A new oleanolic-type triterpene glycoside from<i>Anchusa italica</i>

Chen, Kui-Kui; Xie, Zhou-Jian; Dai, Wei; Wang, Qi

doi:10.1080/14786419.2016.1258557

Cited by 17 publications

(6 citation statements)

References 20 publications

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“…The tri-glycosylated compound 20 and 25 presented a similar glycosylation, with the presence of a glucuronic methyl ester group, observed for the first time in the study of Cartabia et al [ 14 ]. The ability of A. officinalis to produce saponins was already reported in previous studies [ 31 , 38 , 50 ] and their strong accumulation in shoot parts of mycorrhized A. officinalis is in line with the study by Cartabia et al [ 14 ].…”

Section: Discussionsupporting

confidence: 88%

The Metabolic Profile of Anchusa officinalis L. Differs According to Its Associated Arbuscular Mycorrhizal Fungi

et al. 2022

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Anchusa officinalis (L.) interacts with various microorganisms including arbuscular mycorrhizal fungi (AMF). Recently, the AMF Rhizophagus irregularis MUCL 41833 has been shown to modulate the metabolome of A. officinalis. However, little information is available on the impact that different AMF species may have on primary and secondary plant metabolites. In this study, four AMF species belonging to the genus Rhizophagus (R. irregularis MUCL 41833, R. intraradices MUCL 49410, R. clarus MUCL 46238, R. aggregatus MUCL 49408), were evaluated for their potential to modulate A. officinalis metabolome under controlled semi-hydroponic cultivation conditions. An untargeted metabolomic analysis was performed using UHPLC-HRMS followed by a multivariate data analysis. Forty-two compounds were reported to be highly modulated in relation to the different AMF associations. Among them, six new secondary metabolites were tentatively identified including two acetyl- and four malonyl- phenylpropanoid and saponin derivatives, all presenting a common substitution at position C-6 of the glycosidic moiety. In addition, an enhanced accumulation of primary and secondary metabolites was observed for R. irregularis and R. intraradices, showing a stronger effect on A. officinalis metabolome compared to R. clarus and R. aggregatus. Therefore, our data suggest that different AMF species may specifically modulate A. officinalis metabolite production.

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Section: Discussionsupporting

confidence: 88%

The Metabolic Profile of Anchusa officinalis L. Differs According to Its Associated Arbuscular Mycorrhizal Fungi

et al. 2022

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“…Their content is influenced by various biotic stimuli, such as herbivory and pest attack or related to plant-microorganism symbiosis (Hussain et al, 2017 ). Interestingly, the ability to produce these compounds has been already reported for Anchusa spp., specifically oleanane-type glycosidic derivatives mainly present in the foliar part of the plants (Koz et al, 2009 ; Chen et al, 2017 ). In our analysis, and in opposition to phenolic compounds, saponins 17, 32, 33, and 34 showed maximum accumulation in M shoots, with a fold change increment ranking from 1.73 to 2.26.…”

Section: Discussionmentioning

confidence: 99%

The Arbuscular Mycorrhizal Fungus Rhizophagus irregularis MUCL 41833 Modulates Metabolites Production of Anchusa officinalis L. Under Semi-Hydroponic Cultivation

