Xanthohumol
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| General | |||||||||||||||||||
| Surname | Xanthohumol | ||||||||||||||||||
| other names |
1- [2,4-Dihydroxy-6-methoxy-3- (3-methyl-but-2-enyl) -phenyl] -3- (4-hydroxyphenyl) -propenone |
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| Molecular formula | C 21 H 22 O 5 | ||||||||||||||||||
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| properties | |||||||||||||||||||
| Molar mass | 354.40 g · mol -1 | ||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
172 ° C |
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| solubility |
0.0013 g l −1 in water (23 ° C) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
In xanthohumol is a prenylated plant polyphenol that the chalcones is assigned and so far only in hops could be detected. The bitter hop varieties have a significantly higher content of xanthohumol than aroma varieties. During the brewing process, xanthohumol is largely converted into isoxanthohumol by heating .
In tests, xanthohumol has been shown to be effective against the formation and development of cancer cells. The chemopreventive effect of isoxanthohumol is significantly lower. The Hoepfner private brewery developed a process patented in 2004 to brew beer with an increased xanthohumol content.
Laboratory tests at Lanzhou University in China have shown that xanthohumol can protect the nerve cells of the brain and thus could possibly help to slow down the course of diseases such as Alzheimer's or Parkinson's.
literature
- Chadwick LR, Pauli GF, Farnsworth NR: The pharmacognosy of Humulus lupulus L. (hops) with an emphasis on estrogenic properties . In: Phytomedicine . 13, No. 1-2, January 2006, pp. 119-131. PMID 16360942 . PMC 1852439 (free full text).
- Overk CR, Guo J, Chadwick LR, et al. : In vivo estrogenic comparisons of Trifolium pratense (red clover) Humulus lupulus (hops), and the pure compounds isoxanthohumol and 8-prenylnaringenin . In: Chemico-Biological Interactions . 176, No. 1, October 2008, pp. 30-39. PMID 18619951 . PMC 2574795 (free full text).
- Koo JH, Kim HT, Yoon HY, et al. : Effect of xanthohumol on melanogenesis in B16 melanoma cells . In: Experimental & Molecular Medicine . 40, No. 3, June 2008, pp. 313-319. PMID 18587269 . PMC 2679287 (free full text).
- Christoph Michael Dorn: Analysis of the effects of xanthohumol on hepatic homeostasis, inflammation, fibrosis and cancerogenesis. Dissertation, University of Regensburg, 2009. urn : nbn: de: bvb: 355-opus-13613
Individual evidence
- ↑ a b c Entry on xanthohumol. In: Römpp Online . Georg Thieme Verlag, accessed on March 3, 2012.
- ↑ a b Xanthohumol data sheet from Sigma-Aldrich , accessed on May 8, 2017 ( PDF ).
- ↑ a b A. Forster, A. Gahr, M. Ketterer, B. Beck and S. Massinger: Xanthohumol in beer - possibilities and limits of an enrichment. In: Monthly for Brewing Science 55 (9/10): 184-194, 2002.
- ↑ Gerhauser C, Alt A, Heiss E, et al. : Cancer chemopreventive activity of xanthohumol, a natural product derived from hop . In: Molecular Cancer Therapeutics . 1, No. 11, September 2002, pp. 959-969. PMID 12481418 . Retrieved September 25, 2010.
- ↑ Process for the production of a beverage - Document DE10320250A1 .
- ↑ Does beer ingredient stop Alzheimer's and Parkinson's? In: aponet.de. January 30, 2015, accessed August 13, 2015 .