No description available.

No description available.

Sesquiterpene lactones contain £\,£]-unsaturated-£^-lactone as a major structural feature, which in recent studies have been shown to be associ- ated with anti-tumor, cytotoxic, anti-microbial and phytotoxic activities. Previous researchers isolated sesquiterpene lactones from Eupatorium formosanum Hay. Thus, we studied Eupatorium hualienense, a unique speces in Taiwan that grows near the eastern coast. Five new sesquiter- pene lactones of the germacranolide type, eupahualins A-E (1-5) along with the known lactone, eupasimplicin B (6). Their structures were determined by 1D-NMR(1H-NMR,13C-NMR) and 2D-NMR(COSY¡BNOESY¡BHMQC¡BHMBC). Eupahualin A (1) exhibits an aldehyde at C-10 and an a,b-unsatura ted acyl group at C-8. Eupahualin B (2) also has an aldehyde at C-10. The Z-form of C-4, C-5 double bond in eupahualin B (2) is the main difference from the trans-form C-4, C-5 double bond in eupahualin A (1). The difference of eupahualin C (3) and eupahualin A (1) lies in structure of a ester group at C-8. The methyl at C-4' in eupahualin A (1) was changed into hydroxy methyl while the hydroxy methyl of eupahualin A (1) was changed to methyl in eupahualin C (3). Eupahualin D (4) shows exocyclic double bond at C-10, OH at C-1 and OAc at C-3. An carboxylic group (COOH) at C-10 in eupahualin E (5) is the only difference from which in eupahualin A (1).

No description available.

No description available.

No description available.

Thesis (Ph.D.)--York University, 2008. Graduate Programme in Chemistry. / Typescript. Includes bibliographical references (leaves 136-150). Also available on the Internet. MODE OF ACCESS via web browser by entering the following URL: http://gateway.proquest.com/openurl?url_ver=Z39.88-2004&res_dat=xri:pqdiss&rft_val_fmt=info:ofi/fmt:kev:mtx:dissertation&rft_dat=xri:pqdiss:NR51683

