Papers by Gianluca Gilardoni
Chemistry & biodiversity, 2015
Coussarea macrophylla (Mart.) Müll.Arg. (Rubiaceae) was collected in Ecuador, and the bark was ex... more Coussarea macrophylla (Mart.) Müll.Arg. (Rubiaceae) was collected in Ecuador, and the bark was extracted with AcOEt. Chromatographic separation afforded six novel 3,4-secocycloartane and 3,4-secodammarane triterpenes, named macrocoussaric acids A-F, together with the known metabolites secaubryenol and 3,4-secodammara-4(28),20,24-triene-3,26-dioic acid. The structures of the new compounds were determined on the basis of their spectroscopic data. This is the first report of 3,4-secocycloartane and 3,4-secodammarane triterpenes occurring in a Coussarea species. Macrocoussaric acids A and B (2 and 3, resp.) were found to be moderately cytotoxic against five different tumor cell lines.
Journal of Natural Products
Five new naturally occurring anthracene derivatives, 1,4,10-trimethoxyanthracene-2-carbaldehyde (... more Five new naturally occurring anthracene derivatives, 1,4,10-trimethoxyanthracene-2-carbaldehyde (1), (1,4,10-trimethoxy-2-anthracen-2-yl)methanol (2), 1,4,8,10-tetramethoxyanthracene-2-carbaldehyde (3), 1,4,10-trimethoxyanthracene-2-carboxylic acid (4), and 1,3-dimethoxy-2-methoxymethylanthraquinone (5), were isolated from Coussarea macrophylla along with three known compounds, 3-hydroxy-1-methoxy-2-methoxymethylanthraquinone (6), scopoletin, and 3-epi-pomolic acid. The structures of 1-5 were determined on the basis of analysis of their spectroscopic data and by total synthesis.
Natural product communications, 2014
The results of the first investigation of secondary metabolites occurring in intact and damaged f... more The results of the first investigation of secondary metabolites occurring in intact and damaged fruiting bodies of the European mushrooms Lactarius aurantiacus, L. subdulcis, and Russula sanguinaria are reported. The pattern of sesquiterpenes in injured R. sanguinaria is dramatically different from that of Lactarius. The structure of the new furanolactarane 4, isolated from L. aurantiacus, was established on the basis of spectral data.
Fitoterapia, 2006
Four enyne derivatives (1-4) and quercitrin were isolated during a bioassay-guided chromatographi... more Four enyne derivatives (1-4) and quercitrin were isolated during a bioassay-guided chromatographic separation of a methanolic extract of Erigeron apiculatus. Matricarialactone (1) and lachnophyllumlactone (2) showed a high fungitoxic activity against Pyricularia oryzae. Matricaria acid methyl ester (3) and lachnophyllum acid methyl ester (4) were, instead, less active.
Natural product communications, 2011
Phytochemical investigation of secondary metabolites of the Ecuadorian plant Schistocarpha eupato... more Phytochemical investigation of secondary metabolites of the Ecuadorian plant Schistocarpha eupatorioides (Fenzl) Kuntze (Asteraceae) afforded three phytyl fatty acid esters along with a mixture of unidentified polyprenols, the very well known sterols beta-sitosterol and stigmasterol, and their corresponding fatty acid esters and glucosyl derivatives. The structures of the compounds were elucidated on the basis of various spectroscopic means. In addition, a volatile fraction was separated the composition of which, comprising sesquiterpene hydrocarbons as the main fraction, was determined by GC-MS.
Phytochemistry, 2014
The results of the first investigation on secondary metabolites occurring in intact and damaged f... more The results of the first investigation on secondary metabolites occurring in intact and damaged fruiting bodies of Russula nobilis growing in Europe, are reported. Intact mushrooms contain fatty acid esters of velutinal, while three new sesquiterpenoids, russulanobilines A-C, along with eight known ones were isolated from extracts of injured fruiting bodies. The structures of the new compounds were elucidated on the basis of spectral data, molecular modeling, and 13 C NMR spectra calculation. This pattern of sesquiterpenes constitutes a new variant of a chemical defense machinery which protects mushrooms against predators, parasites, and microorganisms.
Journal of Natural Products, 2007
Chrysotriones A (1) and B (2), two new 2-acylcyclopentene-1,3-dione derivatives, were isolated fr... more Chrysotriones A (1) and B (2), two new 2-acylcyclopentene-1,3-dione derivatives, were isolated from the fruiting bodies of the Basidiomycete Hygrophorus chrysodon, and their structures were established by spectroscopic data and synthesis of compound 2. They represent the first examples of 2-acylcyclopentene-1,3-diones found in mushrooms and suggest an unprecedented biosynthetic pathway, starting from fatty acid derivatives. Initial tests indicated interesting antifungal activity of chrysotriones against Fusarium Verticillioides, one of the common worldwide pathogens of cultivated plants.
Journal of Ethnopharmacology, 2010
Fitoterapia, 2006
Four enyne derivatives (1-4) and quercitrin were isolated during a bioassay-guided chromatographi... more Four enyne derivatives (1-4) and quercitrin were isolated during a bioassay-guided chromatographic separation of a methanolic extract of Erigeron apiculatus. Matricarialactone (1) and lachnophyllumlactone (2) showed a high fungitoxic activity against Pyricularia oryzae. Matricaria acid methyl ester (3) and lachnophyllum acid methyl ester (4) were, instead, less active.
Journal of Chromatography A, 2007
An essential oil, obtained by steam distillation of Clinopodium tomentosum (Kunth) Govaerts (Lami... more An essential oil, obtained by steam distillation of Clinopodium tomentosum (Kunth) Govaerts (Lamiaceae), collected in Ecuador, was analyzed by gas chromatography-olfactometry (GC-O) and GC-MS techniques. To our knowledge, the composition of this essential oil is described here for the first time, both from the chemical and olfactometric viewpoints. A preliminary analysis by GC-MS and using Kovats' retention indexes, lead to characterize and quantify the oil constituents, while GC-O was then applied for the identification of the main odorants. By the incremental dilution method (AEDA, CHARM Analysis), applied to the GC-O technique, the flavor dilution (FD) chromatogram was obtained. In order to calculate the TOC values of the main odorants, the relationship between the odorant concentration at the sniffing port and that one in the injected solution was established. This relationship was calculated by comparing the injected amount with the TOC value of a reference compound (limonene), obtained by dynamic dilution olfactometry. A good agreement was found between calculated and measured TOC values of few odorants.
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Papers by Gianluca Gilardoni