脱乙酰壳多糖抑制真菌生长的构效关系

本研究目标是研究脱乙酰壳多糖的化学结构(乙酰化程度DA和聚合程度DP)与它的抑制真菌生长能力之间的构效关系. 选用了12个分属于3个系列、化学结构相关而又不同的、结构清晰的脱乙酰壳多糖和3种不同的真菌(Fusarium solani, Fusarium graminearum和Ustilago maydis). 通过分别测定每个脱乙酰壳多糖对3种真菌的生长曲线和最低抑制浓度(MIC, minimum inhibitory concentration); 比较各个系列脱乙酰壳多糖的MIC和它的化学结构(DA和DP)之间的关系. 结果显示对同一种真菌, 不同脱乙酰壳多糖的抑制真菌生长曲线形态和MIC是各不相同的; 同样同一脱乙酰壳多糖, 对不同真菌也有其特殊的生长曲线和MIC; 通常随着脱乙酰壳多糖中DA的递增, MIC是增加的, 其抑制真菌的活性是降低的; 在DA相同的条件下, 随着DP的递增, MIC也是增加的, 其抑制真菌的活性是减低的. 所以可以说, 脱乙酰壳多糖抑制真菌生长的能力与其化学结构紧密相关, 在本实验的条件下, 脱乙酰壳多糖分子越小, 分子中的自由氨基越多, 抑制真菌的活性越大.     

Chemical composition and antimicrobial activity of the essential oil of the leaves of Feronia elephantum (Rutaceae) from north west Karnataka

The essential oil of the leaves of Feronia elephantum Corr. was analyzed by gas chromatography and gas chromatography/mass spectrometry. The main constituents were beta-pinene (28.4%), Z-anethole (22.1%), methyl chavicol (12.0%) and E-anethole (8.1%), among thirty-three identified compounds, which represented 92.6% of the total oil. The antimicrobial activity was tested against five Gram-positive and eight Gram-negative bacteria, and four fungi. The oil was active against Micrococcus luteus (Gram-positive bacterium), Proteus mirabilis (Gram-negative bacterium), Penicillium chrysogenum and Aspergillus niger (fungi) with MIC values of 0.31 +/- 0.06, 0.52 +/- 0.10, 0.20 +/- 0.50 and 0.26 +/- 0.52 mg/mL, respectively.     

Chemical composition and antimicrobial activities of the essential oils from Ocimum selloi and Hesperozygis myrtoides

Ocimum selloi, a traditional medicinal plant from Brazil, is sold in open-air markets at Rio de Janeiro State. Hesperozygis myrtoides is a very aromatic small bush found in the State of Minas Gerais, Brazil, growing at an altitude of 1800m. The chemical composition of both essential oils was analyzed as well as their antimicrobial activity against fungi and bacteria. For all specimens of Ocimum selloi obtained at open-air markets, methylchavicol was major compound found (93.6% to 97.6%) in their essential oils. The major compounds identified in the oil of H. myrtoides were pulegone (44.4%), isomenthone (32.7%), and limonene (3.5%). Both oils displayed antimicrobial activity against all tested microorganisms but Candida albicans was the most susceptible one. Combinations of the two oils in different proportions were tested to verify their antimicrobial effect against C. albicans, which, however, was not modified in any of the concentrations tested. The minimum inhibitory concentration (MIC) was determined to confirm the antimicrobial activity against C. albicans as well as other clinical isolates (C. glabrata, C. krusei, C. parapsilosis and C. tropicalis).     

Biological activities of α-pinene and β-pinene enantiomers

The antimicrobial activities of the isomers and enantiomers of pinene were evaluated against bacterial and fungal cells. The agar diffusion test showed that only the positive enantiomers of the α- and β-isomers of pinene were active. The minimal inhibitory concentration (MIC) and minimal microbicidal concentration (MMC) of these monoterpenes were also determined, confirming that the positive enantiomers exhibited microbicidal activity against all fungi and bacteria tested with MICs ranging from 117 to 4,150 μg/mL. However, no antimicrobial activity was detected with the negative enantiomers up to 20 mg/mL. Time-kill curves showed that (+)-α-pinene and (+)-β-pinene were highly toxic to Candida albicans, killing 100% of inoculum within 60 min. By contrast, the bactericidal effect occurred after 6 h in methicillin-resistant Staphylococcus aureus (MRSA). In combination with commercial antimicrobials, ciprofloxacin plus (+)-α-pinene or (+)-β-pinene presented synergistic activity against MRSA whereas an indifferent effect against all fungi was detected when amphotericin B was combined with the positive enantiomers of pinene. The potential of (+)-α-pinene and (+)-β-pinene to inhibit phospholipase and esterase activities was also evaluated, and the best inhibition results were obtained with Cryptococcus neoformans. C. albicans biofilm formation was prevented with the MIC concentration of (+)-α-pinene and twice the MIC value of (+)-β-pinene. Finally, the cytotoxicity of the positive enantiomers of pinene to murine macrophages was evaluated, and 250 μg/mL of (+)-α-pinene and (+)-β-pinene reduced the cell viability to 66.8% and 57.7%, respectively.     

