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Volumn 46, Issue 2, 1998, Pages 590-598

Isolation of Lolicine A, Lolicine B, Lolitriol, and Lolitrem N from Lolium perenne Infected with Neotyphodium lolii and Evidence for the Natural Occurrence of 31-Epilolitrem N and 31-Epilolitrem F

Author keywords

Acremonium lolii; Biosynthesis; Endophyte; Lolicine; Lolitrem; Lolitriol; Lolium perenne; Mycotoxin; Neotyphodium lolii; Neurotoxin; Paspaline; Ryegrass staggers; Tremorgen

Indexed keywords

FUNGI; LOLIUM; LOLIUM PERENNE; NEOTYPHODIUM LOLII; STAPHYLOCOCCUS PHAGE 3A;

EID: 0000542715     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9706787     Document Type: Article
Times cited : (47)

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