Investigation of Chemical Composition and Biological Activities of Ajuga pyramidalis—Isolation of Iridoids and Phenylethanoid Glycosides

Abstract

Despite several studies on the Ajuga L. genus, the chemical composition of Ajuga pyramidalis, an alpine endemic species, is still largely unknown. The purpose of this study was to therefore deeper describe it, particularly from the phytochemistry and bioactivity perspectives. In that respect, A. pyramidalis was investigated and 95% of the extracted mass of the plant was characterized by chromatography and mass spectrometry. Apart from the already determined chemical compounds, namely, harpagide and 8-O-acetylharpagide, two iridoids, and neoajugapyrin A, a neo-clerodane diterpene, and three polyphenols (echinacoside, verbascoside and teupoloside) were identified for the first time in A. pyramidalis. Incidentally, the first RX structure of a harpagoside derivative is also described in this paper. The extracts and isolated compounds were then evaluated for various biochemical or biological activities; notably a targeted action on the renewal of the epidermis was highlighted with potential applications in the cosmetic field for anti-aging.

Mass Spectrometric Identification of Metabolites after Magnetic-Pulse Treatment of Infected Pyrus communis L. Microplants

“…Adducts of aucubin ([M+Na] + or [M+NH 4 ] + ) at m/z 269 [11] and 364 [15] have been observed, depending on the experimental MS conditions. The analyte fragmentation in positive polarity is associated with the cleavage of D-glucose (Glc) fragments [16,17], thus producing [M-162] + ions at m/z 184 from charged iridoid glucoside [16]. The molecular [M] + ions appear at m/z 346 [16,18].…”

Probing Antioxidant-Related Properties for Phenolic Compounds

“…Antioxidant compounds have been widely recognized by the scientific community as important auxiliaries in slowing the aging process. − In this sense, although the establishment of an elixir for eternal life seems to be unreachable from a realistic perspective, consumption of dietetic antioxidants (in particular when ingested on a regular basis and combined with better choices regarding other aspects of life) is ascribed to be a promising strategy for preventing several diseases and postponing death, , as these species are able to neutralize free radicals . Among a variety of compounds that present considerable antioxidant activity, phenolic entities, more precisely, polyphenols, are a class of molecules that has been heavily studied over the years. − Beyond their antioxidant potential, these chemical species are known for presenting desired health-related properties such as anti-inflammatory, antiviral, antidiabetic, and antitumor actions and, thus, there is a continuously increasing interest in searching for new polyphenolic species either through isolation/identification of naturally occurring species or via structural modification through synthesis. − In the latter case, the use of computational-based protocols may provide useful insights and contribute to optimizing the strategies for performing specific modifications in polyphenol structures aiming to yield compounds with enhanced properties.…”