Chemical composition and antimicrobial activity of the volatile oil from Fusarium tricinctum, the endophytic fungus in Paris polyphylla var. yunnanensis

The volatile oil, obtained by hydro-distillation from Fusarium tricinctum, the endophytic fungus isolated from Paris polyphylla var. yunnanensis, was analyzed by gas chromatography-mass spectrometry (GC-MS). trans-1,2,3,3a,4,7a-Hexahydro-7a-methyl-5H-inden-5-one (73.1%), 2-methylene-4,8,8-trimethyl-4-vinyl bicyclo [5.2.0] nonane (12.0%), and 2,6-dimethyl-6-(4-methyl-3-pentenyl) bicyclo [3.1.1] hept-2-ene (4.5%) were the major compounds of the 15 identified components accounting for 95.4% of the volatile oil. The antimicrobial activity of the volatile oil was assayed against eight bacteria and two fungi. The minimum inhibitory concentration (MIC) values of the volatile oil against the test bacteria ranged from 25 to 45 microg/mL. The MIC values against the fungi Candida albicans and Magnaporthe oryzae were 100 and 225 microg/mL, respectively. The mean inhibitory concentration (IC50) values of the volatile oil against the test bacteria ranged from 17.8 to 31.6 microg/mL, and those of the volatile oil against C. albicans and M. oryzae were 84.3 and 204.3 microg/mL, respectively.     

Comparison of antimicrobial activities of naphthoquinones from Impatiens balsamina

Lawsone (1), lawsone methyl ether (2), and methylene-3,3'-bilawsone (3) are the main naphthoquinones in the leaf extracts of Impatiens balsamina L. (Balsaminaceae). Antimicrobial activities of these three naphthoquinones against dermatophyte fungi, yeast, aerobic bacteria and facultative anaerobic and anaerobic bacteria were evaluated by determination of minimal inhibitory concentrations (MICs) and minimal bactericidal or fungicidal concentrations (MBCs or MFCs) using a modified agar dilution method. Compound 2 showed the highest antimicrobial activity. It showed antifungal activity against dermatophyte fungi and Candida albicans with the MICs and MFCs in the ranges of 3.9-23.4 and 7.8-23.4?μg?mL(-1), respectively, and also had some antibacterial activity against aerobic, facultative anaerobic and anaerobic bacteria with MICs in the range of 23.4-93.8, 31.2-62.5 and 125?μg?mL(-1), respectively. Compound 1 showed only moderate antimicrobial activity against dermatophytes (MICs and MFCs in the ranges of 62.5-250 and 125-250?μg?mL(-1), respectively), but had low potency against aerobic bacteria, and was not active against C. albicans and facultative anaerobic bacteria. In contrast, 3 showed significant antimicrobial activity only against Staphylococus epidermidis and Bacillus subtilis (MIC and MBC of 46.9 and 93.8?μg?mL(-1), respectively).     

Chemical composition and in vitro antimicrobial activity of the essential oil of the flowers of Tridax procumbens

The essential oil of the flowers of Tridax procumbens L. was obtained by hydro-distillation and analyzed by gas chromatography equipped with a flame ionization detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC/MS). Twenty-six compounds were identified, which comprised 90.6% of the total constituents. The most abundant compound was (Z)-falcarinol (25.9%), followed by alpha-selinene (15.3%), limonene (8.3%) and zerumbone (4.3%). Antimicrobial activity was tested against six Gram-positive and eight Gram-negative bacteria, and three fungi. The oil was active against the tested Gram-positive bacteria at a concentration range of 0.14 +/- 0.03 - 0.57 +/- 0.05 mg/mL, while 0.67 +/- 0.12 - 4.58 +/- 0.41 mg/mL was effective against the studied Gram-negative bacteria. Remarkable antifungal activity was found against the tested fungi at a concentration range of 0.06 +/- 0.008 - 0.10 +/- 0.01 mg/mL.     

