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. 2023 Jan 14;13(1):128.
doi: 10.3390/metabo13010128.

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

Anthonin Gori  1   2 , Benjamin Boucherle  1 , Aurélien Rey  2 , Maxime Rome  3 , Caroline Barette  4 , Emmanuelle Soleilhac  4 , Christian Philouze  5 , Marie-Odile Fauvarque  4 , Nicola Fuzzati  2 , Marine Peuchmaur  1
Affiliations

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

Anthonin Gori et al. Metabolites. .

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.

Keywords: Ajuga pyramidalis; antioxidant; chemical composition; epidermal renewal; iridoids; phenylethanoid glycosides.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Compounds already isolated from A. pyramidalis.
Figure 2
Figure 2
RPC18 HPLC chemical profile of A. pyramidalis: (a) apolar extract, (b) intermediate extract, (c) polar extract (UV chromatogram, 280 nm, at the top and ELSD chromatogram below for each extract).
Figure 3
Figure 3
Chemical structures of new polyphenols isolated from A. pyramidalys.
Scheme 1
Scheme 1
Acetylation of harpagoside (C1 and C8 are numbered in line with the RX structure below).
Figure 4
Figure 4
RX structure of a synthesized pentaacetylated harpagoside derivative.
Figure 5
Figure 5
Effect of the three extracts on the nuclear translocation of NF-κB/p65 induced by TNFα and on autophagy. (A) Images of nuclei and NF-κB/p65 staining of HEK293T cells treated with DMSO or each of the extract, with or w/o TNFα. (B) Images of nuclei and autophagosomes (GFP-LC3 staining) of HeLa GFP-LC3 cells treated with DMSO, rapamycin (inductor of autophagy) or the extracts. (A,B) The results obtained at the lowest non-toxic dilution of extracts (as indicated) are shown. Scale bar = 40 µm.
Figure 6
Figure 6
Effect of the three extracts on the autophagy in HeLa GFP-LC3 cells. Cells were treated with 0.25% DMSO, 250 nM of rapamycin, an inhibitor of mTOR and, consequently, an activator of autophagy, or each of the extract. The results obtained at the lowest non-toxic dilution of extracts (as indicated) are shown. Histograms represent the cell classification regarding their content in autophagosomes (less than three; between three and eight; up to eight ATG/cell).
Figure 7
Figure 7
Phytochemical profile of Ajuga pyramidalis ethanolic extracts of roots (blue), flowers (red) and remaining aerial parts (green): (a) HPLC-DAD and (b) HPLC-ELSD chromatograms.
Figure 8
Figure 8
Phytochemical profile of the ethanolic extract of A. pyramidalis (pink), A. reptans (green), A. chamaepitys (red) and A. genevensis (blue): (a) HPLC-DAD and (b) HPLC-ELSD chromatograms.
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