Lupulone | CAS#468-28-0 | Beta-acid

MedKoo Cat#: 528077 | Name: Lupulone

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lupulon, also known as Lupulone, is a beta-acid that has been found in the hop plant, H. lupulus, and has diverse biological activities, including antibacterial, antioxidant, and anticarcinogenic properties. Lupulone is active against B. subtilis and S. aureus as well as T. b. brucei and L. m. mexicana. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals and reduces proliferation, migration, and capillary tube formation in human umbilical vein endothelial cells (HUVECs). Lupulone also activates the extrinsic apoptotic death pathway in SW480 and SW620 colon cancer cells.

Chemical Structure

Lupulone

CAS#468-28-0

Theoretical Analysis

MedKoo Cat#: 528077

Name: Lupulone

CAS#: 468-28-0

Chemical Formula: C26H38O4

Exact Mass: 414.2770

Molecular Weight: 414.59

Elemental Analysis: C, 75.32; H, 9.24; O, 15.44

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 250.00	2 weeks

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Related CAS #

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Synonym

Lupulon, Lupulone

IUPAC/Chemical Name

2,4-Cyclohexadien-1-one, 3,5-dihydroxy-4-isovaleryl-2,6,6-tris(3-methyl-2-butenyl)-

InChi Key

WPVSVIXDXMNGGN-UHFFFAOYSA-N

InChi Code

InChI=1S/C26H38O4/c1-16(2)9-10-20-23(28)22(21(27)15-19(7)8)25(30)26(24(20)29,13-11-17(3)4)14-12-18(5)6/h9,11-12,19,28,30H,10,13-15H2,1-8H3

SMILES Code

O=C1C(C/C=C(C)\C)=C(O)C(C(CC(C)C)=O)=C(O)C1(C/C=C(C)\C)C/C=C(C)\C

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lupulone is a beta-acid from the hop plant H. lupulus with diverse biological activities including antibacterial, antioxidant, and anticarcinogenic properties.

In vitro activity:

Lupulone (40 microg/ml) up-regulated expression of TRAIL DR4/DR5 death receptors at the cell surface of both cell lines, even in the absence of exogenous TRAIL ligand. Cell death induced by lupulone was inhibited in SW480 and SW620 cells exposed to blocking anti-DR4/DR5 antibodies. Reference: Apoptosis. 2008 Oct;13(10):1232-42. https://pubmed.ncbi.nlm.nih.gov/18726190/

In vivo activity:

Here, the effect of lupulone was evaluated for its effect on the microbiota of the chicken intestine. Lupulone at 125 mg L(-1) significantly decreased the C. perfringens subgroup 16S rRNA gene Cluster I, which contains several pathogenic species, in both the midgut and the cecum and Lactobacillus in the midgut. Reference: FEMS Microbiol Ecol. 2011 Aug;77(2):395-403. https://pubmed.ncbi.nlm.nih.gov/21517917/

Preparing Stock Solutions

The following data is based on the product molecular weight 414.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Mouratidis PX, Colston KW, Charolidi N, Pirianov G. Differential role of apoptosis and autophagy associated with anticancer effect of lupulone (hop β-acid) derivatives on prostate cancer cells. Anticancer Agents Med Chem. 2014;14(8):1169-78. doi: 10.2174/1871520614666140623123006. PMID: 24954859. 2. Lamy V, Roussi S, Chaabi M, Gossé F, Lobstein A, Raul F. Lupulone, a hop bitter acid, activates different death pathways involving apoptotic TRAIL-receptors, in human colon tumor cells and in their derived metastatic cells. Apoptosis. 2008 Oct;13(10):1232-42. doi: 10.1007/s10495-008-0250-5. PMID: 18726190. 3. Tillman GE, Haas GJ, Wise MG, Oakley B, Smith MA, Siragusa GR. Chicken intestine microbiota following the administration of lupulone, a hop-based antimicrobial. FEMS Microbiol Ecol. 2011 Aug;77(2):395-403. doi: 10.1111/j.1574-6941.2011.01119.x. Epub 2011 May 18. PMID: 21517917. 4. Bousserouel S, Lamy V, Gossé F, Lobstein A, Marescaux J, Raul F. Early modulation of gene expression used as a biomarker for chemoprevention in a preclinical model of colon carcinogenesis. Pathol Int. 2011 Feb;61(2):80-7. doi: 10.1111/j.1440-1827.2010.02621.x. Epub 2010 Dec 6. PMID: 21255184.

