Page last updated: 2024-12-06

lupulon

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Lupulon is a bitter hop compound that is a precursor to the α-acid, humulone. Lupulon is a prenylated chalcone, and its structure features a 2-methylbut-2-en-1-yl group, which is thought to be essential for its bitterness. The compound is found in hop cones and is extracted with solvents such as ethanol or hexane. Lupulon is a potent antioxidant and has been shown to exhibit anti-inflammatory and antibacterial properties. It is also studied for its potential role in reducing the risk of certain cancers and neurodegenerative diseases. Lupulon is a naturally occurring compound that is present in hops and is thought to contribute to the bitter flavor and aroma of beer. While lupulon is generally considered safe for consumption, it is possible that some individuals may experience adverse effects such as allergic reactions.'

lupulon: antibiotic from hops; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

lupulone : A beta-bitter acid in which the acyl group is specified as 3-methylbutanoyl. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

beta-bitter acid : An alicyclic ketone obtained by prenylation at positions 4, 6 and 6 of any 2-acylphloroglucinol. beta-bitter acids are well known for their contribution to the bitter taste of beer. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID68051
CHEMBL ID480267
CHEBI ID6574
SCHEMBL ID819253
SCHEMBL ID2431439
MeSH IDM0052026

Synonyms (39)

Synonym
3,5-dihydroxy-2,6,6-tris(3-methylbuten-2-yl)-4-(3-methyl-1-oxobutyl)cyclohexa-2,4-dien-1-one
lupulon
b'' -acid
einecs 207-405-3
2,4-cyclohexadien-1-one, 3,5-dihydroxy-4-isovaleryl-2,6,6-tris(3-methyl-2-butenyl)-
beta-bitter acid
3,5-dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
beta-lupulic acid
lupulone
468-28-0
3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one
FT-0650864
chebi:6574 ,
CHEMBL480267
b7425usg94 ,
unii-b7425usg94
2,4-cyclohexadien-1-one,3,5-dihydroxy-2,6,6-tris(3-methyl-2-buten-1-yl)-4-(3-methyl-1-oxobutyl)-
AKOS015896772
lupulon [mi]
.beta.-bitter acid
.beta.-lupulic acid
SCHEMBL819253
hop beta-acid
SCHEMBL2431439
3,5-dihydroxy-4-(3-methylbutanoyl)-2,6,6-tris(3-methyl-2-butenyl)-2,4-cyclohexadien-1-one #
2,4-cyclohexadien-1-one, 3,5-dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-
3,5-dihydroxy-2,6,6-tris(3-methyl-2-buten-1-yl)-4-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
lupolon
DTXSID00875553
Q55939056
3,5-dihydroxy-2,6,6-tris(3-methylbut-2-enyl)-4-(3-methyl-1-oxobutyl)cyclohexa-2,4-dien-1-one
3,5-dihydroxy-2,6,6-tris(3-methylbut-2-enyl)-4-(3-methylbutanoyl)cyclohexa-2,4-dienone
Q27107249
HY-124923
CS-0089577
gtpl12445
AKOS040744749
PD118550

Research Excerpts

Overview

Lupulone is a compound extracted from Hops (Hurnulus lupulus) It exhibits a good antimicrobial activity against M.  M.

ExcerptReferenceRelevance
"Lupulone is a compound extracted from Hops (Hurnulus lupulus), which exhibits a good antimicrobial activity against M."( Genome-wide transcription analyses in Mycobacterium tuberculosis treated with lupulone.
Guo, N; Liang, J; Meng, R; Shi, Q; Tang, X; Wei, J; Yu, L; Yuan, P, 2014
)
1.35

Treatment

ExcerptReferenceRelevance
"Lupulone treatment enhanced the expression of the anti-apoptotic Mcl-1 protein by 60% favoring the preservation of mitochondrial integrity."( Lupulone triggers p38 MAPK-controlled activation of p53 and of the TRAIL receptor apoptotic pathway in human colon cancer-derived metastatic cells.
Bousserouel, S; Gossé, F; Lamy, V; Lobstein, A; Minker, C; Raul, F, 2011
)
2.53

Bioavailability

ExcerptReferenceRelevance
" Further studies are needed to determine the bioavailability of these compounds and their possible beneficial health effects when taken by moderate beer consumption."( Beer and beer compounds: physiological effects on skin health.
Becker, T; Chen, W; Qian, F; Ring, J, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
antimicrobial agentA substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
apoptosis inducerAny substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
angiogenesis inhibitorAn agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
beta-bitter acidAn alicyclic ketone obtained by prenylation at positions 4, 6 and 6 of any 2-acylphloroglucinol. beta-bitter acids are well known for their contribution to the bitter taste of beer.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID376758Cytotoxicity against mouse RAW264.7 cells after 16 hrs by MTT assay2005Journal of natural products, Jan, Volume: 68, Issue:1
Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus).
AID376752Inhibition of LPS/IFN-gamma-induced NO production in mouse RAW264.7 cells after 16 hrs2005Journal of natural products, Jan, Volume: 68, Issue:1
Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus).
AID600520Antioxidant activity assessed as inhibition of lipid peroxidation2009Journal of natural products, Jun, Volume: 72, Issue:6
Hop (Humulus lupulus)-derived bitter acids as multipotent bioactive compounds.
AID600519Antioxidant activity assessed as DPPH radical scavenging activity2009Journal of natural products, Jun, Volume: 72, Issue:6
Hop (Humulus lupulus)-derived bitter acids as multipotent bioactive compounds.
AID376757Inhibition of LPS/IFN-gamma-induced NO production in mouse RAW264.7 cells at non cytotoxic concentration after 16 hrs2005Journal of natural products, Jan, Volume: 68, Issue:1
Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus).
AID600510Antiangiogenic activity in mouse at 0.01%, po for 21 days2009Journal of natural products, Jun, Volume: 72, Issue:6
Hop (Humulus lupulus)-derived bitter acids as multipotent bioactive compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (51)

TimeframeStudies, This Drug (%)All Drugs %
pre-199013 (25.49)18.7374
1990's1 (1.96)18.2507
2000's10 (19.61)29.6817
2010's24 (47.06)24.3611
2020's3 (5.88)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.75

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index28.75 (24.57)
Research Supply Index3.97 (2.92)
Research Growth Index5.53 (4.65)
Search Engine Demand Index34.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.75)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (3.85%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other50 (96.15%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]