Bioprospecting, chemical investigations and drug discovery from Chilean plants

Persistent Link:
http://hdl.handle.net/10150/284167
Title:
Bioprospecting, chemical investigations and drug discovery from Chilean plants
Author:
Flagg, Melissa L.
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, completed as part of an International Cooperative Biodiversity Group (ICBG) Program, encompasses the field collection, taxonomic determination, bioassay-guided isolation, and chemical characterization of three plants native to Chile, each of which was collected using a distinct collection approach. Chuquiraga ulicina ssp. ulicina , collected by the ecological or environmental strategy, yielded ten compounds including four novel taraxastane-type triterpenoids, 3β-acetoxy-6β-hydroxytaraxasta-20-ene (1), 6β-hydroxytaraxast-20-en-3-one (2), 6β-hydroxytaraxasta-20-ene 3β-palmitate (3), and 3β, 6β-dihydroxytaraxasta-20-ene (4), together with the known triterpenoids lupeol (5), lupenyl acetate (6), lupenone (7), friedelinol ( 8), 3β-acetoxy-30-nor-lupan-20-one (9), and 30-norlupan-3β-ol-20-one (10). Lupeol (5) was the only compound to show antitubercular activity. Sphacele salviae, collected by the ethnobotanical or ethnomedical approach, allowed the isolation of three known compounds, including the two abietane diterpenoids carnosol ( 11) and rosmadial (12), as well as one pentacyclic triterpenoid, ursolic acid (13). Greigia sphacelata, collected according to the random approach, afforded nine compounds. These include the two novel flavanones 5,7,3'-trihydroxy-6,4' ,5'-trimethoxy flavanone (14) and 5,3'-dihydroxy-6,7,4',5 '-tetramethoxy flavanone (15), as well as four known phenylpropanoids, 1,3-O-di-trans-p-coumaroylglycerol (16), 1-O-trans-cournaroylglycerol (17 ), 1-(ω-feruloyldocosanoyl)glycerol and 1-(ω-feruloyltetracosanoyl)glycerol (18), and trans-ferulic acid 22-hydroxy docosanoic acid ester (19), and three known pentacyclic triterpenoids, arborinone (20), arborinol (21), and isoarborinol (22).
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Chemistry, Pharmaceutical.; Health Sciences, Pharmacy.
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.titleBioprospecting, chemical investigations and drug discovery from Chilean plantsen_US
dc.creatorFlagg, Melissa L.en_US
dc.contributor.authorFlagg, Melissa L.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, completed as part of an International Cooperative Biodiversity Group (ICBG) Program, encompasses the field collection, taxonomic determination, bioassay-guided isolation, and chemical characterization of three plants native to Chile, each of which was collected using a distinct collection approach. Chuquiraga ulicina ssp. ulicina , collected by the ecological or environmental strategy, yielded ten compounds including four novel taraxastane-type triterpenoids, 3β-acetoxy-6β-hydroxytaraxasta-20-ene (1), 6β-hydroxytaraxast-20-en-3-one (2), 6β-hydroxytaraxasta-20-ene 3β-palmitate (3), and 3β, 6β-dihydroxytaraxasta-20-ene (4), together with the known triterpenoids lupeol (5), lupenyl acetate (6), lupenone (7), friedelinol ( 8), 3β-acetoxy-30-nor-lupan-20-one (9), and 30-norlupan-3β-ol-20-one (10). Lupeol (5) was the only compound to show antitubercular activity. Sphacele salviae, collected by the ethnobotanical or ethnomedical approach, allowed the isolation of three known compounds, including the two abietane diterpenoids carnosol ( 11) and rosmadial (12), as well as one pentacyclic triterpenoid, ursolic acid (13). Greigia sphacelata, collected according to the random approach, afforded nine compounds. These include the two novel flavanones 5,7,3'-trihydroxy-6,4' ,5'-trimethoxy flavanone (14) and 5,3'-dihydroxy-6,7,4',5 '-tetramethoxy flavanone (15), as well as four known phenylpropanoids, 1,3-O-di-trans-p-coumaroylglycerol (16), 1-O-trans-cournaroylglycerol (17 ), 1-(ω-feruloyldocosanoyl)glycerol and 1-(ω-feruloyltetracosanoyl)glycerol (18), and trans-ferulic acid 22-hydroxy docosanoic acid ester (19), and three known pentacyclic triterpenoids, arborinone (20), arborinol (21), and isoarborinol (22).en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectChemistry, Pharmaceutical.en_US
dc.subjectHealth Sciences, Pharmacy.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.proquest9972115en_US
dc.identifier.bibrecord.b40640541en_US
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