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Article: The antimycobacterial constituents of dill (Anethum graveolens).

Stavri, Michael / Gibbons, Simon

2005 Volume 19, Issue 11, Page(s) 938–941

Abstract: As part of a project to characterize selected members of the Kuwaiti flora for their phytochemistry and antimycobacterial activity, a new furanocoumarin, 5-[4''-hydroxy-3''-methyl-2''-butenyloxy]-6,7-furocoumarin (3), was isolated from the whole herb of ... ...

Abstract	As part of a project to characterize selected members of the Kuwaiti flora for their phytochemistry and antimycobacterial activity, a new furanocoumarin, 5-[4''-hydroxy-3''-methyl-2''-butenyloxy]-6,7-furocoumarin (3), was isolated from the whole herb of Anethum graveolens. The known compounds oxypeucedanin (1), oxypeucedanin hydrate (2) and falcarindiol (4) were also isolated from this plant. The structure of each compound was determined by interpretation of NMR and mass spectrometric data. The three known compounds exhibited antibacterial activity against a panel of rapidly growing mycobacteria with minimum inhibitory concentration (MIC) values in the range 2-128 microg/mL.
MeSH term(s)	Anethum graveolens/chemistry ; Anti-Bacterial Agents/chemistry ; Anti-Bacterial Agents/isolation & purification ; Anti-Bacterial Agents/pharmacology ; Diynes ; Fatty Alcohols/chemistry ; Fatty Alcohols/isolation & purification ; Fatty Alcohols/pharmacology ; Furocoumarins/chemistry ; Furocoumarins/isolation & purification ; Furocoumarins/pharmacology ; Microbial Sensitivity Tests ; Molecular Structure ; Spectrum Analysis
Chemical Substances	5-(4''-hydroxy-3''-methyl-2''-butenyloxy)-6,7-furocoumarin ; Anti-Bacterial Agents ; Diynes ; Fatty Alcohols ; Furocoumarins ; falcarindiol (55297-87-5) ; oxypeucadanin (S1Y67F37PI)
Language	English
Publishing date	2005-11
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	639136-9
ISSN	1099-1573 ; 0951-418X
ISSN (online)	1099-1573
ISSN	0951-418X
DOI	10.1002/ptr.1758
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Article ; Online: Hydraphiles enhance antimicrobial potency against Escherichia coli, Pseudomonas aeruginosa, and Bacillus subtilis.

Patel, Mohit B / Garrad, Evan C / Stavri, Ariel / Gokel, Michael R / Negin, Saeedeh / Meisel, Joseph W / Cusumano, Zachary / Gokel, George W

Bioorganic & medicinal chemistry

2016 Volume 24, Issue 12, Page(s) 2864–2870

Abstract: Hydraphiles are synthetic amphiphiles that form ion-conducting pores in liposomal membranes. These pores exhibit open-close behavior when studied by planar bilayer conductance techniques. In previous work, we showed that when co-administered with various ...

Abstract	Hydraphiles are synthetic amphiphiles that form ion-conducting pores in liposomal membranes. These pores exhibit open-close behavior when studied by planar bilayer conductance techniques. In previous work, we showed that when co-administered with various antibiotics to the DH5α strain of Escherichia coli, they enhanced the drug's potency. We report here potency enhancements at low concentrations of hydraphiles for the structurally and mechanistically unrelated antibiotics erythromycin, kanamycin, rifampicin, and tetracycline against Gram negative E. coli (DH5α and K-12) and Pseudomonas aeruginosa, as well as Gram positive Bacillus subtilis. Earlier work suggested that potency increases correlated to ion transport function. The data presented here comport with the function of hydraphiles to enhance membrane permeability in addition to, or instead of, their known function as ion conductors.
MeSH term(s)	Anti-Bacterial Agents/pharmacokinetics ; Anti-Bacterial Agents/pharmacology ; Bacillus subtilis/drug effects ; Bacillus subtilis/metabolism ; Erythromycin/pharmacokinetics ; Erythromycin/pharmacology ; Escherichia coli/drug effects ; Escherichia coli/metabolism ; Escherichia coli Infections/drug therapy ; Humans ; Kanamycin/pharmacokinetics ; Kanamycin/pharmacology ; Microbial Sensitivity Tests ; Permeability/drug effects ; Pseudomonas Infections/drug therapy ; Pseudomonas aeruginosa/drug effects ; Pseudomonas aeruginosa/metabolism ; Rifampin/pharmacokinetics ; Rifampin/pharmacology ; Surface-Active Agents/chemistry ; Surface-Active Agents/pharmacology ; Tetracycline/pharmacokinetics ; Tetracycline/pharmacology
Chemical Substances	Anti-Bacterial Agents ; Surface-Active Agents ; Kanamycin (59-01-8) ; Erythromycin (63937KV33D) ; Tetracycline (F8VB5M810T) ; Rifampin (VJT6J7R4TR)
Language	English
Publishing date	2016-06-15
Publishing country	England
Document type	Journal Article
ZDB-ID	1161284-8
ISSN	1464-3391 ; 0968-0896
ISSN (online)	1464-3391
ISSN	0968-0896
DOI	10.1016/j.bmc.2016.04.058
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Article ; Online: Antimycobacterial polyacetylenes from Levisticum officinale.

