Leonurine | CAS#24697-74-3 | pseudoalkaloid

MedKoo Cat#: 598581 | Name: Leonurine

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Description:

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

Leonurine has neuroprotective activity, and is isolated from leaves of Leonurus artemisia. Leonurine has uterotonic effect.

Chemical Structure

Leonurine

CAS#24697-74-3

Theoretical Analysis

MedKoo Cat#: 598581

Name: Leonurine

CAS#: 24697-74-3

Chemical Formula: C14H21N3O5

Exact Mass: 311.1481

Molecular Weight: 311.34

Elemental Analysis: C, 54.01; H, 6.80; N, 13.50; O, 25.69

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
5g	USD 650.00	2 Weeks
10g	USD 950.00	2 Weeks

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Synonym

Leonurine;

IUPAC/Chemical Name

4-guanidinobutyl 4-hydroxy-3,5-dimethoxybenzoate

InChi Key

WNGSUWLDMZFYNZ-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H21N3O5/c1-20-10-7-9(8-11(21-2)12(10)18)13(19)22-6-4-3-5-17-14(15)16/h7-8,18H,3-6H2,1-2H3,(H4,15,16,17)

SMILES Code

O=C(OCCCCNC(N)=N)C1=CC(OC)=C(O)C(OC)=C1

Appearance

Solid powder

Purity

>97% (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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Leonurine is an alkaloid isolated from Leonurus artemisia, with anti-oxidative and anti-inflammatory activity.

In vitro activity:

In vitro, interleukin-1 beta (IL-1β) induced over-production of prostaglandin E2, nitric oxide, inducible nitric oxide synthase, cyclooxygenase-2, interleukin-6 and tumor necrosis factor alpha were all inhibited significantly by the pretreatment of LN (leonurine) at a dose-dependent manner (5, 10, and 20 µM). Moreover, the expression of thrombospondin motifs 5 (ADAMTS5) and metalloproteinase 13 (MMP13) was downregulated by LN. All these changes led to the IL-1β induced degradation of extracellular matrix. Reference: J Cell Physiol. 2019 May;234(5):6940-6950. https://pubmed.ncbi.nlm.nih.gov/30417459/

In vivo activity:

Administration of leonurine (60 mg/kg) for 4 weeks significantly alleviated depression-like behaviors of chronic mild stress mice, including increased sucrose preference and reduced immobility time in forced swimming test and tail suspension test. Furthermore, leonurine (60 mg/kg) significantly inhibited the production of proinflammatory cytokine interleukin-1β, interleukin-6 and TNF-α, and suppressed the nuclear factor kappa B signaling pathway. Reference: Int J Neuropsychopharmacol. 2017 Nov 1;20(11):886-895. https://pubmed.ncbi.nlm.nih.gov/29016795/

	Solvent	mg/mL	mM
Solubility
	DMSO	18.2	58.34
	Water	1.0	3.21

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 311.34 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. Hu ZC, Gong LF, Li XB, Fu X, Xuan JW, Feng ZH, Ni WF. Inhibition of PI3K/Akt/NF-κB signaling with leonurine for ameliorating the progression of osteoarthritis: In vitro and in vivo studies. J Cell Physiol. 2019 May;234(5):6940-6950. doi: 10.1002/jcp.27437. Epub 2018 Nov 11. PMID: 30417459. 2. Zhang L, Li HX, Pan WS, Khan FU, Qian C, Qi-Li FR, Xu X. Novel hepatoprotective role of Leonurine hydrochloride against experimental non-alcoholic steatohepatitis mediated via AMPK/SREBP1 signaling pathway. Biomed Pharmacother. 2019 Feb;110:571-581. doi: 10.1016/j.biopha.2018.12.003. Epub 2018 Dec 8. PMID: 30537674. 3. Jia M, Li C, Zheng Y, Ding X, Chen M, Ding J, Du R, Lu M, Hu G. Leonurine Exerts Antidepressant-Like Effects in the Chronic Mild Stress-Induced Depression Model in Mice by Inhibiting Neuroinflammation. Int J Neuropsychopharmacol. 2017 Nov 1;20(11):886-895. doi: 10.1093/ijnp/pyx062. PMID: 29016795; PMCID: PMC5737563. 4. Jiang T, Ren K, Chen Q, Li H, Yao R, Hu H, Lv YC, Zhao GJ. Leonurine Prevents Atherosclerosis Via Promoting the Expression of ABCA1 and ABCG1 in a Pparγ/Lxrα Signaling Pathway-Dependent Manner. Cell Physiol Biochem. 2017;43(4):1703-1717. doi: 10.1159/000484031. Epub 2017 Oct 18. PMID: 29045950.