Esta tese de doutorado aborda alguns aspectos do estudo de plantas medicinais e de princípios ativos naturais. Os procedimentos experimentais incluíram o estudo fitoquímico de uma planta medicinal da família Asteraceae, o desenvolvimento de um método analítico com validação das análises empregadas e o estudo de atividades biológicas relativas ao processo inflamatório. A primeira etapa compreendeu o estudo fitoquímico da planta medicinal Smallanthus sonchifolius (Asteraceae), envolvendo o isolamento de metabólitos secundários da classe dos terpenóides. Do extrato de lavagem foliar foram isoladas as seguintes lactonas sesquiterpênicas (LSTs): enidrina, uvedalina, sonchifolina, fluctuanina, polimatina B, (1Z,4E)-8β-metacriloilóxi-9α-acetoilóxi-germacra-1(10),4,11(13)-trien-6α,12-olido-14-oato de metila, (1Z,4E)-8β-angeloilóxi-14-oxo-germacra-1(10),4,11(13)-trien-6α,12-olido, (1Z,4E)-8β-metacriloilóxi-germacra-1(10),4,11(13)-trien-6α,12-olido-14-oato de metila, ácido (1Z,4E)-8β-angeloilóxi-germacra-1(10),4,11(13)-trien-6α,12-olido-14-óico e (1Z)-3α,4β-epóxi-8β-[(1Z,4E)-(2S,3R)-2-hidróxi-3-óxi-(8β-angeloilóxi-germacra-1(10),4,11(13)-trien-6α,12-olido)]-9α-acetoilóxi-germacra-1(10),11(13)-dien-6α,12-olido-14-oato de metila. A segunda etapa tratou do desenvolvimento de método e validação das análises para controle de qualidade químico de S. sonchifolius em cromatografia líquida de alta eficiência (CLAE). Além disso, foi realizada a quantificação do principal metabólito secundário isolado nos extratos glandulares e de lavagem foliar, a LST enidrina. Esta substância compõe 0,97 % do peso seco das folhas de S. sonchifolius. A terceira etapa refere-se às atividades biológicas, as quais foram avaliadas empregando-se diversos ensaios. Também foi realizada a otimização de método para avaliação da secreção de elastase por neutrófilos humanos e o estudo da estimulação basal de neutrófilos. Ainda foram investigados os efeitos de produtos fitoterápicos, como gel de Arnica montana e extrato de Harpagophytum procumbens, e de metabólitos secundários, como LSTs e alcalóides, na atividade enzimática de elastase, na secreção de elastase por neutrófilos, na ativação do fator de transcrição NF-κB via EMSA, na produção de luciferase por meio de reporter gen assay e de interleucina-8 via ELISA. Com exceção de dois alcalóides, todas as substâncias e produtos testados apresentaram atividades de inibição dos processos inflamatórios investigados. / This Ph.D. thesis deals with some aspects of the study of medicinal plants and their biologically active natural compounds. The experimental procedures comprised the phytochemical study of a plant from the family Asteraceae, the development of an analytical method with validation of the employed analysis and the study of the biological activities related to the inflammatory process. The first step comprised the phytochemical study of the medicinal plant Smallanthus sonchifolius (Asteraceae) and the isolation of secondary metabolites. From the leaf rinse extract were isolated the sesquiterpene lactones (STLs) enhydrin, uvedalin, sonchifolin, fluctuanin, polymatin B, methyl (1Z,4E)-8β-metacryloyloxy-9α-acetoyloxy-germacra-1(10),4,11(13)-trien-6α,12-olide-14-ate, (1Z,4E)-8β-angeloyloxy-14-oxo-germacra-1(10),4,11(13)-trien-6α,12-olide, methyl (1Z,4E)-8β-metacryloyloxy-germacra-1(10),4,11(13)-trien-6α,12-olide-14-ate, (1Z,4E)-8β-angeloyloxy-germacra-1(10),4,11(13)-trien-6α,12-olide-14-oic acid, methyl (1Z)-3α,4β-epoxy-8β-[(1Z,4E)-(2S,3R)-2-hydroxy-3-oxy-(8β-angeloyloxy-germacra-1(10),4,11(13)-trien-6α,12-olide)]-9α-acetoyloxy-germacra-1(10),11(13)-dien-6α,12-olide-14-ate. The second part was related to the development and validation of a chromatographic method for the chemical quality control of S. sonchifolius using high performance liquid chromatography (HPLC). Furthermore, the quantification of the main secondary metabolite, the STL enhydrin on glandular and leaf rinse extracts was also performed. This compound comprises 0,97 % of dried leaves weight of the plant. The third part deals with biological activities, which were investigated through different assays. One method for the study of the elastase release from human neutrophils was evaluated and the basal stimulation of neutrophils was studied. The effects of phytoterapeutic agents, like Arnica montana gel and Harpagophytum procumbens extract, and of the secondary metabolites, like LSTs and alkaloids, on the enzymatic activity of elastase, on elastase release from neutrophils, on the activation of the transcription factor NF-κB through EMSA, on luciferase production through reporter gene assay and on interleucina-8 production through ELISA were also carried out. Both phytoterapeutic agents as well as the great majority of the tested compounds showed some inhibitory activity over the investigated inflammatory processes.

Thesis (M. Sc.)(Chemistry)--University of Pretoria, 2005. / Includes bibliographical references. Available on the Internet via the World Wide Web.

