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

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??g/?L, only 2 was active on Sonchus arvensis while 1 caused around 75% larval mortality on Artemia salina larvae at 0.1??g/?L.


Tutti gli autori

  • M. Evidente; A. Cimmino; M.C. Zonno; M. Masi; E. Santoro; S. Vergura; A. Berestetskiy; S. Superchi; M. Vurro; A. Evidente

Titolo volume/Rivista

Tetrahedron


Anno di pubblicazione

2016

ISSN

0040-4020

ISBN

Non Disponibile


Numero di citazioni Wos

Nessuna citazione

Ultimo Aggiornamento Citazioni

Non Disponibile


Numero di citazioni Scopus

Non Disponibile

Ultimo Aggiornamento Citazioni

Non Disponibile


Settori ERC

Non Disponibile

Codici ASJC

Non Disponibile