In-vitro antibacterial properties of crude aqueous and n-hexane extracts of the husk of Cocos nucifera

The increasing numbers of cases of antibiotic resistance among pathogenic bacteria such as Vibrio species poses a major problem to the food and aquaculture industries, as most antibiotics are no longer effective in controlling pathogenic bacteria affecting these industries. Therefore, this study was carried out to assess the antibacterial potentials of crude aqueous and n-hexane extracts of the husk of Cocos nucifera against some selected Vibrio species and other bacterial pathogens including those normally implicated in food and wound infections. The crude extracts were screened against forty-five strains of Vibrio pathogens and twenty-five other bacteria isolates made up of ten Gram positive and fifteen Gram negative bacteria. The aqueous extract was active against 17 of the tested bacterial and 37 of the Vibrio isolates; while the n-hexane extract showed antimicrobial activity against 21 of the test bacteria and 38 of the test Vibrio species. The minimum inhibitory concentrations (MICs) of the aqueous and n-hexane extracts against the susceptible bacteria ranged between 0.6-5.0 mg/mL and 0.3-5.0 mg/mL respectively, while the time kill study result for the aqueous extract ranged between 0.12 Log?? and 4.2 Log?? cfu/mL after 8 hours interaction in 1 x MIC and 2 x MIC. For the n-hexane extract, the log reduction ranged between 0.56 Log?? and 6.4 Log?? cfu/mL after 8 hours interaction in 1 x MIC and 2 x MIC. This study revealed the huge potential of C. nucifera extracts as alternative therapies against microbial infections.     

A new bioactive triterpenoid saponin from the seeds of Lactuca scariola Linn

A new triterpenoid saponin, 3-O-[beta-D-galactopyranosyl-(1 --> 3)-O-beta-D-xylopyranosyl-(1 --> 4)-O-alpha-L-rhamnopyranosyl]-oleanolic acid; has been isolated from the seeds of Lactuca scariola. Its structure was determined by various spectral analysis and chemical degradations. This compound shows antimicrobial activity against various bacteria and fungi.     

Composition and antimicrobial activity of the essential oil of Heracleum thomsonii (Clarke) from the cold desert of the western Himalayas

Volatile oil composition of hydro-distilled (HD) and supercritical carbon dioxide (SC-CO(2)) essential oil of freshly collected aerial parts of Heracleum thomsonii (Umbeliferae) from the western Himalayas was studied by GC-FID and GC-MS. Results revealed qualitative and quantitative dissimilarity in the composition of hydro-distilled and SC-CO(2) extracted oils. Nineteen constituents, which accounted for 89.32% of total constituents in HD oil, represented by limonene (4.31%), (Z)-β-ocimene (3.69%), terpinolene (22.24%), neryl acetate (36.19%), nerol (9.51%) and p-cymene-8-ol (2.61%) were identified. In SC-CO(2) extracted oil, 24 constituents representing 89.95% of total constituents were identified. Terpinolene (5.08%), germacrene D (2.17%), neryl acetate (51.62%), nerol (9.78%), geranyl acetate (2.06%), α-bisabolol (2.48%) and 1-nonadecanol (4.96%) were the dominating constituents. In?vitro antimicrobial activity of hydro-distilled oil was conducted against microrobial strains including two Gram-positive (Staphylococcus aureus and Bacillus subtilis) and five Gram-negative (Burkholderia cepacia, Escherichia coli, Enterobacter cloacae, Klebseilla pneumoniae and Pseudomonas aeruginosa) bacteria as well as seven fungi (Candida albicans, Issatchenkia orientalis, Aspergillus flavus, Aspergillus niger, Aspergillus parasiticus, Aspergillus sydowii and Trichophyton rubrum) using broth microdilution method. The results of bioassay showed that the oil exhibited moderate to high antimicrobial activity against fungi C. albicans (MIC 625 μg?ml(-1)), A. parasiticus (MIC 312.5 μg?ml(-1)), A. sydowii (MIC 312.5 μg?ml(-1)), T. rubrum (MIC 625 μg?ml(-1)), Gram-positive bacteria B. subtilis (MIC 625?μg?ml(-1)) and Gram-negative bacteria P. aeruginosa (MIC 312.5 μg?ml(-1)).     

Chemical composition and antibacterial activity of the essential oil of Espeletia nana

The essential oil of the leaves of Espeletia nana Cuatrec., obtained by hydrodistillation, was analyzed by GC-MS, which allowed the identification of 24 components, which made up 99.9% of the oil. The most abundant compounds were a-pinene (38.1%), beta-pinene (17.2%), myrcene (15.0%), spathulenol (4.2%), bicyclogermacrene (4.0%), a-zingiberene (4.0%), and gamma-himachalene (3.7%). Antibacterial activity was tested against Gram-positive and Gram-negative bacteria using the agar disk diffusion method. Activity was observed only against Gram-positive bacteria. MIC values were determined for Staphylococcus aureus ATCC 25923 (200 microg/mL) and Enterococcusfaecalis ATCC 29212 (600 microg/mL).     

