Cirsilineol and cubreuva lactone from Artemisia umbrosa and their biological activity

Tashenov, Yerbolat; Джалмаханбетова, Р. И.; Smagulova, F. M.; Дудкин, Р. В.; Горовой, П. Г.; Suleiman, E. M.; Ross, Samir A.

doi:10.1007/s10600-013-0517-0

Cited by 10 publications

(6 citation statements)

References 5 publications

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“…On the basis of physicochemical properties, spectral data (UV, IR, 1D NMR, 2D NMR, EI-MS). Compound 1 have oxygenation patterns as apigenin 5,7,4′, Compounds 2 and 3 have oxygenation patterns as luteolin 5,7,3′,4′ and compound 4 is a 6-luteolin substituted and by comparing the data with the literature values the structures were identified to be 5-hydroxy-7,4′-dimethoxyflavone 1 [ 28 ], 5-hydroxy-7,3′,4′-trimethoxyflavone 2 [ 29 , 30 ], 5,4′-dihydroxy-7, 3′-dimethoxyflavone, velutin 3 [ 30 - 32 ], 5,4′-dihydroxy-6,7,3′-trimethoxyflavone, cirsilineol 4 [ 33 , 34 ]. 5,4′-dihydroxy-7,3′-dimethoxyflavone, velutin 3 was isolated earlier from several plants [ 32 , 35 , 36 ].…”

Section: Resultsmentioning

confidence: 99%

Antioxidant activities of Lampaya medicinalis extracts and their main chemical constituents

Morales

Paredes

2014

BMC Complement Altern Med

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BackgroundLampaya medicinalis Phil. (Verbenaceae) is a plant used by Aymara and Quechua ethnic groups from Northern Chile as folk medicine in the treatment and cure of various diseases. The aim of this study was to investigate the in vitro antioxidant activity, total phenols content, total flavonoids content, total antioxidant activity, reducing power, brine shrimp cytotoxicity and identify the principal chemical constituents.MethodsThe crude hydroethanolic extract (HEE) and its partitioned fraction: hexane (HF), dichloromethane (DF), ethyl acetate (EAF), n-butanol (BF) and soluble residual aqueous fraction (RWF) were evaluated for their antioxidant activity using different assays namely, DPPH, ABTS, FRAP, β-carotene bleaching assay. The content of total phenolics and total flavonoids were measured by Folin-Ciocalteau and by the AlCl3 colorimetric method, respectively. Reducing power was determined by phosphomolybdate and hexacyanoferrate (III) methods. Biotoxicity assays were performed on shrimps of Artemia salina. The EAF was fractionated using chromatographic methods.ResultsConsiderable amount of phenolic and flavonoid contents were recorded in the hydroethanolic extract (HEE) and its derived fractions. Although HEE and all its derived fractions exhibited good antioxidant activities, the most distinguished radical scavenging potential was observed for ethyl acetate fraction (EAF). EAF showed the higher radical scavenging activity by DPPH (95%) and by ABTS (98%), antioxidant activity by FRAP (158.18 ± 5.79 mg equivalent Trolox/g fraction), β-carotene bleaching assay (86.8%), the highest total phenols content (101.26 ± 1.07 mg GAE/g fraction), the highest total flavonoids content (66.26 ± 3.31 μg quercetin/g fraction). The EAF extract showed an reducing power of 78% and 65% using the phosphomolybdate and hexacyanoferrate (III) assays, respectively.Four flavonoids, two p-hydroxyacetophenone derivatives and one iridoid were isolated from Lampaya medicinalis for the first time.ConclusionEtOAc soluble fraction (EAF) shows the strongest antioxidant activity, and it can be attributed to its high content in phenolic and flavonoid compounds. It can be concluded that L.medicinalis can be used as an effective natural source of antioxidant, as ethnomedicine and as a commercial basis for the development of nutraceuticals.

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Section: Resultsmentioning

confidence: 99%

Antioxidant activities of Lampaya medicinalis extracts and their main chemical constituents

Morales

Paredes

2014

BMC Complement Altern Med

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“…Lastly, with regard to chemical profile of Siberian artemisias, the known data had been very limited. Some terpenoids were detected in A. anethifolia (Evstratova and Sinyukhin, 1971 ; Bakhshyeva et al, 2011 ); essential oil (Zhu et al, 2013 ) and flavonoid aglycones (Wang J.-L. et al, 2016 ) in A. integrifolia ; sesquiterpenes in A. latifolia (Adekenov et al, 1984 ); essential oil (Shoaib et al, 2015 ) and sesquiterpenes (Shoaib et al, 2017 ) in A. macrocephala ; flavonoids in A. palustris (Chemesova et al, 1978 ); coumarins in A. tanacetifolia (Szabó et al, 1985 ); and sesquiterpenes (Tashenov et al, 2013 ) and essential oil (Suleimen et al, 2014 ) in A. umbrosa . There is no chemical information about A. commutata, A. desertorum, A. leucophylla, A. messerschmidtiana , and A. sericea .…”

