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MedKoo Cat#: 584564 | Name: Lupenone
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Description:

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

Lupenone inhibits adipocyte differentiation through downregulation of related transcription factor, particularly the PPARγ gene.

Chemical Structure

Lupenone
Lupenone
CAS#1617-70-5

Theoretical Analysis

MedKoo Cat#: 584564

Name: Lupenone

CAS#: 1617-70-5

Chemical Formula: C30H48O

Exact Mass: 424.3705

Molecular Weight: 424.71

Elemental Analysis: C, 84.84; H, 11.39; O, 3.77

Price and Availability

Size Price Availability Quantity
1mg USD 250.00 2 Weeks
5mg USD 570.00 2 Weeks
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Related CAS #
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Synonym
Lupenone
IUPAC/Chemical Name
Lup-20(29)-en-3-one
InChi Key
GRBHNQFQFHLCHO-BHMAJAPKSA-N
InChi Code
InChI=1S/C30H48O/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/h20-23,25H,1,9-18H2,2-8H3/t20-,21+,22-,23+,25+,27+,28-,29+,30+/m0/s1
SMILES Code
CC1(C)C(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])=O
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
>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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Lupenone shows various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity.
In vitro activity:
This study found that the treatment of SH-SY5y cells with an optimal concentration of lupenone could lead to protection against cell death induced by METH. AnnexinV/PI apoptosis analysis revealed a dramatically reduced level of the apoptotic cell population in lupenon and METH treated SH-SY5y cells. Moreover, diminished expression of anti-apoptotic proteins, including Bcl-2, Caspase3, Caspase7, and Caspase8 in METH-exposed SH-SY5y cells, was significantly recovered by treatment with lupenone. Reference: Int J Mol Sci. 2020 Feb 27;21(5):1617. https://pubmed.ncbi.nlm.nih.gov/32120831/
In vivo activity:
Compared to the model group, LUP (lupenone) (8.0 mg/kg) significantly decreased the levels of FBG (22.3%), LEP (9.5%), HbA1c (14.9%) and MDA (12.3%), increased the ADPN (24.2%) levels and GSH-PX activity (12.4%) (p < 0.05), improved oxidative stress, lipid metabolism disorders and pancreas pathological changes, increased the mRNA and protein expression of InsR (3.7-fold and 1.3-fold), IRS-1 (3-fold and 2-fold), IRS-2 (2-fold and 1.6-fold), GLUT-4 (2-fold and 2.4-fold) in skeletal muscle and IRS-1 (6-fold and 1.6-fold), IRS-2 (5.8-fold and 1.5-fold), GLUT-4 (2.5-fold and 1.7-fold) and PPAR-γ (7-fold and 1.4-fold) in adipose tissue (p < 0.05) in insulin resistant rats. Reference: Pharm Biol. 2022 Dec;60(1):997-1010. https://pubmed.ncbi.nlm.nih.gov/35635284/
Solvent mg/mL mM comments
Solubility
DMF 2.0 4.71
DMSO 5.0 11.77
Ethanol 7.5 17.66
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 424.71 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.

