Two new zinniol-related phytotoxins from Alternaria solani.
Bioassay-guided purification of the organic crude extract of Alternaria solani resulted in the isolation of three metabolites responsible for causing necrosis on potato leaves. These phytotoxins were identified as 2-(2",3"-dimethyl-but-1-enyl)-zinniol (1), 8-zinniol methyl ether (2). and 8-zinniol methyl ether based on their spectroscopic data (IR, MS, 1H and 13CNMR). Metabolites 1 and 2 have been identified as new phytotoxins structurally related to zinniol (4). Additionally, 5-(3',3'-dimethylallyloxy)-7-methoxy-6-methyl-phthalide and 8-zinniol-2-(phenyl)-ethyl ether (3) were also isolated during the purification process.
Moreno-Escobar
Jorge
J
Grupo de Química Orgánica, Unidad de Biotecnología, Centro de Investigación Científica de Yucatán, A.C., Calle 43 No. 130, col. Chuburná, Mérida, Yucatán, Mexico.
Puc-Carrillo
Alejandra
A
Cáceres-Farfán
Mirbella
M
Peña-Rodríguez
Luis M
LM
Gamboa-Angulo
M Marcela
MM
D000528:Alternaria / Q000737:chemistry*; D002073:Butanes / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity*; D004987:Ethers / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity*; D009336:Necrosis; D018515:Plant Leaves; D011198:Solanum tuberosum; D013057:Spectrum Analysis; D014992:Xylenes / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity*
C504177:2-(2'',3''-dimethyl-but-1-enyl)-zinniol; C504176:8-zinniol methyl ether; D002073:Butanes; D004987:Ethers; D014992:Xylenes; C051798:zinniol