In-vitro prenylation of aromatic intermediates in the biosynthesis of bitter acids in humulus lupulus

Zuurbier, Karin W.M.; Fung, Suen‐Ying; Scheffer, J. J. C.; Verpoorte, Robert

doi:10.1016/s0031-9422(98)00179-4

Cited by 46 publications

(42 citation statements)

References 22 publications

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“…The building blocks, γ,γ-dimethylallyl pyrophosphate and the isomeric 2-isopentenyl pyrophosphate, may arise from either the mevalonate pathway or the deoxyxylulose pathway 5 , since they are both operative in plants. Prenyltransferases are involved, but prenylations at different positions of an aromatic structure catalysed by different enzymes have been described 22 . The fate of prenylation seems rather unclear and Zuurbier et al proclaimed that "other prenylations of aromatic structures should occur as well" 22 .…”

Section: -2863(9'8-32mentioning

confidence: 99%

“…Prenyltransferases are involved, but prenylations at different positions of an aromatic structure catalysed by different enzymes have been described 22 . The fate of prenylation seems rather unclear and Zuurbier et al proclaimed that "other prenylations of aromatic structures should occur as well" 22 . However, diverse mechanisms have not been detailed until now and alternative pathways remain unexplored.…”

Section: -2863(9'8-32mentioning

confidence: 99%

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Modulation of the Phytoestrogenicity of Beer by Monoterpene Alcohols Present in Various Hop Oil Fractions

Heyerick

Keukeleire

Peteghem

et al. 2002

Journal of the Institute of Brewing

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The estrogenicity of beer, due to prenylated flavonoids, mainly 8-prenylnaringenin, can be modulated under suitable conditions, whereby monoterpene alcohols present in hop oils act as precursors for prenylation of flavonoids. Four hop oil fractions, 'citrussy', 'estery', 'floral', and 'spicy', respectively, were investigated as potential sources. The main constituents were separated and identified by gas chromatography -mass spectroscopy (GC-MS). They were related to 8-prenylnaringenin via their MS features, while the ability to deliver a prenyl residue was evaluated by selected ion monitoring of fragment ions m/z 69 and m/z 41. In particular, the citrussy hop oil fraction proved to be a rich source of precursors for prenyl residues and linalool, the main constituent in the citrussy and spicy hop oil fractions, was shown to be most prominent. The process was highlighted by an increase in the content of 8-prenylnaringenin on forced ageing of acidified beer spiked with naringenin and linalool.

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Section: -2863(9'8-32mentioning

confidence: 99%

Section: -2863(9'8-32mentioning

confidence: 99%

Modulation of the Phytoestrogenicity of Beer by Monoterpene Alcohols Present in Various Hop Oil Fractions

Heyerick

Keukeleire

Peteghem

et al. 2002

Journal of the Institute of Brewing

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“…In conclusion, these results suggest that there is strong tissue specific regulation of the chs_H1 gene. Once expression of chs_H1 is clearly induced in glandular tissue, one has to suggest unambiguously the responsibility of chs_H1 for true chalcone synthase activity, as detected in glandular tissue by Zuurbier et al (1995), as well as the involvement of CHS_H1 in biosynthesis of prenylated flavonoids.…”

Section: Expression Of True Chalcone Synthase In Glandular Tissuementioning

confidence: 99%

“…CHS activity was detected in protein extracts from hop cones by Zuurbier et al (1995), however, corresponding gene(s) encoding true hop CHS has not yet been characterised. Recently cloned phlorisovalerophenone synthase (VPS) was the first CHS homologue isolated from hop Humulus lupulus cones.…”

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confidence: 99%

Analysis of the chalcone synthase from Humulus lupulus L. and biotechnology aspects of medicinal hops

Matoušek¹,

Novák²,

Patzak³

et al. 2002

PLANT SOIL ENVIRON

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The complete sequence hop gene, which corresponds to true chalcone synthase (EC 2.3.1.74), was amplified using a combination of PCR, RT PCR and inverse PCR methods and cloned from Czech Osvald's clone 72. The gene designated chs_H1 was found to be specifically expressed on glandular trichomes, whereas negligible level of specific mRNA was found in leaves. Thus, chs_H1 may co-determine biosynthesis of prenylated chalcones, compounds valuable as anticancer and antiproliferative components of lupulin. It was shown by the comparative analyses and by the structure modelling that the true hop chalcone synthase differs from previously described CHS-like protein, phlorisovalerophenone synthase, which is involved in biosynthesis of bitter acids. Several hop cultivars were analysed for the presence of genes homologous to chs_H1 using chs_H1 cDNA as probe. 2-4 HindIII specific genomic fragments were detected by Southern blots, depending on cultivar. More detailed analysis revealed at least six homologous genes in Osvald's 72 hop, suggesting a great potential of this hop also as a genetic source for modern biotechnology. High level of xanthohumol in some Osvald's 72-derived hybrid cultivars like cv. Sládek, as well as a comparatively high level of prenylated flavonoids in some comprehensive hops, suggest also the presence of additional, regulatory genes co-determining levels of prenylated flavonoids valuable for medicinal hops.

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“…There are two main classes of MPAPs: the diprenylated α-acids (7) and triprenylated β-acids (8) (Figure 12.3). α-Acids are responsible for the flavor and bitter taste of beer [25] while β-acids show, among other properties, free radical scavenger activity [7,26]. Labeling and enzymological experiments have provided evidence that bitter acids are biosynthesized via condensation of three malonyl-CoA and one acyl-CoA, such as isobutyryl-CoA (9) (Scheme 12.1) [27][28][29][30].…”

Section: Introduction and Chemical Classificationmentioning

confidence: 99%

Polyprenylated Phloroglucinols and Xanthones

Theodorakis

2011

Biomimetic Organic Synthesis

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In-vitro prenylation of aromatic intermediates in the biosynthesis of bitter acids in humulus lupulus

Cited by 46 publications

References 22 publications

Modulation of the Phytoestrogenicity of Beer by Monoterpene Alcohols Present in Various Hop Oil Fractions

Modulation of the Phytoestrogenicity of Beer by Monoterpene Alcohols Present in Various Hop Oil Fractions

Analysis of the chalcone synthase from Humulus lupulus L. and biotechnology aspects of medicinal hops

Polyprenylated Phloroglucinols and Xanthones

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