The absolute configurations of regiolone and isosclerone, two enantiomeric bioactive naphthalenone pentaketides produced by fungi and plants, have been unambiguously assigned by ab initio computational prediction of their theoretical optical rotatory powers and electronic circular dichroism spectra. Isosclerone is produced by the plant pathogen Botrytis cinerea, whereas regiolone is produced by B. fabae. The phytotoxic activities of the two compounds were tested for comparison on faba bean (host of both pathogens) and vine plants (host of only B. cinerea); the (R) configuration at C-4 was found to be a fundamental structural feature for bioactivity.

Regiolone and isosclerone, two enantiomeric phytotoxic naphthalenone pentaketides: Computational assignment of absolute configuration and its relationship with phytotoxic activity / Evidente A.; Superchi S.; Cimmino A.; Mazzeo G.; Mugnai L.; Rubiales D.; Andolfi A.; Villegas-Fernández A.M.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 28:(2011), pp. 5564-5570. [10.1002/ejoc.201100941]

Regiolone and isosclerone, two enantiomeric phytotoxic naphthalenone pentaketides: Computational assignment of absolute configuration and its relationship with phytotoxic activity.

MUGNAI, LAURA;
2011

Abstract

The absolute configurations of regiolone and isosclerone, two enantiomeric bioactive naphthalenone pentaketides produced by fungi and plants, have been unambiguously assigned by ab initio computational prediction of their theoretical optical rotatory powers and electronic circular dichroism spectra. Isosclerone is produced by the plant pathogen Botrytis cinerea, whereas regiolone is produced by B. fabae. The phytotoxic activities of the two compounds were tested for comparison on faba bean (host of both pathogens) and vine plants (host of only B. cinerea); the (R) configuration at C-4 was found to be a fundamental structural feature for bioactivity.
2011
28
5564
5570
Evidente A.; Superchi S.; Cimmino A.; Mazzeo G.; Mugnai L.; Rubiales D.; Andolfi A.; Villegas-Fernández A.M.
File in questo prodotto:
File Dimensione Formato  
Evidente_et_al-2011-European_Journal_of_Organic_Chemistry.pdf

Accesso chiuso

Tipologia: Pdf editoriale (Version of record)
Licenza: Tutti i diritti riservati
Dimensione 307.5 kB
Formato Adobe PDF
307.5 kB Adobe PDF   Richiedi una copia

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

Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/549675
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 60
  • ???jsp.display-item.citation.isi??? 60
social impact