Anti-HIV-1 protease activity of lanostane triterpenes from the vietnamese mushroom Ganoderma colossum

Four new lanostane triterpenes, colossolactone V (1), colossolactone VI (2), colossolactone VII (3), and colossolactone VIII (4), were isolated from the fruiting bodies of the Vietnamese mushroom Ganoderma colossum, together with the known compound colossolactone E (5). The structures of 1- 4 were assigned on the basis of spectroscopic evidence, and their absolute configurations were determined by CD spectroscopy and the Mosher ester method. Compounds 1- 5, as well as two previously isolated compounds [schisanlactone A (6) and colossolactone G (7)] from the same mushroom, were evaluated for inhibition of HIV-1 protease, with IC 50 values for the most potent compounds ranging from 5 to 13 microg/mL.     

Isolation and antibacterial activity of phenylpropanoid derivatives from Ballota nigra

In addition to the previously isolated phenylpropanoid glycosides verbascoside 1, forsythoside B 2, arenarioside 3 and ballotetroside 4, another four compounds were isolated from generative aerial parts of Ballota nigra: three phenylpropanoid glycosides, alyssonoside 5, lavandulifolioside 6 and angoroside A 7 and a non-glycosidic derivative (+)-(E)-caffeoyl-L-malic acid 8. The antibacterial activity of the five major compounds (1-4 and 8) was tested against gram-positive and gram-negative bacteria. Three of them (1-3) exhibited a moderate antimicrobial activity against Proteus mirabilis and Staphylococcus aureus including one methicillin-resistant strain.     

New antimicrobial cycloartane triterpenes from Acalypha communis

Three new cycloartane-type triterpenes, 16 alpha-hydroxymollic (1), 15 alpha-hydroxymollic (2), and 7 beta,16 beta-dihydroxy-1,23-dideoxyjessic acids (3), were isolated from the aerial parts of Acalypha communis. The structures of the novel triterpenes were determined by spectroscopic methods as well as chemical derivatization. These compounds were tested for their antimicrobial activity against Gram-positive and -negative bacteria. Compounds 1-3 exhibited moderate antimicrobial activity (MIC 8, 32, 8 microg/mL, respectively) against vancomycin-resistant enterococci. In addition, compound 1 was found to be active against methicillin-resistant staphylococci. In contrast, compounds 1-3 were poorly active against Gram-negative bacteria. Compound 3 was tested in an in vivo model; it did not provide protection to mice infected with Staphylococcus aureus.     

Phenolic compounds from Brazilian propolis with pharmacological activities

Four compounds were isolated from Brazilian propolis. They are identified as: (1) 3-prenyl-4-hydroxycinnamic acid (PHCA), (2) 2,2-dimethyl-6-carboxyethenyl-2H-1-benzopyrane (DCBEN), (3) 3,5-diprenyl-4-hydroxycinnamic acid (DHCA), and (4) 2,2-dimethyl-6-carboxyethenyl-8-prenyl-2H-1-benzopyran (DPB). The structures of the compounds were determined by MS and NMR techniques. All compounds were assayed against Trypanosoma cruzi and the bacteria Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Streptococcus faecalis. Compounds (1) to (4) were active against T. cruzi. Except (1), all compounds presented activity against the bacteria tested. When compounds (1)-(3) were tested in the guinea pig isolated trachea, all induced a relaxant effect similar to propolis extract.     

