Greger Harald, Hofer Margit, Teichmann Klaus, Schinnerl Johann, Pannell Caroline M, Vajrodaya Srunya, Hofer Otmar
Comparative and Ecological Phytochemistry, Faculty Center of Botany, University of Vienna, Rennweg 14, A-1030 Wien, Austria.
Phytochemistry. 2008 Feb;69(4):928-38. doi: 10.1016/j.phytochem.2007.10.015. Epub 2007 Dec 21.
Six amide-esters and two sulphur-containing bisamides were isolated from the leaves, stem and root bark of Aglaia tenuicaulis together with two bisamides from the leaves of A. spectabilis. Their structures were elucidated by spectroscopic methods. The co-occurrence of amide-esters and bisamides suggests close biosynthetic connections replacing only one nitrogen atom of putrescine with oxygen. Putrescine appears to be the common building block linked to various acids from which the cinnamoyl moiety represents the prerequisite for an incorporation of bisamides into flavaglines. Corresponding amide-esters are apparently not incorporated, but closely related amide-alcohol derivatives were found as part of benzopyran and benzofuran flavaglines. The structure of a amide-alcohol is described, representing an artifact due to hydrolysis of an amide-ester during TLC purification. A hypothetical amide-amine building block is suggested to form the characteristic pyrimidinone structures only found in benzofuran flavaglines. Structural and biosynthetic connections between amide-esters, bisamides and flavaglines are discussed and the chemotaxonomic significance of accumulating specific derivatives within the genus Aglaia is highlighted.
从细轴米仔兰的叶、茎和根皮中分离出六种酰胺酯和两种含硫双酰胺，同时从壮丽米仔兰的叶中分离出两种双酰胺。通过光谱方法阐明了它们的结构。酰胺酯和双酰胺的共存表明存在密切的生物合成联系，即腐胺中的一个氮原子被氧取代。腐胺似乎是与各种酸相连的共同结构单元，其中肉桂酰部分是双酰胺并入黄皮酰胺类化合物的前提条件。相应的酰胺酯显然未被并入，但发现密切相关的酰胺醇衍生物是苯并吡喃和苯并呋喃黄皮酰胺类化合物的一部分。描述了一种酰胺醇的结构，它是在薄层色谱纯化过程中由于酰胺酯水解而产生的一种假象。有人提出一种假设的酰胺胺结构单元可形成仅在苯并呋喃黄皮酰胺类化合物中发现的特征性嘧啶酮结构。讨论了酰胺酯、双酰胺和黄皮酰胺类化合物之间的结构和生物合成联系，并强调了米仔兰属植物中积累特定衍生物的化学分类学意义。