Section: Introductionmentioning

confidence: 99%

Bioactive Phenolics of the Genus Artemisia (Asteraceae): HPLC-DAD-ESI-TQ-MS/MS Profile of the Siberian Species and Their Inhibitory Potential Against α-Amylase and α-Glucosidase

et al. 2018

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Artemisia genus of Asteraceae family is a source of medicinal plants known worldwide and used as ethnopharmacological remedies for the treatment of diabetes in Northern Asia (Siberia). The aim of this study was to determine the phenolic profile of 12 Siberian Artemisia species (A. anethifolia, A. commutata, A. desertorum, A. integrifolia, A. latifolia, A. leucophylla, A. macrocephala, A. messerschmidtiana, A. palustris, A. sericea, A. tanacetifolia, A. umbrosa) and to test the efficacy of plant extracts and pure compounds for antidiabetic potential. Finally, by HPLC-DAD-ESI-TQ-MS/MS technique, 112 individual phenolic compounds were detected in Artemisia extracts in a wide range of concentrations. Some species accumulated rare plant phenolics, such as coumarin-hemiterpene ethers (lacarol derivatives) from A. latifolia and A. tanacetifolia; melilotoside from A. tanacetifolia; dihydrochalcones (davidigenin analogs) from A. palustris; chrysoeriol glucosides from A. anethifolia, A. sericea, and A. umbrosa; eriodictyol glycosides from A. messerschmidtiana; and some uncommon flavones and flavonols. The predominant phenolic group from Artemisia species herb was caffeoylquinic acid (CQAs), and in all species, the major CQAs were 5-O-CQA (20.28–127.99 μg/g) and 3,5-di-O-CQA (7.35–243.61 μg/g). In a series of in vitro bioassays, all studied Artemisia extracts showed inhibitory activity against principal enzymes of carbohydrate metabolism, such as α-amylase (IC50 = 150.24–384.14 μg/mL) and α-glucosidase (IC50 = 214.42–754.12 μg/mL). Although many phenolic compounds can be inhibitors, experimental evidence suggests that the CQAs were key to the biological response of Artemisia extracts. Mono-, di- and tri-substituted CQAs were assayed and showed inhibition of α-amylase and α-glucosidase, with IC50 values of 40.57–172.47 μM and 61.08–1240.35 μM, respectively, and they were more effective than acarbose, a well-known enzyme inhibitor. The results obtained in this study reveal that Siberian Artemisia species and CQAs possess a pronounced inhibitory activity against α-amylase and α-glucosidase and could become a complement to synthetic antidiabetic drugs for controlling blood glucose level.

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“…For example, anhydroaustricin, epiashantin, and matricarin are biologically active compounds that were isolated from A. albida [19], A. sieversiana [20], and A. austriaca [21], respectively. Besides, cirsineol is an active lactone that was reported in A. umbrosa [22]. Also, the presence of sesquiterpene lactones and flavonoids were reported in A. tschernieviana [23], A. albida [24], and A. santolinifolia [25], respectively.…”

Section: Introductionmentioning

confidence: 89%

Isolation and In Silico Anti-SARS-CoV-2 Papain-Like Protease Potentialities of Two Rare 2-Phenoxychromone Derivatives from Artemisia spp.

et al. 2022

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Two rare 2-phenoxychromone derivatives, 6-demethoxy-4`-O-capillarsine (1) and tenuflorin C (2), were isolated from the areal parts of Artemisia commutata and A. glauca, respectively, for the first time. Being rare in nature, the inhibition potentialities of 1 and 2 against SARS-CoV-2 was investigated using multistage in silico techniques. At first, molecular similarity and fingerprint studies were conducted for 1 and 2 against co-crystallized ligands of eight different COVID-19 enzymes. The carried-out studies indicated the similarity of 1 and 2 with TTT, the co-crystallized ligand of COVID-19 Papain-Like Protease (PLP), (PDB ID: 3E9S). Therefore, molecular docking studies of 1 and 2 against the PLP were carried out and revealed correct binding inside the active site exhibiting binding energies of −18.86 and −18.37 Kcal/mol, respectively. Further, in silico ADMET in addition to toxicity evaluation of 1 and 2 against seven models indicated the general safety and the likeness of 1 and 2 to be drugs. Lastly, to authenticate the binding and to investigate the thermodynamic characters, molecular dynamics (MD) simulation studies were conducted on 1 and PLP.

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Cirsilineol and cubreuva lactone from Artemisia umbrosa and their biological activity

Cited by 10 publications

References 5 publications

Antioxidant activities of Lampaya medicinalis extracts and their main chemical constituents

Antioxidant activities of Lampaya medicinalis extracts and their main chemical constituents

Bioactive Phenolics of the Genus Artemisia (Asteraceae): HPLC-DAD-ESI-TQ-MS/MS Profile of the Siberian Species and Their Inhibitory Potential Against α-Amylase and α-Glucosidase

Isolation and In Silico Anti-SARS-CoV-2 Papain-Like Protease Potentialities of Two Rare 2-Phenoxychromone Derivatives from Artemisia spp.

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