The triterpenes 3β-Lup-20(29)-en-3-ol and 3β-Lup-20(29)-en-3-yl acetate and the carbohydrate 1,2,3,4,5,6-Hexa-O-acetyl-dulcitol as photosynthesis light reactions inhibitors.

Detalhes bibliográficos
Autor(a) principal: Oliveira, Djalma Menezes de
Data de Publicação: 2011
Outros Autores: Aguilar, Maria Isabel, Díaz, Beatriz King, Vieira Filho, Sidney Augusto, Duarte, Lucienir Pains, Silva, Grácia Divina de Fátima, Hennsen, Blas Lotina
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UFOP
Texto Completo: http://www.repositorio.ufop.br/handle/123456789/3859
https://doi.org/10.3390/molecules16129939
Resumo: Three compounds were isolated from Maytenus acanthophylla Reissek (Celastraceae): the pentacyclic triterpenes lup-20(29)-en-3β-ol (lupeol, 1) and 3β-lup- 20(29)-en-3-yl acetate (2) and the carbohydrate 1,2,3,4,5,6-hexa-O-acetyldulcitol (3); lupeol was also isolated from Xylosma flexuosa. The compounds’ structures were elucidated by spectroscopic and spectrometric analysis. Compound 1 acts as an energy transfer inhibitor, interacting with isolated CF1 bound to thylakoid membrane, and dulcitol hexaacetate 3 behaves as a Hill reaction inhibitor and as an uncoupler, as determined by polarography. Chlorophyll a (Chl a) fluorescence induction kinetics from the minimum yield F0 to the maximum yield FM provides information of the filling up from electrons coming from water to plastoquinone pool with reducing equivalents. In this paper we have examined the effects of compounds 1 and 3 on spinach leaf discs. Compound 1 induces the appearance of a K-band, which indicates that it inhibits the water splitting enzyme. In vivo assays measuring the fluorescence of chl a in P. ixocarpa leaves sprayed with compound 1, showed the appearance of the K-band and the PSII reaction centers was transformed to “heat sinks” or silent reaction centers unable to reduce QA. However, 3 also induced the appearance of a K band and a new band I appears in P. ixocarpa plants, therefore it inhibits at the water splitting enzyme complex and at the PQH2 site on b6f complex. Compounds 1 and 3 did not affect chlorophyll a fluorescence of L. perenne plants.
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spelling Oliveira, Djalma Menezes deAguilar, Maria IsabelDíaz, Beatriz KingVieira Filho, Sidney AugustoDuarte, Lucienir PainsSilva, Grácia Divina de FátimaHennsen, Blas Lotina2014-11-14T18:35:38Z2014-11-14T18:35:38Z2011OLIVEIRA, D. M. et al. The triterpenes 3β-Lup-20(29)-en-3-ol and 3β-Lup-20(29)-en-3-yl acetate and the carbohydrate 1,2,3,4,5,6-Hexa-O-acetyl-dulcitol as photosynthesis light reactions inhibitors. Molecules, v. 16, p. 9939-9956, 2011. Disponível em: <http://www.mdpi.com/1420-3049/16/12/9939>. Acesso em: 20 ago. 2014.1420-3049http://www.repositorio.ufop.br/handle/123456789/3859https://doi.org/10.3390/molecules16129939Three compounds were isolated from Maytenus acanthophylla Reissek (Celastraceae): the pentacyclic triterpenes lup-20(29)-en-3β-ol (lupeol, 1) and 3β-lup- 20(29)-en-3-yl acetate (2) and the carbohydrate 1,2,3,4,5,6-hexa-O-acetyldulcitol (3); lupeol was also isolated from Xylosma flexuosa. The compounds’ structures were elucidated by spectroscopic and spectrometric analysis. Compound 1 acts as an energy transfer inhibitor, interacting with isolated CF1 bound to thylakoid membrane, and dulcitol hexaacetate 3 behaves as a Hill reaction inhibitor and as an uncoupler, as determined by polarography. Chlorophyll a (Chl a) fluorescence induction kinetics from the minimum yield F0 to the maximum yield FM provides information of the filling up from electrons coming from water to plastoquinone