Rutaecarpine | NSC 258317 | CAS#84-26-4

MedKoo Cat#: 329838 | Name: Rutaecarpine

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Description:

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

Rutaecarpine, also known as NSC 258317, is a quinazolinone alkaloid originally isolated from E. rutaecarpa that has diverse biological activities. Rutaecarpine prevented dysfunction of endothelial gap junction induced by Ox-LDL via activation of TRPV1. Rutaecarpine inhibits angiotensin II-induced proliferation in rat vascular smooth muscle cells. Rutaecarpine ameliorates hyperlipidemia and hyperglycemia in fat-fed, streptozotocin-treated rats via regulating the IRS-1/PI3K/Akt and AMPK/ACC2 signaling pathways.

Chemical Structure

Rutaecarpine

CAS#84-26-4

Theoretical Analysis

MedKoo Cat#: 329838

Name: Rutaecarpine

CAS#: 84-26-4

Chemical Formula: C18H13N3O

Exact Mass: 287.1059

Molecular Weight: 287.32

Elemental Analysis: C, 75.25; H, 4.56; N, 14.63; O, 5.57

Price and Availability

Size	Price	Availability	Quantity
200mg	USD 350.00
500mg	USD 750.00
1g	USD 1,150.00

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Synonym

Rutaecarpine; NSC 258317; NSC-258317; NSC258317.

IUPAC/Chemical Name

8,13-dihydro-indolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one

InChi Key

ACVGWSKVRYFWRP-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2

SMILES Code

O=C1N2C(C(NC3=C4C=CC=C3)=C4CC2)=NC5=C1C=CC=C5

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Rutaecarpine inhibits COX-2 and COX-1 dependent phases of PGD2 generation in BMMC in a concentration-dependent manner with an IC50 of 0.28 μM and 8.7 μM, respectively. It inhibits COX-2-dependent conversion of exogenous arachidonic acid to PGE2 in a dose-dependent manner by the COX-2-transfected HEK293 cells.

In vitro activity:

Rutacarpine demonstrated significant in vitro activity against high glucose (HG)-induced cardiomyocyte injury. It effectively inhibited apoptosis and oxidative stress in H9c2 cardiomyocyte cells exposed to HG levels. Additionally, rutacarpine activated TRPV1, inducing autophagy, which further contributed to its protective effects against HG-induced cellular damage. Reference: Bratisl Lek Listy. 2023;124(9):699-706. https://pubmed.ncbi.nlm.nih.gov/37635668/

In vivo activity:

Rutacarpine demonstrated promising in vivo activity in a mouse model of osteoarthritis (OA). It effectively reduced inflammation, cartilage degradation, chondrocyte apoptosis, senescence, and autophagy impairment induced by interleukin-1β. Rutacarpine mediated the PI3K/Akt/NF-κB and MAPK pathways, protecting cartilage. These findings highlight the potential therapeutic benefits of Rutacarpine for osteoarthritis treatment. Reference: Int J Mol Med. 2023 Oct;52(4):97. https://pubmed.ncbi.nlm.nih.gov/37654229/

	Solvent	mg/mL	mM
Solubility
	DMSO	50.0	174.02

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 287.32 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. Song C, Gong Z, Ji Y. Rutaecarpine ameliorates cardiomyocyte injury induced by high glucose by promoting TRPV1-mediated autophagy. Bratisl Lek Listy. 2023;124(9):699-706. doi: 10.4149/BLL_2023_107. PMID: 37635668. 2. Lv J, Ji M, Yang H, Wang C, Zhang L, Ni H. Rutaecarpine attenuates high glucose-induced damage in AC16 cardiomyocytes by suppressing the MAPK pathway. J Appl Toxicol. 2023 Sep;43(9):1306-1318. doi: 10.1002/jat.4465. Epub 2023 Mar 29. PMID: 36928891. 3. Wan J, Li M, Yuan X, Yu X, Chen A, Shao M, Kang H, Cheng P. Rutaecarpine ameliorates osteoarthritis by inhibiting PI3K/AKT/NF‑κB and MAPK signalling transduction through integrin αVβ3. Int J Mol Med. 2023 Oct;52(4):97. doi: 10.3892/ijmm.2023.5300. Epub 2023 Sep 1. PMID: 37654229. 4. Xu M, Shi Z, He Z, Ling X, Wang W, Liu H, Gong M. Rutaecarpine alleviates migraine in nitroglycerin-induced mice by regulating PTEN/PGK1 signaling pathway to activate NRF2 antioxidant system. Biomed Pharmacother. 2023 Aug 7;166:115300. doi: 10.1016/j.biopha.2023.115300. Epub ahead of print. PMID: 37557014.

