New Tricholomalides D-G from the Mushroom Tricholoma ustaloides Grown in an Italian Beech Wood.

Four novel seconeodolastane diterpenoids, named tricholomalides D-G, were isolated, together with the known tricholomalide C, from the fruiting bodies of Tricholoma ustaloides Romagn., a species belonging to the large Tricholoma genus of higher mushrooms (Basidiomycota, family Tricholomataceae). They were isolated through multiple chromatographic separations, and the structures, including the absolute configuration, were established through a detailed analysis of MS, NMR, and CD spectral data and comparison with related compounds reported in the literature, which has been thoroughly revised.

New Tricholidic Acid Triterpenoids from the Mushroom Tricholoma ustaloides Collected in an Italian Beech Wood.

The secondary metabolites produced by Tricholoma ustaloides Romagn., a mushroom species belonging to the large Tricholoma genus (Basidiomycota, Tricholomataceae), are unknown. Therefore, encouraged by the interesting results obtained in our previous chemical analyses of a few Tricholoma species collected in Italian woods, we aimed to investigate the secondary metabolites of Tricholoma ustaloides. The chemical analysis involved the isolation and characterization of secondary metabolites through an extensive chromatographic study. The structures of isolated metabolites, including the absolute configuration, were established based on a detailed analysis of MS, NMR spectroscopic, optical rotation, and circular dicroism data, and on comparison with those of related compounds reported in the literature. Two novel lanostane triterpenoids, named tricholidic acids B and C, together with triglycerides, a mixture of free fatty acids, five unidentified metabolites, and the known rare saponaceolides F and J, tricholidic acid, and tricholomenyn C, were isolated from an EtOAc extract of fruiting bodies of Tricholoma ustaloides that were collected in an Italian beech wood. This is the second example of isolation of tricholidic acid derivatives from a natural source. Saponaceolides F and J exhibited high cytotoxicity (IC50 values ≤ 10 µM) against a panel of five human cancer cell lines. The toxicity against myeloid leukemia (HL-60), lung cancer (A-549), hepatocellular cancer (HepG2), renal cancer (Caki-1), and breast cancer (MCF-7) cells was higher than that shown by the very well-known cytotoxic drug cisplatin.

Ethnobotanical Research at the Kutukú Scientific Station, Morona-Santiago, Ecuador.

This work features the results of an ethnobotanical study on the uses of medicinal plants by the inhabitants of the region near to the Kutukú Scientific Station of Universidad Politécnica Salesiana, located in the Morona-Santiago province, southeast of Ecuador. In the surroundings of the station, one ethnic group, the Shuar, has been identified. The survey hereafter reports a total of 131 plant species, with 73 different therapeutic uses.

Phytochemistry and Ethnopharmacology of Medicinal Plants Used on Safeen Mountain in the Kurdistan Region of Iraq.

In remote villages of Kurdistan-Iraq, such as in those on Safeen Mountain, decoctions, potions, and oils from the local herbal tradition have provided the only medicinal remedies for centuries, up to today. A variety of diseases are treated with different plant preparations, ranging from simple rheumatism to diarrhea, skin diseases, and highly complicated kidney and heart problems. This survey describes, for the first time, the mostly used medicinal plants, resulting from several interviews with local herbal healers. The bioactivity of some isolated compounds is, indeed, strictly related to traditional uses of plants in Safeen Mountain Province. We also report the preliminary results of our ongoing research project on the constituents of the still uninvestigated plant Pterocephalus nestorianus Nab., which is traditionally used against inflammation and oral diseases. Luteolin-7-0-glucoside, 3,5-di-O-caffeoylquinic acid and loganic acid were isolated.

New 3,4-Secocycloartane and 3,4-Secodammarane Triterpenes from the Ecuadorian Plant Coussarea macrophylla.

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.

Determination of the threshold odor concentration of main odorants in essential oils using gas chromatography-olfactometry incremental dilution technique.

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.

Cucurbitane triterpenoids from Leucopaxillus gentianeus.

In addition to the known bioactive triterpene cucurbitacin B (1), two new cucurbitane triterpenoids, namely, leucopaxillones A (3) and B (4), exhibiting a new oxygenation pattern among cucurbitacins, have been isolated from the mushroom Leucopaxillus gentianeus (syn. L. amarus). Cucurbitacin B (1) imparts a bitter taste to the flesh of the fungus; however, it occurs in the fruiting bodies mainly esterified as tasteless fatty acid esters 2a-c. In vitro growth inhibitory effects of compounds 1-4 on proliferation of four different human tumor cell lines (A549, CAKI-1, HepG2, MCF-7) were evaluated by using a 1-day MTT assay. Only cucurbitacin B was highly active on all lines. Free cucurbitacin B is presumed to be formed in vivo by an enzyme-mediated scission of esters 2a-c, thus constituting a chemical weapon that protects the mushrooms against parasites and predators. Compounds 1-4 are structurally different from the other few cucurbitacins isolated from Basidiomycetes, being, instead, more similar to those occurring in plants. In particular, cucurbitacin B (1) seems to represent an interesting example of secondary metabolite convergence between distant taxa such as fungi and vascular plants, where they likely exert a similar role of protection. The structures of the compounds were established by means of spectroscopic methods and X-ray diffraction on a single crystal. The absolute configuration of leucopaxillone A has been assigned on the basis of CD chirality rules.

New anthracene derivatives from Coussarea macrophylla.

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.

Compuestos furánicos en el senecio canescens humb

El senecio canescens Humb., conocido vulgarmente como "orejas de conejo", es usado en la medicina popular para curar infecciones, dolores de cabeza y reumatismos. La investigación de las partes aéreas y de las raíces condujo a la determinación de compuestos furanoeremofilanos, entre los cuales se elució el primer furanoeremofilano hidroperóxido natural y dos nuevos derivados de la cacalohastina, uno de los cuales es un dimero. La fracción volatil fue analizada por GC-MS.