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Megalanthine, a Bioactive Sesquiterpenoid from Heliotropium megalanthum, its Degradation Products and their Bioactivities

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Abstract

The new bioactive sesquiterpenoid (3R,6E)-2,6,10-trimethyl-3-(3-p-hydroxyphenylpropanoyloxy)-dodeca-6,11-diene-2,10-diol, named megalanthine, was isolated from the resinous exudates of Heliotropium megalanthum. The degradation products of this compound were identified. Several plant-defensive properties (insecticidal, antifungal, and phytotoxic) were evaluated after obtaining positive results in a preliminary etiolated wheat coleoptile bioassay. This bioassay showed the need to have both the phenolic and sesquiterpene moieties of the natural product present to achieve a biological effect. This result was confirmed in phytotoxicity bioassays. Megalanthine was ruled out as a significant plant–plant defense agent because of its lack of stability. The positive results recorded in the antifungal and antifeedant tests suggest, however, that this chemical is relevant in several ecological interactions involving H. megalanthum.

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Acknowledgments

This research was supported by the Ministerio de Educación y Ciencia, Spain (MEC; Project No. AGL-2006-10570-AGR), by grants DICTY-Chile (USACH), and a Collaborative Research Grant CSIC-USACH (2004CL0010).

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Authors and Affiliations

  1. Grupo de Alelopatía, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, C/Avda. República Saharaui, s/n, 11510, Puerto Real, Cádiz, Spain

    Francisco A. Macías, Ana M. Simonet & Claudia C. Maya

  2. Dipartimento di Science della Vita, II Università di Napoli, via Vivaldi 43, 81100, Caserta, Italy

    Brigida D’Abrosca

  3. Instituto de Productos Naturales y Agrobiología, CSIC, 38206, La Laguna, Tenerife, Spain

    Matías Reina

  4. Centro de Ciencias Medioambientales, CSIC, Madrid, Spain

    Azucena González-Coloma

  5. Fitopatología, Departamento de Biología Vegetal, Facultad de Biología, Universidad de La Laguna, Avda. Astrofísico Francisco Sánchez s/n, 38206, La Laguna, Tenerife, Spain

    Raimundo Cabrera & Cristina Giménez

  6. Facultad de Química y Biología, Universidad de Santiago de Chile, Casilla 40, Correo-33, Santiago, Chile

    Luis Villarroel

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  1. Francisco A. Macías
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  2. Ana M. Simonet
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  3. Brigida D’Abrosca
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  4. Claudia C. Maya
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  5. Matías Reina
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  6. Azucena González-Coloma
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  7. Raimundo Cabrera
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  8. Cristina Giménez
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  9. Luis Villarroel
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Correspondence to Francisco A. Macías.

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Macías, F.A., Simonet, A.M., D’Abrosca, B. et al. Megalanthine, a Bioactive Sesquiterpenoid from Heliotropium megalanthum, its Degradation Products and their Bioactivities. J Chem Ecol 35, 39–49 (2009). https://doi.org/10.1007/s10886-008-9574-4

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  • DOI: https://doi.org/10.1007/s10886-008-9574-4

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