In vitro protocol:

In vivo protocol:

1. Jia M, Li C, Zheng Y, Ding X, Chen M, Ding J, Du R, Lu M, Hu G. Leonurine Exerts Antidepressant-Like Effects in the Chronic Mild Stress-Induced Depression Model in Mice by Inhibiting Neuroinflammation. Int J Neuropsychopharmacol. 2017 Nov 1;20(11):886-895. doi: 10.1093/ijnp/pyx062. PMID: 29016795; PMCID: PMC5737563. 2. Jiang T, Ren K, Chen Q, Li H, Yao R, Hu H, Lv YC, Zhao GJ. Leonurine Prevents Atherosclerosis Via Promoting the Expression of ABCA1 and ABCG1 in a Pparγ/Lxrα Signaling Pathway-Dependent Manner. Cell Physiol Biochem. 2017;43(4):1703-1717. doi: 10.1159/000484031. Epub 2017 Oct 18. PMID: 29045950.

1: Song X, Wang T, Zhang Z, Jiang H, Wang W, Cao Y, Zhang N. Leonurine exerts anti-inflammatory effect by regulating inflammatory signaling pathways and cytokines in LPS-induced mouse mastitis. Inflammation. 2015 Feb;38(1):79-88. doi: 10.1007/s10753-014-0009-9. PubMed PMID: 25189466. 2: Tan B, Cai W, Zhang J, Zhou N, Ma G, Yang P, Zhu Q, Zhu Y. Identification of UDP-glucuronosyltransferase isoforms responsible for leonurine glucuronidation in human liver and intestinal microsomes. Xenobiotica. 2014 Sep;44(9):775-84. doi: 10.3109/00498254.2014.898808. Epub 2014 Mar 17. PubMed PMID: 24635759. 3: Yuan FL, Xu RS, Jiang DL, He XL, Su Q, Jin C, Li X. Leonurine hydrochloride inhibits osteoclastogenesis and prevents osteoporosis associated with estrogen deficiency by inhibiting the NF-κB and PI3K/Akt signaling pathways. Bone. 2015 Jun;75:128-37. doi: 10.1016/j.bone.2015.02.017. Epub 2015 Feb 21. PubMed PMID: 25708053. 4: Liu C, Yin H, Gao J, Xu X, Zhang T, Yang Z. Leonurine ameliorates cognitive dysfunction via antagonizing excitotoxic glutamate insults and inhibiting autophagy. Phytomedicine. 2016 Dec 1;23(13):1638-1646. doi: 10.1016/j.phymed.2016.10.005. Epub 2016 Oct 8. PubMed PMID: 27823628. 5: Zhu Q, Zhang J, Yang P, Tan B, Liu X, Zheng Y, Cai W, Zhu Y. Characterization of metabolites of leonurine (SCM-198) in rats after oral administration by liquid chromatography/tandem mass spectrometry and NMR spectrometry. ScientificWorldJournal. 2014 Feb 24;2014:947946. doi: 10.1155/2014/947946. eCollection 2014. PubMed PMID: 24772041; PubMed Central PMCID: PMC3956552. 6: Mao F, Zhang L, Cai MH, Guo H, Yuan HH. Leonurine hydrochloride induces apoptosis of H292 lung cancer cell by a mitochondria-dependent pathway. Pharm Biol. 2015;53(11):1684-90. doi: 10.3109/13880209.2014.1001406. Epub 2015 Apr 9. PubMed PMID: 25856714. 7: Cheng H, Bo Y, Shen W, Tan J, Jia Z, Xu C, Li F. Leonurine ameliorates kidney fibrosis via suppressing TGF-β and NF-κB signaling pathway in UUO mice. Int Immunopharmacol. 2015 Apr;25(2):406-15. doi: 10.1016/j.intimp.2015.02.023. Epub 2015 Feb 26. PubMed PMID: 25727888. 8: Liu XH, Pan LL, Deng HY, Xiong QH, Wu D, Huang GY, Gong QH, Zhu YZ. Leonurine (SCM-198) attenuates myocardial fibrotic response via inhibition of NADPH oxidase 4. Free Radic Biol Med. 2013 Jan;54:93-104. doi: 10.1016/j.freeradbiomed.2012.10.555. Epub 2012 Nov 2. PubMed PMID: 23127783. 9: Huang L, Yang X, Peng A, Wang H, Lei X, Zheng L, Huang K. Inhibitory effect of leonurine on the formation of advanced glycation end products. Food Funct. 2015 Feb;6(2):584-9. doi: 10.1039/c4fo00960f. PubMed PMID: 25518982. 