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.
Autor(a) principal: | |
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Data de Publicação: | 2011 |
Outros Autores: | , , , , , |
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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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 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
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. |
dc.identifier.uri.fl_str_mv |
http://www.repositorio.ufop.br/handle/123456789/3859 |
dc.identifier.issn.none.fl_str_mv |
1420-3049 |
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 |
url |
http://www.repositorio.ufop.br/handle/123456789/3859 https://doi.org/10.3390/molecules16129939 |
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eng |
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