = 3.13-6.25 microg/ml). .     

Antibacterial activity, structure and CMC relationships of alkanediyl alpha,omega-bis(dimethylammonium bromide) surfactants

Some alpha,omega-alkanediyl bis-dimethylammonium bromide compounds (gemini surfactants) referred as "m-s-m" have been synthesized, purified and characterized by usual spectroscopic methods. These compounds have been screened for antibacterial activity against Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus. Their activity was compared. The compounds tested showed excellent in vitro antibacterial activity against Staphylococcus aureus ranging from 1.5 to 20 microg/ml and had variable activity against E. coli with minimum minimum inhibitory concentration (MIC) of 50 microg/ml. These compounds are less active against P. aeruginosa. On the other hand, contrary to the antibacterial activity of these products against S. aureus, a relation between the MIC and the critical micellar concentration (CMC) was found and relationship between chain's Length and antibacterial activity was found.     

Antibacterial activity of extracts and neolignans from Piper regnellii (Miq.) C. DC. var. pallescens (C. DC.) Yunck

The evaluation of the activity of the aqueous and ethyl acetate extracts of the leaves of Piper regnellii was tested against gram-positive and gram-negative bacteria. The aqueous extract displayed a weak activity against Staphylococcus aureus and Bacillus subtilis with minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) of 1000 micrograms/ml. The ethyl acetate extract presented a good activity against S. aureus and B. subtilis with MIC and MBC at 15.62 micrograms/ml. In contrast to the relative low MICs for gram-positive bacteria, gram-negative bacteria were not inhibited by the extracts at concentrations < or = 1000 mg/ml. The ethyl acetate extract was fractionated on silica gel into nine fractions. The hexane and chloroform fractions were active against S. aureus (MIC at 3.9 micrograms/ml) and B. subtilis (MIC at 3.9 and 7.8 micrograms/ml, respectively). Using bioactivity-directed fractionation, the hexane fraction was rechromatographed to yield the antimicrobial compounds 1, 2, 5, and 6 identified as eupomatenoid-6, eupomatenoid-5, eupomatenoid-3, and conocarpan, respectively. The pure compounds 1 and 2 showed a good activity against S. aureus with MIC of 1.56 micrograms/ml and 3.12 micrograms/ml, respectively. Both compounds presented MIC of 3.12 micrograms/ml against B. subtilis. The pure compound 6 named as conocarpan was quite active against S. aureus and B. subtilis with MIC of 6.25 micrograms/ml. The antibacterial properties of P. regnellii justify its use in traditional medicine for the treatment of wounds, contaminated through bacteria infections.     

A new dihydroagarofuranoid sesquiterpene from Microtropis fokienensis with antituberculosis activity

A new dihydroagarofuran-based sesquiterpene, 8-acetoxymutangin (1), was isolated from the stems of Microtropis fokienensis, together with eight known compounds, including mutangin (2). Their structures were determined through in-depth spectroscopic and mass-spectrometric analyses. Among the isolated compounds, 1 exhibited potent in vitro antituberculosis activity, with an MIC value of 10.0 microg/ml against Mycobacterium tuberculosis 90-221387, which is considerably better than that of mutangin (2). The activity of 1 lies in the same range as that of the clinic drug ethambutol (MIC 6.25 microg/ml), despite completely different chemical structures, which indicates different modes of action.     

Six new constituents from the roots of Erythrina variegata

Three new isoflavonoids, eryvarins M-O (1-3), two new 2-arylbenzofurans, eryvarins P and Q (4 and 5), and a new 3-aryl-2,3-dihydrobenzofuran, eryvarin R (6), together with three known compounds, were isolated from the roots of Erythrina variegata. The structures of these compounds were established by spectroscopic analysis. Eryvarin R (6) is an unusual 3-aryl-2,3-dihydrobenzofuran derivative with a formyl (CHO) group. Eryvarin Q (5) showed potent antibacterial activity against methicillin-resistant Staphylococcus aureus.     

