A new tetrasubstituted octanoic acid, named hyfraxinic acid (1), was isolated together with known 1-deoxyviridiol (2), viridiol (3), nodulisporiviridin M (4), and demethoxyviridiol (5) from the organic extract of Hymenoscyphus fraxineus responsible for ash (Fraxinus excelsior L.) dieback in Europe. Hyfraxinic acid (1) was characterized, using spectroscopic methods, as 2,4-dihydroxy-7-methyl-6-methyleneoctanoic acid. Furthermore, the advanced Mosher method was used to determine the absolute configuration (3R) of 1-deoxyviridiol. Nodulisporiviridin M (4) was isolated for the first time from H. fraxineus. The phytotoxicity of each compound was tested by a leaf puncture assay on Celtis australis L., Quercus suber L., Hedera elix L., Juglans regia L., and Fraxinus angustifolia L. leaves. Compounds 1, 3, and 5 exhibited remarkable phytotoxicity on all plants tested, inducing necrotic lesions at concentrations of 1.0 and 0.5 mg/mL, while compounds 2 and 4 were found to be inactive in this bioassay. These results could contribute to a deeper understanding of the pathogenicity of H. fraxineus.

Hyfraxinic Acid, a Phytotoxic Tetrasubstituted Octanoic Acid, Produced by the Ash (Fraxinus excelsior L.) Pathogen Hymenoscyphus fraxineus Together with Viridiol and Some of Its Analogues / Masi, M.; Di Lecce, R.; Tuzi, A.; Linaldeddu, B. T.; Montecchio, L.; Maddau, L.; Evidente, A.. - In: JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. - ISSN 0021-8561. - 67:49(2019), pp. 13617-13623. [10.1021/acs.jafc.9b06055]

Hyfraxinic Acid, a Phytotoxic Tetrasubstituted Octanoic Acid, Produced by the Ash (Fraxinus excelsior L.) Pathogen Hymenoscyphus fraxineus Together with Viridiol and Some of Its Analogues

Linaldeddu B. T.;Maddau L.;Evidente A.
2019

Abstract

A new tetrasubstituted octanoic acid, named hyfraxinic acid (1), was isolated together with known 1-deoxyviridiol (2), viridiol (3), nodulisporiviridin M (4), and demethoxyviridiol (5) from the organic extract of Hymenoscyphus fraxineus responsible for ash (Fraxinus excelsior L.) dieback in Europe. Hyfraxinic acid (1) was characterized, using spectroscopic methods, as 2,4-dihydroxy-7-methyl-6-methyleneoctanoic acid. Furthermore, the advanced Mosher method was used to determine the absolute configuration (3R) of 1-deoxyviridiol. Nodulisporiviridin M (4) was isolated for the first time from H. fraxineus. The phytotoxicity of each compound was tested by a leaf puncture assay on Celtis australis L., Quercus suber L., Hedera elix L., Juglans regia L., and Fraxinus angustifolia L. leaves. Compounds 1, 3, and 5 exhibited remarkable phytotoxicity on all plants tested, inducing necrotic lesions at concentrations of 1.0 and 0.5 mg/mL, while compounds 2 and 4 were found to be inactive in this bioassay. These results could contribute to a deeper understanding of the pathogenicity of H. fraxineus.
Hyfraxinic Acid, a Phytotoxic Tetrasubstituted Octanoic Acid, Produced by the Ash (Fraxinus excelsior L.) Pathogen Hymenoscyphus fraxineus Together with Viridiol and Some of Its Analogues / Masi, M.; Di Lecce, R.; Tuzi, A.; Linaldeddu, B. T.; Montecchio, L.; Maddau, L.; Evidente, A.. - In: JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. - ISSN 0021-8561. - 67:49(2019), pp. 13617-13623. [10.1021/acs.jafc.9b06055]
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11388/230841
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 8
  • ???jsp.display-item.citation.isi??? 8
social impact