96(P14) 9-デオキシコチレノール誘導体の合成と活性(ポスター発表の部)

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Cotylenins and fusicoccins, fungal diterpenoid glycosides, are known to have identical, yet unique, plant growth-regulating activities. These compounds widen the stomatal pore, stimulate cell elongation, break seed dormancy, and stimulate rhizogenesis. Because of these plant-hormone like activities, fusicoccin, a representative of this family, has been widely utilized in plant physiology. Action of mechanism of this class of compounds has recently been demonstrated by binding with a 14-3-3 protein in plant signal transductions. Here, several 9-deoxycotylenol derivatives were synthesized according to the previously reported method which was utilized in the first total synthesis of cotylenol (3). The method involves the coupling reaction of two parts of appropriately functionalized iridoid synthons and the eight-membered ring formation by an intramolecular ene reaction. The evaluation of the biological activity of 9-deoxycotylenol derivatives was carried out by checking the germination-stimulating activity using lettuce seeds. The retention of the activity in 9-deoxycotylenol (6) clearly suggested that the 9α-hydroxy group and the sugar moiety on it are not essential for the biological activities. Other analogs, i.e., 3α-thio- and 3α-amino-9-deoxy-19-methoxymethoxycotylenols (7 and 8) were also synthesized. The key synthetic processes were the rearrangement of O-allyl dithiocarbonate to S-allyl dithiocarbonate for 7 and the rearrangement of allyl cyanate to allyl isocyanate for 8. These analogs were, however, mostly inactive on the germination of lettuce seeds. Further studies, including the evaluation of H^+-ATPase activating activity of these compounds, are in progress.
天然有機化合物討論会の論文
1998-08-31

96(P14) 9-デオキシコチレノール誘導体の合成と活性(ポスター発表の部)

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