New C9-polyacetylenes from the essential oil of the highly endangered species Baccharis palustris Heering (Asteraceae) |
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| Institution: | 1. Laboratorio de Biotecnología de Aromas (LaBiotA), Departamento de Química Orgánica, Facultad de Química, Universidad de la República (UdelaR), Av. General Flores 2124, CP: 11800, Montevideo, Uruguay;2. Espacio de Ciencia y Tecnología Química. Centro Universitario Regional Noreste, Sede Tacuarembó. Universidad de la República (UdelaR). Ruta No. 5, km 386, CP: 45000, Tacuarembó, Uruguay;3. Departamento de Botánica. Museo Nacional de Historia Natural (MNHN), Ministerio de Educación y Cultura, 25 de mayo 582, CP: 11000, Montevideo, Uruguay;4. Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, CP: T4000INI, San Miguel de Tucumán, Argentina;1. National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, China;2. Key Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, Wuhan 430064, China;3. Tobacco Research Institute of Hubei Province, Wuhan 430030, China;1. Division of Biochemistry, Indian Agricultural Research Institute, New Delhi, India;2. Basic Sciences Division, Indian Institute of Pulses Research, Kanpur, U.P., India;1. Departamento de Ciências Farmacêuticas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Avenida do Café, s/n, 14040-903, Ribeirão Preto, SP, Brazil;2. Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Avenida Bandeirantes, 3900, 14040-901, Ribeirão Preto, SP, Brazil;1. London Research and Development Center, Agriculture and Agri-Food Canada, London, ON N5V 4T3, Canada;2. Department of Chemistry, University of Western Ontario, London, ON N6A 5B7, Canada;3. Department of Chemistry, Carleton University, Ottawa, ON, K1S 5B6, Canada;4. Department of Biochemistry, University of Western Ontario, London, ON N6A 5B7, Canada;1. Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, T4000INI San Miguel de Tucumán, Tucumán, Argentina;2. Laboratorio de Biotecnología de Aromas, Departamento de Química Orgánica, Facultad de Química, Universidad de la República, General Flores 2124, Montevideo, 11800, Uruguay;3. Cátedra de Química General, Instituto de Química Inorgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, T4000INI San Miguel de Tucumán, Tucumán, Argentina |
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| Abstract: | The essential oil composition of the aerial parts from Baccharis palustris Heering (Asteraceae), a highly endangered species, was analyzed by GC/qMS, GC/HRMS-TOF, FT-IR, UV–vis and NMR spectroscopy using 1D and 2D techniques. To our knowledge, this is the first report on the essential oil composition of B. palustris, as well as the first phytochemical study on this plant species. The volatile extracts were obtained from different phenologicals stages of plant, at flowering stage (FS) and vegetative stage (VS), where 51 components were identified accounting for 96.3 % and 99.0 % of the oil, respectively. The oil was rich in polyacetylene compounds (> 75 %), being the main components identified the new natural C9-polyacetylenes 1-nonene-3,5-diyne (1, here named as baccharisdiyne) (52.7–65.0 %), 1,7(Z)-nonadiene-3,5-diyne 2, 7(Z)-dehydro-baccharisdiyne] (14.4–17.8 %), and 1,7(E)-nonadiene-3,5-diyne 3, 7(E)-dehydro-baccharisdiyne] (1.5–2.4 %). In addition, the known polyacetylenic compounds (Z)-lachnophyllum acid methyl ester (4) (4.3–5.3 %) and (E)-lachnophyllum acid methyl ester (5) (0.2 %) were also identified. Moreover, GC/qMS analysis allowed the identification of other 46 components in the essential oil samples, mainly mono- and sesquiterpenoids. In B. palustris, C9-polyacetylenes probably derive biogenetically from a C10 precursor: baccharisdiyne (1) would be derived from either or both lachnophyllum methyl ester geometric isomers (4 or 5), by enzymatic hydrolysis followed by decarboxylation. Dehydro-baccharisdiynes (2 and 3) could be produced by a similar pathway starting from the corresponding matricaria acid methyl ester isomers, one of which was tentatively identified at trace-level in B. palustris essential oil. |
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| Keywords: | Asteraceae Essential oil Biogenesis |
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