Recalculate based on batch purity %
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. Lee HS, Kim EN, Jeong GS. Lupenone Protects Neuroblastoma SH-SY5y Cells Against Methamphetamine-Induced Apoptotic Cell Death via PI3K/Akt/mTOR Signaling Pathway. Int J Mol Sci. 2020 Feb 27;21(5):1617. doi: 10.3390/ijms21051617. PMID: 32120831; PMCID: PMC7084488. 2. Xu F, Zhang M, Wu H, Wang Y, Yang Y, Wang X. Study on the mechanism of lupenone for treating type 2 diabetes by integrating pharmacological evaluation and network pharmacology. Pharm Biol. 2022 Dec;60(1):997-1010. doi: 10.1080/13880209.2022.2067568. PMID: 35635284; PMCID: PMC9154797.
In vitro protocol:
Lee HS, Kim EN, Jeong GS. Lupenone Protects Neuroblastoma SH-SY5y Cells Against Methamphetamine-Induced Apoptotic Cell Death via PI3K/Akt/mTOR Signaling Pathway. Int J Mol Sci. 2020 Feb 27;21(5):1617. doi: 10.3390/ijms21051617. PMID: 32120831; PMCID: PMC7084488.
In vivo protocol:
Xu F, Zhang M, Wu H, Wang Y, Yang Y, Wang X. Study on the mechanism of lupenone for treating type 2 diabetes by integrating pharmacological evaluation and network pharmacology. Pharm Biol. 2022 Dec;60(1):997-1010. doi: 10.1080/13880209.2022.2067568. PMID: 35635284; PMCID: PMC9154797.
1: 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. 2: Ahn EK, Oh JS. Lupenone isolated from Adenophora triphylla var. japonica extract inhibits adipogenic differentiation through the downregulation of PPARγ in 3T3-L1 cells. Phytother Res. 2013 May;27(5):761-6. doi: 10.1002/ptr.4779. Epub 2012 Jul 31. PubMed PMID: 22848028. 3: Xu F, Wu H, Wang X, Yang Y, Wang Y, Qian H, Zhang Y. RP-HPLC characterization of lupenone and β-sitosterol in rhizoma musae and evaluation of the anti-diabetic activity of lupenone in diabetic Sprague-Dawley rats. Molecules. 2014 Sep 9;19(9):14114-27. doi: 10.3390/molecules190914114. PubMed PMID: 25207716. 4: Xu F, Wu H, Wang Y, Yang Y, Gao Y, Wang X. Determination of lupenone and β-sitosterol in Rhizoma Musae by UPLC with DAD and ELSD. J Chromatogr Sci. 2015 Nov-Dec;53(10):1714-9. doi: 10.1093/chromsci/bmv079. Epub 2015 Jun 29. PubMed PMID: 26126840. 5: Villareal MO, Han J, Matsuyama K, Sekii Y, Smaoui A, Shigemori H, Isoda H. Lupenone from Erica multiflora leaf extract stimulates melanogenesis in B16 murine melanoma cells through the inhibition of ERK1/2 activation. Planta Med. 2013 Mar;79(3-4):236-43. doi: 10.1055/s-0032-1328189. Epub 2013 Feb 13. PubMed PMID: 23408272. 6: Polanco-Hernández G, Escalante-Erosa F, García-Sosa K, Rosado ME, Guzmán-Marín E, Acosta-Viana KY, Giménez-Turba A, Salamanca E, Peña-Rodríguez LM. Synergistic Effect of Lupenone and Caryophyllene Oxide against Trypanosoma cruzi. Evid Based Complement Alternat Med. 2013;2013:435398. doi: 10.1155/2013/435398. Epub 2013 May 20. PubMed PMID: 23762135; PubMed Central PMCID: PMC3671683. 7: Na M, Kim BY, Osada H, Ahn JS. Inhibition of protein tyrosine phosphatase 1B by lupeol and lupenone isolated from Sorbus commixta. J Enzyme Inhib Med Chem. 2009 Aug;24(4):1056-9. doi: 10.1080/14756360802693312. PubMed PMID: 19548777. 8: Biabani F, Singh SK, Kumar S, Raj K, Pathak A. The Willgerodt-Kindler reaction on lupenone: unusual oxidative dimerization. Nat Prod Lett. 2002 Oct;16(5):297-300. PubMed PMID: 12434983. 9: WINTERSTEINER O, KRAKOWER G, MOORE M. LUPENONE AND 18-ALPHA-OLEANAN-19-ALPHA-OL-3-ONE FROM SAMADERA INDICA. J Org Chem. 1965 Aug;30:2847-9. PubMed PMID: 14342874. 10: Leslie Gunatilaka AA, Sotheeswaran S, Sriyani B, Balasubramaniam S. Isoboldine and lupenone from Neolitsea fuscata. Planta Med. 1981 Nov;43(11):309-10. PubMed PMID: 17402053. 11: Chander MP, Kumar KV, Shriram AN, Vijayachari P. Anti-leptospiral activities of an endemic plant Glyptopetalum calocarpum (Kurz.) Prain used as a medicinal plant by Nicobarese of Andaman and Nicobar Islands. Nat Prod Res. 2015;29(16):1575-7. doi: 10.1080/14786419.2014.985679. Epub 2014 Dec 6. PubMed PMID: 25482276. 12: Suttiarporn P, Chumpolsri W, Mahatheeranont S, Luangkamin S, Teepsawang S, Leardkamolkarn V. Structures of phytosterols and triterpenoids with potential anti-cancer activity in bran of black non-glutinous rice. Nutrients. 2015 Mar 6;7(3):1672-87. doi: 10.3390/nu7031672. PubMed PMID: 25756784; PubMed Central PMCID: PMC4377873. 13: Xu F, Huang X, Wu H, Wang X. Beneficial health effects of lupenone triterpene: A review. Biomed Pharmacother. 2018 Jul;103:198-203. doi: 10.1016/j.biopha.2018.04.019. Epub 2018 Apr 24. Review. PubMed PMID: 29653365. 14: Al Muqarrabun LM, Ahmat N, Aris SR, Shamsulrijal N, Baharum SN, Ahmad R, Rosandy AR, Suratman MN, Takayama H. A new sesquiterpenoid from Scaphium macropodum (Miq.) Beumee. Nat Prod Res. 2014;28(9):597-605. doi: 10.1080/14786419.2014.886211. Epub 2014 Feb 25. PubMed PMID: 24568340. 15: Aminudin NI, Ahmad F, Taher M, Zulkifli RM. α-Glucosidase and 15-Lipoxygenase Inhibitory Activities of Phytochemicals from Calophyllum symingtonianum. Nat Prod Commun. 2015 Sep;10(9):1585-7. PubMed PMID: 26594765. 16: Li H, Webster D, Johnson JA, Gray CA. Anti-mycobacterial triterpenes from the Canadian medicinal plant Alnus incana. J Ethnopharmacol. 2015 May 13;165:148-51. doi: 10.1016/j.jep.2015.02.042. Epub 2015 Feb 25. PubMed PMID: 25725435. 17: Seong SH, Roy A, Jung HA, Jung HJ, Choi JS. Protein tyrosine phosphatase 1B and α-glucosidase inhibitory activities of Pueraria lobata root and its constituents. J Ethnopharmacol. 2016 Dec 24;194:706-716. doi: 10.1016/j.jep.2016.10.007. Epub 2016 Oct 18. PubMed PMID: 27769948. 18: Li L, Sun Z, Shang X, Li J, Wang R, Zhu J. [Triterpene compounds from Cirsium setosum]. Zhongguo Zhong Yao Za Zhi. 2012 Apr;37(7):951-5. Chinese. PubMed PMID: 22792796. 19: Rodrigues VF, Oliveira RR, Vega MR. A new isocoumarin from Cajanus cajan (Fabaceae). Nat Prod Commun. 2014 Apr;9(4):493-4. PubMed PMID: 24868865. 20: Bourjot M, Leyssen P, Eydoux C, Guillemot JC, Canard B, Rasoanaivo P, Guéritte F, Litaudon M. Chemical constituents of Anacolosa pervilleana and their antiviral activities. Fitoterapia. 2012 Sep;83(6):1076-80. doi: 10.1016/j.fitote.2012.05.004. Epub 2012 May 14. PubMed PMID: 22613073.