et al. 2021

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Anchusa officinalis is recognized for its therapeutic properties, which are attributed to the production of different metabolites. This plant interacts with various microorganisms, including the root symbiotic arbuscular mycorrhizal fungi (AMF). Whether these fungi play a role in the metabolism of A. officinalis is unknown. In the present study, two independent experiments, associating A. officinalis with the AMF Rhizophagus irregularis MUCL 41833, were conducted in a semi-hydroponic (S-H) cultivation system. The experiments were intended to investigate the primary and secondary metabolites (PMs and SMs, respectively) content of shoots, roots, and exudates of mycorrhized (M) and non-mycorrhized (NM) plants grown 9 (Exp. 1) or 30 (Exp. 2) days in the S-H cultivation system. Differences in the PMs and SMs were evaluated by an untargeted ultrahigh-performance liquid chromatography high-resolution mass spectrometry metabolomics approach combined with multivariate data analysis. Differences in metabolite production were shown in Exp. 1. Volcano-plots analysis revealed a strong upregulation of 10 PMs and 23 SMs. Conversely, in Exp. 2, no significant differences in PMs and SMs were found in shoots or roots between M and NM plants whereas the coumarin scoparone and the furanocoumarin byakangelicin, accumulated in the exudates of the M plants. In Exp. 1, we noticed an enhanced production of PMs, including organic acids and amino acids, with the potential to act as precursors of other amino acids and as building blocks for the production of macromolecules. Similarly, SMs production was significantly affected in Exp 1. In particular, the phenolic compounds derived from the phenylpropanoid pathway. Fifteen di-, tri-, and tetra-meric C6-C3 derivatives of caffeic acid were induced mainly in the roots of M plants, while four oleanane-types saponins were accumulated in the shoots of M plants. Two new salvianolic acid B derivatives and one new rosmarinic acid derivative, all presenting a common substitution pattern (methylation at C-9”' and C-9' and hydroxylation at C-8), were detected in the roots of M plants. The accumulation of diverse compounds observed in colonized plants suggested that AMF have the potential to affect specific plant biosynthetic pathways.

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“…Plants are an important source of phenolic compounds, which are known for their antibacterial properties and can have applications as natural preservatives either in the food field or in the cosmetic field [4,[12][13][14]. Previous chemical studies have shown that Anchusa italic Retz is rich in polyphenols, flavonoids, saponins, tannins, vitamin E [15][16][17][18]. The seeds of the plant are rich in saturated fatty acids, unsaturated fatty acids, and alkaloids [19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial and Antioxidant Properties of Total Polyphenols of Anchusa italica Retz

et al. 2022

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Anchusa italica Retz has been used for a long time in phytotherapy. The aim of the present study was to determine the antioxidant and antibacterial activities of extracts from the leaves and roots of Anchusa italica Retz. We first determined the content of phenolic compounds and flavonoids using Folin–Ciocalteu reagents and aluminum chloride (AlCl3). The antioxidant activity was determined using three methods: reducing power (FRAP), 2.2-diphenyl-1-picrylhydrazyl (DPPH), total antioxidant capacity (TAC). The antimicrobial activity was investigated against four strains of Escherichia coli, two strains of Klebsiella pneumoniae and coagulase-negative Staphylococcus, and one fungal strain of Candida albicans. The results showed that the root extract was rich in polyphenols (43.29 mg GAE/g extract), while the leave extract was rich in flavonoids (28.88 mg QE/g extract). The FRAP assay showed a strong iron reduction capacity for the root extract (IC50 of 0.11 µg/mL) in comparison to ascorbic acid (IC50 of 0.121 µg/mL). The DPPH test determined an IC50 of 0.11 µg/mL for the root extract and an IC50 of 0.14 µg/mL for the leaf extract. These values are low compared to those for ascorbic acid (IC50 of 0.16 µg/mL) and BHT (IC50 0.20 µg/mL). The TAC values of the leaf and root extracts were 0.51 and 0.98 mg AAE/g extract, respectively. In vitro, the extract showed inhibitory activity against all strains studied, with diameters of zones of inhibition in the range of 11.00–16.00 mm for the root extract and 11.67–14.33 mm for the leaf extract. The minimum inhibitory concentration was recorded for the leaf extract against E. coli (ATB:57), corresponding to 5 mg/mL. Overall, this research indicates that the extracts of Anchusa italica Retz roots and leaves exert significant antioxidant and antibacterial activities, probably because of the high content of flavonoids and polyphenols.

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A new oleanolic-type triterpene glycoside fromAnchusa italica

Cited by 17 publications

References 20 publications

The Metabolic Profile of Anchusa officinalis L. Differs According to Its Associated Arbuscular Mycorrhizal Fungi

The Metabolic Profile of Anchusa officinalis L. Differs According to Its Associated Arbuscular Mycorrhizal Fungi

The Arbuscular Mycorrhizal Fungus Rhizophagus irregularis MUCL 41833 Modulates Metabolites Production of Anchusa officinalis L. Under Semi-Hydroponic Cultivation

Antimicrobial and Antioxidant Properties of Total Polyphenols of Anchusa italica Retz

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