Schinkovitz, Andreas / Stavri, Michael / Gibbons, Simon / Bucar, Franz

Phytotherapy research : PTR

2008 Volume 22, Issue 5, Page(s) 681–684

Abstract: No conflicts of interest concerning financial matters or personal relationships exist between the authors and those who might bias this work. The present work is in part included the PhD thesis of A. Schinkovitz (University of Graz) but has not been ... ...

Abstract	No conflicts of interest concerning financial matters or personal relationships exist between the authors and those who might bias this work. The present work is in part included the PhD thesis of A. Schinkovitz (University of Graz) but has not been published elsewhere previously. The dichloromethane extract of the roots of Levisticum officinale L. (Apiaceae) exhibited significant antimycobacterial activity against Mycobacterium fortuitum and Mycobacterium aurum in a microtiter plate dilution assay and was further analysed following a bioassay-guided fractionation strategy. 3(R)-Falcarinol (3(R)-(-)-1,9-heptadecadien-4,6-diin-3-ol] and 3(R)-8(S)-falcarindiol [3(R)-8(S)-(+)-1,9-heptadecadien-4,6-diin-3,8-diol] could be identified as the active components in this extract. The minimal inhibitory concentration (MIC) of 3(R)-falcarinol against M. fortuitum and M. aurum was 16.4 microM while that of 3(R)-8(S)-falcarindiol was 30.7 microM against M. fortuitum and 61.4 microm against M. aurum, respectively. Previously, 3(R),8(R)-dehydrofalcarindiol was isolated from Artemisia monosperma and surprisingly this polyacetylene exhibited no antimycobacterial activity at 128 microg/mL. This indicates that the terminal methyl group is vital for retention of antimycobacterial activity. Reference antibiotics ethambutol and isoniazid exhibited an activity of 115.5 microM and 14.6 microM against M. fortuitum, and 3.4 microM and 29.2 microM against M. aurum, respectively.
MeSH term(s)	Apiaceae/chemistry ; Diynes/chemistry ; Diynes/pharmacology ; Fatty Alcohols/chemistry ; Fatty Alcohols/pharmacology ; Methylene Chloride/chemistry ; Microbial Sensitivity Tests ; Molecular Structure ; Mycobacterium/drug effects ; Mycobacterium fortuitum/drug effects ; Plant Extracts/chemistry ; Plant Extracts/pharmacology ; Plant Roots/chemistry ; Polyacetylenes/chemistry ; Polyacetylenes/pharmacology
Chemical Substances	Diynes ; Fatty Alcohols ; Plant Extracts ; falcarinol (21852-80-2) ; Polyacetylenes (25067-58-7) ; falcarindiol (55297-87-5) ; Methylene Chloride (588X2YUY0A)
Language	English
Publishing date	2008-05
Publishing country	England
Document type	Journal Article
ZDB-ID	639136-9
ISSN	1099-1573 ; 0951-418X
ISSN (online)	1099-1573
ISSN	0951-418X
DOI	10.1002/ptr.2408
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Article: Bacterial efflux pump inhibitors from natural sources.

