PHENOL OXIDATION AND BIOSYNTHESIS .6. BIOGENESIS OF AMARYLLIDACEAE ALKALOIDS
PHENOL OXIDATION AND BIOSYNTHESIS .6. BIOGENESIS OF AMARYLLIDACEAE ALKALOIDS
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DOI：
10.1039/jr9630004545
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发表时间：
1963-01-01
期刊：
影响因子：
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通讯作者：
THOMAS, GM
中科院分区：
文献类型：
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作者：
BARTON, DHR;TAYLOR, JB;THOMAS, GM
研究了阿尔弗雷德王水仙花产生的生物碱加兰他敏、加兰他敏和血红素中四种二酚 (Ia)、(Ib)、(Ic) 和 (Id) 的掺入情况。前体已根据需要标记在 N-Me、O-Me 和位置 1 上。生物碱的降解表明标签没有混乱并且前体完整地掺入。特别阐述了多重标记前体的应用。还进行了中间捕获实验。通过对 O-Me 上 1 位双标记的前体 (Ic) 进行的决定性实验，证明了血红胺的亚甲二氧基在自然界中是通过 (Ic) 的 O-甲氧基苯酚基团环化形成的。这种现象的普遍性和机制存在争议。
The incorporation of the four diphenols (Ia),(Ib),(Ic), and (Id) into the alkaloids galanthamine, galanthine, and haemanthamine produced by the King Alfred daffodil has been investigated. The precursors have been labelled on the N-Me, on the O-Me, and at position 1 as appropriate. Degradation of the alkaloids demonstrated that there was no scrambling of the labels and that the precursors are incorporated intact. The application of multiply labelled precursors has been specially illustrated. Intermediate trapping experiments have also been made.By a decisive experiment with the precursor (Ic), doubly labelled on O-Me and at position 1, it has been proved that the methylenedioxy-group of haemanthamine is formed in Nature by cyclisation of the O-methoxyphenol group of (Ic). The generalisation and mechanism of this phenomenon are debated.