Bioassay-guided fractionation of the fermentation extract of Xylaria sp. XC-16;
an endophyte from Toona sinensis led to the isolation of two new cytochalasans cytochalasin Z27;
1;
and cytochalasin Z28;
2;
along with three known compounds seco-cytochalasin E;
3;
and cytochalasin Z18;
4;
and cytochalasin E;
5. The structures of 1 and 2 were elucidated by spectroscopic and electronic circular dichroism methods. Compound 5 was shown to be potently cytotoxic against brine shrimp (LC50 = 2.79 μM);
comparable to that of the positive agent toosendanin (LC50 = 4.03 μM);
and also exhibited potential phytotoxic effects on Lactuca sativa and Raphanus sativus L. seedlings;
which are higher than that of the positive control glyphosate. Additionally;
the fungicidal effect of 2 against the phytopathogen Gibberella saubinetti was better than that of hymexazol. This is the first report of the three types of cytochalasins present in genus Xylaria. A structure-phytotoxicity activity relationship is also discussed. © 2014 American Chemical Society;