On the structure of humulinone

Shoolery, James Ν.; Verzele, M.; Alderweireldt, F. C.

doi:10.1016/0040-4020(60)80016-6

Cited by 17 publications

(15 citation statements)

References 4 publications

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“…Those with chiral centers on the prenyl unit can all be envisioned to arise from a theoretical prenyl-epoxide intermediate. In addition to the compounds detailed above, the known hop constituents α,β-dihydroxanthohumol ( 2 ), xanthohumol D ( 3 ), desmethylxanthohumol ( 7 ), 5‘-prenylxanthohumol ( 8 ), 6,8-diprenylnaringenin ( 14 ), 8-prenylnaringenin ( 15 ), ,,,,,, 6-prenylnaringenin ( 16 ), ,,,,, isoxanthohumol ( 17 ), ,,,,,, humulinone ( 20 ), , and cohumulinone ( 21 ) 40,41 were also isolated from spent hops and identified by comparison with literature data.…”

Section: Resultsmentioning

confidence: 99%

Estrogens and Congeners from Spent Hops (Humuluslupulus)

et al. 2004

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Estrogenicity-directed fractionation of a methanol extract of the strobiles of Humulus lupulus that had been extracted previously with supercritical CO(2), known as "spent hops", led to the isolation and identification of 22 compounds including 12 prenylated chalcones (1-8, 10-13), five prenylflavanones (14-17), 4-hydroxybenzaldehyde (18), sitosterol-3-O-beta-glucopyranoside (19), humulinone (20), and cohumulinone (21). In addition, the prenylated chalcone xanthohumol C (9a) was obtained as a 6:1 mixture along with its 1' ',2' '-dihydro derivative (9b). Three new chalcones (4, 11, 12) and four previously unreported constituents of hops (5, 6, 9b, 13) are reported. The structures of the new compounds were determined through a combination of spectrometric techniques including 1D and 2D NMR, HRESIMS, and ESIMS-MS. Full 1H NMR spin system analyses were performed to characterize the higher-order glucopyranosyl, prenyl, and chalcone B-ring spectra of the isolates. The principle estrogen 8-prenylnaringenin (15) from hops is an artifact formed along with its positional isomer 6-prenylnaringenin (16) through the spontaneous isomerization of the pro-estrogenic chalcone DMX (7).

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Section: Resultsmentioning

confidence: 99%

Estrogens and Congeners from Spent Hops (Humuluslupulus)

et al. 2004

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“…This cluster analysis clearly demonstrate a rather similar evolution pattern of these compounds throughout the entire brewing process, thus being well in line with the proposed reaction routes for the formation of isoxanthohumol (2) from 1, the iso-R-acids (6-11), humulinones (12)(13)(14), and cis-and trans-humulinic acids (40-45) from the R-acids (3)(4)(5), and hulupinic acid (36) from the β-acids (15)(16)(17) (Figure 3). An amount of 77.2, 51.8, and 82.5% of the starting dosage of R-acids (3)(4)(5) were isomerized to the corresponding iso-R-acids (6)(7)(8)(9)(10)(11) in the final beer VII (Table 3), which is in the range to be expected for a Pilsner-type beer (32,33). In addition, 6.6-7.4% of the parent R-acids were found to be transformed into humulinones (12)(13)(14) and humulinic acids (40-45).…”

Section: Concentrations Of Sensometabolites Adsorbed At Filter Materimentioning

confidence: 99%

Quantitative Sensomics Profiling of Hop-Derived Bitter Compounds Throughout a Full-Scale Beer Manufacturing Process

Haseleu

Lagemann²,

Stephan³

et al. 2010

J. Agric. Food Chem.

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Although the complex taste profile of beer is well accepted to be reflected by the molecular blueprint of its sensometabolites, the knowledge available on the process-induced transformation of hop-derived phytochemicals into key sensometabolites during beer manufacturing is far from comprehensive. The objective of the present investigation was, therefore, to develop and apply a suitable HPLC-MS/MS method for the simultaneous and comprehensive quantitative monitoring of a total of 69 hop-derived sensometabolites in selected intermediary products throughout a full-scale beer manufacturing process. After data normalization, the individual sensometabolites were arranged into different clusters by means of agglomerative hierarchical analysis and visualized using a sensomics heatmap to verify the structure-specific reaction routes proposed for their formation during the beer brewing process.

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“…Proton magnetic resonance spectroscopy was first applied to hop chemistry in 1959 in order to distinguish between the five-(CXI) and six-membered (CX) ring structures for humulinone (340). The spectra of humulone (I), dihydrohumulone (CLXXVI), and humulinone were recorded in deuteriochloroform at 60 Me/sec, and by comparison of the spectra of humulone and dihydrohumulone it was possible to allocate all the signals to the relevant protons, in particular, the signals associated with the methylene groups of the dimethylallyl side chains F and G, which in humulone were doublets at r 6.79 and 7.41, respectively.…”

Section: Nuclear Magnetic Resonance Spectroscopymentioning

confidence: 99%

“…-di(3'-methylbutyl)phlorisobutyrophenone (CX-III) by Clemmensen reduction of tetrahydrocohumulone (CXII), they obtained the same product, albeit Clemmensen only in 1% yield by Clemmensen reduction of tetrahydrocohumulinone. It was later shown by proton magnetic resonance spectroscopy that humulinone had the five-membered ring structure CXI,Howard and Slater's results being explained by the fact that at high concentrations humulone can form an insoluble sodium salt and so contaminates the more insoluble sodium salt of humulinone(340).…”

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confidence: 99%