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Molecules 2011, 16(12), 9939-9956; doi:10.3390/molecules16129939

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

1
Departamento de Química, Universidad Federal de Minas Gerais, Avenida Antonio Carlos 6627, Pampulha, 31270-901, Belo Horizonte, MG, Brazil
2
Departamento de Bioquímica, Facultad de Química, Universidad Nacional Autónoma de México, México D. F. 04510, Mexico
*
Author to whom correspondence should be addressed.
Received: 28 September 2011 / Revised: 25 November 2011 / Accepted: 28 November 2011 / Published: 1 December 2011
(This article belongs to the Section Natural Products)
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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 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.
Keywords: chlorophyll a fluorescence; energy transfer inhibitor; 1,2,3,4,5,6-hexa-O-acetyldulcitol; Hill reaction inhibitors; 3β-lup-20(29)-en-3-yl acetate; lupeol; lup-20(29)-en-3β-ol; Maytenus acanthophylla; uncoupler; Xylosma flexuosa chlorophyll a fluorescence; energy transfer inhibitor; 1,2,3,4,5,6-hexa-O-acetyldulcitol; Hill reaction inhibitors; 3β-lup-20(29)-en-3-yl acetate; lupeol; lup-20(29)-en-3β-ol; Maytenus acanthophylla; uncoupler; Xylosma flexuosa
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Menezes-de-Oliveira, D.; Aguilar, M.-I.; King-Díaz, B.; Vieira-Filho, S.A.; Pains-Duarte, L.; Silva, G.-D.; Lotina-Hennsen, B. 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 2011, 16, 9939-9956.

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