In vitro protocol:

In vivo protocol:

1. Tillman GE, Haas GJ, Wise MG, Oakley B, Smith MA, Siragusa GR. Chicken intestine microbiota following the administration of lupulone, a hop-based antimicrobial. FEMS Microbiol Ecol. 2011 Aug;77(2):395-403. doi: 10.1111/j.1574-6941.2011.01119.x. Epub 2011 May 18. PMID: 21517917. 2. Bousserouel S, Lamy V, Gossé F, Lobstein A, Marescaux J, Raul F. Early modulation of gene expression used as a biomarker for chemoprevention in a preclinical model of colon carcinogenesis. Pathol Int. 2011 Feb;61(2):80-7. doi: 10.1111/j.1440-1827.2010.02621.x. Epub 2010 Dec 6. PMID: 21255184.

1: Schulz C, Fritz N, Sommer T, Krofta K, Friedland K, Pischetsrieder M. Activation of membrane-located Ca(2+) channels by hop beta acids and their tricyclic transformation products. Food Chem. 2018 Jun 30;252:215-227. doi: 10.1016/j.foodchem.2018.01.073. Epub 2018 Jan 10. PubMed PMID: 29478534. 2: Bogdanova K, Röderova M, Kolar M, Langova K, Dusek M, Jost P, Kubelkova K, Bostik P, Olsovska J. Antibiofilm activity of bioactive hop compounds humulone, lupulone and xanthohumol toward susceptible and resistant staphylococci. Res Microbiol. 2018 Apr;169(3):127-134. doi: 10.1016/j.resmic.2017.12.005. Epub 2018 Jan 31. PubMed PMID: 29407045. 3: Cermak P, Olsovska J, Mikyska A, Dusek M, Kadleckova Z, Vanicek J, Nyc O, Sigler K, Bostikova V, Bostik P. Strong antimicrobial activity of xanthohumol and other derivatives from hops (Humulus lupulus L.) on gut anaerobic bacteria. APMIS. 2017 Nov;125(11):1033-1038. doi: 10.1111/apm.12747. Epub 2017 Sep 28. PubMed PMID: 28960474. 4: Matoušek J, Kocábek T, Patzak J, Bříza J, Siglová K, Mishra AK, Duraisamy GS, Týcová A, Ono E, Krofta K. The "putative" role of transcription factors from HlWRKY family in the regulation of the final steps of prenylflavonid and bitter acids biosynthesis in hop (Humulus lupulus L.). Plant Mol Biol. 2016 Oct;92(3):263-77. doi: 10.1007/s11103-016-0510-7. Epub 2016 Jul 8. PubMed PMID: 27392499. 5: Gaid M, Haas P, Beuerle T, Scholl S, Beerhues L. Hyperforin production in Hypericum perforatum root cultures. J Biotechnol. 2016 Mar 20;222:47-55. doi: 10.1016/j.jbiotec.2016.02.016. Epub 2016 Feb 10. PubMed PMID: 26876610. 6: Wang L, Shen C. Survival of Unstressed and Acid-, Cold-, and Starvation-Stress-Adapted Listeria monocytogenes in Ham Extract with Hops Beta Acids and Consumer Acceptability of HBA on Ready-to-Eat Ham. Biomed Res Int. 2015;2015:817042. doi: 10.1155/2015/817042. Epub 2015 Oct 11. PubMed PMID: 26539527; PubMed Central PMCID: PMC4619879. 7: Li H, Ban Z, Qin H, Ma L, King AJ, Wang G. A heteromeric membrane-bound prenyltransferase complex from hop catalyzes three sequential aromatic prenylations in the bitter acid pathway. Plant Physiol. 2015 Mar;167(3):650-9. doi: 10.1104/pp.114.253682. Epub 2015 Jan 6. PubMed PMID: 25564559; PubMed Central PMCID: PMC4348772. 