Stavri, Michael / Piddock, Laura J V / Gibbons, Simon

The Journal of antimicrobial chemotherapy

2007 Volume 59, Issue 6, Page(s) 1247–1260

Abstract: The rapid spread of bacteria expressing multidrug resistance (MDR) has necessitated the discovery of new antibacterials and resistance-modifying agents. Since the initial discovery of bacterial efflux pumps in the 1980s, many have been characterized in ... ...

Abstract	The rapid spread of bacteria expressing multidrug resistance (MDR) has necessitated the discovery of new antibacterials and resistance-modifying agents. Since the initial discovery of bacterial efflux pumps in the 1980s, many have been characterized in community- and hospital-acquired Gram-positive and Gram-negative pathogens, such as Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli and, more recently, in mycobacteria. Efflux pumps are able to extrude structurally diverse compounds, including antibiotics used in a clinical setting; the latter are rendered therapeutically ineffective. Antibiotic resistance can develop rapidly through changes in the expression of efflux pumps, including changes to some antibiotics considered to be drugs of last resort. It is therefore imperative that new antibiotics, resistance-modifying agents and, more specifically, efflux pump inhibitors (EPIs) are characterized. The use of bacterial resistance modifiers such as EPIs could facilitate the re-introduction of therapeutically ineffective antibiotics back into clinical use such as ciprofloxacin and might even suppress the emergence of MDR strains. Here we review the literature on bacterial EPIs derived from natural sources, primarily those from plants. The resistance-modifying activities of many new chemical classes of EPIs warrant further studies to assess their potential as leads for clinical development.
MeSH term(s)	ATP Binding Cassette Transporter, Sub-Family B/antagonists & inhibitors ; Animals ; Anti-Bacterial Agents/pharmacology ; Bacteria/genetics ; Bacteria/metabolism ; Biological Products/pharmacology ; Drug Evaluation, Preclinical ; Drug Synergism ; Fungi/drug effects ; Fungi/metabolism ; Humans ; Plants/chemistry
Chemical Substances	ATP Binding Cassette Transporter, Sub-Family B ; Anti-Bacterial Agents ; Biological Products
Language	English
Publishing date	2007-06
Publishing country	England
Document type	Journal Article ; Review
ZDB-ID	191709-2
ISSN	1460-2091 ; 0305-7453
ISSN (online)	1460-2091
ISSN	0305-7453
DOI	10.1093/jac/dkl460
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Article ; Online: Antibacterial diterpenes from Plectranthus ernstii.

Stavri, Michael / Paton, Alan / Skelton, Brian W / Gibbons, Simon

Journal of natural products

2009 Volume 72, Issue 6, Page(s) 1191–1194

Abstract: Three new diterpenoids including two pimaranes (1 and 2) and a labdane (3) were isolated from the whole herb of Plectranthus ernstii. The structures of these compounds were determined as rel-15(zeta),16-epoxy-7alpha-hydroxypimar-8,14-ene (1) and rel-15( ... ...

Abstract	Three new diterpenoids including two pimaranes (1 and 2) and a labdane (3) were isolated from the whole herb of Plectranthus ernstii. The structures of these compounds were determined as rel-15(zeta),16-epoxy-7alpha-hydroxypimar-8,14-ene (1) and rel-15(zeta),16-epoxy-7-oxopimar-8,14-ene (2), and compound 3 was elucidated as 1R,11S-dihydroxy-8R,13R-epoxylabd-14-ene on the basis of single-crystal X-ray structural analysis. Compound 1 exhibited moderate antistaphylococcal activity against a range of multidrug-resistant (MDR) and methicillin-resistant (MRSA) strains of Staphylococcus aureus with a minimum inhibitory concentration (MIC) of 32 microg/mL. All three diterpenes exhibited antimycobacterial activity against three strains of rapidly growing mycobacteria with MIC values ranging from 8 to 128 microg/mL.
MeSH term(s)	Anti-Bacterial Agents/chemistry ; Anti-Bacterial Agents/isolation & purification ; Anti-Bacterial Agents/pharmacology ; Crystallography, X-Ray ; Diterpenes/chemistry ; Diterpenes/isolation & purification ; Diterpenes/pharmacology ; Drug Resistance, Multiple/drug effects ; Methicillin-Resistant Staphylococcus aureus/drug effects ; Microbial Sensitivity Tests ; Molecular Conformation ; Molecular Structure ; Plectranthus/chemistry ; Stereoisomerism ; United Kingdom
Chemical Substances	Anti-Bacterial Agents ; Diterpenes ; labdane ; rel-15(zeta),16-epoxy-7alpha-hydroxypimar-8,14-ene
Language	English
Publishing date	2009-06
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/np800581s
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Article: Antimicrobial constituents of Scrophularia deserti.

