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Identification and Quantitation of Allelochemicals from the Lichen Lethariella canariensis: Phytotoxicity and Antioxidative Activity

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Abstract

Phytotoxicity-based extraction and fractionation were employed to separate allelochemicals contained in an extract of Lethariella canariensis. Twelve phenolic substances were isolated from the phytotoxic fraction “Letharal” of the thalli. These were identified by spectroscopic methods, physicochemical constants, and HPLC chemical correlation, and determined to be atranol (2), chloroatranol (3), hematommic acid (4), chlorohematommic acid (5), methyl hematommate (6), methyl chlorohematommate (7) (new compound), ethyl hematommate (8), ethyl chlorohematommate (9), methyl β-orsellinate (10), atranorin (11), chloroatranorin (12), and (+)-usnic acid (13). Further identification and quantification of these allelochemicals in the environment were conducted by HPLC. Several phenolic compounds showed moderate antimicrobial activity. The cytostatic activity of the polyphenols was investigated on U937 and HL-60 cells. All compounds were assayed, with the exception of 10. The “Letharal” mixture decreased cell viability in both cell lines. Protection against lipid peroxidation was investigated using brain homogenates. Compounds 2, 3, 6, 8, 11, and Letharal decreased H2O2/Fe+2 induced lipid peroxidation in a concentration-dependent manner, while 10 and 13 were unable to protect tissue against oxidative stress.

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Authors and Affiliations

  1. Dpto. de Química, Universidad de Las Palmas de Gran Canaria, Canary Islands, Spain

    F. J. Toledo Marante, A. García Castellano, F. Estévez Rosas & J. Quintana Aguiar

  2. Instituto de Productos Naturales y Agrobiología del CSIC, Instituto de Bio-Orgánica “A. González”, Avda. Astrofisico Francisco Sánchez 2, 38206, La Laguna, Tenerife, Canary Islands, Spain

    J. Bermejo Barrera

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  1. F. J. Toledo Marante
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  2. A. García Castellano
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  3. F. Estévez Rosas
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  4. J. Quintana Aguiar
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  5. J. Bermejo Barrera
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Correspondence to J. Bermejo Barrera.

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Marante, F.J.T., Castellano, A.G., Rosas, F.E. et al. Identification and Quantitation of Allelochemicals from the Lichen Lethariella canariensis: Phytotoxicity and Antioxidative Activity. J Chem Ecol 29, 2049–2071 (2003). https://doi.org/10.1023/A:1025682318001

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