| Co-Investigator(Kenkyū-buntansha) |
KODAMA Motoichirou Tottori University, Dept. Agriculture, Assistant Professor, 農学部, 講師 (00183343)
OKAMOTO Yoshiharu Tottori University, Dept. Agriculture, Associate Professor, 農学部, 助教授 (50194410)
YAMAMOTO Fukujyu Tottori University, Dept. Agriculture, Professor, 農学部, 教授 (60112322)
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| Research Abstract |
Four kinds of natural type phenylpropanoid glycosides, acteoside (1), conandroside (2), plantamajoside (3) and isoacteoside (4) were synthesized, which are partial members in phenylpropanoid library. These are the first examples for the total chemical synthesis of the four compounds.
Syntheses of above compounds were accomplished by newly developing method. To a key intermediate, 2-(3,4-dihydroxyphenyl)ethyl 2,6-di-O-acetyl-4-O-caffeoyl-β-D-glucopyranoside, sugar residues (rhamnosyl, xylosyl and glucosyl residues) were introduced by the imidate method giving each derivative of compound 1, 2 and 3. These derivatives were deacetylated with methylamine and debenzylated with 1,4-cyclohexadiene (as a proton source) / paradium-carbon to obtain compounds 1, 2 and 3. In the deacetylation process, a reaction conditions for conversion of compound 1 into compound 4 was established.
In addition, a protective group for catechol group was modified ; tert-butyldimethylsilyl group was employed instead of benzyl group, which increase the total yield from 3 % to 7 %.
Synthesized four kinds of phenylpropanoid glycosides were examined as anti-fungi agents against Altanaria altanata Japanese pear pathotype (O-276) and Non pathogenic Altanaria altanata (O-94) using spore testing method. In the results, plantamajoside was found to have a promoting activities in germination, which suggested that the phenylpropanoid glycosides have specific bio-activities related with their chemical structure.
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