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

MedKoo CAT#: 584631

CAS#: 464-99-3

Description: Lupane has antineoplastic activity.


Price and Availability

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Lupane is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 584631
Name: Lupane
CAS#: 464-99-3
Chemical Formula: C30H52
Exact Mass: 412.4069
Molecular Weight: 412.746
Elemental Analysis: C, 87.30; H, 12.70


Synonym: Lupane

IUPAC/Chemical Name: (1R,3aR,5aR,5bR,11aS)-3a,5a,5b,8,8,11a-hexamethyl-1-propan-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene

InChi Key: NKMDIWKRKQFYPH-DONWXUBYSA-N

InChi Code: InChI=1S/C30H52/c1-20(2)21-12-16-27(5)18-19-29(7)22(25(21)27)10-11-24-28(6)15-9-14-26(3,4)23(28)13-17-30(24,29)8/h20-25H,9-19H2,1-8H3/t21-,22?,23?,24?,25?,27-,28+,29-,30-/m1/s1

SMILES Code: CC([C@H]1CC[C@@]2(C)C1C3CCC4[C@@]5(C)CCCC(C)(C)C5CC[C@@]4(C)[C@]3(C)CC2)C


Technical Data

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).

Harmonized System Code:
2934.99.03.00


References

1: Valencia-Chan LS, García-Cámara I, Torres-Tapia LW, Moo-Puc RE, Peraza-Sánchez SR. Lupane-Type Triterpenes of Phoradendron vernicosum. J Nat Prod. 2017 Nov 22;80(11):3038-3042. doi: 10.1021/acs.jnatprod.7b00177. Epub 2017 Nov 9. PubMed PMID: 29120172.

2: Zhang J, Liu C, Huang RZ, Chen HF, Liao ZX, Sun JY, Xia XK, Wang FX. Three new C-27-carboxylated-lupane-triterpenoid derivatives from Potentilla discolor Bunge and their in vitro antitumor activities. PLoS One. 2017 Apr 7;12(4):e0175502. doi: 10.1371/journal.pone.0175502. eCollection 2017. PubMed PMID: 28388692; PubMed Central PMCID: PMC5384777.

3: Dat LD, Thao NP, Luyen BTT, Tai BH, Jeong MH, Woo MH, Kim YH. Identification of six new lupane-type triterpenoids from Acanthopanax koreanum leaves and their tyrosinase inhibitory activities. Bioorg Med Chem Lett. 2016 Feb 1;26(3):1061-1067. doi: 10.1016/j.bmcl.2015.12.020. Epub 2015 Dec 8. PubMed PMID: 26786496.

4: Kang KB, Jun JB, Kim JW, Kim HW, Sung SH. Ceanothane- and lupane-type triterpene esters from the roots of Hovenia dulcis and their antiproliferative activity on HSC-T6 cells. Phytochemistry. 2017 Oct;142:60-67. doi: 10.1016/j.phytochem.2017.06.014. Epub 2017 Jul 4. PubMed PMID: 28686899.

5: Czarnotta E, Dianat M, Korf M, Granica F, Merz J, Maury J, Baallal Jacobsen SA, Förster J, Ebert BE, Blank LM. Fermentation and purification strategies for the production of betulinic acid and its lupane-type precursors in Saccharomyces cerevisiae. Biotechnol Bioeng. 2017 Nov;114(11):2528-2538. doi: 10.1002/bit.26377. Epub 2017 Aug 17. PubMed PMID: 28688186.

6: Lacouth-Silva F, Xavier CV, da S Setúbal S, Pontes AS, Nery NM, de Castro OB, Fernandes CF, Honda ER, Zanchi FB, Calderon LA, Stábeli RG, Soares AM, Silva-Jardim I, Facundo VA, Zuliani JP. The effect of 3β, 6β, 16β-trihydroxylup-20(29)-ene lupane compound isolated from Combretum leprosum Mart. on peripheral blood mononuclear cells. BMC Complement Altern Med. 2015 Nov 25;15(1):420. doi: 10.1186/s12906-015-0948-1. PubMed PMID: 26608735; PubMed Central PMCID: PMC4659216.

7: Lee S, Jung K, Lee D, Lee SR, Lee KR, Kang KS, Kim KH. Protective effect and mechanism of action of lupane triterpenes from Cornus walteri in cisplatin-induced nephrotoxicity. Bioorg Med Chem Lett. 2015 Dec 1;25(23):5613-8. doi: 10.1016/j.bmcl.2015.10.035. Epub 2015 Oct 22. PubMed PMID: 26592171.

8: Khusnutdinova EF, Smirnova IE, Giniyatullina GV, Medvedeva NI, Yamansarov EY, Kazakov DV, Kazakova OB, Linh PT, Viet do Q, Huong DT. Inhibition of Alpha-Glucosidase by Synthetic Derivatives of Lupane, Oleanane, Ursane and Dammarane Triterpenoids. Nat Prod Commun. 2016 Jan;11(1):33-5. PubMed PMID: 26996014.