Evaluation of the antimicrobial potential of medicinal plants from the Ivory Coast

A total of 148 crude ethanol extracts from 115 plant species were tested in vitro against Gram-negative strains (Escherichia coli, Pseudomonas aeruginosa) and the Gram-positive Staphylococcus aureus and Enterococcus faecalis. Moreover, they were submitted to antifungal assays against Candida albicans and Cladosporium cucumerinum, a human and a plant pathogenic microorganism, respectively, known to be good indicators of antifungal activity. No activity was detected against the Gram-negative bacteria, while 14.8% and 10.8% of the extracts showed Gram-positive bactericidal or bacteriostatic effects on S. aureus and E. faecalis, respectively. An antifungal activity was observed with 15 extracts (10.1%). Two species were particularly active against the fungi: Dioscorea minutiflora and Erythrina vogelii. The young tubers of D. minutiflora contain metabolites with a specific effect on fungi and were not active against the bacteria. On the other hand, E. vogelii was highly effective against the Gram-positive bacteria and the fungi.     

狼毒大戟抗肿瘤活性成分

目的:筛选狼毒大戟抗肿瘤活性馏分,分离活性单体化合物并对构效关系进行探讨。利用超高效液相色谱-质谱联用技术(UPLC-Q-TOF-MS)对活性馏分的化学成分进行鉴定。方法:采用噻唑蓝(MTT)法对狼毒大戟乙醇提取物的石油醚、乙酸乙酯、正丁醇和水萃取部位的抗肿瘤活性进行测试。综合运用多种现代色谱分离手段对活性萃取层石油醚层进行分离。利用核磁(NMR)和质谱(MS)技术鉴定化合物的化学结构。质谱使用ESI离子源,正离子模式下采集数据,结合狼毒大戟相关文献以及对照品信息进行数据分析,解析活性馏分的化合物结构。结果:从活性馏分层石油醚层分离得到6个单体化合物,分别为岩大戟内酯A,岩大戟内酯B,17-羟-岩大戟内酯A,17-羟-岩大戟内酯B,euphopilolide,atis-16-en-13(s)-hydroxy-3,14-dione。对这些化合物的抗肿瘤活性的构效关系进行了探讨。利用UPLC-Q-TOF-MS对狼毒大戟乙醇提取物的石油醚萃取部位化学成分进行鉴定,共鉴定化合物23个,其中二萜类成分19个,酚类成分2个,脂肪酸类成分1个,三萜类成分1个。峰18和峰21初步鉴定为新化合物。结论:狼毒大戟的活性馏分层为石油醚层,其主要成分为二萜类,具有较好的抗肿瘤活性。UPLC-Q-TOF-MS技术能够快速准确地鉴定狼毒大戟活性馏分的化学成分结构,为其质量评价和活性物质基础研究提供了参考。     

Antioxidant and neurosedative properties of polyphenols and iridoids from Lippia alba

The neurosedative and antioxidative properties of some major compounds isolated from a citral chemotype of Lippia alba were investigated. Binding assays were performed on two CNS inhibitory targets: benzodiazepine and GABA(A) receptors. The most active compound was luteolin-7-diglucuronide, with half maximal inhibitory concentrations (IC(50)) of 101 and 40 microm, respectively. Fifteen compounds isolated from Lippia alba were tested for their radical scavenging capacities against DPPH. Four of the major compounds (verbascoside, calceolarioside E, luteolin-7-diglucuronide and theveside) were also tested for their antioxidant activity against superoxide radical-anion in cell-free (hypoxanthine-xanthine oxidase) and cellular (PMA-stimulated neutrophil granulocytes) systems.     

HCV-NS3/4A protease inhibitory iridoid glucosides and dimeric foliamenthoic acid derivatives from Anarrhinum orientale

Four new compounds were isolated from the methanol extract of the aerial parts of Anarrhinum orientale: 6'-O-cinnamoylmussaenosidic acid (1), 6'-O-cinnamoyl-8-O-(6'-O-cinnamoylglucopyranosyl)mussaenosidic acid (2), (2E,6E)-8-{[(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoyl]oxy}-2,6-dimethylocta-2,6-dienoic acid (3), and (2E,6E)-8-{[(2E,6E)-8-acetoxy-2,6-dimethylocta-2,6-dienoyl]oxy}-2,6-dimethylocta-2,6-dienoic acid (4). The known 8-O-cinnamoylmussaenosidic acid (5) was also identified. All five compounds were tested for inhibition of the hepatitis C virus (HCV) protease. Compounds 1 and 5 exhibited moderate activity, while 2 and 3 showed weak effects. No inhibitory activity on the human serine protease was observed for any of these compounds, which may infer the selectivity toward the viral protease. A computational docking study of the isolated compounds against HCV protease was used to formulate a hypothetical mechanism for the inhibitory activity of the active compounds on the enzymes tested.     