In vitro protocol:

In vivo protocol:

1. Wan J, Li M, Yuan X, Yu X, Chen A, Shao M, Kang H, Cheng P. Rutaecarpine ameliorates osteoarthritis by inhibiting PI3K/AKT/NF‑κB and MAPK signalling transduction through integrin αVβ3. Int J Mol Med. 2023 Oct;52(4):97. doi: 10.3892/ijmm.2023.5300. Epub 2023 Sep 1. PMID: 37654229. 2. Xu M, Shi Z, He Z, Ling X, Wang W, Liu H, Gong M. Rutaecarpine alleviates migraine in nitroglycerin-induced mice by regulating PTEN/PGK1 signaling pathway to activate NRF2 antioxidant system. Biomed Pharmacother. 2023 Aug 7;166:115300. doi: 10.1016/j.biopha.2023.115300. Epub ahead of print. PMID: 37557014.

1: Chen MM, Guo X, Li TQ, He XX, Wen DY, Hang XC, Lu AD, Zhou ZH, Wang QM, Wang ZW. Discovery of new pesticide candidates from nature: design, synthesis and bioactivity research of rutaecarpine derivatives. Pest Manag Sci. 2024 Sep 23. doi: 10.1002/ps.8430. Epub ahead of print. PMID: 39311339. 2: Yang Y, Gong Z, Yang J, Cai Y, Hong S, Mao W, Guo Z, Qiu M, Fan Z, Cui B. Exploring shared mechanisms between ulcerative colitis and psoriasis and predicting therapeutic natural compounds through bioinformatics and molecular docking. Heliyon. 2024 Sep 7;10(18):e37624. doi: 10.1016/j.heliyon.2024.e37624. PMID: 39309918; PMCID: PMC11416260. 3: Shimu MSS. Computational screening and molecular docking of compounds from Traditional Chinese Medicine (TCM) by targeting DNA topoisomerase I to design potential anticancer drugs. PLoS One. 2024 Sep 12;19(9):e0310364. doi: 10.1371/journal.pone.0310364. PMID: 39264927; PMCID: PMC11392414. 4: Wan M, Gao H, Liu X, Zhang Y. Rutaecarpine Aggravates Acetaminophen-Induced Acute Liver Injury by Inducing CYP1A2. Toxics. 2024 Jul 18;12(7):515. doi: 10.3390/toxics12070515. PMID: 39058167; PMCID: PMC11280960. 5: 5-Fluorouracil Combined with Rutaecarpine Synergistically Suppresses the Growth of Colon Cancer Cells by Inhibiting STAT3 [Retraction]. Drug Des Devel Ther. 2024 Jun 19;18:2403-2404. doi: 10.2147/DDDT.S483041. PMID: 38911031; PMCID: PMC11193980. 6: Yadav M, Roy N, Mandal K, Nagpure M, Santra MK, Guchhait SK. Rutaecarpine- inspired scaffold-hopping strategy and Ullmann cross-coupling based synthetic approach: Identification of pyridopyrimidinone-indole based novel anticancer chemotypes. Bioorg Med Chem. 2024 Jul 15;109:117799. doi: 10.1016/j.bmc.2024.117799. Epub 2024 Jun 13. PMID: 38897138. 7: Lin S, Wang X, Tang RW, Duan R, Leung KW, Dong TT, Webb SE, Miller AL, Tsim KW. Computational Docking as a Tool in Guiding the Drug Design of Rutaecarpine Derivatives as Potential SARS-CoV-2 Inhibitors. Molecules. 2024 Jun 3;29(11):2636. doi: 10.3390/molecules29112636. PMID: 38893512; PMCID: PMC11173897. 8: Xu M, Qian LH, Wang JX, He ZY, Ling XY, Wang WH, Wang JW, Hu Y, Gong MJ. Rutaecarpine Alleviates Early Brain Injury-Induced Inflammatory Response Following Subarachnoid Hemorrhage via SIRT6/NF-[Formula: see text]B Pathway. Am J Chin Med. 2024;52(3):799-819. doi: 10.1142/S0192415X24500320. Epub 2024 May 16. PMID: 38752843. 9: Wang L, Hao H, Meng X, Zhang W, Zhang Y, Chai T, Wang X, Gao Z, Zheng Y, Yang J. A novel isoquinoline alkaloid HJ-69 isolated from Zanthoxylum bungeanum attenuates inflammatory pain by inhibiting voltage-gated sodium and potassium channels. J Ethnopharmacol. 2024 Aug 10;330:118218. doi: 10.1016/j.jep.2024.118218. Epub 2024 Apr 25. PMID: 38677570. 