title: Absolute configurations of phytotoxic inuloxins B and C based on experimental and computational analysis of chiroptical properties.
abstract: The absolute configuration of phytotoxins inuloxins B and C, produced by Inula viscosa, and with potential herbicidal activity for the management of parasitic plants, has been determined by Time-dependent density functional theory computational prediction of electronic circular dichroism and optical rotatory dispersion spectra. The inuloxin B has been converted to its 5-O-acetyl derivative, which due to its more constrained conformational features facilitated the computational analysis of its chiroptical properties. The analysis based on experimental and computed data led to assignment of absolute configuration to naturally occurring (+)-inuloxin B and (-)-inuloxin C as (7R,8R,10S,11S) and (5S,7S,8S,10S), respectively.
authors: Department of Chemical Sciences, University of Naples "Federico II", Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126, Napoli, Italy; Department of Chemistry, Columbia University, 3000 Broadway, 3114, New York, NY 10027, USA.
authors: Marco
authors: M
authors: Evidente
authors: Department of Sciences, University of Basilicata, Via dell'Ateneo Lucano 10, 85100 Potenza, Italy.
authors: Ernesto
authors: E
authors: Santoro
authors: Department of Chemistry, Columbia University, 3000 Broadway, 3114, New York, NY 10027, USA; Department of Life Sciences, New York Institute of Technology (NYIT), 1855 Broadway, New York, NY 10023, USA.
authors: Ana G
authors: AG
authors: Petrovic
authors: Department of Chemical Sciences, University of Naples "Federico II", Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126, Napoli, Italy.
authors: Alessio
authors: A
authors: Cimmino
authors: JASCO Corporation, Hachioji-shi, Tokyo 192-8537, Japan.
authors: Jun
authors: J
authors: Koshoubu
authors: Department of Chemical Sciences, University of Naples "Federico II", Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126, Napoli, Italy. Electronic address: evidente@unina.it.
authors: Antonio
authors: A
authors: Evidente
authors: Department of Chemistry, Columbia University, 3000 Broadway, 3114, New York, NY 10027, USA. Electronic address: ndb1@columbia.edu.
authors: Nina
authors: N
authors: Berova
authors: Department of Sciences, University of Basilicata, Via dell'Ateneo Lucano 10, 85100 Potenza, Italy. Electronic address: stefano.superchi@unibas.it.
authors: Stefano
authors: S
authors: Superchi
mesh_terms: D019659:Asteraceae / Q000737:chemistry*; D002942:Circular Dichroism; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009905:Optical Rotatory Dispersion; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013237:Stereoisomerism; D013997:Time Factors
chemical_list: D012717:Sesquiterpenes; C000614413:inuloxin B; C000614415:inuloxin C
keywords: Absolute configuration; Asteraceae; Electronic circular dichroism; Inula viscosa; Inuloxins; Optical rotation; Phytotoxins; TDDFT computations