C<sub>19</sub> Benzylisoquinoline Alkaloid with Unprecedented Architecture from <i>Hypecoum erectum</i>
Hai-Lian Yuan, Yun‐Li Zhao, Kun Hu, Yingjie He, Xing‐Wei Yang, Xiao‐Dong Luo
Abstract
Hyperectumine (1), the first C19 benzylisoquinoline alkaloid with a complicated ring system, was isolated from Hypecoum erectum and structurally characterized. Its biosynthetic origin should involve a hybrid pattern of C8 + C8 + C1 + C2, from which a C17 benzylisoquinoline alkaloid might be further attacked by a malonamic acid and undergo decarboxylation and cyclization to produce 1. Compound (−)-1 exhibited moderate anti-inflammatory activity via suppression of LPS-activated inflammatory mediators in RAW 264.7 macrophage cells.
Topics & Concepts
BenzylisoquinolineChemistryAlkaloidDecarboxylationStereochemistryOrganic chemistryBiosynthesisCatalysisEnzymeBerberine and alkaloids researchAlkaloids: synthesis and pharmacologyTraditional and Medicinal Uses of Annonaceae