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 2 was active on Sonchus arvensis while 1 caused around 75% larval mortality on Artemia salina larvae at 0.1 μg/μL.
Chenopodolans E and F, two new furopyrans produced by Phoma chenopodiicola and absolute configuration determination of chenopodolan B / Evidente, Marco; Cimmino, Alessio; Zonno, Maria Chiara; Masi, Marco; Santoro, Ernesto; Vergura, Stefania; Berestetskiy, Alexander; Superchi, Stefano; Vurro, Maurizio; Evidente, Antonio. - In: TETRAHEDRON. - ISSN 0040-4020. - 72:51(2016), pp. 8502-8507. [10.1016/j.tet.2016.11.024]
Chenopodolans E and F, two new furopyrans produced by Phoma chenopodiicola and absolute configuration determination of chenopodolan B
CIMMINO, ALESSIO;MASI, MARCO;EVIDENTE, ANTONIO
2016
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 2 was active on Sonchus arvensis while 1 caused around 75% larval mortality on Artemia salina larvae at 0.1 μg/μL.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
