Antioxidant, Cytotoxic, and Antimicrobial Activity of Alnus incana (L.) ssp. incana Moench and A. viridis (Chaix) DC ssp. viridis Extracts

Stević, Tatjana; Šavikin, Katarina; Zdunić, Gordana; Stanojković, Tatjana; Juranić, Zorica D.; Janković, Teodora; Menković, Nebojša

doi:10.1089/jmf.2009.0111

Cited by 24 publications

(15 citation statements)

References 12 publications

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“…japonica (Novaković et al 2014a), which may be significant for taxonomic considerations. Hydrophilic bark extractives of black and gray alder were found to exhibit antioxidant, cytotoxic, antimicrobial, antidiabetic and antiadipogenic activities (Spoor et al 2006;Frédérich et al 2009;Martineau et al 2010;Stević et al 2010;Telysheva et al 2011;Dahija et al 2014). The main constituents of these extractives are diarylheptanoids and condensed tannins.…”

Section: Resultsmentioning

confidence: 99%

Significance of diarylheptanoids for chemotaxonomical distinguishing between Alnus glutinosa and Alnus incana

et al. 2017

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Diarylheptanoids are a group of secondary metabolites widely distributed in the Betulaceae family and characteristic for Alnus species. In this study, the chemotaxonomic power of diarylheptanoids, such as hirsutanonol-5-O-β-d-glucopyranoside, rubranoside A, oregonin, platyphylloside, alnuside A and hirsutanonol, has been investigated in combination with principal component analysis (PCA) for differentiation of Alnus species. Concentrations of six diarylheptanoids in the bark extracts of two natural populations of Alnus glutinosa (black alder) and Alnus incana (gray alder) were determined by ultraperformance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). PCA clearly shows the separation of three groups. Populations I (A. glutinosa) and II (A. incana) both consisted of individuals of the corresponding species. Four individuals from both sampled populations formed a separate group (population III), which possibly represents a hybrid group. Accordingly, diarylheptanoids may serve in combination with PCA as chemotaxonomic markers at the species level, which may also reveal hybrid species.

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Section: Resultsmentioning

confidence: 99%

Significance of diarylheptanoids for chemotaxonomical distinguishing between Alnus glutinosa and Alnus incana

et al. 2017

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“…Methanol extracts of A. viridis and A. incana barks exhibited antimicrobial activity against fifteen microorganisms with MIC values of 0.225-0.297 mg/mL (Stević et al 2010). The most sensitive species on the methanol extract of the A. incana bark were E. coli, Salmonella enterica subsp.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial activity of the diarylheptanoids from the black and green alder

Novaković

Cvetković

et al. 2015

Braz. J. Bot

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Antimicrobial activity of fourteen diarylheptanoids isolated from the bark of black and green alder against twelve bacterial species (five Gram-positive and seven Gram-negative) and eight fungal strains has been reported. The most sensitive bacterial species were Klebsiella pneumoniae and Pseudomonas aeruginosa (Gramnegative), and Streptosporangium longisporum and Bacillus subtilis (Gram-positive). Among fungal strains the most sensitive to the diarylheptanoids were Fusarium equiseti, F. tricinctum, Candida albicans, and Saccharomyces cerevisiae. Oregonin (8), platyphyllenone (13), hirsutenone (14), (5S)-5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-one-5-O-b-D-apiofuranosyl(1 ? 6)-b-D-glucopyranoside (2), and platyphylloside (1) were the most active diarylheptanoids against both bacteria and fungi, especially against fungi. Eleven of fourteen investigated diarylheptanoids exhibited stronger antifungal activity than standards nystatin and fluconazole against C. albicans and eight against S. cerevisiae. Structure/activity analysis revealed the importance of the enone moiety in the structure of diarylheptanoids for the antifungal activity. Significant antifungal activity and high content of oregonin (8) and hirsutenone (14) in the black alder bark chloroform/ methanol (1:1) extract recommend the use of these compounds as easily accessible potential antifungal remedies.

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“…In addition, these compounds possessed a higher activity than seselinonol, a flavonoid that exhibited a significant capability to decrease DNA damage in the same assay [38]. Since the extracts of A. glutinosa have previously shown strong antioxidant activities [5], the observed outstanding protective behavior of diarylheptanoids was expected. Diarylheptanoids that possess a pronounced protective activity in this assay have a 3-keto group in the heptanoid skeleton and two 3,4-dihydroxyphenyl (catechol) moieties.…”

Section: Resultsmentioning

confidence: 88%

“…When young, the leaves are somewhat glutinous, hence its name. In different pharmacological studies, extracts of Alnus species exhibited anti-inflammatory, antiobesity and antioxidative effects [2][3][4][5]. Alnus japonica, A. hirsuta, A. incana, and A. rubra have been the most intensively investigated of all the Alnus species.…”

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confidence: 99%

Diarylheptanoids from Alnus glutinosa Bark and Their Chemoprotective Effect on Human Lymphocytes DNA

et al. 2013

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A study of secondary metabolites from the bark of Alnus glutinosa led to the isolation of fourteen diarylheptanoids: oregonin (1), platyphylloside (2), rubranoside A (3), rubranoside B (4), hirsutanonol (5), hirsutenone (6), hirsutanonol-5-O-β-D-glucopyranoside (7), platyphyllonol-5-O-β-D-xylopyranoside (8), aceroside VII (9), alnuside A (10), alnuside B (11), 1,7-bis-(3,4-dihydoxyphenyl)-5-hydroxy-heptane-3-O-β-D-xylopyranoside (12), (5S)-1-(4-hydroxyphenyl)-7-(3,4-dihydroxyphenyl)-5-O-β-D-glucopyranosyl-heptan-3-one (13), and (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-O-β-D-[6-(3,4-dimethoxycinnamoylglucopyranosyl)]-heptan-3-one (14). All of the diarylheptanoids, except 1 and 5, were found in A. glutinosa for the first time, while 13 and 14 were new compounds. The structures were determined by spectroscopic techniques: 1D and 2D NMR, HR-ESI-MS, FTIR, UV, and CD. All isolated compounds were analyzed for an in vitro protective effect on chromosome aberrations in peripheral human lymphocytes using the cytokinesis-block micronucleus assay. The majority of them, including the new compounds 13 and 14, exerted a pronounced effect in decreasing DNA damage in human lymphocytes. Diarylheptanoids 1, 2, 5, 13, and 14 at a concentration of 1 µg/mL decreased the frequency of micronuclei by 52.8 %, 43.8 %, 63.6 %, 44.4 %, and 56.0 %, respectively, exerting a much stronger effect than the synthetic protector amifostine (17.2 %, c = 1 µg/mL).

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Antioxidant, Cytotoxic, and Antimicrobial Activity of Alnus incana (L.) ssp. incana Moench and A. viridis (Chaix) DC ssp. viridis Extracts

Cited by 24 publications

References 12 publications

Significance of diarylheptanoids for chemotaxonomical distinguishing between Alnus glutinosa and Alnus incana

Significance of diarylheptanoids for chemotaxonomical distinguishing between Alnus glutinosa and Alnus incana

Antimicrobial activity of the diarylheptanoids from the black and green alder

Diarylheptanoids from Alnus glutinosa Bark and Their Chemoprotective Effect on Human Lymphocytes DNA

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