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Helikauranoside A, a New Bioactive Diterpene

Author:
Macías, Francisco A., López, Adriana, Varela, Rosa M., Torres, Ascensión, Molinillo, José M. G.
Source:
Journal of chemical ecology 2008 v.34 no.1 pp. 65-69
ISSN:
0098-0331
Subject:
Helianthus annuus, plant extracts, chemical constituents of plants, glucosides, diterpenoids, chemical structure, bioactive properties, chemical concentration, allelopathy, Triticum aestivum, wheat, coleoptiles, bioassays
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.
Agid:
718649