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

三萜类化合物 3β-lup-20(29)-烯-3-醇和 3β-lup-20(29)-烯-3-基乙酸酯以及碳水化合物 1,2,3,4,5,6-六-O-乙酰基-半乳糖醇作为光合作用光反应抑制剂

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作者:Djalma Menezes-de-Oliveira, Maria-Isabel Aguilar, Beatriz King-Díaz, Sidney Augusto Vieira-Filho, Lucinier Pains-Duarte, Grácia-Divina de Fátima Silva, Blas Lotina-Hennsen

Abstract

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 CF&sub1; 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 F&sub0; to the maximum yield F(M )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 Q(A). 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 PQH&sub2; site on b₆f complex. Compounds 1 and 3 did not affect chlorophyll a fluorescence of L. perenne plants.

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