8: Dušek M, Olšovská J, Krofta K, Jurková M, Mikyška A. Qualitative determination of β-acids and their transformation products in beer and hop using HR/AM-LC-MS/MS. J Agric Food Chem. 2014 Aug 6;62(31):7690-7. doi: 10.1021/jf501852r. Epub 2014 Jul 28. PubMed PMID: 25099125. 9: Mouratidis PX, Colston KW, Charolidi N, Pirianov G. Differential role of apoptosis and autophagy associated with anticancer effect of lupulone (hop β-acid) derivatives on prostate cancer cells. Anticancer Agents Med Chem. 2014;14(8):1169-78. PubMed PMID: 24954859. 10: Wei J, Liang J, Shi Q, Yuan P, Meng R, Tang X, Yu L, Guo N. Genome-wide transcription analyses in Mycobacterium tuberculosis treated with lupulone. Braz J Microbiol. 2014 Apr 18;45(1):333-41. doi: 10.1590/S1517-83822014005000032. eCollection 2014. PubMed PMID: 24948953; PubMed Central PMCID: PMC4059319. 11: Harlow BE, Lawrence LM, Kagan IA, Flythe MD. Inhibition of fructan-fermenting equine faecal bacteria and Streptococcus bovis by hops (Humulus lupulus L.) β-acid. J Appl Microbiol. 2014 Aug;117(2):329-39. doi: 10.1111/jam.12532. Epub 2014 May 14. PubMed PMID: 24775300. 12: Mouratidis PX, Colston KW, Tucknott ML, Tyrrell E, Pirianov G. An investigation into the anticancer effects and mechanism of action of hop β-acid lupulone and its natural and synthetic derivatives in prostate cancer cells. Nutr Cancer. 2013;65(7):1086-92. doi: 10.1080/01635581.2013.850963. Epub 2013 Oct 29. PubMed PMID: 24168111. 13: Chen W, Becker T, Qian F, Ring J. Beer and beer compounds: physiological effects on skin health. J Eur Acad Dermatol Venereol. 2014 Feb;28(2):142-50. doi: 10.1111/jdv.12204. Epub 2013 Jun 27. Review. PubMed PMID: 23802910. 14: de Almeida NE, do Nascimento ES, Cardoso DR. On the reaction of lupulones, hops β-acids, with 1-hydroxyethyl radical. J Agric Food Chem. 2012 Oct 24;60(42):10649-56. doi: 10.1021/jf302708c. Epub 2012 Oct 12. PubMed PMID: 23031058. 15: Saugspier M, Dorn C, Czech B, Gehrig M, Heilmann J, Hellerbrand C. Hop bitter acids inhibit tumorigenicity of hepatocellular carcinoma cells in vitro. Oncol Rep. 2012 Oct;28(4):1423-8. doi: 10.3892/or.2012.1925. Epub 2012 Jul 20. PubMed PMID: 22825405. 16: Degrandi-Hoffman G, Ahumada F, Probasco G, Schantz L. The effects of beta acids from hops (Humulus lupulus) on mortality of Varroa destructor (Acari: Varroidae). Exp Appl Acarol. 2012 Dec;58(4):407-21. doi: 10.1007/s10493-012-9593-2. Epub 2012 Jul 6. PubMed PMID: 22767150; PubMed Central PMCID: PMC3487002. 17: Lamy V, Bousserouel S, Gossé F, Minker C, Lobstein A, Raul F. Lupulone triggers p38 MAPK-controlled activation of p53 and of the TRAIL receptor apoptotic pathway in human colon cancer-derived metastatic cells. Oncol Rep. 2011 Jul;26(1):109-14. doi: 10.3892/or.2011.1273. Epub 2011 Apr 20. PubMed PMID: 21519792. 18: Tillman GE, Haas GJ, Wise MG, Oakley B, Smith MA, Siragusa GR. Chicken intestine microbiota following the administration of lupulone, a hop-based antimicrobial. FEMS Microbiol Ecol. 2011 Aug;77(2):395-403. doi: 10.1111/j.1574-6941.2011.01119.x. Epub 2011 May 18. PubMed PMID: 21517917.