Pulcaffeate, a Trimeric Caffeic Acid Derivative from Bourreria pulchra

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2023-07-01 DOI:10.29356/jmcs.v67i3.1985

Gilda Erosa-Rejón, Alejandro Yam-Puc, L. Peña‐Rodríguez, O. Sterner

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Abstract

Abstract. The trimeric caffeic acid derivative pulcaffeate (1) was isolated from the organic crude extract of the roots of Bourreria pulchra (Boraginaceae). The biosynthesis of 1 appears to involve an intramolecular Diels-Alder reaction between a cyclohexa-1,3-diene intermediate, generated by the oxidation of the aromatic ring of a cinnamic acid unit, and the conjugated double bond of a caffeic acid unit. The structure of the new metabolite was elucidated through a detailed analysis of its 1H and 13C NMR spectroscopic data. This is the first report of a trimeric metabolite occurring in B. pulchra. Resumen. Pulcafeato (1) un derivado trimérico del ácido cafeico fue aislado del extracto orgánico crudo de las raíces de Bourreria pulchra (Boraginaceae). La biosíntesis de 1 parece llevarse a cabo mediante una reacción intramolecular de Diels-Alder entre un intermediario de cyclohexa-1,3-dieno, generado durante la oxidación del anillo aromático de una unidad de ácido cinámico, y el doble enlace conjugado de una unidad de ácido cafeico. La estructura del nuevo metabolito fue elucidada mediante el análisis detallado de sus datos espectroscópicos de RMN de 1H y 13C. Este es el primer reporte sobre la presencia de un metabolito trimérico en B. pulchra.

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咖啡酸盐，一种三聚体咖啡酸衍生物

摘要三聚体咖啡酸衍生物pulcaffeate(1)是从波兰科波兰根有机粗提物中分离得到的。1的生物合成似乎涉及环己-1,3-二烯中间体(由肉桂酸单元的芳香环氧化产生)和咖啡酸单元的共轭双键之间的分子内Diels-Alder反应。通过对其1H和13C NMR数据的详细分析，阐明了新代谢物的结构。这是首次报道一种三聚体代谢物出现在白杨中。Resumen。蒲草科(1)蒲草科(1)蒲草科(1)蒲草科(1)蒲草科(1)蒲草科(1)蒲草科(1)蒲草科(1)蒲草科(1)蒲草科(1)蒲草科(1)蒲草科(1)蒲草科)La biosíntesis de 1 parece llevarse a cabo mediante una reacción分子内de Diels-Alder中心和中间体de cyclohexa-1,3-dieno, generado durante La oxidación del anillo aromático de una unidad de ácido cinámico, el双链共轭物de una unidad de ácido cafeico。La structure del nuevo metabolito futureelucidada mediante el análisis detallado de sus datos espectroscópicos de RMN de 1H y 13C。Este和el primer报道了在B. pulchra中有明显的代谢性trimica存在。

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来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.