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Master's Dissertation
DOI
10.11606/D.46.1984.tde-02032011-153249
Document
Author
Full name
Massuo Jorge Kato
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 1984
Supervisor
Title in Portuguese
Policetídeos e lignóides do tegumento de virola elongata warb. (Myristicaceae)
Keywords in Portuguese
Fitoquímica
Lignanas
Policetídeos
Abstract in Portuguese
A presente dissertação descreve o isolamento e elucidação estrutural de alguns constituíntes químicos do tegumento de V. elongata, espécie envolvida em usos etnofarmacológicos. 0 extrato clorofórmico forneceu além de ésteres alifáticos e triglicerídeos dois policetídeos do tipo diarilalcanoílicos: 1-(2',6'- Dihidroxi-4'-metoxifeni1)-12-fenil-dodecan-1-ona (inédito) e 1-(2',4',6'- Trihidroxi-3',4'-dihidrofeni1)-11-fenil-undecan-1-ona (conhecido) ; três lignanas furofufurânicas: (1R,2S,5R,6R)-6-(3',4'-Dimetoxifeni1)-2-(3",4"-metilenodioxifeni1)-3,7-dioxabiciclo‌3.3.0‌ octano (fargesina); (1R,2S,5R,6R)-2,6-Bis-(3",4" -dimetoxifeni1)-3,7-dioxabiciclo- ‌3.3.0‌ octano (epieudesmina) e (1R,2S,5R,6S)-2,6-Bis-(3",4" -dimetoxifenil)-3,7-dioxabiciclo ‌3.3.0‌ octano (eudesmina); e duas neolignanas tetraidrofurânicas: (1S,2S,5R,6R)-1-Metil - 2-(3",4"-metilenodioxifeni1)-5-(α-hidroxi-3" 1,4'"-dimetoxibenzil)-tetraidrofurano (inédita) e (15,2S,5R,6R)-1-Metil-2-(3",4"-dimetoxifeni1)-5-(α-hidroxi-3'",4'"-dimetoxibenzil)-tetraidrofurano (magnostelina A). 0 isolamento dos constituíntes químicos foi baseada em técnicas cromatográficas e a elucidação estrutural em métodos espectrométricos usuais (UV, IV, DRO, RMN de 1H e de 13C). A comprovação da estrutura do policetídeo Ve-6 foi baseada na aromatização por desidratação em meio ácido. A determinação da configuração relativa das neolignanas tetreidrofurânicas foi baseada em estudo envolvendo o reagente de deslocamento Eu(fod)3. A determinação da configuração absoluta foi baseada na conversão em uma neolignana tetralínica e comparação de sua curva de DRO com compostos modêlos.
Title in English
Poliketides and lignoids of the Tegument from Virola elongata (Spr. ex Benth) Warb.
Keywords in English
Lignans
Phytochemistry
Poliketides
Abstract in English
The present dissertation describe isolation and structural elucidation of some chemicals constituents of tegument from V. elongata, involved in ethnopharmacology uses. The chloroform extract afford besides aliphatics esthers and triglycerides, two poliketides of the diarylalkanoyl type: 1-(2',6'-Dihydroxypheny1)-12-dodecan-l-one and 1-(2',4',6'-Trihydroxy-3',5'-dihydropheny1)-11-phenyl-undecan-1-one, the former is unknown and the latter is known; three furofuranic lignans type: (1R, 2S, 5R, 6R) -6- (3',4'-Dimethoxypheny1)-2-(3",4" -methylenedioxypheny1)-3,7-dioxabicycle‌3.3.0‌ octane (fargesin); (1R,2S,5R,6R)-2,6-Bis-(3",4"-dimethoxypheny1)-3,7-dioxabicycle‌3.3.0‌octane (epieudesmin) and (1R,2S,5R,6S)-2,6-Bis-(3",4" -dimethoxypheny1)-3,7-dioxabicycle‌3.3.0‌ octane (eudesmin); and two neolignans of the tetrahydrofuranic type:(1S,2S,5R,6R)-1-Methy1-2-(3",4" -methylenedioxypheny1)-5-(α-hydroxy-3'",4'" -dimethoxybenzy1)-tetrahydrofuran (unknow) and (1S,2S,5R,6R)-1-Methy1-2-(3",4" -dimethoxypheni1)-5-(α-hydroxy-3'",4'"-dimethoxybenzy1)-tetrahydrofuran (magnostelin A). Isolation of chemical constituents was based on chromatographic techniques and structural determination on usual spectrometric methods (UV, IR, MS, ORD, 1H and 13C NMR). Poliketyde skeleton was elucidated by acid catalized dehydration yielding a diarylic compound. The relative structure of tetrahydrofuranic neolignans was based in lanthanide induced shift reagent. The absolute configuration was based on chemical transformation to tetralinic neolignan and comparison of its ORD curve with model compounds curves.
 
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Publishing Date
2011-03-02
 
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