Term Name: stemphyloxin I
Synonyms: (2S,3R,4R,4aS,5R,7R,8aS)-2,7-dihydroxy-3-[(2R)-1-hydroxybutan-2-yl]-4-[(2Z)-3-hydroxyprop-2-enoyl]-2,4,5,7-tetramethyloctahydronaphthalen-1(2H)-one, deacyl-FR 225654, stemphyloxin I
Definition: An octahydronaphthalene that is 2,4,5,7-tetramethyloctahydronaphthalen-1(2H)-one which is substituted by hydroxy groups at positions 2 and 7, a (2R)-1-hydroxybutan-2-yl group at position 3, and a (2Z)-3-hydroxyprop-2-enoyl group at position 4 (the 2S,3R,4R,4aS,5R,7R,8aS stereoisomer). Isolated from the endophytic fungus Stemphylium botryosum, it is the causal agent of leaf spot and foliage blight disease in tomatoes. Its phytotoxcity is at least 200 times greater than that of stemphyloxin II. It shows high affinity for Fe(3+) (but not Fe(2+)) ions.
Ontology: ChEBI [CHEBI:145070]  ( EBI )

Relationships
is a type of: 3-oxo aldehyde alpha-hydroxy ketone cyclic ketone enol octahydronaphthalenes primary alcohol tertiary alcohol tetrol
has_role: fungal metabolite iron chelator phytotoxin
inverse has_functional_parent: dihydrostemphyloxin I