五味子提取液抑菌活性研究

目的:探究五味子提取液的抑菌活性。方法:采用水提醇沉法提取五味子活性成分,以大肠埃希菌、枯草芽孢杆菌、沙门菌、金黄色葡萄球菌4种标准菌株和环丙沙星耐药及敏感的大肠杆菌野株为供试菌,以环丙沙星为对照药物,采用牛津杯法测定供试菌分别培养16,32,48,64 h后五味子提取液的抑菌圈直径,监测五味子提取液的抑菌活性和抑菌活性的变化趋势,同时采用试管双倍稀释法测定五味子提取液对大肠杆菌耐药株的最低抑菌浓度(MIC)和最低杀菌浓度(MBC)。结果:五味子提取液对各供试菌的抑菌圈直径在20.16~30.06 mm,五味子提取液对环丙沙星耐药大肠埃希菌的最低抑菌质量浓度在0.0156 3~0.062 5 g·mL-1,最低杀菌质量浓度在0.312 5~0.062 5 g·mL-1。五味子提取液对所有供试菌都有明显的抑制作用,与环丙沙星相比,五味子提取液对环丙沙星耐药菌的抑制作用表现出极大的优势。环丙沙星与五味子提取液对供试菌的抑菌活性都呈逐渐下降趋势。结论:五味子提取液不仅具有广谱抗菌活性,对环丙沙星耐药菌也具有显著的抑制活性,可开发为新型抗菌剂。     

Antimicrobial activity of the methanolic extracts and compounds from Vismia laurentii De Wild (Guttiferae)

Methanolic extracts prepared from the leaves, twigs and the roots of Vismia laurentii De Wild as well as nine compounds isolated from these crude extracts, were tested for their antimicrobial activity against Gram-positive bacteria (six species), Gram-negative bacteria (12 species) and two Candida species using disc diffusion and well micro-dilution methods. The disc diffusion assay indicated that the crude extract was active against all the pathogens tested, whereas isolated compounds showed selective activities. The degree of sensitivity of the test organisms to purified compounds varied from 25 to 90%. Fridelin (8) was found to be the most active compound, while Bivismiaquinone (3) was the least active. The lowest minimum inhibition concentration (MIC) values as obtained by the micro-dilution assays were 19.53 and 1.22 microg/ml for the crude extracts and purified compounds, respectively. The lowest value for the purified compounds (1.22 microg/ml) was obtained with O(1)-demethyl-3',4'-deoxypsorospermin-3',4'-diol (6) on Candida gabrata and Bacillus subtilis; 1,8-dihydroxy-6-methoxy-3-methylanthraquinone (5) on Bacillus subtilis and 6-deoxyisojacareubin (7) on Bacillus stearothermophilus. These results provide promising baseline information for the potential use of these crude extracts as well as some of the isolated compounds in the treatment of bacterial and fungal infections.     

Bioactive metabolites from the Caribbean sponge Aka coralliphagum

The chemistry of the burrowing sponge Aka coralliphagum was investigated to identify chemically labile secondary metabolites. The HPLC-MS analysis of the two growth forms typica and incrustans revealed different metabolites. The previously unknown sulfated compounds siphonodictyals B1 to B3 (6-8), corallidictyals C (9) and D (10), and siphonodictyal G (11) were isolated, and their structures were elucidated by NMR and MS experiments. The compounds were tested in a DPPH assay, in antimicrobial assays against bacteria, yeasts, and fungi, and in antiproliferation assays using cultures of mouse fibroblasts. The biological activity was linked to the presence of the ortho-hydroquinone moiety.     

