Chenopodolans E and F, two new furopyrans produced by Phoma chenopodiicola and absolute configuration determination of chenopodolan B

July 28, 2017

Title

Chenopodolans E and F, two new furopyrans produced by Phoma chenopodiicola and absolute configuration determination of chenopodolan B

Author

Marco Evidente, Alessio Cimmino, Maria Chiara Zonno, Marco Masi, Ernesto Santoro, Stefania Vergura, Alexander Berestetskiy, Stefano Superchi, Maurizio Vurro, Antonio Evidente

Year

2016

Journal

Tetrahedron

Abstract

Two new furopyrans, named chenopodolans E and F (1 and 2), were isolated from the liquid culture of Phoma chenopodiicola, a fungal pathogen proposed for the biological control of Chenopodium album, a common worldwide weed of arable crops. They were characterized using spectroscopic methods as 3-(3-methoxy-2,6-dimethyl-7aH-furo[2,3b]pyran-4-yl)-but-2-enoic acid methyl ester and 1-(3-methoxy-2,6-dimethyl-7aH-furo[2,3b]pyran-4-yl)-ethanone, respectively. Furthermore, the absolute configuration of chenopodolan B (3) was established to be (7aR,9S) by a combined application of the advanced Mosher's method and of quantum mechanical calculations of chiroptical (ECD and ORD) properties. When 1 and 2 were assayed on punctured leaves at 2 μg/μL, only 2was active on Sonchus arvensis while 1 caused around 75% larval mortality on Artemia salina larvae at 0.1 μg/μL.

Instrument

J-815

Keywords

Circular dichroism, Absolute configuration, Agricultural and environmental