Arboridinine Structure Elucidation

S.P. Wong  et al investigated the alkaloid content of K. arborea Blume, and reported the isolation and structure determination of a new pentacyclic monoterpenoid indole alkaloid, Arboridinine (molecular formula C₁₉H₂₂N₂O), characterized by an unprecedented molecular skeleton.

In a 2023 article published in Eur. J. Org. Chem, the incorrect structures of two natural products and their subsequent reassignment was discussed. Here we discuss how Structure Elucidator Suite was used to verify these structures.

The structure of Boerelasin B (molecular formula C₂₉H₃₅NO₄) was determined from 1D and 2D NMR spectra as well as by comparison of the spectroscopic data with those of a known similar structure isolated from the same fungus. The NMR data obtained were used by us for challenging Structure Elucidator Suite.

Kim et al isolated and identified two unprecedented phosphorus-containing iodinated polyacetylenes, Phosphoiodyn A and B, from a Korean marine sponge Placospongia sp. Here we will describe the structural elucidation of Phosphoiodyn A (molecular formula C₁₆H₂₄O₄PI).

A reinvestigation of the NMR and IR results for natural schizocommunin led the researchers to propose a revised structure, quinazolinone. We suggested that if a CASE approach were used elucidate the structure when this compound was firstly isolated, the structure revision would be not necessary: for final structure confirmation X-ray crystallographic analysis would be sufficient.

Here we describe a total synthesis of a hypothetical alternative structure and its spectroscopic confirmation, representing a huge amount of work done by the authors to disprove the original structure. We used their example to ask what solution would be obtained if the authors used ACD/Structure Elucidator Suite for processing the spectroscopic data of the unknown.

Tronoharine was isolated in a small amount as a minor alkaloid from a sample of T. corymbosa and given a proposed structure. In a more recent work, it was obtained in a more significant amount, which enabled the authors to reevaluate the previously proposed structure. Structure Elucidator Suite was used to confirm the newly proposed structure of Tronoharine ((molecular formula C₂₁H₂₄N₂O₂).

Kim and coworkers isolated a new neolignan, piperkadsin C, and elucidated its structure. However, the structure was revised by the same group in their next article. Structure Elucidator Suite was used to confirm the proposed structure #2, molecular formula C₂₀H₂₀O₆.

El Aouad at al isolated a new naphthopyrone (structure 1) named Lasionectrin (molecular formula C₁₉H₂₀O₆) with antiplasmodial properties from fermentation broths of a Lasionectria species. The article constitutes the first account on the isolation of a natural product from fungi of this genus.