9: Barros NB, Migliaccio V, Facundo VA, Ciancaglini P, Stábeli RG, Nicolete R, Silva-Jardim I. Liposomal-lupane system as alternative chemotherapy against cutaneous leishmaniasis: macrophage as target cell. Exp Parasitol. 2013 Oct;135(2):337-43. doi: 10.1016/j.exppara.2013.07.022. Epub 2013 Aug 6. PubMed PMID: 23933281.

10: Rajan R, Venkataraman R, Baby S. A new lupane-type triterpenoid fatty acid ester and other isolates from Ophiorrhiza shendurunii. Nat Prod Res. 2016 Oct;30(19):2197-203. doi: 10.1080/14786419.2016.1160232. Epub 2016 Mar 16. PubMed PMID: 26979490.

11: Ying YM, Li CY, Chen Y, Xiang JG, Fang L, Yao JB, Wang FS, Wang RW, Shan WG, Zhan ZJ. Lupane- and Friedelane-Type Triterpenoids from Celastrus stylosus. Chem Biodivers. 2015 Aug;12(8):1222-8. doi: 10.1002/cbdv.201400269. PubMed PMID: 26265574.

12: Li D, Li W, Higai K, Koike K. Protein tyrosine phosphatase 1B inhibitory activities of ursane- and lupane-type triterpenes from Sorbus pohuashanensis. J Nat Med. 2014 Apr;68(2):427-31. doi: 10.1007/s11418-013-0804-x. Epub 2013 Oct 6. PubMed PMID: 24096553.

13: Lomchid P, Nasomjai P, Kanokmedhakul S, Boonmak J, Youngme S, Kanokmedhakul K. Bioactive Lupane and Hopane Triterpenes from Lepisanthes senegalensis. Planta Med. 2017 Feb;83(3-04):334-340. doi: 10.1055/s-0042-116438. Epub 2016 Sep 12. PubMed PMID: 27617903.

14: Ye Y, Zhang T, Yuan H, Li D, Lou H, Fan P. Mitochondria-Targeted Lupane Triterpenoid Derivatives and Their Selective Apoptosis-Inducing Anticancer Mechanisms. J Med Chem. 2017 Jul 27;60(14):6353-6363. doi: 10.1021/acs.jmedchem.7b00679. Epub 2017 Jul 18. PubMed PMID: 28671831.

15: Peng LY, Xu G, He J, Wu XD, Dong LB, Gao X, Cheng X, Su J, Li Y, Dong WM, Zhao QS. Nor-lupane triterpenoid and guaiane sesquiterpenoids from Schefflera venulosa. Fitoterapia. 2015 Jun;103:294-8. doi: 10.1016/j.fitote.2015.05.005. Epub 2015 May 9. PubMed PMID: 25964186.

16: Yang H, Kim HW, Kim YC, Sung SH. Cytotoxic activities of naturally occurring oleanane-, ursane-, and lupane-type triterpenes on HepG2 and AGS cells. Pharmacogn Mag. 2017 Jan-Mar;13(49):118-122. doi: 10.4103/0973-1296.196308. PubMed PMID: 28216894; PubMed Central PMCID: PMC5307894.

17: Cai S, Risinger AL, Nair S, Peng J, Anderson TJ, Du L, Powell DR, Mooberry SL, Cichewicz RH. Identification of Compounds with Efficacy against Malaria Parasites from Common North American Plants. J Nat Prod. 2016 Mar 25;79(3):490-8. doi: 10.1021/acs.jnatprod.5b00874. Epub 2015 Dec 21. PubMed PMID: 26722868; PubMed Central PMCID: PMC5558429.

18: Khlebnicova TS, Piven YA, Baranovsky AV, Lakhvich FA, Shishkina SV, Zicāne D, Tetere Z, Rāviņa I, Kumpiņš V, Rijkure I, Mieriņa I, Peipiņš U, Turks M. Synthesis of novel lupane triterpenoid-indazolone hybrids with oxime ester linkage. Steroids. 2017 Jan;117:77-89. doi: 10.1016/j.steroids.2016.08.002. Epub 2016 Aug 5. PubMed PMID: 27500691.

19: Xu QM, Shu Z, Zhu WF, Liu YL, Li XR, Yang SL. Lupane-type triterpenoidal saponins from Pulsatilla chinensis and their anticomplement activities through the classical pathway. Planta Med. 2013 Apr;79(6):506-12. doi: 10.1055/s-0032-1328323. Epub 2013 Mar 21. PubMed PMID: 23519791.

20: Kang KB, Kim JW, Oh WK, Kim J, Sung SH. Cytotoxic Ceanothane- and Lupane-Type Triterpenoids from the Roots of Ziziphus jujuba. J Nat Prod. 2016 Sep 23;79(9):2364-75. doi: 10.1021/acs.jnatprod.6b00525. Epub 2016 Sep 12. PubMed PMID: 27617953.