Structural and synthetic studies of bioactive natural products

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dc.contributor.authorHeltzel, Carl E.en
dc.contributor.committeechairKingston, David G. I.en
dc.contributor.committeememberBell, Harold M.en
dc.contributor.committeememberCastagnoli, Neal Jr.en
dc.contributor.committeememberMerola, Joseph S.en
dc.contributor.committeememberTaylor, Larry T.en
dc.contributor.departmentChemistryen
dc.date.accessioned2014-03-14T21:21:55Zen
dc.date.adate2005-10-21en
dc.date.available2014-03-14T21:21:55Zen
dc.date.issued1993-10-26en
dc.date.rdate2005-10-21en
dc.date.sdate2005-10-21en
dc.description.abstractBioassay directed fractionation of the methyl ethyl ketone extract of Crescentia cujete resulted in the isolation of nine bioactive compounds, and detailed spectroscopic interpretation led to the assignment of their structures as (2S,3S)-3-hydroxy-5,6-dimethoxy dehydroiso-α-Iapachone [2.10], (2R)-5,6- dimethoxydehydroiso-α-Iapachone [2.11], (2R)-5-methoxy dehydroiso-alapachone [2.12], 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b ]furan-4,9-dione [2.13], 2-(1 '-hydroxyethyl)naphtho[2,3-b ]furan-4,9-dione [2.14]' 2-isopropenylnaphtho[ 2,3-b ]furan-4,9-dione [2.15], 5-hydroxydehydro-iso-a-Iapachone [2.16], 3-hydroxymethylfuro[3,2-b ]naphtho[2,3-d]furan-5,10-dione [2.17], and 9- hydroxy-3-hydroxymethylfuro[3,2-b ]naphtho[2,3-d]furan-5,10-dione [2.18]. Compounds 2.10-2.12 are new, showing selective activity towards DNA repair-deficient yeast mutants. The selective DNA damaging activity of known compounds 2.13-2.16 is reported herein for the first time. Compounds 2.17 and 2.18 also show DNA damaging activity, and possess a novel fused ring system. The bioactive sterols ergosta-5-24(28)-diene-3β,7α-diol [3.1] and 24,28- epoxyergost-5-ene-3β,7α-diol [3.2], originally isolated from <i>Pseudobersama mossambicensis</i>, have been synthesized from stigmasterol. In addition to these sterols, some of their analogs were prepared, and the bioactivity of all compounds were assessed.en
dc.description.degreePh. D.en
dc.format.extentxii, 148 leavesen
dc.format.mediumBTDen
dc.format.mimetypeapplication/pdfen
dc.identifier.otheretd-10212005-123005en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-10212005-123005/en
dc.identifier.urihttp://hdl.handle.net/10919/40067en
dc.language.isoenen
dc.publisherVirginia Techen
dc.relation.haspartLD5655.V856_1993.H459.pdfen
dc.relation.isformatofOCLC# 30698161en
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subject.lccLD5655.V856 1993.H459en
dc.subject.lcshPlant bioactive compoundsen
dc.titleStructural and synthetic studies of bioactive natural productsen
dc.typeDissertationen
dc.type.dcmitypeTexten
thesis.degree.disciplineChemistryen
thesis.degree.grantorVirginia Polytechnic Institute and State Universityen
thesis.degree.leveldoctoralen
thesis.degree.namePh. D.en

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