Cytochalasins Z1, Z2 and Z3, three 24-oxa[14]cytochalasans produced by Pyrenophora semeniperda.
Three new cytochalasans, named cytochalasins Z1, Z2 and Z3, were isolated from the wheat culture of Pyrenophora semeniperda, a fungus proposed to biologically control grass weeds. Other cytochalasins isolated from the same organic extract were identified as the already known cytochalasins F, T, deoxaphomin and cytochalasins B, the latter being produced in very large amounts. All three new cytochalasins were characterized as 24-oxa[14]cytochalasans by extensive use of NMR and MS techniques. Cytochalasins Z1 and Z2 proved to be structurally related to cytochalasin T, whereas cytochalasin Z3 was related to cytochalasin B. When assayed on wheat and tomato seedlings, cytochalasin Z3, in comparison to the new cytochalasins, cytochalasin B, its 21,22-dihydroderivative, cytochalasin F and deoxaphomin showed a remarkable ability to inhibit root elongation. The possibility of using these metabolites in biological control strategies is discussed.
Evidente
Antonio
A
Dipartimento di Scienze del Suolo, della Pianta e dell'Ambiente, Università di Napoli Federico II, Via Università 100, I-80055 Portici, Italy. evidente@unina.it
Andolfi
Anna
A
Vurro
Maurizio
M
Zonno
Maria Chiara
MC
Motta
Andrea
A
D003572:Cytochalasins / Q000302:isolation & purification* / Q000633:toxicity*; D005658:Fungi / Q000737:chemistry* / Q000502:physiology; D006540:Herbicides / Q000302:isolation & purification / Q000633:toxicity; D018551:Solanum lycopersicum / Q000187:drug effects / Q000254:growth & development; D013058:Mass Spectrometry; D015394:Molecular Structure; D018515:Plant Leaves / Q000187:drug effects; D018517:Plant Roots / Q000187:drug effects / Q000254:growth & development; D013057:Spectrum Analysis; D014908:Triticum / Q000187:drug effects / Q000254:growth & development / Q000382:microbiology
D003572:Cytochalasins; D006540:Herbicides