Chemical investigations of South American plants: Applications to drug discovery, biodiversity conservation and economic development

Persistent Link:
http://hdl.handle.net/10150/279829
Title:
Chemical investigations of South American plants: Applications to drug discovery, biodiversity conservation and economic development
Author:
Caldwell, Colby G.
Issue Date:
2000
Publisher:
The University of Arizona.
Rights:
Copyright © 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.
Abstract:
This dissertation describes chemical investigations involving 11 Argentinean plant species and a sample of Chilean propolis. In total, 18 known and four novel compounds were isolated and identified. The compounds were tested in various antimicrobial assays. Three novel triterpenes, 3,4- seco-olean-12-en-3,28-dioic acid (4), 3alpha,-hydroxyolean-11-en-28,13 beta-olide (5), and 3alpha-hydroxyolean-11:13(18)-dien-28-oic acid ( 6) were isolated from the aerial parts of the Argentinean shrub, Junellia tridens (Lag.) Mold. (Verbenaceae). Another five compounds, oleanolic acid (1), oleanonic acid (2) and epioleanolic acid (3), all biosynthetically related to the three new oleananes, as well as epibetulinic acid (7) and sitosterol (8), were also isolated. LC-MS data are provided on the occurrence of these triterpenes in six other species of Junellia. We report the minimum inhibitory concentrations (MICs) of compounds 1--8 against Mycobacterium tuberculosis, and conclude that they are responsible for the antitubercular activity originally observed in the crude plant extract. Four other plants showing preliminary antitubercular activity were also investigated. The EtOAc extracts of Acantholippia seriphioides and Adesmia ameghinoi contained oleanolic acid (1) as their main constituent. The organic soluble portions of Chiliotrichium diffusum and Lathyrus magellanicus contained large amounts of ursolic acid (12) and sitosterol (8), respectively. Bioassay of the predominant compounds in these plants indicated that triterpenes were responsible for the antitubercular activity observed in the crude extracts. Fractionation of propolis (a product of honey beehives) from Colliguay in Central Chile led to the isolation, identification and bioassay of a novel gamma-lactone (14), five flavonoids (15--19), two diarylheptanoids (20--21), and a prenylated coumarin (22). All structures were elucidated primarily by 1D and 2D NMR and mass spectrometry. Based on the traditional use of propolis as an antimicrobial agent, the bioactivity of the purified compounds was determined against Staphylococcus aureus, Escherichia coli, Enterococcus faecium, and Candida albicans . Microscopic analysis of pollen present in the propolis provided clues to its botanical origins.
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Chemistry, Organic.; Chemistry, Pharmaceutical.
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Graduate College; Pharmaceutical Sciences
Degree Grantor:
University of Arizona
Advisor:
Timmermann, Barbara N.

Full metadata record

DC FieldValue Language
dc.language.isoen_USen_US
dc.titleChemical investigations of South American plants: Applications to drug discovery, biodiversity conservation and economic developmenten_US
dc.creatorCaldwell, Colby G.en_US
dc.contributor.authorCaldwell, Colby G.en_US
dc.date.issued2000en_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.description.abstractThis dissertation describes chemical investigations involving 11 Argentinean plant species and a sample of Chilean propolis. In total, 18 known and four novel compounds were isolated and identified. The compounds were tested in various antimicrobial assays. Three novel triterpenes, 3,4- seco-olean-12-en-3,28-dioic acid (4), 3alpha,-hydroxyolean-11-en-28,13 beta-olide (5), and 3alpha-hydroxyolean-11:13(18)-dien-28-oic acid ( 6) were isolated from the aerial parts of the Argentinean shrub, Junellia tridens (Lag.) Mold. (Verbenaceae). Another five compounds, oleanolic acid (1), oleanonic acid (2) and epioleanolic acid (3), all biosynthetically related to the three new oleananes, as well as epibetulinic acid (7) and sitosterol (8), were also isolated. LC-MS data are provided on the occurrence of these triterpenes in six other species of Junellia. We report the minimum inhibitory concentrations (MICs) of compounds 1--8 against Mycobacterium tuberculosis, and conclude that they are responsible for the antitubercular activity originally observed in the crude plant extract. Four other plants showing preliminary antitubercular activity were also investigated. The EtOAc extracts of Acantholippia seriphioides and Adesmia ameghinoi contained oleanolic acid (1) as their main constituent. The organic soluble portions of Chiliotrichium diffusum and Lathyrus magellanicus contained large amounts of ursolic acid (12) and sitosterol (8), respectively. Bioassay of the predominant compounds in these plants indicated that triterpenes were responsible for the antitubercular activity observed in the crude extracts. Fractionation of propolis (a product of honey beehives) from Colliguay in Central Chile led to the isolation, identification and bioassay of a novel gamma-lactone (14), five flavonoids (15--19), two diarylheptanoids (20--21), and a prenylated coumarin (22). All structures were elucidated primarily by 1D and 2D NMR and mass spectrometry. Based on the traditional use of propolis as an antimicrobial agent, the bioactivity of the purified compounds was determined against Staphylococcus aureus, Escherichia coli, Enterococcus faecium, and Candida albicans . Microscopic analysis of pollen present in the propolis provided clues to its botanical origins.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectChemistry, Organic.en_US
dc.subjectChemistry, Pharmaceutical.en_US
thesis.degree.namePh.D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.disciplinePharmaceutical Sciencesen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.advisorTimmermann, Barbara N.en_US
dc.identifier.proquest3002527en_US
dc.identifier.bibrecord.b41426885en_US
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