The antimicrobial activities of Psidium guajava and Juglans regia leaf extracts to acne-developing organisms

This study aims to present the in vitro inhibitory effect of Psidium guajava and Juglans regia leaf extracts on the main developer of acne lesions, Propionibacterium acnes (P. acnes), and other organisms that are isolated from acne lesions. Thirty-eight subjects (males and females) who had various types of acne were enrolled in the study. The contents of the acne lesions were cultured and the frequency of P. acnes (alone and with Staphylococci spp.) was 47%, whereas the frequencies for Staphylococcus aureus and Staphylococcus epidermidis were 13% and 24%, respectively. The antimicrobial activities of Psidium guajava and Juglans regia leaf extracts, determined by disk diffusion method (zone of inhibition), were compared to tea tree oil (TTO), doxycycline and clindamycin antibiotics. The zones of inhibition due to the Psidium guajava and Juglans regia leaf extracts ranged from 15.8-17.6 mm against P. acnes, 11.3-15.7 mm against S. aureus and 12.9-15.5 mm against S. epidermidis, respectively. These zones of inhibition were significantly higher than those of TTO and equivalent in case of Staphylococci spp., but less in case of P. acnes, to those obtained from doxycycline or clindamycin. It can be concluded that Psidium guajava and Juglans regia leaf extracts may be beneficial in treating acne especially when they are known to have anti-inflammatory activities.     

Isoprenylated naphthoquinone dimers firmianones A, B, and C from Firmiana platanifolia

Three new compounds designated as firmianones A, B, and C (1-3), along with 13 known compounds, were isolated from the roots of Firmiana platanifolia. Their structures were elucidated by interpretation of HRESIMS, 1H-1H COSY, HMQC, HMBC, and NOESY. The absolute configurations of firmianones A and B with a rare hexacyclic skeleton were determined by CD exciton-coupling experiments. Firmianones A and B exhibited moderate cytotoxicity to the P388 cancer cell line.     

Antiviral flavonoid from Pterocaulon sphacelatum, an Australian Aboriginal medicine

The antipicornaviral activity of an ethanolic extract of the green aerial parts of the Australian plant Pterocaulon sphacelatum (Labill.) Benth. & Hook. f. ex F. Muell. has been investigated. This plant has been a favoured traditional medicine, used for the treatment of colds by the Australian Aboriginal people. Antiviral activity-guided fractionation of the extract of P. sphacelatum using an inhibition of poliovirus-induced cytopathic effect assay, has yielded the antiviral flavonoid chrysosplenol C (3,7,3'-trimethoxy-5,6,4'-trihydroxyflavone). This compound is a 4'-hydroxy-3-methoxyflavone, one of a group of compounds known to be potent and specific inhibitors of picornaviral replication. These compounds inhibit the replication of rhinoviruses, the most frequent causative agent of the common cold. The coumarin 6,7,8-trimethoxycoumarin was also isolated from the ethanolic extract.     

Antimicrobial activity of some Ganoderma species from Nigeria

The crude n-hexane:diethyl ether, chloroform:acetone and methanol extracts of four species of Ganoderma (Ganoderma colossum (Fr.) C. F. Baker, G. resinaceum Boud., G. lucidum (cf.) (Curtis) P. Karst. and G. boninense (cf.) Pat.), from Nigeria, were tested for antimicrobial activity. The three solvent extracts of all the species of Ganoderma were active against Pseudomonas syringae and Bacillus subtilis, whereas none of the extracts were active against Cladosporium herbarum. Preliminary thin layer chromatography chemical tests on these extracts of Ganoderma showed that they contained compounds that stained blue-violet and blue or green when sprayed with anisaldehyde-sulphuric acid or Dragendorff, respectively. The profile of compounds in the extracts showed some variation among the four species.     

Chemical constituents and antimicrobial activity of medicinal plants from Ghana: Cassia sieberiana, Haematostaphis barteri, Mitragyna inermis and Pseudocedrela kotschyi

The antimicrobial activity of the sequential n-hexane, acetone and 50% aqueous methanol extracts of leaves, stem bark and roots of four species of medicinal plants, Cassia sieberiana DC. (Leguminosae), Haematostaphis barteri Hook. f. (Anacardiaceae), Mitragyna inermis (Willd.) O. Kuntze (Rubiaceae) and Pseudocedrela kotschyi (Schweinf.) Harms (Meliaceae), from Ghana were tested against Bacillus subtilis, Pseudomonas syringae and Cladosporium herbarum using TLC direct-autobiographic methods. Extracts from leaves, stem bark and roots of the four species gave a positive result against at least one test organism. Twelve of the 36 extracts were active against B. subtilis, four extracts were active against P. syringae and six were active against C. herbarum. Preliminary chemical analysis revealed the presence of flavonoids, stilbenes and alkaloids. This is the first report of a stilbene from the Anacardiaceae.     

