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Anti-oxidativeproperties of prenylflavonoids isolated from hops (Humulus lupulus L.)

Agnieszka Kuczyńska ,  Barbara Kąkol ,  Aleksandra M. Szczucińska ,  Jacek Cybulski ,  Bożenna Obukowicz ,  Mirosława Szpakiewicz 

Instytut Chemii Przemysłowej (IChP), Rydygiera 8, Warszawa 01-793, Poland

Abstract

Hop (Humulus lupulus L.) is a genus of flowering plants. The medicinal use of extracts prepared from the parts of the Cannabaceae genus dates back to ancient times. The female flowers, commonly called hops, are used as flavouring agents and stabilisers during beer brewing.

At the base of the hop scales there are two hard nuts covered in aromatic, yellow dust called lupulin. Lupulin contains from 5 to 30% bitter substances including acylphloro-glucides, humulones [1], lupulones; essential oil containing mono- and sesquiterpenes, aroma substances, flavonoids, xanthohumol and other chalcones [2,3]. Isolated prenylflavonoids show interesting biological activities witch may be used as cancer chemopreventive agents, anti-oxidative or as antiviral agents [3].

The purpose of this review is to show an overview of the anti-oxidative activities of prenylflavonoids from hops.

Prenylflavonoids were isolated from supercritical carbon dioxide extracted hops. The particular residues were extracted by solvent extraction. The fractions containing xanthohumol and isoxanthohumol were collected, evaporated in vacuo and purified by repeated column chromatography on silica gel. The structures were confirmed by spectroscopic methods: UV-VIS, IR, 1H NMR.

Anti-oxidative property of xanthohumol and isoxanthohumol from hops were compared with other natural antioxidants extracted from the evening primrose (Oenothera paradoxa L.) and black chokeberry (Aronia melanocarpa).

The induction time and oxidative stability of prenylflavonoids from hops and natural extracts were determined by rancimat test. With the results presented in this study, we concluded that isoxanthohumol and xanthohumol had the highest oxidative stability. Both of those compounds indicate that they are two times stronger in antioxidative activity than the natural extracts from evening primrose and black chokeberry.

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A. Rumuńska, A. Ożarowski; Leksykon roślin leczniczych: Warszawa 1990.

2.        J. F. Stevens, E. Pagaj; Phytochemistry: 2004,65,1317-1330.

Q. Wang, Z. Ding, J. Liu, Y. Zheng; Antiviral Research: 2004,64,189-194.

3.        J. F. Stevens, A.W. Taylor, M. L. Deinzer; Journal of Chro: 1999, 832, 97-107.

M. Anioł, K. Szymańska, A. Żołnierczyk; Tetrahedron: 2008, 64, 9544-9547.

 

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Related papers

Presentation: Poster at VII Multidyscyplinarna Konferencja Nauki o Leku, by Agnieszka Kuczyńska
See On-line Journal of VII Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2010-03-18 10:15
Revised:   2010-04-05 14:44