WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H584407
CAS#: 545-47-1
Description: 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.
Hodoodo Cat#: H584407
Name: Lupeol
CAS#: 545-47-1
Chemical Formula: C30H50O
Exact Mass: 426.39
Molecular Weight: 426.729
Elemental Analysis: C, 84.44; H, 11.81; O, 3.75
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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
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: | |
| In vitro protocol: | |
| In vivo protocol: |
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.
