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Planta Med 2013; 79(06): 499-505
DOI: 10.1055/s-0032-1328301
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

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

Miroslav Novaković
1   Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Belgrade, Serbia
,
Miroslava Stanković
1   Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Belgrade, Serbia
,
Ivan Vučković
2   Faculty of Chemistry, University of Belgrade, Belgrade, Serbia
,
Nina Todorović
1   Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Belgrade, Serbia
,
Snežana Trifunović
2   Faculty of Chemistry, University of Belgrade, Belgrade, Serbia
,
Vele Tešević
2   Faculty of Chemistry, University of Belgrade, Belgrade, Serbia
,
Vlatka Vajs
1   Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Belgrade, Serbia
,
Slobodan Milosavljević
2   Faculty of Chemistry, University of Belgrade, Belgrade, Serbia
› Author Affiliations
Further Information

Publication History

received 08 November 2012
revised 01 February 2013

accepted 07 February 2013

Publication Date:
19 March 2013 (online)

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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).

Key words

Alnus glutinosa - Betulaceae - diarylheptanoids - HPLC-DAD - NMR analysis - protective effect - CBMN assay

Supporting Information

 

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