pool with reducing equivalents. In this paper we have examined the effects of compounds 1 and 3 on spinach leaf discs. Compound 1 induces the appearance of a K-band, which indicates that it inhibits the water splitting enzyme. In vivo assays measuring the fluorescence of chl a in P. ixocarpa leaves sprayed with compound 1, showed the appearance of the K-band and the PSII reaction centers was transformed to “heat sinks” or silent reaction centers unable to reduce QA. However, 3 also induced the appearance of a K band and a new band I appears in P. ixocarpa plants, therefore it inhibits at the water splitting enzyme complex and at the PQH2 site on b6f complex. Compounds 1 and 3 did not affect chlorophyll a fluorescence of L. perenne plants.Chlorophylla fluorescenceLupeolMaytenus acanthophyllaUncouplerXylosma flexuosaThe triterpenes 3β-Lup-20(29)-en-3-ol and 3β-Lup-20(29)-en-3-yl acetate and the carbohydrate 1,2,3,4,5,6-Hexa-O-acetyl-dulcitol as photosynthesis light reactions inhibitors.info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleThis is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Fonte: Molecules <http://www.mdpi.com/1420-3049/18/8/9919>. Acesso em: 08 set. 2014.info:eu-repo/semantics/openAccessengreponame:Repositório Institucional da UFOPinstname:Universidade Federal de Ouro Preto (UFOP)instacron:UFOPLICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://www.repositorio.ufop.br/bitstream/123456789/3859/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52ORIGINALARTIGO_TriterpenesLUPAcetato.pdfARTIGO_TriterpenesLUPAcetato.pdfapplication/pdf310936http://www.repositorio.ufop.br/bitstream/123456789/3859/1/ARTIGO_TriterpenesLUPAcetato.pdf187baf73c74c3ebab50c8d1c6f8bbaf3MD51123456789/38592019-05-09 13:58:44.48oai:localhost: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Repositório InstitucionalPUBhttp://www.repositorio.ufop.br/oai/requestrepositorio@ufop.edu.bropendoar:32332019-05-09T17:58:44Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP)false
dc.title.pt_BR.fl_str_mv The triterpenes 3β-Lup-20(29)-en-3-ol and 3β-Lup-20(29)-en-3-yl acetate and the carbohydrate 1,2,3,4,5,6-Hexa-O-acetyl-dulcitol as photosynthesis light reactions inhibitors.
title The triterpenes 3β-Lup-20(29)-en-3-ol and 3β-Lup-20(29)-en-3-yl acetate and the carbohydrate 1,2,3,4,5,6-Hexa-O-acetyl-dulcitol as photosynthesis light reactions inhibitors.
spellingShingle The triterpenes 3β-Lup-20(29)-en-3-ol and 3β-Lup-20(29)-en-3-yl acetate and the carbohydrate 1,2,3,4,5,6-Hexa-O-acetyl-dulcitol as photosynthesis light reactions inhibitors.
Oliveira, Djalma Menezes de
Chlorophylla fluorescence
Lupeol
Maytenus acanthophylla
Uncoupler
Xylosma flexuosa
title_short The triterpenes 3β-Lup-20(29)-en-3-ol and 3β-Lup-20(29)-en-3-yl acetate and the carbohydrate 1,2,3,4,5,6-Hexa-O-acetyl-dulcitol as photosynthesis light reactions inhibitors.
title_full The triterpenes 3β-Lup-20(29)-en-3-ol and 3β-Lup-20(29)-en-3-yl acetate and the carbohydrate 1,2,3,4,5,6-Hexa-O-acetyl-dulcitol as photosynthesis light reactions inhibitors.
title_fullStr The triterpenes 3β-Lup-20(29)-en-3-ol and 3β-Lup-20(29)-en-3-yl acetate and the carbohydrate 1,2,3,4,5,6-Hexa-O-acetyl-dulcitol as photosynthesis light reactions inhibitors.
title_full_unstemmed The triterpenes 3β-Lup-20(29)-en-3-ol and 3β-Lup-20(29)-en-3-yl acetate and the carbohydrate 1,2,3,4,5,6-Hexa-O-acetyl-dulcitol as photosynthesis light reactions inhibitors.
title_sort The triterpenes 3β-Lup-20(29)-en-3-ol and 3β-Lup-20(29)-en-3-yl acetate and the carbohydrate 1,2,3,4,5,6-Hexa-O-acetyl-dulcitol as photosynthesis light reactions inhibitors.
