ABSTRACT
From the roots of Saliva caespitosa Montbret and Aucher ex. Bentham a new diterpene 6beta-hydroxyisopimaric acid (1) has been isolated together with four known diterpenes, one new triterpenoid, 3-acetylvergatic acid (2), as well as five known triterpenoids, two steroids and a flavone. The structures of the compounds were established by spectroscopic analyses. The isolated compounds were tested against standard bacterial strains. Only the new diterpene, 6beta-hydroxyisopimaric acid has strong activity (MIC 9 microg/ml) against S. aureus and (MIC 18 microg/ml) against S. epidermidis as well as against B. subtilis (MIC 9 microg/ml).
Subject(s)
Anti-Bacterial Agents/isolation & purification , Diterpenes/isolation & purification , Plants, Medicinal/chemistry , Salvia/chemistry , Steroids , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Bacillus subtilis/drug effects , Chromatography, Thin Layer , Diterpenes/chemistry , Diterpenes/pharmacology , Flavonoids/chemistry , Flavonoids/isolation & purification , Flavonoids/pharmacology , Microbial Sensitivity Tests , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Oxidation-Reduction , Plant Roots/chemistry , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , Staphylococcus aureus/drug effects , Staphylococcus epidermidis/drug effects , Steroids/chemistry , Steroids/isolation & purification , Steroids/pharmacology , Triterpenes/chemistry , Triterpenes/isolation & purification , Triterpenes/pharmacology , TurkeyABSTRACT
Three new diterpenes, salviviridinol, viridinol, viridone, five known diterpenes, sugiol, 1-oxoferruginol, ferruginol, aethiopinone and microstegiol, abietane and rearranged abietane diterpenes were isolated from the roots of Salvia viridis. These compounds were assayed against S. aureus ATCC 6538 P, E. coli ATCC 8739, P. mirabilis ATCC 14153, K. pneumonia ATCC 4352, P. aeruginosa ATCC 27853, S. epidermidis ATCC 12228, E. faecalis ATCC 29212 and a yeast C. albicans ATCC 10231. 1-Oxoferruginol showed activity against B. subtilis, S. aureus, S. epidermidis and a modest activity against P. mirabilis, migrostegiol had a little activity against B. subtilis. The structures of the compounds were established by 1D and 2D NMR spectroscopic techniques.
Subject(s)
Anti-Infective Agents/isolation & purification , Diterpenes/isolation & purification , Plants/chemistry , Anti-Bacterial Agents , Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Candida albicans/drug effects , Diterpenes/chemistry , Diterpenes/pharmacology , Gammaproteobacteria/drug effects , Gram-Positive Bacteria/drug effects , Microbial Sensitivity Tests , Plant Roots/chemistryABSTRACT
The roots of Ononis spinosa subsp. leiosperma (Leguminosae) afforded a new glycoside, spinonin (1), possessing a novel skeleton, in addition to the known isoflavonoid glycoside, ononin [7beta-(glucosyloxy)formononetin] (2) and the known pterocarpan, 7-demethoxy-7-D-(glucosyloxy)homopterocarpin (3). The structure of the new isolate was elucidated by spectral methods including 1H and 13C NMR, COSY, APT, HETCOR, HMBC, NOESY, CD, FABMS, HRMS, EIMS, CIMS, and some chemical reactions. Spinonin was inactive against a number of human cancer cell lines and HIV-1 reverse transcriptase. The compounds 1 and 3 showed weak activity against Pseudomonas aeruginosa, whereas 2 was active against beta-hemolytic Streptococcus.
Subject(s)
Anti-Bacterial Agents/isolation & purification , Antineoplastic Agents, Phytogenic/isolation & purification , Glucosides/isolation & purification , HIV Reverse Transcriptase/metabolism , Phenols/isolation & purification , Reverse Transcriptase Inhibitors/isolation & purification , Acetylation , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Bacteria/drug effects , Drug Screening Assays, Antitumor , Glucosides/chemistry , Glucosides/pharmacology , Humans , Hydrolysis , Methylation , Microbial Sensitivity Tests , Phenols/chemistry , Phenols/pharmacology , Reverse Transcriptase Inhibitors/chemistry , Reverse Transcriptase Inhibitors/pharmacology , Tumor Cells, CulturedABSTRACT
Ten sesquiterpene lactones and one sesquiterpene isolated from Tanacetum praeteritum subsp. praeteritum: 1 alpha, 6 alpha -dihydroxyisocostic acid methyl ester (2), 1 alpha-hydroxy-1-deoxoarglanine (3), douglanin (5), santamarin (6), reynosin (7), 1-epitatridin B (8), ludovicin A (10), armexin (12), armefolin (13), armexifolin (14), and 3 alpha-hydroxyreynosin (15) were tested against the human lung carcinoma cell line GLC4 and the colorectal cancer cell line COLO 320 as well as against the bacteria Bacillus subtilis, Staphylococcus aureus, Proteus mirabilis, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Enterococcus, beta-hemolytic Streptococcus, and the yeast Candida albicans. In addition, two germacranolides tatridin A (16) and tamirin (17) were included in the study. All compounds showed cytotoxic activity (IC50 = 124 microM) but most of them were not effective in the antimicrobial tests.
