BIOSYNTHESIS OF PODOPHYLLUM LIGNANS .4. BIOSYNTHETIC RELATIONSHIP OF ARYLTETRALIN LACTONE LIGNANS TO DIBENZYLBUTYROLACTONE LIGNANS
BIOSYNTHESIS OF PODOPHYLLUM LIGNANS .4. BIOSYNTHETIC RELATIONSHIP OF ARYLTETRALIN LACTONE LIGNANS TO DIBENZYLBUTYROLACTONE LIGNANS
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DOI：
10.1016/0031-9422(86)80072-3
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发表时间：
1986-01-01
期刊：
影响因子：
3.8
通讯作者：
DEWICK, PM
中科院分区：
文献类型：
--
作者：
KAMIL, WM;DEWICK, PM
对六脚木质素植物的取食实验表明，二苄基丁内酯木脂素亚蛋白是芳基四脚素木脂素足臼毒素的理想前体。相应的yatein的顺式异构体也被掺入，但程度较小，可能是通过yatein。足酚酚、表足酚酚和无水足酚酚不被纳入足酚毒素，尽管足酚酚和无水足酚酚均存在于六脚藤植物中。提出了一种通过喹啉甲胺中间体从叶黄素合成鬼臼毒素的生物合成序列。这种中间体也可能是氢氢酚和无氢氢氢酚的前体。摘要提出了木质素中芳四烷素三甲氧基和羟基二甲氧基系列的支点化合物。从[s -甲基- 14c]蛋氨酸衍生的鬼臼毒素和4''-去甲基鬼臼毒素的标记模式支持这一建议。
Feeding experiments in Podophyllum hexandrum plants have shown that the dibenzylbutyrolactone lignan yatein is a satisfactory precursor of the aryltetralin lignan podophyllotoxin. The corresponding cis isomer of yatein was also incorporated, but to a lesser extent, and probably via yatein. Podorhizol, epipodorhizol and anhydropodorhizol were not incorporated into podophyllotoxin, despite the demonstrated presence of both podorhizol and anhydropodorhizol in P. hexandrum plants. A biosynthetic sequence from yatein to podophyllotoxin via a key quinonemethide intermediate is proposed. This intermediate is probably also the precursor of both podorhizol and anhydropodorhizol. Matairesinol is proposed as the branchpoint compound to the trimethoxy and hydroxydimethoxy series of aryltetralin lignans in Podophyllum. Labelling patterns in podophyllotoxin and 4''-demethylpodophyllotoxin derived from [S-methyl-14C]methionine support this suggestion.