A Reappraisal of the Structure of Lyaline as the First Naturally Occurring Nacycline Monoterpene Indole Alkaloid,Journal of Natural Products

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A Reappraisal of the Structure of Lyaline as the First Naturally Occurring Nacycline Monoterpene Indole Alkaloid
Journal of Natural Products ( IF 3.3 ) Pub Date : 2021-09-15 , DOI: 10.1021/acs.jnatprod.1c00572
Adrien Jagora ₁ , Jean-François Gallard ₂ , Mehdi A Beniddir ₁ , Pierre Le Pogam ₁

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Lyaline (1) is a monoterpene indole alkaloid that was isolated in 1974 from Pauridiantha lyallii (Rubiaceae) in our laboratory and has not been reported elsewhere since then. Its structure was proposed on the basis of a very limited set of spectroscopic data (viz., ¹H NMR and EIMS) as a structurally bizarre harman-1,4-dihydropyridine derivative. A total synthesis of this proposed structure 30 years later proved this product to be highly unstable, and inconsistencies with the original limited spectroscopic data indicated that the structure proposed for lyaline was incorrect. Having in our laboratory the initial and unique lyaline sample, we decided to reinvestigate it using modern spectroscopic techniques, 47 years after its isolation. Our new spectroscopic data confirmed that the initially assigned harman-1,4-dihydropyridine structure was incorrect, instead establishing lyaline as the first naturally occurring nacycline analogue. This structure revision substantiates a type of chemical reactivity of strictosidine first reported in 1975.

中文翻译：

作为第一个天然存在的 Nacycline 单萜吲哚生物碱的赖氨酸结构的重新评估

Lyaline ( 1 ) 是一种单萜吲哚生物碱，于 1974 年从我们实验室的Pauridiantha lyallii (茜草科) 中分离出来，此后一直没有在其他地方报道过。它的结构是根据一组非常有限的光谱数据提出的（即，¹H NMR 和 EIMS）作为一种结构奇异的哈曼-1,4-二氢吡啶衍生物。30 年后对该结构的全合成证明该产物高度不稳定，与原始有限光谱数据的不一致表明为赖氨酸提出的结构是不正确的。在我们的实验室中获得了初始且独特的赖氨酸样品后，我们决定在其分离 47 年后使用现代光谱技术对其进行重新研究。我们的新光谱数据证实最初分配的哈曼-1,4-二氢吡啶结构不正确，而是将赖氨酸确定为第一个天然存在的萘环素类似物。这种结构修正证实了 1975 年首次报道的胡豆苷的一种化学反应性。

更新日期：2021-09-24

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