Studies on biosynthesis of lignans in woody plants.

木本植物木脂素生物合成的研究。

基本信息

批准号：
05660177
负责人：
OZAWA Shuji
金额：
$ 1.34万
依托单位：
HOKKAIDO UNIVERSITY
依托单位国家：
日本
项目类别：
Grant-in-Aid for General Scientific Research (C)
财政年份：
1993
资助国家：
日本
起止时间：
1993 至 1995
项目状态：
已结题

项目摘要

Lignans and neolignans are a widely distributed, structurally diverse phytochemical class in gymnosperms and angiosperms, with exhibiting various biological activities.As a part of our studies to elucidating biosynthetic pathways of lignans in woody plants, we investigated the formation of lignans in Magnolia kobus DC var. borealis Sarg. and Abies sachalinensis Masters.Based on structural considaratin and possible transformations, we obtained various lignans in recemic ((]SY.+-.]))-form by total synthesis. They were ((]SY.+-.]))-pinoresinol, ((]SY.+-.]))-monomethylpinoresinal, ((]SY.+-.]))-eudesmin, ((]SY.+-.]))-syringaresinol, ((]SY.+-.]))-monomethylsyringaresinol, ((]SY.+-.]))-yangambin, ((]SY.+-.]))-kobusin, ((]SY.+-.]))-fargesin and ((]SY.+-.]))-piperitol. In addition, [9,9-^2H_2, OC^2H_3] coniferyl alcohol and [3-O^<14>CH_3] monomethylpinoresinol were synthesized.In vivo labelling experiments of M.kobus DC var. borealis, it was established that deuterated coniferyl alcohol had been incorporated into pinoresinol, but not fargesin and kobusin. These results suggested that formation of pinoresinol can occur via coupling of two intact coniferyl alcohol moieties. Next, we examined O-methylation reaction of ((]SY.+-.]))-pinoresinol by incubation with cell-free extracts from M.kobus DC var. borealis. It was shown that M.kobus DC var. borealis cell-free extracts catalysed the O-methylation of pinoresinol, suggesting the conversion of pinoresinol into monomethylpinoresinol and eudesmin in Magnolia.In the investigation of lignans of Abies sachalinensis various lignans were isolated. it revealed that lignans of Abies sachalinensis were characterized by a preferential occurerence of lactol-type lignans, which mainly distributed in the sap-and heartwood. it was suggested that abiesol A (phenylpropane trimer) was derived from the coupling of lariciresinol (tetrahydrofuran type lignan) and coniferyl alcohlol. (monolignol).

Lignans and neolignans are a widely distributed, structurally diverse phytochemical class in gymnosperms and angiosperms, with exhibiting various biological activities.As a part of our studies to elucidating biosynthetic pathways of lignans in woody plants, we investigated the formation of lignans in Magnolia kobus DC var. Borealis Sarg。和Abies sachalinensis Masters。基于结构化合物和可能的转化，我们在recemic（（（]sy。+ - 。]）中，我们获得了各种木lignans） - 通过总合成形式。它们是（（（] sy。+ - 。]）） - 丁香醇，（（（]Sy。+ - 。]）） - 单甲基丙肾，（（（（] SY。+ - 。。（（]sy。+ - 。]）） - kobusin，（（（]sy。+ - 。]）） - fargesin and（（（] sy。+ - 。]）） - piperitol。此外，合成了[9,9-^2H_2，OC^2H_3] Coniferyl醇和[3-O^<14> CH_3]单甲基吡啶酚。北极性的，已经确定已将氘化的针叶性酒精掺入了Pinoresinol中，但不远处和无丁素。这些结果表明，可以通过两个完整的针叶醇部分偶联而形成无原醇。接下来，我们通过与M.Kobus DC Var中的无细胞提取物一起孵育（（SY]。+ - 。]））的O-甲基化反应。北方。结果表明M.Kobus DC Var。北极细胞提取物催化了可生石的O-甲基化，这表明在木兰中，小甲醇转化为单甲基甲基酚和eudesmin。它揭示了sachalinensis的脂肪人的特征是乳糖型木lignans的优先出现，乳糖型木质豆体主要分布在树液和心脏木中。有人提出，阿比柴酚A（苯丙烷三聚体）源自幼虫（四氢呋喃型lignan）和coniferyl botherlol的偶联。（单极酚）。