Lupeol | CAS#545-47-1 | anti-inflammatory

MedKoo Cat#: 584407 | Name: Lupeol

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Description:

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

Lupeol is a phytosterol and triterpene widely found in edible fruits, and vegetables. Various in vitro and preclinical animal studies suggest that lupeol has a potential to act as an anti-inflammatory, anti-microbial, anti-protozoal, anti-proliferative, anti-invasive, anti-angiogenic and cholesterol lowering agent. Employing various in vitro and in vivo models, lupeol has also been tested for its therapeutic efficiency against conditions including wound healing, diabetes, cardiovascular disease, kidney disease, and arthritis.

Chemical Structure

Lupeol

CAS#545-47-1

Theoretical Analysis

MedKoo Cat#: 584407

Name: Lupeol

CAS#: 545-47-1

Chemical Formula: C30H50O

Exact Mass: 426.3862

Molecular Weight: 426.73

Elemental Analysis: C, 84.44; H, 11.81; O, 3.75

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 285.00	2 weeks
50mg	USD 500.00	2 Weeks

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Synonym

Lupeol; Clerodol; Fagarasterol; Lupenol; Monogynol B; NSC 90487; β-Viscol

IUPAC/Chemical Name

Lup-20(29)-en-3-ol, (3-beta)-

InChi Key

MQYXUWHLBZFQQO-QGTGJCAVSA-N

InChi Code

InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1

SMILES Code

CC1(C)[C@@H](O)CC[C@]2(C)[C@@]3([H])CC[C@]4([H])[C@@]5([H])[C@H](C(C)=C)CC[C@@](C)5CC[C@](C)4[C@@](C)3CC[C@@]12[H]

Appearance

Solid powder

Purity

>98% (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

>2 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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lupeol is a potent androgen receptor (AR) inhibitor.

In vitro activity:

Cells grown under androgen-rich environment and treated with lupeol were tested for proliferation, AR transcriptional activity, AR competitive ligand binding, AR-DNA binding, and AR-ARE/target gene binding. Lupeol significantly inhibited R1881 (androgen analogue) induced (i) transcriptional activity of AR and (ii) expression of PSA. Lupeol (i) competed antagonistically with androgen for AR, (ii) blocked the binding of AR to AR-responsive genes including PSA, TIPARP, SGK, and IL-6, and (iii) inhibited the recruitment of RNA Pol II to target genes. Reference: Clin Cancer Res. 2011 Aug 15;17(16):5379-91. https://pubmed.ncbi.nlm.nih.gov/21712449/

In vivo activity:

Lupeol (1-2 mg/mouse) 30 min prior to TPA (3.2 nmol/mouse) application onto the skin of CD-1 mice afforded significant inhibition, in a time- and dose-dependent manner, against TPA-mediated increase in (i) skin edema and hyperplasia, (ii) epidermal ornithine decarboxylase (ODC) activity, and (iii) protein expression of ODC, cyclo-oxygenase-2 and nitric oxide synthase. Lupeol showed significantly reduced tumor incidence, lower tumor body burden and a significant delay in the latency period for tumor appearance. Reference: Oncogene. 2004 Jul 1;23(30):5203-14. https://pubmed.ncbi.nlm.nih.gov/15122342/

	Solvent	mg/mL	mM
Solubility
	Ethanol	7.7	17.92
	DMSO	1.5	3.52

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 426.73 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. Saha S, Profumo E, Togna AR, Riganò R, Saso L, Buttari B. Lupeol Counteracts the Proinflammatory Signalling Triggered in Macrophages by 7-Keto-Cholesterol: New Perspectives in the Therapy of Atherosclerosis. Oxid Med Cell Longev. 2020 Sep 27;2020:1232816. doi: 10.1155/2020/1232816. PMID: 33062133; PMCID: PMC7537694. 2. Siddique HR, Mishra SK, Karnes RJ, Saleem M. Lupeol, a novel androgen receptor inhibitor: implications in prostate cancer therapy. Clin Cancer Res. 2011 Aug 15;17(16):5379-91. doi: 10.1158/1078-0432.CCR-11-0916. Epub 2011 Jun 28. PMID: 21712449; PMCID: PMC4573593. 3. Ahmad R, Khan A, Rehman IU, Lee HJ, Khan I, Kim MO. Lupeol Treatment Attenuates Activation of Glial Cells and Oxidative-Stress-Mediated Neuropathology in Mouse Model of Traumatic Brain Injury. Int J Mol Sci. 2022 May 29;23(11):6086. doi: 10.3390/ijms23116086. PMID: 35682768; PMCID: PMC9181489. 4. Saleem M, Afaq F, Adhami VM, Mukhtar H. Lupeol modulates NF-kappaB and PI3K/Akt pathways and inhibits skin cancer in CD-1 mice. Oncogene. 2004 Jul 1;23(30):5203-14. doi: 10.1038/sj.onc.1207641. PMID: 15122342.

