AI Article Synopsis

  • A natural compound, areolal, shows significant variations in its absolute configuration within the same species, with samples displaying different enantiomeric compositions over time from the same geographical area.
  • These variations were measured using NMR data with BINOL as a chiral solvating agent, uncovering a unique phenomenon in the compound’s behavior.
  • The findings highlight potential influences of environmental factors and biochemical processes, emphasizing the importance of careful evaluation of enantiomeric composition for natural products intended for human use.

Article Abstract

The exceptional case of a natural compound that shows drastic absolute configuration variations within the same species was examined. Sequential samples of areolal () isolated from showed dextrorotatory (ee 32%), almost racemic (ee 4%), levorotatory (ee 82%), and again dextrorotatory (ee 10%) values. Enantiomeric compositions of this epoxythymol derivative were determined from individual plant specimens collected from the same geographical location over a 46-day period, which were processed using the same extraction and isolation methods. Detection of this unusual phenomenon was possible by analysis of NMR data recorded in the presence of BINOL as a chiral solvating agent. The absolute configuration of (-)-(8)-areolal followed from vibrational circular dichroism data of an enantiomerically enriched sample, while single-crystal X-ray diffraction and supramolecular analyses revealed interactions that diminish the crystal entropy in -. These results might be related with environmental factors and biochemical processes, suggesting the need of strict evaluations of enantiomeric composition of natural products that could be considered for human applications.

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Source
http://dx.doi.org/10.1021/acs.jnatprod.9b00734DOI Listing

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