Abstract
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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Claims 4
Claim · model-written summary
Isolation and identification of 22 compounds from spent hops (Humulus lupulus strobiles), including 12 prenylated chalcones and five prenylflavanones.
- Taxon
- Humulus lupulus
Humulus lupuluse0 - Organ / stage
- strobilese0
- Outcome
- isolation and identification of 22 compoundse1
- Value
- 22 compoundse1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“strobiles of Humulus lupulus”
e1“led to the isolation and identification of 22 compounds including 12 prenylated chalcones (1-8, 10-13), five prenylflavanones (14-17)”
Claim · model-written summary
Three new chalcones (compounds 4, 11, 12) were identified in spent hops.
- Taxon
- Humulus lupulusHumulus lupuluse0
- Outcome
- new chalconese2
- Value
- Threee2
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“strobiles of Humulus lupulus”
e2“Three new chalcones (4, 11, 12) and four previously unreported constituents of hops (5, 6, 9b, 13) are reported”
Claim · model-written summary
Four previously unreported constituents of hops (compounds 5, 6, 9b, 13) were reported.
- Taxon
- Humulus lupulusHumulus lupuluse0
- Outcome
- previously unreported constituents of hopse2
- Value
- foure2
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“strobiles of Humulus lupulus”
e2“four previously unreported constituents of hops (5, 6, 9b, 13) are reported”
Claim · model-written summary
The principal estrogen 8-prenylnaringenin (15) from hops is an artifact formed with 6-prenylnaringenin through spontaneous isomerization of the chalcone DMX (7).
- Taxon
- Humulus lupulusHumulus lupuluse0
- Compound
- DMX (7)e3
- Outcome
- 8-prenylnaringenin (15) from hops is an artifacte3
- Qualifier
- spontaneous isomerizatione3
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“strobiles of Humulus lupulus”
e3“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)”