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MedKoo Cat#: 558050 | Name: Lespenefril
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Description:

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

Lespenefril is an antioxidant, antimicrobial and anti-inflammatory agent.

Chemical Structure

Lespenefril
Lespenefril
CAS#482-38-2

Theoretical Analysis

MedKoo Cat#: 558050

Name: Lespenefril

CAS#: 482-38-2

Chemical Formula: C27H30O14

Exact Mass: 578.1636

Molecular Weight: 578.52

Elemental Analysis: C, 56.06; H, 5.23; O, 38.72

Price and Availability

Size Price Availability Quantity
10mg USD 285.00 2 Weeks
50mg USD 650.00 2 Weeks
100mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
4-18-00-03292 (Beilstein Handbook Reference); BRN 0073958; Kaempferitrin; Kaempferol 3,7-bisrhamnoside;
IUPAC/Chemical Name
4H-1-Benzopyran-4-one, 3,7-bis((6-deoxy-alpha-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-
InChi Key
PUPKKEQDLNREIM-QNSQPKOQSA-N
InChi Code
InChI=1S/C27H30O14/c1-9-17(30)20(33)22(35)26(37-9)39-13-7-14(29)16-15(8-13)40-24(11-3-5-12(28)6-4-11)25(19(16)32)41-27-23(36)21(34)18(31)10(2)38-27/h3-10,17-18,20-23,26-31,33-36H,1-2H3/t9-,10-,17-,18-,20+,21+,22+,23+,26-,27-/m0/s1
SMILES Code
O=C1C(O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)=C(C3=CC=C(O)C=C3)OC4=CC(O[C@H]5[C@@H]([C@@H]([C@H]([C@H](C)O5)O)O)O)=CC(O)=C14
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
>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:
Kaempferitrin is a natural flavonoid, possesses antinociceptive, anti-inflammatory, anti-diabetic, antitumoral and chemopreventive effects, and activates insulin signaling pathway.
In vitro activity:
Kaempferitrin treatment resulted in an up-regulated level of phosphorylation on insulin receptor beta and insulin receptor substrate 1, and ser473 site in PKB/akt. Kaempferitrin also stimulated more sustained adiponectin secretion than insulin did. This study provided evidence of the dual effects of kaempferitrin. Reference: Eur J Pharmacol. 2009 Apr 1;607(1-3):27-34. https://pubmed.ncbi.nlm.nih.gov/19326566/
In vivo activity:
Also, different doses of KM (kaempferitrin) were injected intraperitoneally daily into athymic mice bearing tumors of HeLa cells during 32 days. KM induces high cytotoxic effects in vitro and in vivo against HeLa cells. The general mechanisms by which KM induces cytotoxic effects include: cell cycle arrest in G1 phase and apoptosis via intrinsic pathway in a caspase dependent pathway. Also, KM exerts chemopreventive and antitumor effects. Reference: J Ethnopharmacol. 2013 Jan 30;145(2):476-89. https://pubmed.ncbi.nlm.nih.gov/23211658/
Solvent mg/mL mM
Solubility
DMSO 25.0 43.21
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 578.52 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. Zhang N, Liu J, Chen Z, Dou W. In vitro inhibitory effects of kaempferitrin on human liver cytochrome P450 enzymes. Pharm Biol. 2019 Dec;57(1):571-576. doi: 10.1080/13880209.2019.1656257. PMID: 31456483; PMCID: PMC6720019. 2. Tzeng YM, Chen K, Rao YK, Lee MJ. Kaempferitrin activates the insulin signaling pathway and stimulates secretion of adiponectin in 3T3-L1 adipocytes. Eur J Pharmacol. 2009 Apr 1;607(1-3):27-34. doi: 10.1016/j.ejphar.2009.01.023. PMID: 19326566. 3. Wang J, Zhao Q. Kaempferitrin inhibits proliferation, induces apoptosis, and ameliorates inflammation in human rheumatoid arthritis fibroblast-like synoviocytes. Phytother Res. 2019 Jun;33(6):1726-1735. doi: 10.1002/ptr.6364. Epub 2019 Jun 2. PMID: 31155798. 4. Alonso-Castro AJ, Ortiz-Sánchez E, García-Regalado A, Ruiz G, Núñez-Martínez JM, González-Sánchez I, Quintanar-Jurado V, Morales-Sánchez E, Dominguez F, López-Toledo G, Cerbón MA, García-Carrancá A. Kaempferitrin induces apoptosis via intrinsic pathway in HeLa cells and exerts antitumor effects. J Ethnopharmacol. 2013 Jan 30;145(2):476-89. doi: 10.1016/j.jep.2012.11.016. Epub 2012 Dec 2. PMID: 23211658.