Antibacterial activity evaluation of microcin J25 against diarrheagenic Escherichia coli

The inhibitory activities of known microcins were evaluated against some diarrheagenic Escherichia coli strains. Some antibacterial properties of microcin J25, the most active one, were studied. A rapid two-step purification was performed. The MIC and the minimum bactericidal concentration of J25 against E. coli O157:H7 were 1 and 100 microg ml(-1), respectively. A 10(4)-CFU ml(-1) contamination by this strain was destroyed in milk and meat extract by 6.25 microg of J25 ml(-1) and in half-diluted egg yolk by 50 microg of J25 ml(-1).     

Blepharismin produced by a protozoan Blepharisma functions as an antibiotic effective against methicillin-resistant Staphylococcus aureus

A ciliated protozoan, Blepharisma japonicum, produces a photosensitive red pigment, blepharismin (BLR). This study showed that the pigment inhibits the growth of Gram-positive bacteria, such as methicillin-resistant Staphylococcus aureus (MRSA) resistant to arbekacin (ABK), which is the most effective aminoglycoside antibiotic against MRSA and used world wide. Although the minimum inhibitory concentration (MIC) of BLR to the ABK-resistant MRSA strain was 6.25 μg/ml in dark, it was decreased to 1.25 μg/ml by irradiation with white light of 65 W/m² for 30 min, suggesting that the antibacterial activity of BLR is photoactivated. Our findings suggested that the antibacterial activity of BLR in dark is due to inhibition of protein synthesis. In addition, we found that BLR is bactericidal and enhances synergistically the antibacterial activity of ABK.     

Anthraquinones from the stem bark of Stereospermum zenkeri with antimicrobial activity

Two anthraquinones, zenkequinones A and B were isolated from the stem bark of Stereospermum zenkeri together with known sterequinone-F, p-coumaric acid, sitosterol-3-O-beta-D-glucopyranoside and 3beta-hydroxyolean-12-en-28-O-beta-D-glucopyranoside. Their structures were established by spectroscopic methods. The antimicrobial activity of the isolated compounds was evaluated against six multiresistant strains of pathogens. Zenkequinone B showed the best antibacterial activity (MIC 9.50 microg/ml) against gram-negative Pseudomonas aeruginosa.     

Synthesis and antimicrobial activity of some novel phenyl and benzimidazole substituted benzyl ethers

In this study, a series of novel phenyl- and benzimidazole-substituted benzyl ethers were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, Methicillin-resistant S. aureus (MRSA), Escherichia coli, Candida albicans, and Candida krusei. Compound 6g exhibited the most potent antibacterial activity with lowest MIC values of 3.12 and 6.25 microg/mL against S. aureus and MRSA, respectively.     

Antimicrobial evaluation of indole-containing hydrazone derivatives

There has been an increasing importance of drug-resistant pathogens in clinical microbiological and antibacterial research. Indoles and hydrazone-type compounds constitute important classes of compounds in the search for effective agents against multidrug-resistant microbial infections. In this study a series of 1-methylindole-3-carboxaldehyde hydrazone derivatives were evaluated for their in vitro antimicrobial activities using the two-fold serial dilution technique against Staphylococcus aureus, methicillin-resistant S. aureus, methicillin-resistant S. aureus isolate, Escherichia coli, Bacillus subtilis, and Candida albicans. The minimum inhibitory concentration (MIC) of the test compounds and the reference standards sultamicillin, ampicillin, fluconazole, and ciprofloxacin was determined. All compounds possessed a broad spectrum of activity having MIC values of 6.25-100 microg/ml against the tested microorganisms. Aromaticity and disubstitution of the phenyl ring with especially fluorine and chlorine atoms were found to be significant for the antimicrobial activity     

In vitro anti-Neisseria gonorrhoeae activity of Terminalia macroptera leaves

We used the agar dilution method to evaluate the antibacterial effect of Terminalia macroptera leaf (Tml) extract against nine reference and clinical Neisseria gonorrhoeae strains, including penicillin- and tetracycline-resistant and -susceptible strains. Tml possesses anti-N. gonorrhoeae activity against all of the strains and the minimum inhibitory concentrations (MIC) were between 100 and 200 microg ml(-1). We then used a liquid-liquid partition method to divide the Tml extract into five fractions and determined the anti-N. gonorrhoeae activity of each of the fractions. All of the fractions showed antibacterial activity. The most active one was identified as the diethyl ether fraction and had MIC values of between 25 and 50 microg ml(-1) against all of the strains.