Benzoic acid derivatives from Piper species and their fungitoxic activity against Cladosporium cladosporioides and C. sphaerospermum

Piper crassinervium, P. aduncum, P. hostmannianum, and P. gaudichaudianum contain the new benzoic acid derivatives crassinervic acid (1), aduncumene (8), hostmaniane (18), and gaudichaudianic acid (20), respectively, as major secondary metabolites. Additionally, 19 known compounds such as benzoic acids, chromenes, and flavonoids were isolated and identified. The antifungal activity of these compounds was evaluated by bioautographic TLC assay against Cladosporium cladosporioides and C. sphaerospermum.     

蒙药玉簪花的化学成分研究

 目的研究玉簪[Hosta plantaginea(Lam.)Aschers]花的化学成分。方法采用硅胶柱色谱,Sephadex LH-20柱色谱进行系统分离。通过理化性质和波谱学方法鉴定化合物结构。结果从体积分数95%乙醇提取物中分离得到了6个化合物,分别鉴定为正二十烷酸(Ⅰ),棕榈酸-α-单甘油酯(Ⅱ),山柰酚(Ⅲ),槲皮素(Ⅳ),山柰酚-3-O-芸香糖苷(Ⅴ),山柰酚-7-O-β-D-葡萄糖苷(Ⅵ)。结论6个化合物均为首次从该植物中得到。化合物Ⅰ,Ⅱ,Ⅲ,Ⅳ,Ⅵ为首次从该属植物中得到。     

Laxiflorolides A and B, epimeric bishomoditerpene lactones from Isodon eriocalyx

Laxiflorolides A (1) and B (2), two unprecedented epimeric bishomoditerpene lactones with a unique C(22) framework, along with laxiflorins P-R (3-5), maoecrystal P (6), maoecrystal C (7), and eriocalyxin B (8), were isolated from the leaves of I. eriocalyx var. laxiflora. The structures of 1 and 2, including the absolute configurations, were determined by spectroscopic methods and single-crystal X-ray diffraction analysis. All of the compounds isolated were evaluated for their cytotoxicity against five tumor cell lines. Compounds 3, 6, and 8 showed remarkable cytotoxic activity against certain cell lines compared with the positive control.     

Pochonins A-F,new antiviral and antiparasitic resorcylic acid lactones from Pochonia chlamydosporia var. catenulata

Monorden (1) and the novel resorcylic acid lactones pochonins A (2), B (4), C (6), D (7), and E (8) as well as tetrahydromonorden (5) and pseurotin A (22) were isolated from cultures of the clavicipitaceous hyphomycete Pochonia chlamydosporia var. catenulata strain P 0297. Fermentation of P 0297 in bromide-containing culture media led to a shift in secondary metabolite production and yielded monocillins III (3) and II (9) as major metabolites besides monorden (1) as well as the novel compounds pochonin F (10) and a monocillin II glycoside (11) as minor metabolites. Most of these compounds showed moderate activities in a cellular replication assay against Herpes Simplex Virus 1 (HSV1) and against the parasitic protozoan Eimeria tenella. In contrast to the structurally related zearalenone derivatives none of the metabolites of strain P 0297 were found to be active in a fluorescence polarization assay for determination of modulatory activities on the human estrogenic receptor ERbeta. Beta-zearalenol (17), but not zearalenone (15) and alpha-zearalenol (16), showed antiherpetic effects. We report the production, isolation, and structure elucidation of compounds 1-11 and their biological characterization.     

Antifungal amides from Piper scutifolium and Piper hoffmanseggianum

Chromatographic fractionation of a dichloromethane extract from the leaves of Piper scutifolium yielded two new isobutyl amides, scutifoliamide A ( 1) and scutifoliamide B ( 2), together with the known compounds piperolactam C ( 3), piperovatine ( 4), piperlonguminine ( 5), corcovadine ( 6), isopiperlonguminine ( 7), and isocorcovadine ( 8). From the dichloromethane extract from the leaves of P. hoffmannseggianum two new isobutyl amides, hoffmannseggiamide A ( 9) and hoffmannseggiamide B ( 10), were obtained together with the known compounds isopiperlonguminine ( 7) and isocorcovadine ( 8), sitosterol, and stigmasterol. The structures of the new compounds were established on the basis of spectroscopic data analysis. The inhibitory activity of compounds 1-10 against the growth of the fungi Cladosporium sphaerospermum and C. cladosporioides was determined by bioautography.     

