Isolation and Structure Elucidation of Additional Alkaloids from the Tropical Rainforest Tree Galbulimima baccata,Journal of Natural Products

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Isolation and Structure Elucidation of Additional Alkaloids from the Tropical Rainforest Tree Galbulimima baccata
Journal of Natural Products ( IF 3.3 ) Pub Date : 2021-09-07 , DOI: 10.1021/acs.jnatprod.1c00537
Nirmal K Chaudhary ₁ , Walter C Taylor ₂ , Lewis N Mander ₃ , Peter Karuso ₁

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The structures of five new natural products (GB 27–GB 31, 1–5), isolated as minor components from the bark of Galbulimima baccata, have been determined by 2D NMR spectroscopy in combination with DFT calculations. Among the alkaloids, GB 31 (5) belongs to Class I, GB 27 (1) and 28 (2) belong to Class II, and GB 30 (4) belongs to Class III GB alkaloids. GB 31 is the first non-nitrogen-containing GB “alkaloid”, being a biosynthetic oxidation product of himbacine, himandravine, or himbeline. GB 29 (3) has an entirely new natural product scaffold but belongs to Class IV (miscellaneous alkaloids). The isolation of a new Galbulimima scaffold has revealed a new pathway in the biosynthesis of the GB alkaloids. The new molecules isolated have shed further light on the biogenetic relationship among these structurally unique and complex groups of alkaloids. We present, for the first time, a unified biogenesis for the GB alkaloids that were first isolated in the 1950s and now number over 40 examples. This work also brings full circle the story of Galbulimima alkaloids. A life-long project of Wal Taylor involving one of his first students (Lew Mander) and one of his last students (Peter Karuso), a story stretching over six decades, has come to a final conclusion.

中文翻译：

热带雨林树Galbulimima baccata中额外生物碱的分离和结构解析

五个新的天然产物（GB 27-GB 31，结构1 - 5），分离为从树皮次要组分Galbulimima山定子，已经由2D NMR光谱与DFT计算组合来确定。生物碱中，GB 31( 5 )属Ⅰ类，GB 27( 1 )、28( 2 )属Ⅱ类，GB 30( 4 )属Ⅲ类国标生物碱。GB 31 是第一种不含氮的 GB“生物碱”，是喜巴碱、喜山树碱或喜白林的生物合成氧化产物。GB 29 ( 3 ) 具有全新的天然产物支架，但属于第四类（杂类生物碱）。新的隔离Galbulimima支架揭示了 GB 生物碱生物合成的新途径。分离出的新分子进一步阐明了这些结构独特且复杂的生物碱组之间的生物遗传关系。我们第一次展示了 GB 生物碱的统一生物起源，这些生物碱在 1950 年代首次被分离出来，现在有 40 多个例子。这部作品也完整地讲述了金雀花生物碱的故事。沃尔·泰勒 (Wal Taylor) 的一项涉及他的第一批学生 (Lew Mander) 和最后一名学生 (Peter Karuso) 的终生项目，一个长达 60 年的故事，已经有了最终结论。

更新日期：2021-09-24

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