Composition and antimicrobial activity of the essential oil of Actinidia macrosperma from China

Actinidia macrosperma is a medicinal plant in China and has been well known for its attraction to cats and activities against leprosy and cancers. The compositions and the antimicrobial activity of its leaf oil were reported for the first time. The oil obtained by hydrodistillation and analyzed by GC and GC-MS, was characterized by the high content of monoterpenes. Linalool (48.14%) is the major component identified, followed by 1,2-dimethyl-lindoline (7.94%), linolenic acid methylester (6.57%) and (E)-phytol (5.29%). The antimicrobial activity of the oil was evaluated against four bacterial and three fungal species. The results showed that it exhibited a mild antibacterial activity against two Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), a significant activity against Gram-negative bacteria (Escherichia coli), and no activity on Pseudomonas aeruginosa. The test fungi were more sensitive to the oil, with a MIC range of 0.78-1.56 microL mL(-1) than bacteria in the range which were significantly higher from 0.78 to 25.50 microL mL(-1).     

Antiproliferative, antimicrobial and apoptosis inducing effects of compounds isolated from Inula viscosa

The antiproliferative and antimicrobial effects of thirteen compounds isolated from Inula viscosa (L.) were tested in this study. The antiproliferative activity was tested against three cell lines using the MTT assay. The microdilution method was used to study the antimicrobial activity against two Gram positive bacteria, two Gram negative bacteria and one fungus. The apoptotic activity was determined using a TUNEL colorimetric assay. Scanning electron microscopy was used to study the morphological changes in treated cancer cells and bacteria. Antiproliferative activity was observed in four flavonoids (nepetin, 3,3'-di-O-methylquercetin, hispidulin, and 3-O-methylquercetin). 3,3'-di-O-Methylquercetin and 3-O-methylquercetin showed selective antiproliferative activity against MCF-7 cells, with IC(50) values of 10.11 and 11.23 μg/mL, respectively. Both compounds exert their antiproliferative effect by inducing apoptosis as indicted by the presence of DNA fragmentation, nuclear condensation, and formation of apoptotic bodies in treated cancer cells. The antimicrobial effect of Inula viscosa were also noticed in 3,3'-di-O-methylquercetin and 3-O-methyquercetin that inhibited Bacillus cereus at MIC of 62.5 and 125 μg/mL, respectively. Salmonella typhimurium was inhibited by both compounds at MIC of 125 μg/mL. 3,3'-di-O-Methylquercetin induced damage in bacterial cell walls and cytoplasmic membranes. Methylated quercetins isolated from Inula viscosa have improved anticancer and antimicrobial properties compared with other flavonoids and are promising as potential anticancer and antimicrobial agents.     

Antimicrobial activities of single aroma compounds

Commercially available aroma samples were evaluated for their olfactory quality by professional perfumers and tested for their antimicrobial activity. Agar diffusion and agar-dilution were used as test methods and a set of two Gram-positive (Staphylococcus aureus and Enterococcus faecalis) and four Gram-negative bacterial strains (Escherichia coli, Pseudomonas aeruginosa, Proteus vulgaris G, Klebsiella pneumoniae and Salmonella abony) and a yeast, Candida albicans, were the test microorganisms. All the investigated compounds were active against Gram-positive bacteria, especially beta-caryophyllene against Enterococcus faecalis (MIC 6 ppm), but only few substances showed activity towards Gram-negative bacteria, except for cinnamic acid, which was active against all (MIC 60 ppm) and Candida albicans, against which cinnamic acid and caryophyllene oxide showed high activity (MIC < 60 ppm).     

Antimicrobial activity of three baccharis species used in the traditional medicine of Northern Chile

The antimicrobial activities of aqueous ethanol and chloroform extracts of three Baccharis species currently used in Northern Chile folk medicine for the treatment of several infectious and inflammatory disorders were tested against Gram-positive and negative bacteria and fungal spp. using the agar-disc diffusion assay. The results indicated that the activity was more pronounced against Gram-positive than against Gram-negative bacteria and yeast. No significant differences on the antibacterial activity were observed in the aqueous ethanol versus chloroform extracts. None of the plant extracts evaluated exhibited any activity against ten fungi tested.     

