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Helikauranoside A, a New Bioactive Diterpene

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Abstract

A new ent-kaurane glucoside, named helikauranoside A (4), was isolated from the aerial parts of Helianthus annuus L. together with three known ent-kaurane-type diterpenoids: (−)-kaur-16-en-19-oic acid (1), grandifloric acid (2), and paniculoside IV (3). The structure of 4 was determined by using a combination of 1D (1H-NMR and 13C-NMR) and 2D (COSY, HSQC, and HMBC) NMR techniques. Bioactivity spectra of isolated compounds were tested by using the etiolated wheat coleoptile bioassay in aqueous solutions at concentrations ranging from 10−3 to 10−6M. Helikauranoside A (4) was the most active (−84%, 10−3M; −56%, 10−4M). These results suggest that this new compound may be involved in defense mechanisms of H. annuus.

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Acknowledgement

This research was supported by the Ministerio de Ciencia y Tecnología, Spain (MCYT; Project No. AGL2005–05190). A.L. acknowledges a fellowship from La Agencia Española de Cooperación Internacional, Ministerio de Asuntos Exteriores, Spain.

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Authors and Affiliations

  1. Grupo de Alelopatía, Departamento de Química Organica, Facultad de Ciencias, Universidad de Cádiz, C/ República Saharaui s/n, Apdo. 40, 11510, Puerto Real, Cádiz, Spain

    Francisco A. Macías, Adriana López, Rosa M. Varela, Ascensión Torres & José M. G. Molinillo

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  1. Francisco A. Macías
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  2. Adriana López
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  3. Rosa M. Varela
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  4. Ascensión Torres
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  5. José M. G. Molinillo
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Correspondence to Francisco A. Macías.

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Macías, F.A., López, A., Varela, R.M. et al. Helikauranoside A, a New Bioactive Diterpene. J Chem Ecol 34, 65–69 (2008). https://doi.org/10.1007/s10886-007-9400-4

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  • DOI: https://doi.org/10.1007/s10886-007-9400-4

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