Esta tese de doutorado aborda alguns aspectos do estudo de plantas medicinais e de princípios ativos naturais. Os procedimentos experimentais incluíram o estudo fitoquímico de uma planta medicinal da família Asteraceae, o desenvolvimento de um método analítico com validação das análises empregadas e o estudo de atividades biológicas relativas ao processo inflamatório. A primeira etapa compreendeu o estudo fitoquímico da planta medicinal Smallanthus sonchifolius (Asteraceae), envolvendo o isolamento de metabólitos secundários da classe dos terpenóides. Do extrato de lavagem foliar foram isoladas as seguintes lactonas sesquiterpênicas (LSTs): enidrina, uvedalina, sonchifolina, fluctuanina, polimatina B, (1Z,4E)-8β-metacriloilóxi-9α-acetoilóxi-germacra-1(10),4,11(13)-trien-6α,12-olido-14-oato de metila, (1Z,4E)-8β-angeloilóxi-14-oxo-germacra-1(10),4,11(13)-trien-6α,12-olido, (1Z,4E)-8β-metacriloilóxi-germacra-1(10),4,11(13)-trien-6α,12-olido-14-oato de metila, ácido (1Z,4E)-8β-angeloilóxi-germacra-1(10),4,11(13)-trien-6α,12-olido-14-óico e (1Z)-3α,4β-epóxi-8β-[(1Z,4E)-(2S,3R)-2-hidróxi-3-óxi-(8β-angeloilóxi-germacra-1(10),4,11(13)-trien-6α,12-olido)]-9α-acetoilóxi-germacra-1(10),11(13)-dien-6α,12-olido-14-oato de metila. A segunda etapa tratou do desenvolvimento de método e validação das análises para controle de qualidade químico de S. sonchifolius em cromatografia líquida de alta eficiência (CLAE). Além disso, foi realizada a quantificação do principal metabólito secundário isolado nos extratos glandulares e de lavagem foliar, a LST enidrina. Esta substância compõe 0,97 % do peso seco das folhas de S. sonchifolius. A terceira etapa refere-se às atividades biológicas, as quais foram avaliadas empregando-se diversos ensaios. Também foi realizada a otimização de método para avaliação da secreção de elastase por neutrófilos humanos e o estudo da estimulação basal de neutrófilos. Ainda foram investigados os efeitos de produtos fitoterápicos, como gel de Arnica montana e extrato de Harpagophytum procumbens, e de metabólitos secundários, como LSTs e alcalóides, na atividade enzimática de elastase, na secreção de elastase por neutrófilos, na ativação do fator de transcrição NF-κB via EMSA, na produção de luciferase por meio de reporter gen assay e de interleucina-8 via ELISA. Com exceção de dois alcalóides, todas as substâncias e produtos testados apresentaram atividades de inibição dos processos inflamatórios investigados. / This Ph.D. thesis deals with some aspects of the study of medicinal plants and their biologically active natural compounds. The experimental procedures comprised the phytochemical study of a plant from the family Asteraceae, the development of an analytical method with validation of the employed analysis and the study of the biological activities related to the inflammatory process. The first step comprised the phytochemical study of the medicinal plant Smallanthus sonchifolius (Asteraceae) and the isolation of secondary metabolites. From the leaf rinse extract were isolated the sesquiterpene lactones (STLs) enhydrin, uvedalin, sonchifolin, fluctuanin, polymatin B, methyl (1Z,4E)-8β-metacryloyloxy-9α-acetoyloxy-germacra-1(10),4,11(13)-trien-6α,12-olide-14-ate, (1Z,4E)-8β-angeloyloxy-14-oxo-germacra-1(10),4,11(13)-trien-6α,12-olide, methyl (1Z,4E)-8β-metacryloyloxy-germacra-1(10),4,11(13)-trien-6α,12-olide-14-ate, (1Z,4E)-8β-angeloyloxy-germacra-1(10),4,11(13)-trien-6α,12-olide-14-oic acid, methyl (1Z)-3α,4β-epoxy-8β-[(1Z,4E)-(2S,3R)-2-hydroxy-3-oxy-(8β-angeloyloxy-germacra-1(10),4,11(13)-trien-6α,12-olide)]-9α-acetoyloxy-germacra-1(10),11(13)-dien-6α,12-olide-14-ate. The second part was related to the development and validation of a chromatographic method for the chemical quality control of S. sonchifolius using high performance liquid chromatography (HPLC). Furthermore, the quantification of the main secondary metabolite, the STL enhydrin on glandular and leaf rinse extracts was also performed. This compound comprises 0,97 % of dried leaves weight of the plant. The third part deals with biological activities, which were investigated through different assays. One method for the study of the elastase release from human neutrophils was evaluated and the basal stimulation of neutrophils was studied. The effects of phytoterapeutic agents, like Arnica montana gel and Harpagophytum procumbens extract, and of the secondary metabolites, like LSTs and alkaloids, on the enzymatic activity of elastase, on elastase release from neutrophils, on the activation of the transcription factor NF-κB through EMSA, on luciferase production through reporter gene assay and on interleucina-8 production through ELISA were also carried out. Both phytoterapeutic agents as well as the great majority of the tested compounds showed some inhibitory activity over the investigated inflammatory processes.