10: Xu D, Chen M, Ren X, Ren X, Wu Y. Leonurine ameliorates LPS-induced acute kidney injury via suppressing ROS-mediated NF-κB signaling pathway. Fitoterapia. 2014 Sep;97:148-55. doi: 10.1016/j.fitote.2014.06.005. Epub 2014 Jun 9. PubMed PMID: 24924288. 11: Zhou C, He Y, Zhang YM, Wang B, Yu JD, Dai Z, Ma SC. [Determination of stachydrine hydrochloride and leonurine hydrochloride in Yimucao preparations by HPLC-MS]. Zhongguo Zhong Yao Za Zhi. 2016 May;41(10):1876-1879. doi: 10.4268/cjcmm20161019. Chinese. PubMed PMID: 28895336. 12: Liu XH, Pan LL, Yang HB, Gong QH, Zhu YZ. Leonurine attenuates lipopolysaccharide-induced inflammatory responses in human endothelial cells: involvement of reactive oxygen species and NF-κB pathways. Eur J Pharmacol. 2012 Apr 5;680(1-3):108-14. doi: 10.1016/j.ejphar.2012.01.012. Epub 2012 Jan 28. PubMed PMID: 22305882. 13: Liu X, Pan L, Wang X, Gong Q, Zhu YZ. Leonurine protects against tumor necrosis factor-α-mediated inflammation in human umbilical vein endothelial cells. Atherosclerosis. 2012 May;222(1):34-42. doi: 10.1016/j.atherosclerosis.2011.04.027. Epub 2011 May 5. PubMed PMID: 22326051. 14: Li B, Wu J, Li X. Simultaneous determination and pharmacokinetic study of stachydrine and leonurine in rat plasma after oral administration of Herba Leonuri extract by LC-MS/MS. J Pharm Biomed Anal. 2013 Mar 25;76:192-9. doi: 10.1016/j.jpba.2012.12.029. Epub 2013 Jan 5. PubMed PMID: 23348611. 15: Lin S, Wu J, Guo W, Zhu Y. Effects of leonurine on intracerebral haemorrhage by attenuation of perihematomal edema and neuroinflammation via the JNK pathway. Pharmazie. 2016 Nov 2;71(11):644-650. doi: 10.1691/ph.2016.6692. PubMed PMID: 29441969. 16: Zhu Q, Cai W, Sha X, Ma G, Zheng Y, Shi X, Zhu Y. Quantification of leonurine, a novel potential cardiovascular agent, in rat plasma by liquid chromatography-tandem mass spectrometry and its application to pharmacokinetic study in rats. Biomed Chromatogr. 2012 Apr;26(4):518-23. doi: 10.1002/bmc.1699. Epub 2011 Sep 1. PubMed PMID: 21882210. 17: Liu H, Zhang X, Du Y, Ji H, Li S, Li L, Xing Y, Zhang X, Dong L, Wang C, Zhao K, Ji Y, Cao X. Leonurine protects brain injury by increased activities of UCP4, SOD, CAT and Bcl-2, decreased levels of MDA and Bax, and ameliorated ultrastructure of mitochondria in experimental stroke. Brain Res. 2012 Sep 20;1474:73-81. doi: 10.1016/j.brainres.2012.07.028. Epub 2012 Jul 27. PubMed PMID: 22842526. 18: Kuchta K, Ortwein J, Rauwald HW. Leonurus japonicus, Leonurus cardiaca, Leonotis leonurus: a novel HPLC study on the occurrence and content of the pharmacologically active guanidino derivative leonurine. Pharmazie. 2012 Dec;67(12):973-9. PubMed PMID: 23346757. 19: Li X, Yuan FL, Zhao YQ, Lu WG, Li CW, He CH. Effect of leonurine hydrochloride on endothelin and the endothelin receptor-mediated signal pathway in medically-induced incomplete abortion in rats. Eur J Obstet Gynecol Reprod Biol. 2013 Jul;169(2):299-303. doi: 10.1016/j.ejogrb.2013.02.022. Epub 2013 Mar 28. PubMed PMID: 23541415. 20: Gao H, Yang X, Gu X, Zhu YZ. Synthesis and biological evaluation of the codrug of Leonurine and Aspirin as cardioprotective agents. Bioorg Med Chem Lett. 2016 Oct 1;26(19):4650-4654. doi: 10.1016/j.bmcl.2016.08.058. Epub 2016 Aug 21. PubMed PMID: 27575471.