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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).

木脂素和新木脂素是裸子植物和被子植物中广泛存在的一类结构多样的植物化学物质，具有多种生物活性。北方藻和高山冷杉Masters。基于结构考虑和可能的转化，我们在外消旋（（]SY.+-.]）-中获得了多种木脂素全合成的形式。他们是（（]SY.+-.]））-松醇，（（]SY.+-.]））-单甲基半夏醛，（（]SY.+-.]））-桉结蛋白，（（）SY.+-.]））-姜黄树脂酚，（（]SY.+-.]））-单甲基双松脂醇，（（[SY.+.]））- yangambin，（（]SY.+-.]））- kobusin，（（]SY.+-.]））- fargesin和（（]SY.+-.]））-胡椒醇此外，还合成了[9，9-^2H_2，OC^2H_3]松柏醇和[3-<14>O^CH_3]单甲基松柏醇。在Borealis中，确定氘代松柏醇已掺入到松醇中，但未掺入到法格辛和kobusin中。这些结果表明，可以通过两个完整的松柏醇部分的偶联来形成松脂醇。接下来，我们检查了（（]SY.+-.]））-的O-甲基化反应。通过与来自M.kobus DC var.北极光结果表明，牦牛绒茧蜂DC var.结果表明，在木兰科植物中，华北冷杉无细胞提取物催化了松醇的O-甲基化反应，表明松醇转化为单甲基松醇和桉叶结蛋白。结果表明，高山冷杉木脂素以乳醇型木脂素为主，主要分布在心材和边材中。结果表明，冷杉醇A（苯基丙烷三聚体）是由落叶松树脂酚（四氢呋喃型木脂素）与松柏醇偶联而得。（monolithyl）。