Cinnamacrins A-C, cinnafragrin D, and cytostatic metabolites with alpha-glucosidase inhibitory activity from Cinnamosma macrocarpa

Two new monomeric and two new dimeric drimane sesquiterpenes, cinnamacrins A-C (1-3) and cinnafragrin D (4), along with bemadienolide (5), capsicodendrin (6), cinnamodial (7), cinnamolide (8), isopolygodial (9), and delta-tocotrienol (10), were isolated from Cinnamosma macrocarpa. The structures of the new compounds were determined by physical, chemical, and spectroscopic evidence. Capsicodendrin (6) and/or cinnamodial (7) are the major compounds in C. fragrans and C. macrocarpa, which are both widely used in Malagasy traditional medicine. The cytostatic activity as well as alpha-glucosidase inhibition and antiviral activities of the major constituents 6 and 7 and the compounds previously isolated from C. fragrans were evaluated.     

Macrolactins O-R, glycosylated 24-membered lactones from Bacillus sp. AH159-1

In the course of screening for inhibitors of Staphylococcus aureus peptide deformylase, four new glycosylated macrolactin compounds, macrolactins O ( 1), P ( 2), Q ( 3), and R ( 4), along with the known macrolactins B ( 5) and C ( 6), have been isolated from the liquid cultures of Bacillus sp. AH159-1. The structures of compounds 1- 4 were assigned on the basis of MS and NMR data. They inhibited S. aureus peptide deformylase and also showed antibacterial activity against Escherichia coli and Staphylococcus aureus.     

Comparison of fascaplysin and related alkaloids: a study of structures, cytotoxicities, and sources

The fascaplysin class of compounds have been further investigated from six organisms consisting of four sponge collections (Fascaplysinopsis reticulata) and two tunicate collections (Didemnum sp.). This work is an extension of an earlier communication and reports the isolation of 12 new fascaplysin derivatives: 10-bromofascaplysin (7), 3,10-dibromofascaplysin (8), homofascaplysate A (9), homofascaplysin B-1 (11), 3-bromohomofascaplysins B (12), B-1 (13), and C (15), 7,14-dibromoreticulatine (17), reticulatol (20), 14-bromoreticulatol (21), and 3-bromosecofascaplysins A (22) and B (23), along with known compounds: fascaplysin (1), reticulatine (4), 3-bromofascaplysin (6), and homofascaplysin C (14). Selected compounds were screened in a cell-based cytotoxicity assay with compounds 1, 6, and fascaplysin A (24) also screened in the NCI 60 cell line panel. A biogenetic pathway for the brominated fascaplysins and brominated related alkaloids is proposed and discussed.     

潞党参甾体类成分及其抗炎活性

目的 研究潞党参Codonopsis pilosula(Franch.)Nannf.甾体类成分及其抗炎活性.方法 潞党参甲醇提取物的分析采用硅胶、TLC进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构.采用脂多糖(LPS)诱导的RAW264.7细胞炎症模型进行体外抗炎活性评价.Griess法测定NO水平,酶联免...     

狗牙根化学成分的研究

目的研究狗牙根的化学成分。方法狗牙根95%乙醇提取物正丁醇部位采用MCI、Rp-C18、半制备HPLC进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。结果从中分离得到13个化合物,分别鉴定为monocerin (1)、绿原酸甲酯(2)、4-O-香豆酰基奎宁酸甲酯(3)、5-O-阿魏酰奎宁酸(4)、异血红酸(5)、麦芽酚-β-D-吡喃葡萄糖苷(6)、1, 4-二甲氧基吩嗪(7)、19α-羟基齐墩果酮酸(8)、3-羟基-1-(4-羟基-3,5-二甲氧基苯基)-2-[4-(3-羟基-1-(E)-丙烯基)-2,6-二甲氧基苯氧基]丙基-β-D-吡喃葡萄糖苷(9)、4,5-二咖啡酰基奎宁酸甲酯(10)、苯甲酸(11)、4-羟基-邻茴香醛(12)、阿替匹林C(13)。结论所有化合物均为首次从该植物中分离得到。     

Benzoic acid derivatives from Piper species and their antiparasitic activity

Piper glabratum and P. acutifolium were analyzed for their content of main secondary constituents, affording nine new benzoic acid derivatives (1, 2, 4, 5, 7, and 10-13), in addition to four known compounds (3, 6, 8, and 9). Their structures were elucidated on the basis of spectroscopic data. Riguera ester reactions and optical rotation measurements established the new compounds as racemates. In the search for antiparasitic agents, the compounds were evaluated in vitro against the promastigote forms of Leishmania spp., Trypanosoma cruzi, and Plasmodium falciparum. Among the evaluated compounds, methyl 3,4-dihydroxy-5-(3'-methyl-2'-butenyl)benzoate (7) exhibited leishmanicidal effect (IC50 13.8-18.5 microg/mL) against the three Leishmania strains used, and methyl 3,4-dihydroxy-5-(2-hydroxy-3-methylbutenyl)benzoate (1), methyl 4-hydroxy-3-(2-hydroxy-3-methyl-3-butenyl)benzoate (3), and methyl 3,4-dihydroxy-5-(3-methyl-2-butenyl) benzoate (7) showed significant trypanocidal activity, with IC50 values of 16.4, 15.6, and 18.5 microg/mL, respectively.     

