Research Project Title

Absolute Configuration Determination of Sequiterpene Lactone Inuloxin A Based on Experimental and Computational Analysis of Chiroptical Properties

Session Type

Poster Presentation

Research Project Abstract

Inuloxin A is a phytotoxin obtained from Inula viscosa, a widespread Mediterranean plant well known for its therapeutic metabolites. Specifically, Inuloxin A displays inhibition towards Leishmania donovani: a parasite responsible for visceral leishmaniasis. The absolute configuration of chiral molecules like Inuloxin A is critical to their bioactivities. Therefore, we used chiroptical spectroscopic measurements and predictions to assign the absolute configuration of Inuloxin A. Using Gaussian09 programs, we optimized the geometry of various enantiomeric conformers of Inuloxin A and then isolated the lowest energy conformers for each enantiomer. After applying a Boltzmann distribution, we interpreted the theoretical spectra against experimental spectrum by visual and quantitative analysis in the CDSpecTech program suite. Chiroptical spectra could not facilitate definitive absolute configuration assignment; however, the absolute configuration (7R,8R,10S) is suggested.

Session Number

PS2

Location

HUB Multipurpose Room

Abstract Number

PS2-aa

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Apr 28th, 11:00 AM Apr 28th, 12:30 PM

Absolute Configuration Determination of Sequiterpene Lactone Inuloxin A Based on Experimental and Computational Analysis of Chiroptical Properties

HUB Multipurpose Room

Inuloxin A is a phytotoxin obtained from Inula viscosa, a widespread Mediterranean plant well known for its therapeutic metabolites. Specifically, Inuloxin A displays inhibition towards Leishmania donovani: a parasite responsible for visceral leishmaniasis. The absolute configuration of chiral molecules like Inuloxin A is critical to their bioactivities. Therefore, we used chiroptical spectroscopic measurements and predictions to assign the absolute configuration of Inuloxin A. Using Gaussian09 programs, we optimized the geometry of various enantiomeric conformers of Inuloxin A and then isolated the lowest energy conformers for each enantiomer. After applying a Boltzmann distribution, we interpreted the theoretical spectra against experimental spectrum by visual and quantitative analysis in the CDSpecTech program suite. Chiroptical spectra could not facilitate definitive absolute configuration assignment; however, the absolute configuration (7R,8R,10S) is suggested.