Subject(s)
Anti-Infective Agents/pharmacology , Antineoplastic Agents, Phytogenic/pharmacology , Bacteria/drug effects , Cell Survival/drug effects , Plants, Medicinal , Sesquiterpenes/pharmacology , Anti-Bacterial Agents , Anti-Infective Agents/isolation & purification , Antineoplastic Agents, Phytogenic/isolation & purification , Candida albicans/drug effects , Carcinoma, Small Cell , Cell Line , Colorectal Neoplasms , Humans , Lactones , Lung Neoplasms , Microbial Sensitivity Tests , Plant Extracts , Sesquiterpenes/isolation & purification , Tumor Cells, CulturedABSTRACT
From the roots of Salvia forskahlei a new diterpenoid, forskalinone, two new aromatic compounds, the octanol esters of cis- and trans-4-O-methyl-caffeic acid dimers, were isolated together with the known compounds stigmast-3-one, sitosterol and alpha-amyrin. The structures of the new and the known compounds were established by spectral data. The antimicrobial activity of forskalinone and the dimeric cinnamic acid esters was tested against standard bacterial strains and a yeast, namely Bacillus subtilis ATCC 6633, Staphylococcus aureus 6538P, S. epidermidis ATCC 12228, Proteus mirabilis ATCC 14153, Escherichia coli ATCC 8739, Klebsiella pneumonia ATC 4352, Pseudomonus aeruginosa ATCC 9027, Enterococcus faecalis ATCC 29212, beta-haemolytic Streptococcus and Candida albicans ATCC 10231. Forskalinone showed moderate resistance against S. epidermidis (670 micrograms ml-1) and slight activity against E. faecalis (168 micrograms ml-1). trans-4-O-Methyl-caffeic acid dimer octanol ester was inactive while the cis isomer showed a slight activity against C. albicans (156 micrograms ml-1).
Subject(s)
Anti-Infective Agents/chemistry , Bacteria/drug effects , Diterpenes/chemistry , Phenols/chemistry , Plants, Medicinal , Anti-Bacterial Agents , Anti-Infective Agents/isolation & purification , Anti-Infective Agents/pharmacology , Bacillus subtilis/drug effects , Candida albicans/drug effects , Diterpenes/isolation & purification , Diterpenes/pharmacology , Enterococcus faecalis/drug effects , Escherichia coli/drug effects , Klebsiella pneumoniae/drug effects , Microbial Sensitivity Tests , Phenols/isolation & purification , Phenols/pharmacology , Plant Roots , Proteus mirabilis/drug effects , Pseudomonas aeruginosa/drug effects , Staphylococcus aureus/drug effects , Staphylococcus epidermidis/drug effects , Streptococcus agalactiae/drug effectsABSTRACT
From an acetone extract of the whole plant Salvia sclarea, seven known diterpenes, sclareol, manool, salvipisone, ferruginol, microstegiol, candidissiol and 7-oxoroyleanone, and two new ones, 2,3-dehydrosalvipisone and 7-oxoferruginol-18-al, as well as two sesquiterpenes, caryophyllene oxide and spathulenol, alpha-amyrin, beta-sitosterol and the flavonoids apigenin, luteolin, 4'-methylapigenin, 6-hydroxyluteolin-6, 7,3',4'-tetramethyl ether, 6-hydroxy apigenin-7,4'-dimethyl ether were obtained. The diterpenoids and the sesquiterpenoids were tested for antimicrobial activity against standard bacterial strains and a yeast. 2,3-Dehydrosalvipisone, sclareol, manool, 7-oxoroyleanone, spathulenol and caryophyllene oxide were found to be active against Staphylococcus aureus, the first and third compound against Candida albicans and the last compound against Proteus mirabilis.