In vitro protocol:
1. Zhang N, Liu J, Chen Z, Dou W. In vitro inhibitory effects of kaempferitrin on human liver cytochrome P450 enzymes. Pharm Biol. 2019 Dec;57(1):571-576. doi: 10.1080/13880209.2019.1656257. PMID: 31456483; PMCID: PMC6720019. 2. Tzeng YM, Chen K, Rao YK, Lee MJ. Kaempferitrin activates the insulin signaling pathway and stimulates secretion of adiponectin in 3T3-L1 adipocytes. Eur J Pharmacol. 2009 Apr 1;607(1-3):27-34. doi: 10.1016/j.ejphar.2009.01.023. PMID: 19326566.
In vivo protocol:
1. Wang J, Zhao Q. Kaempferitrin inhibits proliferation, induces apoptosis, and ameliorates inflammation in human rheumatoid arthritis fibroblast-like synoviocytes. Phytother Res. 2019 Jun;33(6):1726-1735. doi: 10.1002/ptr.6364. Epub 2019 Jun 2. PMID: 31155798. 2. Alonso-Castro AJ, Ortiz-Sánchez E, García-Regalado A, Ruiz G, Núñez-Martínez JM, González-Sánchez I, Quintanar-Jurado V, Morales-Sánchez E, Dominguez F, López-Toledo G, Cerbón MA, García-Carrancá A. Kaempferitrin induces apoptosis via intrinsic pathway in HeLa cells and exerts antitumor effects. J Ethnopharmacol. 2013 Jan 30;145(2):476-89. doi: 10.1016/j.jep.2012.11.016. Epub 2012 Dec 2. PMID: 23211658.
1: Lambev I, Simeonova K, Sedmakova L, Krushkov I, Dimitrov D. [Therapeutic activity of nephroton, lespenefril and furosemide in experimental azotemia]. Eksp Med Morfol. 1985;24(4):27-35. Bulgarian. PubMed PMID: 3833521. 2: Vellosa JC, Regasini LO, Belló C, Schemberger JA, Khalil NM, de Araújo Morandim-Giannetti A, da Silva Bolzani V, Brunetti IL, de Faria Oliveira OM. Preliminary in vitro and ex vivo evaluation of afzelin, kaempferitrin and pterogynoside action over free radicals and reactive oxygen species. Arch Pharm Res. 2015 Jun;38(6):1168-77. doi: 10.1007/s12272-014-0487-1. Epub 2014 Oct 15. PubMed PMID: 25315635. 3: Ma XQ, Han T, Zhang X, Wu JZ, Rahman K, Qin LP, Zheng CJ. Kaempferitrin prevents bone lost in ovariectomized rats. Phytomedicine. 2015 Dec 1;22(13):1159-62. doi: 10.1016/j.phymed.2015.09.003. Epub 2015 Oct 3. PubMed PMID: 26598914. 4: Onkokesung N, Reichelt M, van Doorn A, Schuurink RC, Dicke M. Differential Costs of Two Distinct Resistance Mechanisms Induced by Different Herbivore Species in Arabidopsis. Plant Physiol. 2016 Feb;170(2):891-906. doi: 10.1104/pp.15.01780. Epub 2015 Nov 24. PubMed PMID: 26603653; PubMed Central PMCID: PMC4734589. 5: Puchalski Z, Kala E. [Clinical significance of lespenefril in modern therapy]. Wiad Lek. 1966 Sep 1;19(17):1333-6. Polish. PubMed PMID: 5977817. 6: Zhao S, Li X, Cho DH, Arasu MV, Al-Dhabi NA, Park SU. Accumulation of kaempferitrin and expression of phenyl-propanoid biosynthetic genes in kenaf (Hibiscus cannabinus). Molecules. 2014 Oct 23;19(10):16987-97. doi: 10.3390/molecules191016987. PubMed PMID: 25342553. 7: Da Silva D, Casanova LM, Marcondes MC, Espindola-Netto JM, Paixão LP, De Melo GO, Zancan P, Sola-Penna M, Costa SS. Antidiabetic activity of Sedum dendroideum: metabolic enzymes as putative targets for the bioactive flavonoid kaempferitrin. IUBMB Life. 2014 May;66(5):361-70. doi: 10.1002/iub.1270. Epub 2014 May 10. PubMed PMID: 24817132. 