title: Reassessment of Melittis melissophyllum L. subsp. melissophyllum iridoidic fraction.
abstract: The analysis of the polar fraction of Melittis melissophyllum L. subsp. melissophyllum led to the identification of several iridoid glycosides: monomelittoside (1), melittoside (2), harpagide (3), acetyl-harpagide (4) and ajugoside (5). Compounds 3 and 4 are considered marker compounds for the genus and, as well as compounds 1, 2 and 5, were already evidenced in a previous study on the nominal species. It was noteworthy of the presence of allobetonicoside (6) which was never reported for this genus. The isolation of 6 is very relevant because of its allose residue on the structure. Allose has been often found in the species of the subfamily Lamioideae even if it mostly regarded flavonoids considered of chemotaxonomical relevance for some correlated genera of Lamiaceae. Same as allosyl-glycosidic flavonoids, the presence of allosyl-glycosidic iridoids may also be an additional chemosystematic evidence of botanical relationships among Lamiaceae species and genera.
authors.affiliation: a Dipartimento di Chimica Piazzale Aldo Moro , Università di Roma "La Sapienza", 5 , 00185 Rome , Italy.|b Dipartimento di Biologia Ambientale Piazzale Aldo Moro , Università di Roma "La Sapienza", 5 , 00185 Rome , Italy.
authors.forename: A
authors.initials: A
authors.lastname: Venditti
authors.affiliation: b Dipartimento di Biologia Ambientale Piazzale Aldo Moro , Università di Roma "La Sapienza", 5 , 00185 Rome , Italy.
authors.forename: C
authors.initials: C
authors.lastname: Frezza
authors.affiliation: a Dipartimento di Chimica Piazzale Aldo Moro , Università di Roma "La Sapienza", 5 , 00185 Rome , Italy.|d Pharmaceutical Chemistry and Technologies, Sapienza-University of Rome , P.le A. Moro, 5, 00185 Rome , Italy.
authors.forename: L
authors.initials: L
authors.lastname: Guarcini
authors.affiliation: c School of Pharmacy, University of Camerino , Camerino , Italy.
authors.forename: F
authors.initials: F
authors.lastname: Maggi
authors.affiliation: a Dipartimento di Chimica Piazzale Aldo Moro , Università di Roma "La Sapienza", 5 , 00185 Rome , Italy.
authors.forename: A
authors.initials: A
authors.lastname: Bianco
authors.affiliation: b Dipartimento di Biologia Ambientale Piazzale Aldo Moro , Università di Roma "La Sapienza", 5 , 00185 Rome , Italy.
authors.forename: M
authors.initials: M
authors.lastname: Serafini
mesh_terms: D005960:Glucosides / Q000032:analysis; D057889:Iridoid Glycosides / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification; D039823:Iridoids / Q000032:analysis / Q000737:chemistry*; D019686:Lamiaceae / Q000737:chemistry* / Q000145:classification; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D011714:Pyrans / Q000032:analysis
chemical_list: D005960:Glucosides; D057889:Iridoid Glycosides; D039823:Iridoids; D011714:Pyrans; C477173:ajugoside; C033250:harpagide
keywords: Lamiaceae; Melittis melissophyllum L. subsp. melissophyllum; allobetonicoside; chemotaxonomy; iridoids