壳多糖抑制细菌生长的构效关系

运用化学结构已清楚, 分属4大系列的29种壳多糖, 以4种不同类型的细菌(革兰氏阳性菌Ecoli K1、革兰氏阴性菌Bacillus cereus、Bacillus megaterium和Staphlylococcu aureus)为研究对象, 进行了壳多糖抑菌能力构效关系的研究. 在实验中采用96孔平板, 用计算机\|吸光值读数仪直接测定每个孔的吸光值, 获得了各个细菌在不同壳多糖浓度中的生长曲线和壳多糖抑制细菌生长的最低抑制浓度(MIC, Minimum inhibit concentration). 通过比较同一(各个)系列的壳多糖在这些相同(不同)细菌的MIC变化规律与壳多糖的化学结构的关系, 发现同一壳多糖对不同的细菌的MIC值是不相同的, 因而壳多糖抑制细菌生长的能力首先与细菌本身特点有关, 但与是否为革兰氏阳性菌或阴性菌无直接的相关性; 同一细菌对不同化学结构的壳多糖有一定的相关性, 在壳多糖的聚合程度(DP)相同的条件下, 壳多糖中氨基被乙酰化(DA)的程度越低, 壳多糖抑制细菌生长的MIC值越低, 壳多糖抑制细菌生长的能力就越强; 同样,在DA相同的情况下, 分子越小, 壳多糖抑制细菌生长的MIC值越低, 抑制细菌生长的能力越强. 根据上述实验结果, 初步推测壳多糖抑制细菌生长的机制可能与其在溶液中所带的正电荷多少有关.     

The influence of chemical structure on the antimicrobial activities of thiosemicarbazone-chitosan

We have previously reported the preparation of acetyl and benzoyl phenyl-thiosemicarbazone derivatives of chitosan and their antimicrobial activities. The purpose of this study was to further assess the relationship between chemical structure and antimicrobial activity of chloracetyl phenyl-thiosemicarbazone-chitosan. Ten new chloracetyl phenyl-thiosemicarbazone-chitosans were prepared, and their structures were characterized using FT-IR and elemental analysis. The synthesized compounds were tested against four species of bacteria and four crop-threatening pathogenic fungi. Different molecular weights and concentrations were evaluated. The antifungal activities of the synthesized compounds were related to the positive polarity of the N₄ atom and the distribution of the electron atmosphere in the C=S group. All chitosan compounds had inhibitory effects when tested with bacteria. The minimum MIC and MBC with Escherichia coli were 7.03 and 56.25 μg mL^?1, respectively.     

Synthesis and Antibacterial Activities of N-[(1-Aryl-3-phenyl-pyrazol-4-yl)methylene]-2-(halo-o-hydroxyphenyl)hydrazide Derivatives

A series of novel N-[(1-aryl-3-phenyl-pyrazol-4-yl)methylene]-2-(halo-o-hydroxyphenyl)hydrazide derivatives was synthesized and the antibacterial activity of each of them was evaluated. The supposed reaction mechanism of acquiring compounds 3a—3d is that catalytic activity is enhanced by the electron-donating groups of the first phenyl ring while decreased by electron-withdrawing groups of that ring. The result of preliminary bioassay shows that the lowest minimal inhibitory concentration(MIC) of the title compounds against Escherichia coli is 2 μg/mL. MIC values against Monilia albican and Staphlococcus aureus are as low as 4 μg/mL. They will be a series of potential antibacterial compounds against fungi and gram-negative bacteria.     

Synthesis and Antimicrobial Activity of Some New 4H-Pyrrolo[1,2-a]benzimidazoles

Some new 4H-pyrrolo[1,2-a]benzimidazoles（2a-2f） have been synthesized. The structures of these compounds were confirmed by IR, tH NMR, mass spectroscopy and elemental analysis. Compound 2a was further confirmed by X-ray diffraction. The in vitro antimicrobial activities of these compounds were determined against some gram-positive bacteria, gram-negative bacteria and fungi and their drug-resistant isolates in comparison with standard drugs. Antimicrobial results indicate that compounds 2c, 2d and 2e show moderately active antibacterial properties, their minimum inhibitory concentrations are from 12.5 μg/mL to 125 μg/mL. In the series, the most active compound against C. albicans is compound 2fwith an MIC value of 31.25 μg/mL.     

New hemisynthetic manoyl oxide derivatives with antimicrobial activity.

The synthesis and antimicrobial activity of ten labdane-type diterpenes derived from ent-3-beta-hydroxy-13-epi-manoyl oxide (ribenol) is reported. The chloroethyl carbamidic ester 9 showed the strongest antimicrobial activity against all the tested gram (+), gram (-) bacteria and pathogenic fungi. Moreover, the glycoside 11 exhibited an interesting activity against the three tested fungi.