Daryamides A-C, weakly cytotoxic polyketides from a marine-derived actinomycete of the genus Streptomyces strain CNQ-085

In the course of our continuing search for new antitumor-antibiotics from marine-derived actinomycete bacteria, four new cytotoxic compounds, designated as daryamides A (1), B (2), and C (3) and (2E,4E)-7-methylocta-2,4-dienoic acid amide (4), were isolated from the culture broth of a marine-derived Streptomyces strain CNQ-085. The structures of these new compounds were assigned by detailed interpretation of spectroscopic data. The relative configuration of 1 was determined by comprehensive NMR analysis, while the absolute configuration of 1 was determined as 4S,5R using the modified Mosher method. The daryamides show weak to moderate cytotoxic activity against the human colon carcinoma cell line HCT-116 and very weak antifungal activities against Candida albicans.     

胶州湾具抗菌活性海洋链霉菌的筛选及菌株M097的代谢产物

目的:筛选具有抗菌活性的海洋链霉菌并分离鉴定其代谢产物。方法:利用8株受试菌作为抗菌活性筛选模型,以杯碟法对采集自胶州湾海洋的256株链霉菌进行抗菌活性的筛选;对具有抗菌活性的海洋链霉菌M097进行发酵条件的优化,采用乙酸乙酯提取和柱层析等方法,分离发酵液中的代谢产物。结果:具有抗菌活性海洋链霉菌的比例为22%;通过ESI-MS、EI-MS、NMR等波谱数据进行分析,鉴定了3个活性代谢产物的结构。结论:具有抗菌活性的海洋链霉菌的比例很高;海洋链霉菌M097在M 2培养基中产生的3个活性代谢产物均属于大环内酯类抗生素,与Streptomyces griseus产生的feigrisolides A、B和C的结构一致。     

Antibacterial activity of flavonoids from the stem bark of Erythrina caffra thunb.

The antibacterial activity of the stem bark of Erythrina caffra Thunb. was investigated against different bacterial strains. The antibacterial activity was determined by a micro broth dilution assay. Antibacterial compounds were isolated and identified using a Bruker Avance III LPO NMR spectrometer. Four known flavonoids, abyssione‐V 4′‐O‐methyl ether, 6,8‐diprenylgenistein, alpinumisoflavone and burttinone, were isolated. All the compounds were active against both Gram‐negative and Gram‐positive bacteria. The minimum inhibitory concentration values obtained (MIC) ranged from 3.9 μg/mL to 125 μg/mL. This is the first report of antibacterial activity of burttinone and the isolation of these compounds from E. caffra. Copyright © 2010 John Wiley & Sons, Ltd.     

Diterpenoids from the roots of Salvia hypargeia

From the root extracts of Salvia hypargeia, in addition to the known diterpenoids cryptanol and horminone, six new abietane diterpenoids were isolated. The structures of the new and the known compounds were established by spectral data. The new compounds, hypargenins A, B, C, D, and F, showed antibacterial activity, while hypargenin F was also active against Mycobacterium tuberculosis. Hypargenin E did not exhibit antibacterial activity.     

