Phomentrioloxin: A phytotoxic pentasubstituted geranylcyclohexentriol produced by Phomopsis sp., a potential mycoherbicide for Carthamus lanatus Biocontrol.
A new phytotoxic geranylcyclohexenetriol, named phomentrioloxin, was isolated from the liquid culture of Phomopsis sp., a fungal pathogen proposed for the biological control of Carthamus lanatus, a widespread and troublesome thistle weed belonging to the Asteraceae family causing severe crop and pastures losses in Australia. The structure of phomentrioloxin was established by spectroscopic, X-ray, and chemical methods as (1S,2S,3S,4S)-3-methoxy-6-(7-methyl-3-methylene-oct-6-en-1-ynyl)cyclohex-5-ene-1,2,4-triol. At a concentration of 6.85 mM, the toxin causes the appearance of necrotic spots when applied to leaves of both host and nonhost plants. It also causes growth and chlorophyll content reduction of fronds of Lemna minor and inhibition of tomato rootlet elongation. Finally, in preliminary bioassays, phomentrioloxin did not show any antibacterial, fungicidal, or zootoxic activities.
Dipartimento di Scienze del Suolo, della Pianta, dell'Ambiente e delle Produzioni Animali (DISSPAPA), Università di Napoli Federico II, Via Università 100, 80055 Portici, Italy.
Alessio
A
Cimmino
Anna
A
Andolfi
Maria C
MC
Zonno
Ciro
C
Troise
Antonello
A
Santini
Angela
A
Tuzi
Maurizio
M
Vurro
Gavin
G
Ash
Antonio
A
Evidente
D001203:Ascomycota / Q000737:chemistry*; D001315:Australia; D031178:Carthamus / Q000382:microbiology*; D018360:Crystallography, X-Ray; D003511:Cyclohexanols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D006540:Herbicides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D018551:Solanum lycopersicum / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000187:drug effects
D003511:Cyclohexanols; D006540:Herbicides; C574853:phomentrioloxin