1. Diarylheptanoids from Alnus glutinosa Bark and Their Chemoprotective Effect on Human Lymphocytes DNA.
- Author
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Novaković, Miroslav, Stanković, Miroslava, Vučković, Ivan, Todorović, Nina, Trifunović, Snežana, Tešević, Vele, Vajs, Vlatka, and Milosavljević, Slobodan
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ANALYSIS of variance , *BARK , *BIOLOGICAL assay , *DNA , *HIGH performance liquid chromatography , *LYMPHOCYTES , *MASS spectrometry , *MEDICINAL plants , *MOLECULAR structure , *NUCLEAR magnetic resonance spectroscopy , *RESEARCH funding , *PHYTOCHEMICALS , *SOLID phase extraction , *QUANTITATIVE research , *DATA analysis software , *IN vitro studies - Abstract
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). [ABSTRACT FROM AUTHOR]
- Published
- 2013
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