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. 2023 Jan 15;12(2):402.
doi: 10.3390/plants12020402.

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

Stefano Salamone  1   2 , Nicola Aiello  3 , Pietro Fusani  3 , Antonella Rosa  4 , Mariella Nieddu  4 , Giovanni Appendino  1 , Federica Pollastro  1   2
Affiliations

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

Stefano Salamone et al. Plants (Basel). .

Abstract

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.

Keywords: Achillea erba-rotta subsp. moschata; guaianolides; lipophilic flavonoids; xanthomicrol.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
The guaianolides biosynthesis through the Δ1,3-diene [4 + 2] photocycloaddition of oxygen followed by rearrangement to a diepoxide leading to 8 and, after hydrolysis of one of the two epoxide functions, to 9.
Figure 1
Figure 1
Musk yarrow constituents identified: xanthomicrol 1, taraxasterol 2, matricarin 3, tanetin 4, penduletin 5, 1(10)-secocariophyllane 6, apigenin 7, canin 8, 1α,2β-epoxy-3β,4α,10 α-trihydroxyguaian 6α,12-olide 9, eupatilin 10, artemetin 11.
Figure 2
Figure 2
Viability (MTT assay) expressed as % of the control (Ctrl), induced by incubation for 24 h with different amounts (5–200 μM) of xanthomicrol 1 in cancer HeLa cells and 3T3 fibroblasts. Three independent experiments were performed, and data are presented as mean ± SD (n = 16); a = p < 0.001 versus Ctrl (One-way ANOVA and Bonferroni post-test); *** = p < 0.001 for Hela cells versus 3T3 fibroblasts (Student’s unpaired t-test with Welch’s correction).
Figure 3
Figure 3
Representative images of phase contrast of control HeLa cells and cells treated for 24 h with DMSO (2%) and different amounts (5–200 μM) of xanthomicrol 1. Bar = 100 µm. Clear cytotoxic activity is evidenced as a result of an increase in dosage.
Figure 4
Figure 4
Flow cytometric analysis of the cell cycle distribution of control HeLa cells (Ctrl) and cells treated for 24 h with xanthomicrol 1 at concentrations of 5, 10, and 25 μM. Percentage values of the HeLa cells in cell cycle patterns (sub G1, G0/G1, S, and G2/M phases) are reported in the lower panel.
See this image and copyright information in PMC

References

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