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dc.contributor.advisorHoffmann, Joseph J.en_US
dc.contributor.authorDentali, Steven John.en_US
dc.creatorDentali, Steven John.en_US
dc.date.accessioned2011-10-31T17:40:10Z
dc.date.available2011-10-31T17:40:10Z
dc.date.issued1991en_US
dc.identifier.urihttp://hdl.handle.net/10150/185511
dc.description.abstractThe dichloromethane extracts of twelve US Southwestern herbal remedies were tested against Staphylococcus aureus (9-29 UA), Bacillus subtilis (2-27 UA), Klebsiella pneumoniae (3-9 UA), and Candida brassicae (IFO 1664) in an agar dilution-streak bioassay at 1000 μg/ml. All twelve plants inhibited the growth of B. subtilis. Anemopsis californica, Berberis fendleri, Cacalia decomposita, and Eriodictyon angustifolium inhibited the growth of at least two organisms. Salvia apiana was the only plant in this study to completely inhibit the growth of all four test organisms. After a literature search led to the elimination of A. californica, B. fendleri, and C. decomposita from further study due to reports of their bioactive compounds, Eriodictyon angustifolium Nutt. and Salvia apiana Jeps. were subjected to a detailed bioassay directed chemical investigation. Compounds were isolated by solvent extraction, fractionation and standard chromatographic techniques. They were identified by infrared, mass, and nuclear magnetic resonance spectral analyses, comparison with published spectra and comparison with authentic samples when available. Benzyl-trans-4-coumarate was isolated from E. angustifolium following high performance reverse phase liquid chromatography and subsequently synthesized through the condensation of p-coumaric acid and benzyl alcohol. Estimated at 2.9% of the dichloromethane extract, benzylcoumarate was active against S. aureus (100 μg/ml), B. subtilis (50 μg/ml), and C. albicans (25 μg/ml). Also isolated from E. angustifolium were five flavanones: 4',5,7-trihydroxy-flavanone (naringenin), 4',5-dihydroxy-7-methoxy-flavanone (sakuranetin), 3'-methoxy-4', 5',7-trihydroxy-flavanone (homoeriodictyol), 4',5-dihydroxy-3',7-dimethoxy-flavanone, and 5,7-dihydroxy-3',4'-dimethoxy-flavanone. The dichloromethane extract of S. apiana gave an acid fraction from which the abietane diterpenes carnosic acid and its 16-hydroxy derivative were isolated as their methyl ester acetates. Unstable as free carboxylic acids, these compounds retained activity after methylation but lost activity upon acetylation. Methylation without prior acetylation lead to the formation of 11-methoxy-methylcarnosate, 12-methoxy-methylcarnosate, 16-hydroxy-methylcarnosate, 16-hydroxy-11-methoxy-methylcarnosate, 16-hydroxy-12-methoxy-methylcarnosate, and 11,12-dimethoxy-16-hydroxy-methylcarnosate. At 500 μg/ml 12-methoxy-methylcarnosate was inactive while 16-hydroxy-12-methoxy-methylcarnosate was active against S. aureus, B. subtilis, and C. albicans at 250 μg/ml. From this result it was inferred that the introduction of a 16-hydroxy group increased the bioactivity of carnosic acid.
dc.language.isoenen_US
dc.publisherThe University of Arizona.en_US
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en_US
dc.subjectDissertations, Academicen_US
dc.subjectPharmaceutical chemistry.en_US
dc.titlePotential antiinfective agents from Eriodictyon angustifolium Nutt. and Salvia apiana Jeps.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.identifier.oclc710856344en_US
thesis.degree.grantorUniversity of Arizonaen_US
thesis.degree.leveldoctoralen_US
dc.contributor.committeememberMartin, Arnold R.
dc.contributor.committeememberTimmermann, Barbara
dc.identifier.proquest9136843en_US
thesis.degree.disciplinePharmaceutical Sciencesen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.namePh.D.en_US
refterms.dateFOA2018-05-29T11:45:48Z
html.description.abstractThe dichloromethane extracts of twelve US Southwestern herbal remedies were tested against Staphylococcus aureus (9-29 UA), Bacillus subtilis (2-27 UA), Klebsiella pneumoniae (3-9 UA), and Candida brassicae (IFO 1664) in an agar dilution-streak bioassay at 1000 μg/ml. All twelve plants inhibited the growth of B. subtilis. Anemopsis californica, Berberis fendleri, Cacalia decomposita, and Eriodictyon angustifolium inhibited the growth of at least two organisms. Salvia apiana was the only plant in this study to completely inhibit the growth of all four test organisms. After a literature search led to the elimination of A. californica, B. fendleri, and C. decomposita from further study due to reports of their bioactive compounds, Eriodictyon angustifolium Nutt. and Salvia apiana Jeps. were subjected to a detailed bioassay directed chemical investigation. Compounds were isolated by solvent extraction, fractionation and standard chromatographic techniques. They were identified by infrared, mass, and nuclear magnetic resonance spectral analyses, comparison with published spectra and comparison with authentic samples when available. Benzyl-trans-4-coumarate was isolated from E. angustifolium following high performance reverse phase liquid chromatography and subsequently synthesized through the condensation of p-coumaric acid and benzyl alcohol. Estimated at 2.9% of the dichloromethane extract, benzylcoumarate was active against S. aureus (100 μg/ml), B. subtilis (50 μg/ml), and C. albicans (25 μg/ml). Also isolated from E. angustifolium were five flavanones: 4',5,7-trihydroxy-flavanone (naringenin), 4',5-dihydroxy-7-methoxy-flavanone (sakuranetin), 3'-methoxy-4', 5',7-trihydroxy-flavanone (homoeriodictyol), 4',5-dihydroxy-3',7-dimethoxy-flavanone, and 5,7-dihydroxy-3',4'-dimethoxy-flavanone. The dichloromethane extract of S. apiana gave an acid fraction from which the abietane diterpenes carnosic acid and its 16-hydroxy derivative were isolated as their methyl ester acetates. Unstable as free carboxylic acids, these compounds retained activity after methylation but lost activity upon acetylation. Methylation without prior acetylation lead to the formation of 11-methoxy-methylcarnosate, 12-methoxy-methylcarnosate, 16-hydroxy-methylcarnosate, 16-hydroxy-11-methoxy-methylcarnosate, 16-hydroxy-12-methoxy-methylcarnosate, and 11,12-dimethoxy-16-hydroxy-methylcarnosate. At 500 μg/ml 12-methoxy-methylcarnosate was inactive while 16-hydroxy-12-methoxy-methylcarnosate was active against S. aureus, B. subtilis, and C. albicans at 250 μg/ml. From this result it was inferred that the introduction of a 16-hydroxy group increased the bioactivity of carnosic acid.


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