Abstract：
:Two phytotoxins 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. The two phytotoxins appeared to be a new tetrasubstituted furopyran and a new ent-pimaradiene. From the same culture a new tetrasubstituted isocoumarin was also isolated. These compounds were characterized by using spectroscopic (essentially 1D and 2D NMR and HR ESI MS) and chemical methods as 3-(3-methoxy-2,6-dimethyl-7aH-furo[2,3-b]pyran-4-yl)-but-2-en-1-ol (chenopodolan D, 1) (1S,2S,3S,4S,5S,9R,10S,12S,13S)-1,3,12-triacetoxy-2,hydroxy-6-oxo-ent-pimara-7(8),15-dien-18-oic acid 2,18-lactone (chenopodolin B, 3), and, 4,5,7-trihydroxy-3-methyl-isochroman-1-one (chenisocoumarin, 2) The absolute configuration of chenisocoumarin was assigned by applying an advanced Mosher's method through the derivatization of its secondary hydroxylated carbon C-4, while that of chenopodolan D by application of quantum mechanical calculations of chiroptical (ECD and ORD) properties. When assayed by leaf puncture against non-host weeds, chenopodolan D and chenopodolin B showed phytotoxicity while chenisocoumarin and the 9-O-acetyl derivative of chenopodolan D were inactive. These results confirm that the nature of the side chain at C-4 in chenopodolans, and in particular its hydroxylation, are important features for activity. The activity of chenopodolin B could also be explained by its possible hydrolysis to chenopodolin.
journal_name
Phytochemistryjournal_title
Phytochemistryauthors
Evidente M,Cimmino A,Zonno MC,Masi M,Berestetskyi A,Santoro E,Superchi S,Vurro M,Evidente Adoi
10.1016/j.phytochem.2015.07.008subject
Has Abstractpub_date
2015-09-01 00:00:00pages
482-488eissn
0031-9422issn
1873-3700pii
S0031-9422(15)30047-9journal_volume
117pub_type
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