title: Farinose alpine Primula species: phytochemical and morphological investigations.
abstract: This work investigated the epicuticular and tissue flavonoids, the volatiles and the glandular trichome structure of the leaves of four species of Primula L. that grow in the Italian Eastern Alps. Primula albenensis Banfi and Ferlinghetti, P. auricula L., P. farinosa L., P. halleri Gmelin produce farinose exudates that are deposited on the leaf surface as filamentous crystalloids. In addition to compounds already known, a new flavone, the 3,5-dihydroxyflavone, was isolated from the acetone extract of leaf farinas and three new flavonol glycosides, 3'-O-(β-galactopyranosyl)-2'-hydroxyflavone, isorhamnetin 3-O-α-rhamnopyranosyl-(1→3)-O-[α-rhamnopyranosyl-(1→6)]-O-β-galactopyranoside, quercetin 3-O-α-rhamnopyranosyl-(1→3)-O-[α-rhamnopyranosyl-(1→6)]-O-β-galactopyranoside, were isolated from the MeOH extract of the leaves. All the structures were elucidated on the basis of their (1)H and (13)C NMR data and 2D NMR techniques, as well as on HPLC-MS. The leaf-volatiles emitted by these Primula species were mainly sesquiterpene hydrocarbons, with the exception of P. albenensis, which produced almost exclusively a non-terpene derivative; P. halleri flowers were also examined and the volatiles emitted by the flower parts (corolla and calyx) were compared with the corresponding leaves.
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, 20133 Milano, Italy; Orto Botanico G.E. Ghirardi, Dipartimento di Scienze Farmaceutiche, Via Religione 25, Toscolano Maderno, Brescia, Italy. Electronic address: paola.colombo6@studenti.unimi.it.
authors.forename: Paola S
authors.initials: PS
authors.lastname: Colombo
authors.affiliation: Dipartimento di Farmacia, Università degli Studi di Pisa, via Bonanno 33, 56126 Pisa, Italy. Electronic address: flamini@farm.unipi.it.
authors.forename: Guido
authors.initials: G
authors.lastname: Flamini
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, 20133 Milano, Italy. Electronic address: michael.christodoulou@unimi.itc.
authors.forename: Michael S
authors.initials: MS
authors.lastname: Christodoulou
authors.affiliation: Dipartimento di Bioscienze, Università degli Studi di Milano,via Celoria 26, 20133 Milano, Italy. Electronic address: graziella.rodondi@unimi.it.
authors.forename: Graziella
authors.initials: G
authors.lastname: Rodondi
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, 20133 Milano, Italy; Orto Botanico G.E. Ghirardi, Dipartimento di Scienze Farmaceutiche, Via Religione 25, Toscolano Maderno, Brescia, Italy. Electronic address: sara.vitalini@unimi.it.
authors.forename: Sara
authors.initials: S
authors.lastname: Vitalini
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, 20133 Milano, Italy. Electronic address: daniele.passarella@unimi.it.
authors.forename: Daniele
authors.initials: D
authors.lastname: Passarella
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, 20133 Milano, Italy; Orto Botanico G.E. Ghirardi, Dipartimento di Scienze Farmaceutiche, Via Religione 25, Toscolano Maderno, Brescia, Italy. Electronic address: gelsomina.fico@unimi.it.
authors.forename: Gelsomina
authors.initials: G
authors.lastname: Fico
mesh_terms: D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification*; D035264:Flowers / Q000737:chemistry; D015394:Molecular Structure; D055668:Photochemical Processes; D018515:Plant Leaves / Q000737:chemistry; D031825:Primula / Q000737:chemistry*; D013045:Species Specificity; D064201:Trichomes / Q000737:chemistry*; D055549:Volatile Organic Compounds / Q000737:chemistry / Q000302:isolation & purification*
chemical_list: D005419:Flavonoids; D055549:Volatile Organic Compounds
keywords: Farina; Flavonoids; Phytochemistry; Primula albenensis, P. auricula, P. farinosa, P. halleri; Primulaceae; Trichome micromorphology; Volatile compounds