In vitro protocol:

In vivo protocol:

1. Ahmad R, Khan A, Rehman IU, Lee HJ, Khan I, Kim MO. Lupeol Treatment Attenuates Activation of Glial Cells and Oxidative-Stress-Mediated Neuropathology in Mouse Model of Traumatic Brain Injury. Int J Mol Sci. 2022 May 29;23(11):6086. doi: 10.3390/ijms23116086. PMID: 35682768; PMCID: PMC9181489. 2. Saleem M, Afaq F, Adhami VM, Mukhtar H. Lupeol modulates NF-kappaB and PI3K/Akt pathways and inhibits skin cancer in CD-1 mice. Oncogene. 2004 Jul 1;23(30):5203-14. doi: 10.1038/sj.onc.1207641. PMID: 15122342.

1: Siveen KS, Nguyen AH, Lee JH, Li F, Singh SS, Kumar AP, Low G, Jha S, Tergaonkar V, Ahn KS, Sethi G. Negative regulation of signal transducer and activator of transcription-3 signalling cascade by lupeol inhibits growth and induces apoptosis in hepatocellular carcinoma cells. Br J Cancer. 2014 Sep 23;111(7):1327-37. doi: 10.1038/bjc.2014.422. Epub 2014 Aug 7. PubMed PMID: 25101566; PubMed Central PMCID: PMC4183851. 2: Bhandari P, Patel NK, Bhutani KK. Synthesis of new heterocyclic lupeol derivatives as nitric oxide and pro-inflammatory cytokine inhibitors. Bioorg Med Chem Lett. 2014 Aug 1;24(15):3596-9. doi: 10.1016/j.bmcl.2014.05.032. Epub 2014 May 22. PubMed PMID: 24909081. 3: Jin Y, Lyu Y, Tang X, Zhang Y, Chen J, Zheng D, Liang Y. Lupeol enhances radiosensitivity of human hepatocellular carcinoma cell line SMMC-7721 in vitro and in vivo. Int J Radiat Biol. 2015 Feb;91(2):202-8. doi: 10.3109/09553002.2015.966209. Epub 2015 Jan 27. PubMed PMID: 25241960. 4: Kim MJ, Bae GS, Choi SB, Jo IJ, Kim DG, Shin JY, Lee SK, Kim MJ, Song HJ, Park SJ. Lupeol Protects Against Cerulein-Induced Acute Pancreatitis in Mice. Phytother Res. 2015 Oct;29(10):1634-9. doi: 10.1002/ptr.5423. Epub 2015 Jul 16. PubMed PMID: 26179197. 5: Kim SJ, Cho HI, Kim SJ, Kim JS, Kwak JH, Lee DU, Lee SK, Lee SM. Protective effects of lupeol against D-galactosamine and lipopolysaccharide-induced fulminant hepatic failure in mice. J Nat Prod. 2014 Nov 26;77(11):2383-8. doi: 10.1021/np500296b. Epub 2014 Oct 17. PubMed PMID: 25325613. 6: Kwon HH, Yoon JY, Park SY, Min S, Kim YI, Park JY, Lee YS, Thiboutot DM, Suh DH. Activity-guided purification identifies lupeol, a pentacyclic triterpene, as a therapeutic agent multiple pathogenic factors of acne. J Invest Dermatol. 2015 Jun;135(6):1491-1500. doi: 10.1038/jid.2015.29. Epub 2015 Feb 3. PubMed PMID: 25647437. 7: Kallubai M, Rachamallu A, Yeggoni DP, Subramanyam R. Comparative binding mechanism of lupeol compounds with plasma proteins and its pharmacological importance. Mol Biosyst. 2015 Apr;11(4):1172-83. doi: 10.1039/c4mb00635f. PubMed PMID: 25710711. 8: Khan MF, Maurya CK, Dev K, Arha D, Rai AK, Tamrakar AK, Maurya R. Design and synthesis of lupeol analogues and their glucose uptake stimulatory effect in L6 skeletal muscle cells. Bioorg Med Chem Lett. 2014 Jun 15;24(12):2674-9. doi: 10.1016/j.bmcl.2014.04.059. Epub 2014 Apr 24. PubMed PMID: 24813738. 9: Deyrup ST, Asghar KB, Chacko A, Hebert JM, Samson E, Talone CJ. Chemical investigation of the medicinal and ornamental plant Angelonia angustifolia Benth. reveals therapeutic quantities of lupeol. Fitoterapia. 2014 Oct;98:174-8. doi: 10.1016/j.fitote.2014.08.005. Epub 2014 Aug 10. PubMed PMID: 25111011. 