author Oliveira, Djalma Menezes de
author_facet Oliveira, Djalma Menezes de
Aguilar, Maria Isabel
Díaz, Beatriz King
Vieira Filho, Sidney Augusto
Duarte, Lucienir Pains
Silva, Grácia Divina de Fátima
Hennsen, Blas Lotina
author_role author
author2 Aguilar, Maria Isabel
Díaz, Beatriz King
Vieira Filho, Sidney Augusto
Duarte, Lucienir Pains
Silva, Grácia Divina de Fátima
Hennsen, Blas Lotina
author2_role author
author
author
author
author
author
dc.contributor.author.fl_str_mv Oliveira, Djalma Menezes de
Aguilar, Maria Isabel
Díaz, Beatriz King
Vieira Filho, Sidney Augusto
Duarte, Lucienir Pains
Silva, Grácia Divina de Fátima
Hennsen, Blas Lotina
dc.subject.por.fl_str_mv Chlorophylla fluorescence
Lupeol
Maytenus acanthophylla
Uncoupler
Xylosma flexuosa
topic Chlorophylla fluorescence
Lupeol
Maytenus acanthophylla
Uncoupler
Xylosma flexuosa
description Three compounds were isolated from Maytenus acanthophylla Reissek (Celastraceae): the pentacyclic triterpenes lup-20(29)-en-3β-ol (lupeol, 1) and 3β-lup- 20(29)-en-3-yl acetate (2) and the carbohydrate 1,2,3,4,5,6-hexa-O-acetyldulcitol (3); lupeol was also isolated from Xylosma flexuosa. The compounds’ structures were elucidated by spectroscopic and spectrometric analysis. Compound 1 acts as an energy transfer inhibitor, interacting with isolated CF1 bound to thylakoid membrane, and dulcitol hexaacetate 3 behaves as a Hill reaction inhibitor and as an uncoupler, as determined by polarography. Chlorophyll a (Chl a) fluorescence induction kinetics from the minimum yield F0 to the maximum yield FM provides information of the filling up from electrons coming from water to plastoquinone pool with reducing equivalents. In this paper we have examined the effects of compounds 1 and 3 on spinach leaf discs. Compound 1 induces the appearance of a K-band, which indicates that it inhibits the water splitting enzyme. In vivo assays measuring the fluorescence of chl a in P. ixocarpa leaves sprayed with compound 1, showed the appearance of the K-band and the PSII reaction centers was transformed to “heat sinks” or silent reaction centers unable to reduce QA. However, 3 also induced the appearance of a K band and a new band I appears in P. ixocarpa plants, therefore it inhibits at the water splitting enzyme complex and at the PQH2 site on b6f complex. Compounds 1 and 3 did not affect chlorophyll a fluorescence of L. perenne plants.
publishDate 2011
dc.date.issued.fl_str_mv 2011
dc.date.accessioned.fl_str_mv 2014-11-14T18:35:38Z
dc.date.available.fl_str_mv 2014-11-14T18:35:38Z
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dc.identifier.citation.fl_str_mv OLIVEIRA, D. M. et al. The triterpenes 3β-Lup-20(29)-en-3-ol and 3β-Lup-20(29)-en-3-yl acetate and the carbohydrate 1,2,3,4,5,6-Hexa-O-acetyl-dulcitol as photosynthesis light reactions inhibitors. Molecules, v. 16, p. 9939-9956, 2011. Disponível em: <http://www.mdpi.com/1420-3049/16/12/9939>. Acesso em: 20 ago. 2014.
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dc.identifier.doi.none.fl_str_mv https://doi.org/10.3390/molecules16129939
identifier_str_mv OLIVEIRA, D. M. et al. The triterpenes 3β-Lup-20(29)-en-3-ol and 3β-Lup-20(29)-en-3-yl acetate and the carbohydrate 1,2,3,4,5,6-Hexa-O-acetyl-dulcitol as photosynthesis light reactions inhibitors. Molecules, v. 16, p. 9939-9956, 2011. Disponível em: <http://www.mdpi.com/1420-3049/16/12/9939>. Acesso em: 20 ago. 2014.
1420-3049
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