8: Cassani J, Dorantes-Barrón AM, Novales LM, Real GA, Estrada-Reyes R. Anti-depressant-like effect of kaempferitrin isolated from Justicia spicigera Schltdl (Acanthaceae) in two behavior models in mice: evidence for the involvement of the serotonergic system. Molecules. 2014 Dec 19;19(12):21442-61. doi: 10.3390/molecules191221442. PubMed PMID: 25532842. 9: Onkokesung N, Reichelt M, van Doorn A, Schuurink RC, van Loon JJ, Dicke M. Modulation of flavonoid metabolites in Arabidopsis thaliana through overexpression of the MYB75 transcription factor: role of kaempferol-3,7-dirhamnoside in resistance to the specialist insect herbivore Pieris brassicae. J Exp Bot. 2014 May;65(8):2203-17. doi: 10.1093/jxb/eru096. Epub 2014 Mar 11. PubMed PMID: 24619996; PubMed Central PMCID: PMC3991749. 10: Del Carmen Juárez-Vázquez M, Josabad Alonso-Castro A, García-Carrancá A. Kaempferitrin induces immunostimulatory effects in vitro. J Ethnopharmacol. 2013 Jun 21;148(1):337-40. doi: 10.1016/j.jep.2013.03.072. Epub 2013 Apr 12. PubMed PMID: 23588095. 11: Jiang B, Chi C, Fu YW, Zhang QZ, Wang GX. In vivo anthelmintic effect of flavonol rhamnosides from Dryopteris crassirhizoma against Dactylogyrus intermedius in goldfish (Carassius auratus). Parasitol Res. 2013 Dec;112(12):4097-104. doi: 10.1007/s00436-013-3600-3. Epub 2013 Sep 8. PubMed PMID: 24013342. 12: Cazarolli LH, Pereira DF, Kappel VD, Folador P, Figueiredo Mdos S, Pizzolatti MG, Silva FR. Insulin signaling: a potential signaling pathway for the stimulatory effect of kaempferitrin on glucose uptake in skeletal muscle. Eur J Pharmacol. 2013 Jul 15;712(1-3):1-7. doi: 10.1016/j.ejphar.2013.02.029. Epub 2013 Mar 1. Review. PubMed PMID: 23458067. 13: Ortiz-Andrade R, Cabañas-Wuan A, Arana-Argáez VE, Alonso-Castro AJ, Zapata-Bustos R, Salazar-Olivo LA, Domínguez F, Chávez M, Carranza-Álvarez C, García-Carrancá A. Antidiabetic effects of Justicia spicigera Schltdl (Acanthaceae). J Ethnopharmacol. 2012 Sep 28;143(2):455-62. doi: 10.1016/j.jep.2012.06.043. Epub 2012 Jul 20. PubMed PMID: 22819688. 14: Alonso-Castro AJ, Ortiz-Sánchez E, García-Regalado A, Ruiz G, Núñez-Martínez JM, González-Sánchez I, Quintanar-Jurado V, Morales-Sánchez E, Dominguez F, López-Toledo G, Cerbón MA, García-Carrancá A. Kaempferitrin induces apoptosis via intrinsic pathway in HeLa cells and exerts antitumor effects. J Ethnopharmacol. 2013 Jan 30;145(2):476-89. doi: 10.1016/j.jep.2012.11.016. Epub 2012 Dec 2. PubMed PMID: 23211658. 15: Urgaonkar S, Shaw JT. Synthesis of kaempferitrin. J Org Chem. 2007 Jun 8;72(12):4582-5. Epub 2007 May 11. PubMed PMID: 17497804. 16: Zhang Y, Zhang TT. Studies on the chemical constituents from the stem and leaves of Tagetes erecta. Zhong Yao Cai. 2010 Sep;33(9):1412-4. PubMed PMID: 21235096. 17: Hamzah AS, Lajis NH, Sargent MV. Kaempferitrin from the leaves of Hedyotis verticillata and its biological activity. Planta Med. 1994 Aug;60(4):388-9. PubMed PMID: 7938277. 18: Yan W, Fu Y, Ma Y, Li Y, Zhang X, Xin F. [Studies on flavones of Epimedium bevicorum Maxim]. Zhongguo Zhong Yao Za Zhi. 1998 Dec;23(12):735-6, 764. Chinese. PubMed PMID: 12242823. 19: Qu G, Li X, Liu J. [Flavonol glycosides of Sonchus arvensis L]. Zhongguo Zhong Yao Za Zhi. 1996 May;21(5):292-4, 319. Chinese. PubMed PMID: 9388936. 20: Lin TY, Liao JW, Chang ST, Wang SY. Antidyslipidemic activity of hot-water extracts from leaves of Cinnamomum osmophloeum Kaneh. Phytother Res. 2011 Sep;25(9):1317-22. doi: 10.1002/ptr.3408. Epub 2011 Feb 10. PubMed PMID: 21308822.