Role of Caffeic Acid Sugar Esters in Tree Defense-Repair Processing
| Project/Area Number |
05660179
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
林産学
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| Research Institution | IWATE UNIVERSITY |
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Principal Investigator |
OTA Michikazu IWATE UNIVERSITY FACULTY OF AGRICULTURE ASSOCIATE PROFESSOR, 農学部, 助教授 (80111160)
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| Co-Investigator(Kenkyū-buntansha) |
KOFUJITA Hisayoshi IWATE UNIVERSITY FACULTY OF AGRICULTURE RESEARCH ASSOCIATE, 農学部, 助手 (40270798)
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| Project Period (FY) |
1993 – 1995
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| Project Status |
Completed (Fiscal Year 1995)
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| Budget Amount *help |
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1995: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1994: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1993: ¥1,400,000 (Direct Cost: ¥1,400,000)
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| Keywords | Tree / Defense-Repair Processing / Caffeic Sugar Esters / Peroxidase / Polymeric Substance / Acteoside / Synthesis / (3', 4'-dihydroxyphenyl)-ethyl beta-D-glucose / 合成中間体 / (3′,4′-diacetoxyphenyl)-ethyl2-O-benzoyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside. / 桐 / ベルオキシダーゼ / カフェー酸 / ^<13>Cラベル標識化合物 / フェノール性OH / TBDPS保護基 / 酵素的酸化反応 / ペルオキシダーゼ / 4-O-caffeoyl-β-D-glucose |
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| Research Abstract |
Caffeic sugar esters were postulated to play a role of defense-repair processing in response to wounding, based on the observation that acteoside changed to a polymeric substance, catalyzed by a crude enzyme preparation from paulownia and horse radish peroxidase : This substance was strongly resisted to acid or base hydrolysis. A preparation of acteoside of which the caffeoyl moiety is labelled with ^<13>C atom was planned to confirm this view in vitro and in vivo.
A synthetic scheme comprises 14 steps, starting with D-glucose : in the 7th step, (3', 4'-diacetoxyphenyl)-ethyl2-0-benzoyl-4,6-0-benzylidene-3-0- (2,3,4-tri-0 acetyl-alpha-L-rhamnophyranosyl)-beta-D-glucopyranoside was prepared with an average yield of 80.2%. The further step is now inprogress.
Caffeic acid labelled at the beta position of the side chain with ^<13>C atom is to be prepared in 9 steps, starting with veratrol.
(3', 4'-dihydroxyphenyl)-ethyl beta-D-glucose was prepared as one of the model compounds to interpret the hydrolysis behavior of an enzymatically oxidized acteoside : It was synthesized in the 6 steps with an average yield of 70.2%, starting with (3,4-dihydroxyphenyl) acetic acid.
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Report
(4 results)
Research Products
(6 results)
