Direct infusion ESI‐IT‐MSn alkaloid profile and isolation of tetrahydroharman and other alkaloids from Bocageopsis pleiosperma maas (Annonaceae). Issue 5 (24th June 2015)

• Record Type: Journal Article
• Authors: Soares, Elzalina R.; da Silva, Felipe M. A.; de Almeida, Richardson A.; de Lima, Bruna R.; da Silva Filho, Francinaldo A.; Barison, Andersson; Koolen, Hector H. F.; Pinheiro, Maria Lúcia B.; de Souza, Afonso D. L.
• Is Part Of: Phytochemical analysis. Volume 26:Issue 5(2015:Sep.)
• Page Start: 339
• Page End: 345
• Publication Date: 2015-06-24
• Subjects: Plants -- Analysis -- Periodicals; Plants -- chemistry -- Periodicals; 572.2
• DOI: 10.1002/pca.2568
• Languages: English
• ISSNs: 0958-0344

Abstract

<abstract abstract-type="main"> <title>Abstract</title> <sec id="pca2568-sec-0001" sec-type="section"> <title>Introduction</title> <p>The Annonaceae family is known as a promising abundant source of secondary metabolites, especially annonaceous acetogenins, terpenoids and isoquinoline‐derived alkaloids. Although widely investigated from the phytochemical viewpoint, this family still presents some largely unexplored genera, e.g. the <italic>Bocageopsis</italic>.</p> </sec> <sec id="pca2568-sec-0002" sec-type="section"> <title>Objective</title> <p>To investigate the alkaloid content of <italic>Bocageopsis pleiosperma</italic> Maas using direct infusion electrospray ionisation ion trap tandem mass spectrometry (ESI‐IT‐MS<italic><sup>n</sup></italic>) analysis.</p> </sec> <sec id="pca2568-sec-0003" sec-type="section"> <title>Methodology</title> <p>Dichloromethane extracts of aerial parts were subjected to acid–base partitioning to yield the alkaloidal fractions. These fractions were analysed by direct infusion into a (+)ESI‐IT‐MS<italic><sup>n</sup></italic> system. The alkaloidal fraction from the leaves was also obtained on a large scale and subjected to chromatographic separation.</p> </sec> <sec id="pca2568-sec-0004" sec-type="section"> <title>Results</title> <p>The tentative MS<italic><sup>n</sup></italic>‐based identification of alkaloids in leaves, twigs and trunk bark showed that aporphine alkaloids were restricted to the leaves and twigs, tetrahydroprotoberberine alkaloids were only found in the twigs and trunk bark while benzylisoquinoline alkaloids were found in the leaves, twigs and trunk bark. Chromatographic separation of the leaf alkaloidal fraction yielded the aporphine alkaloids nornuciferine, asimilobine and isoboldine, the β‐carboline alkaloid tetrahydroharman and some mixtures containing benzylisoquinoline and aporphine alkaloids, all described for the first time in the <italic>Bocageopsis</italic> genus. Furthermore, tetrahydroharman has not previously been reported in the Magnoliales order.</p> </sec> <sec id="pca2568-sec-0005" sec-type="section"> <title>Conclusion</title> <p>Direct infusion ESI‐IT‐MS<italic><sup>n</sup></italic> analysis of alkaloids allowed fast recognition of alkaloidal classes previously reported in the Annonaceae family, aiding the chromatographic step and allowing a selective isolation of compounds previously not identified in the <italic>Bocageopsis</italic> genus. Copyright © 2015 John Wiley & Sons, Ltd.</p> </sec> </abstract>