10: Siddique HR, Saleem M. Beneficial health effects of lupeol triterpene: a review of preclinical studies. Life Sci. 2011 Feb 14;88(7-8):285-93. doi: 10.1016/j.lfs.2010.11.020. Epub 2010 Nov 29. Review. PubMed PMID: 21118697. 11: Kumari A, Kakkar P. Lupeol prevents acetaminophen-induced in vivo hepatotoxicity by altering the Bax/Bcl-2 and oxidative stress-mediated mitochondrial signaling cascade. Life Sci. 2012 Apr 20;90(15-16):561-70. doi: 10.1016/j.lfs.2012.01.012. Epub 2012 Feb 2. PubMed PMID: 22326499. 12: Vijay Avin BR, Prabhu T, Ramesh CK, Vigneshwaran V, Riaz M, Jayashree K, Prabhakar BT. New role of lupeol in reticence of angiogenesis, the cellular parameter of neoplastic progression in tumorigenesis models through altered gene expression. Biochem Biophys Res Commun. 2014 May 30;448(2):139-44. doi: 10.1016/j.bbrc.2014.04.090. Epub 2014 Apr 26. PubMed PMID: 24780400. 13: He Y, Liu F, Zhang L, Wu Y, Hu B, Zhang Y, Li Y, Liu H. Growth inhibition and apoptosis induced by lupeol, a dietary triterpene, in human hepatocellular carcinoma cells. Biol Pharm Bull. 2011;34(4):517-22. PubMed PMID: 21467639. 14: Shi D, Kuang Y, Wang G, Peng Z, Wang Y, Yan C. [Mechanism research on the lupeol treatment on MCF-7 breast cancer cells based on cell metabonomics]. Se Pu. 2014 Mar;32(3):278-83. Chinese. PubMed PMID: 24984468. 15: Yoon YP, Lee HJ, Lee DU, Lee SK, Hong JH, Lee CJ. Effects of Lupenone, Lupeol, and Taraxerol Derived from Adenophora triphylla on the Gene Expression and Production of Airway MUC5AC Mucin. Tuberc Respir Dis (Seoul). 2015 Jul;78(3):210-7. doi: 10.4046/trd.2015.78.3.210. Epub 2015 Jun 30. PubMed PMID: 26175774; PubMed Central PMCID: PMC4499588. 16: de Lima FO, Alves V, Barbosa Filho JM, Almeida JR, Rodrigues LC, Soares MB, Villarreal CF. Antinociceptive effect of lupeol: evidence for a role of cytokines inhibition. Phytother Res. 2013 Oct;27(10):1557-63. doi: 10.1002/ptr.4902. Epub 2012 Dec 3. PubMed PMID: 23208998. 17: Saratha V, Subramanian SP. Lupeol, a triterpenoid isolated from Calotropis gigantea latex ameliorates the primary and secondary complications of FCA induced adjuvant disease in experimental rats. Inflammopharmacology. 2012 Feb;20(1):27-37. doi: 10.1007/s10787-011-0095-3. Epub 2011 Oct 16. PubMed PMID: 22002338. 18: Liu Y, Bi T, Wang G, Dai W, Wu G, Qian L, Gao Q, Shen G. Lupeol inhibits proliferation and induces apoptosis of human pancreatic cancer PCNA-1 cells through AKT/ERK pathways. Naunyn Schmiedebergs Arch Pharmacol. 2015 Mar;388(3):295-304. doi: 10.1007/s00210-014-1071-4. Epub 2014 Nov 25. PubMed PMID: 25418891. 19: Nitta M, Azuma K, Hata K, Takahashi S, Ogiwara K, Tsuka T, Imagawa T, Yokoe I, Osaki T, Minami S, Okamoto Y. Systemic and local injections of lupeol inhibit tumor growth in a melanoma-bearing mouse model. Biomed Rep. 2013 Jul;1(4):641-645. Epub 2013 May 28. PubMed PMID: 24649001; PubMed Central PMCID: PMC3917038. 20: Peña-Rodríguez LM, Yam-Puc A, Knispel N, Schramek N, Huber C, Graßberger C, Ramírez-Torres FG, Escalante-Erosa F, García-Sosa K, Hiebert-Giesbrecht MR, Chan-Bacab MJ, Godoy-Hernández G, Bacher A, Eisenreich W. Isotopologue profiling of triterpene formation under physiological conditions. Biosynthesis of lupeol-3-(3'-R-hydroxy)-stearate in Pentalinon andrieuxii. J Org Chem. 2014 Apr 4;79(7):2864-73. doi: 10.1021/jo402677w. Epub 2014 Mar 24. PubMed PMID: 24606167.