Non-Volatile Terpenoids and Lipophilic Flavonoids from Achillea erba-rotta Subsp. moschata (Wulfen) I. Richardson.

Musk yarrow (Achillea erba-rotta subsp. moschata (Wulfen) I. Richardson) is endemic to the Central Alps, and is used to flavour alcoholic beverages. Despite its popularity as aromatizing agent and its alleged beneficial effects on digestion, the phytochemical profile of the plant is still largely unknown and undiscovered. As a consequence, its authentication in aromatized products is impossible beyond sensory analysis allowing forgery. To address these issues, we phytochemically characterized a sample of musk yarrow from the Italian Eastern Alps, identifying, in addition to widespread phytochemicals (taraxasterol, apigenin), the guaianolides 3, 8, 9; the seco-caryophyllane 6; and the polymethoxylated lipophilic flavonoids 1, 4, and 5. The flavonoid xanthomicrol 1, a major constituent of the plant, was cytotoxic to HeLa cells, but only modestly affected primary 3T3 fibroblasts. On account of their stability, detectability by UV absorption, and concentration, the oxygenated flavonoids qualify as markers to validate the supply chain of the plant growers to consumers.

Variability in the Essential Oil Composition of Achillea erba-rotta subsp. moschata (Wulfen) I. Richardson Growing in the Eastern Italian Alps.

Achillea erba-rotta subsp. moschata (Wulfen) I. Richardson is endemic of the Central Alps and distributed in several Italian Regions, where is used for its medicinal and aromatic properties. Nine wild populations of the species were characterized for their essential oil content and composition. In total 45 components were detected of which 40 were identified, accounting from 96.3 % to 98.8 % of the total oil. Monoterpenes represented the main class of compounds (from 84 % to 90.9 %), being cis-thujone (from 1.1 % to 48.4 %), camphor (from 1.8 % to 36.9 %), 1,8-cineole (from 4.9 % to 23.4 %), trans-thujone (from 2.2 % to 33.9 %) and p-cymene (from 1.8 % to 4.8 %) the most abundant ones. The relative amount of chamazulene, detected in some accessions, was here reported for the first time in this species. High variability in the essential oil composition resulted among the investigated accessions, which were grouped by multivariate analysis into four main clusters, in some cases according to their site of origin. Beyond their possible chemo-systematic significance, the obtained results represent useful indications for the selection of interesting chemotypes within the species, especially in the perspective of its future cultivation.

Volatile Composition Variability of Arnica montana Wild Populations of Trentino-Alto Adige, Italy, Determined by Headspace-Solid Phase Microextraction.

Arnica montana is a plant distributed in most of Europe, including the Alpine arc and Apennines in Italy, and traditionally used worldwide for medicinal properties. Twelve natural populations of the species from Trentino-Alto Adige, Italy, were characterized using Headspace-Solid Phase Microextraction analysis for their volatile profile. Fifty-one compounds were detected in flower heads, the most abundant being (E)-Caryophyllene (23.4 %), 2,2,4,6,6-Pentamethylheptane (8.3 %), α- trans-Bergamotene (7.2 %), Germacrene D (5.7 %), and Hexanal (5.3 %). A multivariate analysis performed on the ten most abundant compounds grouped these investigated accessions into five main clusters. Three clusters, comprising together five accessions, were linked to the geographical origin of two collection sites. This work is a complete characterization of volatiles of the species by SPME analysis reported to date. Furthermore, results suggest that the species' volatile profile can be linked to the geographical origin of the natural populations and, therefore, represent a tool for evaluating biodiversity within the species.

Evaluation of the Farming Potential of Echinacea Angustifolia DC. Accessions Grown in Italy by Root-Marker Compound Content and Morphological Trait Analyses.

The Echinacea genus includes a number of species that are commercially employed for the preparation of herbal products. Echinacea angustifolia DC. is one of these and is widely used, mainly for its immunomodulating properties, as it contains a wide range of compounds that belong to different chemical classes. In particular, echinacoside, cynarin and lipophylic alkylamides are the main specialized metabolites of the roots and can be considered to be marker compounds. In this work, 65 E. angustifolia accessions have been compared in a field trial in Italy, with the aim of investigating the variability/stability of the weight and chemical composition of their roots in order to identify the accessions that are most promising for future genetic-improvement programs. The morphological characteristics of the aerial parts have also been investigated. Seventeen samples were discarded due to germination or plantlet-development issues. Seven of the remaining accessions were identified as being different Echinacea species after a combined phytochemical and morphological evaluation. The morphological traits of the epigeal part, the root weight and the chemical composition data of the 41 confirmed E. angustifolia accessions were submitted to multivariate statistical analysis and a moderately homogenous sample distribution, with low selected-marker variability, was observed. Good echinacoside content was detected in almost all roots (>0.5%). However, two groups of accessions stood out because of their interesting features: One group possessed small roots, but had a high concentration of marker compounds, while another had highly developed roots and a good amount of marker compounds. These accessions can therefore be exploited for future selection work.

Research survey on iridoid and phenylethanoid glycosides among seven populations of Euphrasia rostkoviana Hayne from the Alps.

The traditional use of extracts of Euphrasia rostkoviana to relieve ocular inflammation or infections is well documented and supported by clinical studies. Various classes of chemical compounds such as iridoids, phenylethanoids, flavonoids and hydroxycinnamic acids have been reported. The present work aims to assess the chemical diversity among seven populations of Euphrasia rostkoviana found in northern Italy. A meticulous separation of components led to the isolation and structural characterization of two previously unrecorded phenylethanoids methoxycrassifolioside and deoxycrassifolioside and one previously undescribed terpene glucoside (1E,6E)-8-hydroxy-3,7-dimethyl-octa-1,6-dienyl 1-O-ß-D-glucopyranoside. We have also identified known phenylethanoids and iridoids that are reported in this genus for the first time. Finally, a targeted quantitative analysis for the standardization of herbal preparations revealed that iridoids occur in all populations whereas the presence and the levels of rutin and phenylethanoids are highly variable.

Differences in the chemical composition of Arnica montana flowers from wild populations of north Italy.

The flower heads of fourteen wild Arnica montana L. populations were collected in the summer of 2010 in the provinces of Trento, Brescia and Bergamo (Italy). The dried flowers were analyzed to assess their chemical diversity. HLPC-MS analysis led to the identification of phenolic derivatives and sesquiterpene lactones in the samples, confirming literature data. Quali-quantitative analysis of the flower heads showed similar qualitative patterns both for the phenolic as well as sesquiterpene lactone derivatives, while significant variability was obtained in the amounts (HPLC-DAD) of sesquiterpene lactones (0.45-2.31%), phenolic acids (1.44-2.88%) and flavonoids (0.96-2.44%). The highest quantities of sesquiterpene lactones, flavonoids and phenolic acids were found in Malga Fregasoga (1703 m above sea level), Rifugio Camini (1608 m a.s.l.) and Malga Sass (1817 m a.s.l.) samples, respectively.