Antibacterial iridoid glucosides from Eremostachys laciniata

Eremostachys laciniata (L) Bunge (family: Lamiaceae alt. Labiatae; subfamily: Lamioideae) is one of the 15 endemic Iranian herbs of the genus Eremostachys. A decoction of the roots and flowers of E. laciniata has traditionally been taken orally for the treatment of allergies, headache and liver diseases. Three antibacterial iridoid glucosides, phloyoside I (1), phlomiol (2) and pulchelloside I (3) have been isolated from the rhizomes of this plant. The structures of these compounds were elucidated unequivocally by a series of 1D and 2D NMR analyses. The antibacterial activity and brine shrimp toxicity of these compounds were assessed using the resazurin microtitre assay and the brine shrimp lethality assay, respectively. All three iridoid glycosides 1-3 exhibited from low to moderate levels (MIC = 0.05-0.50 mg/mL) of antibacterial activity. Of these compounds, compound 3 was the most active, and displayed antibacterial activity against 9 of 12 different strains tested. The most noteworthy activity of 3 was against Bacillus cereus, penicillin-resistant Escherichia coli, Proteus mirabilis and Staphylococcus aureus with an MIC value of 0.05 mg/mL.     

Antifungal,antioxidant and larvicidal activities of compounds isolated from the heartwood of Mansonia gagei

Eleven compounds isolated from the heartwood of Mansonia gagei were tested for their antifungal activities against Cladosporium cucumerinum and Candida albicans, as well as for their larvicidal activities against Aedes aegypti and radical scavenging properties in a DPPH assay. Mansonone C (4) was found to be the most interesting compound with antifungal activities against Cladosporium cucumerinum and Candida albicans as well as for its larvicidal properties against Aedes aegypti. Mansonone E (5) was active against Cladosporium cucumerinum and Candida albicans. Two coumarin derivatives, mansorin A (1) and mansorin B (2) were also found to be active against Cladosporium cucumerinum, while mansonone N (9) was the only isolated product to show radical scavenging properties.     

Screening of some Cuban medicinal plants for antimicrobial activity

The antimicrobial activities of 23 extracts of 12 Cuban plant species reported in traditional medicine were tested. The agar diffusion method was used to assess the activity against four bacteria and one yeast: Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa and Candida albicans. The results, evaluated as the diameter of the inhibition zone of microbial growth, showed that nine extracts were active against Gram-positive bacteria but only two of these proved to be also active against Gram-negative bacteria. None of the extracts inhibited the growth of the yeast. The most susceptible bacterium was Staphylococcus aureus and the best antibacterial activity was shown by Schinus terebenthifolius.     

Karnatakafurans A and B: two dibenzofurans isolated from the Fungus Aspergillus karnatakaensis

Karnatakafurans A (1) and B (2), two novel dibenzofurans, have been isolated from the Specie Novum Aspergillus karnatakaensis Frisvad. The compounds were the major secondary metabolites and were isolated through UV-guided fractionation of the organic extract. The structures were elucidated by spectroscopic methods including MS and NMR. The compounds were tested for antimicrobial and antimalarial activity and proved to be moderately active against Plasmodium falciparum.     

Efficacy of scopadulcic acid A against Plasmodium falciparum in vitro

Scoparia dulcis is a perennial herb widely distributed in many tropical countries. It is used as an herbal remedy for gastrointestinal and many other ailments, and in Nicaragua extracts are used to treat malaria. Phytochemical screening has shown that scopadulcic acid A (SDA), scopadulcic acid B (SDB), and semisynthetic analogues are pharmacologically active compounds from S. dulcis. SDB has antiviral activity against Herpes simplex virus type 1, antitumor activity in various human cell lines, and direct inhibitory activity against porcine gastric H(+), K(+)-ATPase. A methyl ester of scopadulcic acid B showed the most potent inhibitory activity against gastric proton pumps of 30 compounds tested in one study. Compounds with antiviral, antifungal, and antitumor activity often show activity against Plasmodium falciparum. In P. falciparum, the plasma membrane and food vacuole have H(+)-ATPases and the acidocalcisome has an H(+)-Ppase. These proton pumps are potential targets for antimalarial therapy and may have their function disrupted by compounds known to inhibit gastric proton pumps. We tested pure SDA and found in vitro activity against P. falciparum with an IC(50) of 27 and 19 microM against the D6 and W2 clones, respectively. The IC(50) against the multidrug-resistant isolate, TM91C235, was 23 microM.