| Budget Amount *help |
¥7,200,000 (Direct Cost: ¥7,200,000)
Fiscal Year 1986: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1985: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1984: ¥5,300,000 (Direct Cost: ¥5,300,000)
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| Research Abstract |
The new insecticidal sesquilignans, haedoxane A, D, C-acetate and F-acetate, were isolated from the extract of Phryma leptostachya L.. Their structures were elucidated as 1-hydroxy-6-[trans-7'-methoxy-3'-methoxymethyl-2'-(3,4-methylenedioxy)phenyl-1', 4'-benzodioxan-6'-yl]-2-aryloxy-3,7-dioxabicyclo[3.3.0]octane (Ar=2,6-dimethoxy-4,5-methylenedioxyphenyl for A; 2-methoxy-4, 5-methylenedioxyphenyl for D; 1-acetoxy-3'-hydroxy-haedoxane D for C-acetate; 1-acetoxy-3'-desmethyl-haedoxane D for F-acetate) on the basis of their chemical and spectroscopic informations. The total syntheses of phrymarolin I and haedoxane D were accomplished through 15 and 14 steps to establish their absolute configurations as 1S, 2S, 5R, 6S and 1S, 2S, 5R, 6S, 2'R, 3'R, respectively. By assessing the insecticidal activities of 15 stereoisomers of haedoxane A, D, and E, it was revealed that the high insecticidal activity of haedoxanes corelated to the absolute configuration. Due to the characteristic toxicity on
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insects involving effectiveness on pesticide-resistant insects, haedoxanes were considered prototypes for design of new insecticides. First of all, 50 of polyalkoxy-1, 3-benzodioxoles were synthesized and assessed their insecticidal activities on housefly. However, their activities were much less than those of the natural products. Further investigations on structure-activity relation are undergoing. The tissue culture of Phryma is an interested method to be developed for the production of a mixture of haedoxanes having complex structures and promising available activities for pest control. Culture-conditions for the growth of tissues were established, and productivity of the insecticidal lignans was studied. The insecticidal lignans were not or only in a small amount found in the root-tissue cultures and in the plant entities which did not developed roots. As well as the plants grown in the field, those normally developed from a tissue section mainly accumulated the lignans in the roots. To select the strains able to produce more materials, geographical variations are investigated. Less
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