Macías Francisco A, López Adriana, Varela Rosa M, Torres Ascensión, Molinillo José M G
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.
J Chem Ecol. 2008 Jan;34(1):65-9. doi: 10.1007/s10886-007-9400-4. Epub 2007 Dec 11.
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(-6)M. Helikauranoside A (4) was the most active (-84%, 10(-3)M; -56%, 10(-4)M). These results suggest that this new compound may be involved in defense mechanisms of H. annuus.
从向日葵的地上部分分离出一种新的对映-贝壳杉烷型糖苷，命名为向日葵贝壳杉烷苷A（4），同时还分离出三种已知的对映-贝壳杉烷型二萜类化合物：（-）-贝壳杉-16-烯-19-酸（1）、大花酸（2）和圆锥花苷IV（3）。通过结合一维（1H-NMR和13C-NMR）和二维（COSY、HSQC和HMBC）核磁共振技术确定了4的结构。在浓度范围为10（-3）至10（-6）M的水溶液中，使用黄化小麦胚芽鞘生物测定法测试了分离出的化合物的生物活性谱。向日葵贝壳杉烷苷A（4）活性最高（10（-3）M时为-84%；10（-4）M时为-56%）。这些结果表明，这种新化合物可能参与了向日葵的防御机制。
