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Estudo metabolômico e proteômico em Peperomia blanda (Piperaceae)

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felippe_lg_me_araiq.pdf: 3785380 bytes, checksum: 174ccb573abb8592b9fe951b97fda87c (MD5) / Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) / Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) / O estudo químico das partes aéreas de Peperomia blanda resultou no isolamento de quinze substâncias, incluindo cinco lignanas tetraidrofurâncias (rel-(7R,8S,7’S,8’S)- 4,5,4’,5’-dimetilenodioxi-3,3’-dimetoxi-7,7’-epoxilignana, rel-(7R,8S,7’S,8’S)-4’,5’- metilenodioxi-3,4,5,3’-tetrametoxi-7,7’-epoxilignana, rel-(7R,8S,7’S,8’S)-4-hidroxi- 4’,5’-metilenodioxi-3,5,3’-trimetoxi-7,7’-epoxilignana, rel-(7R,8S,7’S,8’S)-4’-hidroxi- 3,4,5,3’,5’-pentametoxi-7,7’-epoxilignana, rel-(7R,8S,7’S,8’S)-9-hidroxi-4’,5’-metilenodioxi- 3,4,5,3’-tetrametoxi-7,7’-epoxilignana), cinco secolignanas ((2S,3R)-2-metil-3- [bis(4’,5’-metilenodioxi-3’-metoxifenil)metil]butirolactona, rel-(2S,3R)-2-metil-3-[bis (3’,4’,5’-trimetoxifenil)metil]butirolactona, rel-(2R,3R)-2-metil-3-[bis(3’,4’,5’-trimetoxifenil) metil]butirolactona, (2S,3R,5R)-2-metil-3-[5-(3’,4’,5’-trimetoxifenil)-5-(4’’,5’’- metilenodioxi-3’’-metoxifenil)metil]butirolactona, (2R,3R,5R)-2-metil-3-[5-(3’,4’,5’-trimetoxifenil)- 5-(4’’,5’’-metilenodioxi-3’’-metoxifenil)metil]butirolactona), duas flavonas (5-hidroxi-4’,7,8-trimetoxiflavona,5-hidroxi-3’,4’,7,8-tetrametoxiflavona) e três policetídeos (proctoriona C, surinona A, surinona C). As estruturas químicas das substâncias foram determinadas utilizando técnicas espectrométricas, incluindo RMN 1D e 2D. As estereoquímicas relativas das lignanas tetraidrofurânicas e das secolignanas foram determinadas através de experimentos de NOESY 1D e as estereoquímicas absolutas das secolignanas foram determinadas através de dicroísmo circular. Todas as substâncias estão sendo descritas pela primeira vez nessa espécie vegetal, sendo que as lignanas tetraidrofurânicas apresentaram estruturas químicas com estereoquímicas inéditas e as secolignanas haviam sido obtidas... / The phytochemical investigation of aerial parts of Peperomia blanda yielded fifteen compounds, identified as five tetrahydrofuran lignans (rel-(7R,8S,7’S,8’S)- 4,5,4’,5’-dimethylenedioxy-3,3’-dimethoxy-7,7’-epoxylignan, rel-(7R,8S,7’S,8’S)-4’,5’- methylenedioxy-3,4,5,3’-tetramethoxy-7,7’-epoxylignan, rel-(7R,8S,7’S,8’S)-4-hydroxy- 4’,5’-methylenedioxy-3,5,3’-trimethoxy-7,7’-epoxylignan, rel-(7R,8S,7’S,8’S)-4’- hydroxy-3,4,5,3’,5’-pentamethoxy-7,7’-epoxylignan, rel-(7R,8S,7’S,8’S)-9-hydroxy- 4’,5’-methylenedioxy-3,4,5,3’-tetramethoxy-7,7’-epoxylignan), five secolignans ((2S,3R)-2-methyl-3-[bis(4’,5’-methylenedioxy-3’-methoxyphenyl)methyl]butyrolactone, rel-(2S,3R)-2-methyl-3-[bis(3’,4’,5’-trimethoxyphenyl)methyl]butyrolactone, rel- (2R,3R)-2-methyl-3-[bis(3’,4’,5’-trimethoxyphenyl)methyl]butyrolactone, (2S,3R,5R)-2- methyl-3-[5-(3’,4’,5’-trimethoxyphenyl)-5-(4’’,5’’-methylenedioxy-3’’-methoxyphenyl) methyl]butyrolactone and (2R,3R,5R)-2-methyl-3-[5-(3’,4’,5’-trimethoxyphenyl)-5- (4’’,5’’-methylenedioxy-3’’-methoxyphenyl)methyl]butyrolactone), two flavones (5- hydroxy-4’,7,8-trimethoxyflavone, 5-hydroxy-3’,4’,7,8-tetramethoxyflavone) and three polyketides (proctorione C, surinone A, surinone C). The chemical structures were elucidated by interpretation of their spectroscopic data, including 1D and 2D NMR. The relative configurations of tetrahydrofuran lignans and secolignans were determined using NOESY analyses and the absolute configurations were defined by CD spectra. All compounds were described at the first time in this species and all tetrahydrofuran lignans showed novel stereoisomers and the secolignans were previously published as synthetic products. The tetrahydrofuran lignans showed powerful trypanocidal... (Complete abstract click electronic access below)

Identiferoai:union.ndltd.org:IBICT/oai:repositorio.unesp.br:11449/97956
Date27 June 2008
CreatorsFelippe, Lidiane Gaspareto [UNESP]
ContributorsUniversidade Estadual Paulista (UNESP), Furlan, Maysa [UNESP]
PublisherUniversidade Estadual Paulista (UNESP)
Source SetsIBICT Brazilian ETDs
LanguagePortuguese
Detected LanguageEnglish
Typeinfo:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/masterThesis
Format251 f. : il.
SourceAleph, reponame:Repositório Institucional da UNESP, instname:Universidade Estadual Paulista, instacron:UNESP
Rightsinfo:eu-repo/semantics/openAccess
Relation-1, -1

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