Filiferol, a chalconoid analogue from Washingtonia filifera possibly involved in the defence against the Red Palm Weevil Rhynchophorus ferrugineus Olivier.
A chalconoid analogue, 1,3,5-benzentriol 2-[(2S,3R)-3-(3,4-dihydroxylphenyl)-2,3-dihydroxylpropyl], named filiferol (1), has been isolated and purified for the first time from the leaf basal tissues of the palm species Washingtonia filifera. The chemical structure of the isolated compound has been elucidated unambiguously by spectroscopic and chemical methods. Filiferol has been based on a flavonol structure with the reduction of the common flavonoid keto group to give an unprecedented methylene carbon on the three carbon chain. An analogous compound with S stereochemistry at C3 has been obtained as synthetic intermediate for developing an enantioselective synthesis of (2R,3S)-(+)-catechin. Even though 1 proved to be deprived of antifungal properties, it displays a very effective larvicidal activity against Red Palm Weevil, Rhynchophorus ferrugineus, an important pest affecting cultivated and ornamental palms. 1 has been isolated from leaf tissues of W. filifera, a species resistant to this pest, but this molecule seems instead undetectable in tissues of other palm species susceptible to the parasite. The presence of 1 could therefore account for W. filifera natural resistance to the attacks of the Red Palm Weevil (R. ferrugineus).
Consiglio per la Ricerca in Agricoltura e l'Analisi dell'Economia Agraria, Research Unit for Floriculture and Ornamental Species, Corso Inglesi 508, 18038 Sanremo, Italy.
Benedetta
B
Cangelosi
Consiglio per la Ricerca in Agricoltura e l'Analisi dell'Economia Agraria, Research Unit for Floriculture and Ornamental Species, Corso Inglesi 508, 18038 Sanremo, Italy.
Francesca
F
Clematis
Consiglio per la Ricerca in Agricoltura e l'Analisi dell'Economia Agraria, Research Unit for Floriculture and Ornamental Species, Corso Inglesi 508, 18038 Sanremo, Italy.
Fernando
F
Monroy
Consiglio per la Ricerca in Agricoltura e l'Analisi dell'Economia Agraria, Research Centre for Agrobiology and Pedology, Piazza M. D'Azeglio 30, 50121 Firenze, Italy. Electronic address: pio.roversi@entecra.it.
Pio Federico
PF
Roversi
Università degli Studi di Napoli Federico II, Dipartimento di Agraria, Via Università 100, 80055 Portici, Italy.
Raffaele
R
Troiano
Consiglio per la Ricerca in Agricoltura e l'Analisi dell'Economia Agraria, Research Unit for Floriculture and Ornamental Species, Corso Inglesi 508, 18038 Sanremo, Italy. Electronic address: paolo.curir@entecra.it.
Paolo
P
Curir
Università degli Studi di Napoli Federico II, Dipartimento di Agraria, Via Università 100, 80055 Portici, Italy. Electronic address: lanzotti@unina.it.
Virginia
V
Lanzotti
D000818:Animals; D028023:Arecaceae / Q000737:chemistry*; D047188:Chalcones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D007814:Larva / Q000187:drug effects; D015394:Molecular Structure; D048889:Weevils / Q000187:drug effects
D047188:Chalcones; D007306:Insecticides; C000606010:filiferol
Chalconoid; Resistance; Rhynchophorus ferrugineus; Washingtonia filifera