10: Ali D, Okla M, Abuelreich S, Vishnubalaji R, Ditzel N, Hamam R, Kowal JM, Sayed A, Aldahmash A, Alajez NM, Kassem M. Apigenin and Rutaecarpine reduce the burden of cellular senescence in bone marrow stromal stem cells. Front Endocrinol (Lausanne). 2024 Apr 4;15:1360054. doi: 10.3389/fendo.2024.1360054. PMID: 38638133; PMCID: PMC11024792. 11: Krishnamoorthi R, Ganapathy A A, Hari Priya VM, Kumaran A. Future aspects of plant derived bioactive metabolites as therapeutics to combat benign prostatic hyperplasia. J Ethnopharmacol. 2024 Aug 10;330:118207. doi: 10.1016/j.jep.2024.118207. Epub 2024 Apr 16. PMID: 38636573. 12: Ji Z, Zhang C, Feng P, Zhao J. Rutaecarpine Protects Against Cigarette Smoke-Induced Chronic Obstructive Pulmonary Disease (COPD) in Rats. Appl Biochem Biotechnol. 2024 Mar 14. doi: 10.1007/s12010-024-04896-5. Epub ahead of print. PMID: 38483764. 13: Hu HC, Yu SY, Tsai YH, Hsieh PW, Wang HC, Chen YN, Chuang YT, Lee MY, Chang HW, Hu HC, Wu YC, Chang FR, Szatmári I, Fülöp F. Synthesis of bioactive evodiamine and rutaecarpine analogues under ball milling conditions. Org Biomol Chem. 2024 Mar 27;22(13):2620-2629. doi: 10.1039/d4ob00056k. PMID: 38451121. 14: Hu X, Wang J, Jiang L, Liu X, Ge Q, Wang Q, Qi X, Wu Y. Rutaecarpine protects podocytes in diabetic kidney disease by targeting VEGFR2/NLRP3-mediated pyroptosis. Int Immunopharmacol. 2024 Mar 30;130:111790. doi: 10.1016/j.intimp.2024.111790. Epub 2024 Mar 6. PMID: 38447417. 15: Zhao Z, Yan J, Huang L, Yang X. Phytochemicals targeting Alzheimer's disease via the AMP-activated protein kinase pathway, effects, and mechanisms of action. Biomed Pharmacother. 2024 Apr;173:116373. doi: 10.1016/j.biopha.2024.116373. Epub 2024 Mar 4. PMID: 38442672. 16: Li Y, Tan Z, Li W, Li Z, Zhang G. Rutaecarpine ameliorates imiquimod-induced psoriasis-like dermatitis in mice associated with alterations in the gut microbiota. Acta Biochim Biophys Sin (Shanghai). 2024 Mar 25;56(3):345-355. doi: 10.3724/abbs.2024018. PMID: 38419497; PMCID: PMC11292129. 17: Wu T, Zhang H, Jin Y, Zhang M, Zhao Q, Li H, Wang S, Lu Y, Chen S, Du H, Liu T, Guo W, Liu W. The active components and potential mechanisms of Wuji Wan in the treatment of ethanol-induced gastric ulcer: An integrated metabolomics, network pharmacology and experimental validation. J Ethnopharmacol. 2024 May 23;326:117901. doi: 10.1016/j.jep.2024.117901. Epub 2024 Feb 8. PMID: 38341112. 18: Jin SE, Seo CS, Jeon WY, Oh YJ, Shin HK, Jeong HG, Ha H. Evodiae Fructus extract suppresses inflammatory response in HaCaT cells and improves house dust mite-induced atopic dermatitis in NC/Nga mice. Sci Rep. 2024 Jan 4;14(1):472. doi: 10.1038/s41598-023-50257-3. PMID: 38172219; PMCID: PMC10764943. 19: Hou BL, Wu K, Liu R, Liu J, Wang J, Wang C, Liang Y, Wang Z. Natural products fragment-based design and synthesis of a novel pentacyclic ring system as potential MAPK inhibitor. Bioorg Med Chem Lett. 2024 Feb 1;99:129598. doi: 10.1016/j.bmcl.2023.129598. Epub 2023 Dec 31. PMID: 38169246. 20: Lu Y, Dong K, Yang M, Liu J. Network pharmacology-based strategy to investigate the bioactive ingredients and molecular mechanism of Evodia rutaecarpa in colorectal cancer. BMC Complement Med Ther. 2023 Dec 1;23(1):433. doi: 10.1186/s12906-023-04254-8. PMID: 38041080; PMCID: PMC10691004.