Inhibition of Na(+)/K(+) -ATPase by antcins, unique steroid-like compounds in Antrodia camphorate

The inhibition of Na(+)/K(+) -ATPase by versatile steroid-like compounds contributes to the putative therapeutic effects of many Chinese medicinal cardiac products via the same molecular mechanism triggered by cardiac glycosides. Five major steroid-like compounds, antcin A, B, C, H, and K were isolated from Niuchangchih (Antrodia camphorata), a unique Taiwan mushroom, and all inhibited Na(+)/K(+) -ATPase. Antcin A exhibited significantly higher inhibitory potency than the other four antcins, though weaker than ginsenoside Rh2 . In contrast, cortisone (an analogous steroid with anti-inflammatory effects stronger than antcin A) showed no detectable inhibitory potency. Molecular modeling has shown that antcins bind to Na(+)/K(+) -ATPase with the steroidal skeleton structurally upside-down in comparison with ginsenoside Rh2 . The inhibitory potency of antcin A is attributed to steroidal hydrophobic interaction within the binding pocket and the formation of three hydrogen bonds between its carboxyl group and two cationic residues around the cavity entrance of Na(+)/K(+) -ATPase. The presence of an additional carbonyl or hydroxyl group at C7 of the other four antcins leads to severe repulsion in the hydrophobic pocket, and thus significantly reduces inhibitory potency. It is proposed that antcin A is a bi-functional compound that exerts anti-inflammatory effects and that enhances blood circulation via two different molecular mechanisms.     

Alvaradoins E-N, antitumor and cytotoxic anthracenone C-glycosides from the leaves of Alvaradoa haitiensis

Bioactivity-directed fractionation of an extract of the leaves of Alvaradoa haitiensis, using the KB (human oral epidermoid carcinoma) cell line, led to the isolation and identification of 10 new anthracenone C-glycosides, alvaradoins E-N (1-10), along with the known compound chrysophanol (11). The cytotoxicity of all compounds was evaluated, and preliminary structure-activity relationships are suggested. The most potent compounds in the in vitro assays (1 and 2) were evaluated in vivo versus the P388 (murine lymphocytic leukemia) model, and alvaradoin E (1) showed antileukemic activity (125% T/C) at a dose of 0.2 mg kg-1 per injection when administered intraperitoneally.     

Vasorelaxant activity of diterpenes from Croton zambesicus and synthetic trachylobanes and their structure-activity relationships

The diterpenes previously isolated from the leaves of Croton zambesicus were tested to evaluate their vasorelaxant activity on the Wistar rat aorta. Their vasorelaxant effect was compared to a series of synthetic trachylobanes and related polycyclic compounds on KCl- or noradrenaline-induced contractions in order to evaluate structure-activity relationships. We demonstrate the vasorelaxant properties of some pure trachylobane diterpenes at low concentration (IC50 < 10 microM) on KCl-induced contractions, but none have a significant effect in noradrenaline-induced contractions. Comparing structures and activity we observed that a C-14 carbonyl group associated with a C-15 hydroxy or ketone function or a C-3 carbonyl associated with a hydroxymethyl group plays an important role in the vasorelaxant activity of trachylobane diterpenes. We also observed that the absolute configuration or the cleavage of the C13-C16 cyclopropane bond does not have a marked effect on the activity. The cytotoxicity of all of these compounds has also been evaluated on HeLa cells in order to verify that the vasorelaxant activity was not correlated with general cytotoxicity.     

Microbial O-demethylation, hydroxylation, sulfation, and ribosylation of a xanthone derivative from Halenia elliptica

1-Hydroxy-2,3,5-trimethoxyxanthone (1), one of the major xanthone derivatives isolated from Halenia elliptica, was biotransformed by two fungi, Trichothecium roseum and Paecilomyces marquandii. Transformation of 1 by T. roseumgave 1,5-dihydroxy-2,3-dimethoxyxanthone (2), 5-O-sulfate-1-hydroxy-2,3-dimethoxyxanthone (3), 5-O-sulfate-1-hydroxy-2,3,7-trimethoxyxanthone (4), 5-O-beta-ribofuranosyl-1-hydroxy-2,3-dimethoxyxanthone (5), and 1,5,6-trihydroxy-2,3-dimethoxyxanthone (6). Compound 2 was also formed by P. marquandii. The structures of the isolated compounds were elucidated by spectroscopic analyses. Among the five microbial-converted compounds, 3, 4, 5, and 6 are new compounds.