Diarylheptanoids from the bark of black alder inhibit the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cells

Novaković, Miroslav; Pešić, Milica; Trifunović, Snežana; Vučković, Ivan; Todorović, Nina; Podolski-Renić, Ana; Dinić, Jelena; Stojković, Sonja; Tešević, Vele; Vajs, Vlatka; Milosavljević, Slobodan

doi:10.1016/j.phytochem.2013.11.001

Cited by 33 publications

(39 citation statements)

References 28 publications

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“…It is assumed that diarylheptanoids play an ecological role as a part of the chemical defense system against herbivores; for example, diarylheptanoid glycosides isolated from birch phloem show an inhibitory effect on ruminant digestion (Sunnerheim and Bratt 2004). Members of this group of natural products are reported to have antiviral, antimicrobial, anti-adipogenic, anti-inflammatory, cytotoxic and many other activities (Mshvildadze et al 2007;Tung et al 2010;Lai et al 2012;Lee et al 2013;Novaković et al 2014bNovaković et al , 2015.…”

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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“…Diarylheptanoid compounds was shown to have potential for overcoming MDR since they increased accumulation of doxorubicin via modulating Pgp activity (100). It was concluded that diarylheptanoids, which possess better inhibitory activities and selectivity than curcumin, could be used as novel natural compounds with a potential for treating cancer.…”

Section: Natural Product Modulatorsmentioning

confidence: 99%

Natural Product Modulators to Overcome Multidrug Resistance In Cancer

Çört

Özben

2015

Nutrition and Cancer

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Multidrug resistance (MDR) is a condition that makes cells simultaneously unresponsive to different drugs, unrelated to their chemical structure and mechanism of action. MDR caused by the presence and overexpression of ABC transporters makes obstacles in cancer treatment and lower the effectiveness of chemotherapy. Natural products are investigated by many researchers as MDR modulators for their low toxicity and potent, selective behavior. When coadministered, MDR modulators compete with cytotoxic agents for binding to the active site of the membrane transporters and reduce drug efflux. Natural product-based drugs are important in struggling against drug resistance during cancer therapy. This review is focused on the potential mechanisms against drug resistance, the development of inhibitors for ABC drug transporters, natural product modulators, and nanoparticle drug delivery.

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“…Diarylheptanoids investigated in this work were previously isolated from the black and green alder barks from Serbia (Novaković et al 2013(Novaković et al , 2014 by silica-gel column chromatography followed by semipreparative reversed phase HPLC. Their structures were elucidated by means of 1D and 2D NMR, IR, UV, and HR-ESI-MS. Diarylheptanoids from the black alder analyzed in this work are platyphylloside (1) (7), oregonin (8), aceroside VII (9), rubranoside A (12), and hirsutenone (14).…”

Section: Diarylheptanoidsmentioning

confidence: 99%

“…According to earlier investigations in which extracts of the black alder exhibited antibacterial activity (Saxena et al 1995) and earlier determined antibacterial activity of oregonin and hirsutenone (Choi et al 2012), it was expected that compounds isolated from A. glutinosa and A. viridis would possess antimicrobial action on selected bacterial and fungal species. In this work, antimicrobial investigation of fourteen known diarylheptanoids isolated in previous work (Novaković et al 2013(Novaković et al , 2014 from the black and green alder barks against twelve bacterial and eight fungal species is presented. This is the first report of the antibacterial and antifungal activities of diarylheptanoids isolated from A. glutinosa and A. viridis.…”

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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Diarylheptanoids from the bark of black alder inhibit the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cells

Cited by 33 publications

References 28 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

Natural Product Modulators to Overcome Multidrug Resistance In Cancer

Antimicrobial activity of the diarylheptanoids from the black and green alder

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