Stavri, Michael / Mathew, K T / Gibbons, Simon

Phytochemistry

2006 Volume 67, Issue 14, Page(s) 1530–1533

Abstract: 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- ...

Abstract	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.
MeSH term(s)	Anti-Infective Agents/chemistry ; Anti-Infective Agents/isolation & purification ; Anti-Infective Agents/pharmacology ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Mycobacterium/drug effects ; Scrophularia/chemistry ; Staphylococcus aureus/drug effects
Chemical Substances	Anti-Infective Agents
Language	English
Publishing date	2006-07
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2006.05.011
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Article ; Audio / Video: Antibacterial Diterpenes from Plectranthus ernstii

Stavri, Michael / Paton, Alan / Skelton, Brian W / Gibbons, Simon

Journal of natural products. 2009 June 26, v. 72, no. 6

2009

Keywords	Plectranthus ; medicinal plants ; medicinal properties ; phytochemicals ; diterpenoids ; antibacterial properties ; chemical structure ; X-ray diffraction ; Staphylococcus aureus ; multiple drug resistance ; antibiotic resistance ; minimum inhibitory concentration ; Mycobacterium ; animal pathogenic bacteria ; ornamental plants ; nursery crops ; South Africa
Language	English
Dates of publication	2009-0626
Size	p. 1191-1194.
Document type	Article ; Audio / Video
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/np800581s
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Article: A categorization and analysis of the criticisms of Evidence-Based Medicine.

Cohen, Aaron Michael / Stavri, P Zoë / Hersh, William R

International journal of medical informatics

2004 Volume 73, Issue 1, Page(s) 35–43

Abstract: The major criticisms and limitations of Evidence-Based Medicine (EBM) appearing in the literature over the past decade can be summarized and categorized into five recurring themes. The themes include: reliance on empiricism, narrow definition of evidence, ...

Abstract	The major criticisms and limitations of Evidence-Based Medicine (EBM) appearing in the literature over the past decade can be summarized and categorized into five recurring themes. The themes include: reliance on empiricism, narrow definition of evidence, lack of evidence of efficacy, limited usefulness for individual patients, and threats to the autonomy of the doctor/patient relationship. Analysis of EBM according to these themes leads to the conclusion that EBM can be a useful tool, but has severe drawbacks when used in isolation in the practice of individual patient care. Modern medicine must strive to balance an extremely complex set of priorities. To be an effective aid in achieving this balance, the theory and practice of EBM must expand to include new methods of study design and integration, and must adapt to the needs of both patients and the health care system in order to provide patients with the best care at the lowest cost.
MeSH term(s)	Attitude to Health ; Decision Making ; Empirical Research ; Evidence-Based Medicine ; Health Services Research ; Humans ; Knowledge ; Philosophy, Medical ; Physician-Patient Relations ; Professional Autonomy
Language	English
Publishing date	2004-02
Publishing country	Ireland
Document type	Journal Article ; Research Support, U.S. Gov't, P.H.S. ; Review
ZDB-ID	1466296-6
ISSN	1872-8243 ; 1386-5056
ISSN (online)	1872-8243
ISSN	1386-5056
DOI	10.1016/j.ijmedinf.2003.11.002
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Article: Guaianolide sesquiterpenes from Pulicaria crispa (Forssk.) Oliv.

Stavri, Michael / Mathew, K T / Gordon, Andrew / Shnyder, Steven D / Falconer, Robert A / Gibbons, Simon

Phytochemistry

2008 Volume 69, Issue 9, Page(s) 1915–1918

Abstract: A phytochemical study of the asteraceous herb Pulicaria crispa (Forssk.) Oliv. resulted in the characterisation of three guaianolide sesquiterpenes, 2alpha,4alpha-dihydroxy-7alphaH,8alphaH,10alphaH-guaia-1(5),11(13)-dien-8beta,12-olide (1), 1alpha,2alpha- ...

Abstract	A phytochemical study of the asteraceous herb Pulicaria crispa (Forssk.) Oliv. resulted in the characterisation of three guaianolide sesquiterpenes, 2alpha,4alpha-dihydroxy-7alphaH,8alphaH,10alphaH-guaia-1(5),11(13)-dien-8beta,12-olide (1), 1alpha,2alpha-epoxy-4beta-hydroxy-5alphaH,7alphaH,8alphaH,10alphaH-guaia-11(13)-en-8beta,12-olide (2) and 5,10-epi-2,3-dihydroaromatin (3). The structures were assigned on the basis of extensive 1 and 2D NMR experiments. Compound 3 exhibited weak antimycobacterial activity against Mycobacterium phlei with a minimum inhibitory concentration of 0.52 mM and cytotoxicity (IC50 of 5.8+/-0.2 microM) in a human bladder carcinoma cell line, EJ-138.
MeSH term(s)	Magnetic Resonance Spectroscopy ; Molecular Structure ; Pulicaria/chemistry ; Sesquiterpenes, Guaiane/chemistry
Chemical Substances	Sesquiterpenes, Guaiane
Language	English
Publishing date	2008-06
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2008.03.012
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Article: Antimycobacterial polyacetylenes from Levisticum officinale

Schinkovitz, Andreas / Stavri, Michael / Gibbons, Simon / Bucar, Franz

Phytotherapy research. 2008 May, v. 22, no. 5

2008

Abstract	No conflicts of interest concerning financial matters or personal relationships exist between the authors and those who might bias this work. The present work is in part included the PhD thesis of A. Schinkovitz (University of Graz) but has not been published elsewhere previously.The dichloromethane extract of the roots of Levisticum officinale L. (Apiaceae) exhibited significant antimycobacterial activity against Mycobacterium fortuitum and Mycobacterium aurum in a microtiter plate dilution assay and was further analysed following a bioassay-guided fractionation strategy. 3(R)-Falcarinol (3(R)-(-)-1,9-heptadecadien-4,6-diin-3-ol] and 3(R)-8(S)-falcarindiol [3(R)-8(S)-(+)-1,9-heptadecadien-4,6-diin-3,8-diol] could be identified as the active components in this extract. The minimal inhibitory concentration (MIC) of 3(R)-falcarinol against M. fortuitum and M. aurum was 16.4 μm while that of 3(R)-8(S)-falcarindiol was 30.7 μm against M. fortuitum and 61.4 μm against M. aurum, respectively. Previously, 3(R),8(R)-dehydrofalcarindiol was isolated from Artemisia monosperma and surprisingly this polyacetylene exhibited no antimycobacterial activity at 128 μg/mL. This indicates that the terminal methyl group is vital for retention of antimycobacterial activity. Reference antibiotics ethambutol and isoniazid exhibited an activity of 115.5 μm and 14.6 μm against M. fortuitum, and 3.4 μm and 29.2 μm against M. aurum, respectively. Copyright © 2008 John Wiley & Sons, Ltd.
Keywords	Artemisia monosperma ; Levisticum officinale ; Mycobacterium aurum ; Mycobacterium fortuitum ; antibiotics ; fractionation ; isoniazid ; methylene chloride ; minimum inhibitory concentration ; polyacetylenes ; roots
Language	English
Dates of publication	2008-05
Size	p. 681-684.
Publishing place	John Wiley & Sons, Ltd.
Document type	Article
ZDB-ID	639136-9
ISSN	1099-1573 ; 0951-418X
ISSN (online)	1099-1573
ISSN	0951-418X
DOI	10.1002/ptr.2408
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