Koenimbine | CAS#21087-98-9 | anti-inflammatory

MedKoo Cat#: 125212 | Name: Koenimbine

Description:

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

Koenimbine is a carbazole alkaloid isolated from Murraya koenigii, belongs to the Rutaceae family. Koenimbine is a potential novel anti-inflammatory drug candidate in treating inflammatory disorders. Various pharmacological effects such as anti-diabetic, melanogenesis inhibition, anti-diarrheal, anti-cancer, and anti-inflammatory properties of koenimbine have already been reported. Koenimbine significantly attenuated the expression levels of nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in a dose dependent manner and also decreased the production of reactive oxygen species (ROS) in LPS-activated RAW 264.7 cells. Koenimbine blocks NF-κB p65 from translocating into the nucleus and activating inflammatory gene transcription.

Chemical Structure

Koenimbine

CAS#21087-98-9

Theoretical Analysis

MedKoo Cat#: 125212

Name: Koenimbine

CAS#: 21087-98-9

Chemical Formula: C19H19NO2

Exact Mass: 293.1416

Molecular Weight: 293.37

Elemental Analysis: C, 77.79; H, 6.53; N, 4.77; O, 10.91

Price and Availability

Size	Price	Availability
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,650.00	2 Weeks
2g	USD 5,650.00	2 Weeks

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Related CAS #

No Data

Synonym

NSC 127152; NSC-127152; NSC127152; Koenimbin; Kenimbine;

IUPAC/Chemical Name

8-methoxy-3,3,5-trimethyl-3,11-dihydropyrano[3,2-a]carbazole

InChi Key

OSERHKINMDLESD-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H19NO2/c1-11-9-15-14-10-12(21-4)5-6-16(14)20-17(15)13-7-8-19(2,3)22-18(11)13/h5-10,20H,1-4H3

SMILES Code

CC1=CC2=C(C3=C1OC(C=C3)(C)C)NC4=C2C=C(C=C4)OC

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 293.37 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

1: Tanty DK, Sahu PR, Mohapatra R, Sahu SK. Antidiabetic potency and molecular insights of natural products bearing indole moiety: A systematic bioinformatics investigation targeting AKT1. Comput Biol Chem. 2024 Mar 23;110:108059. doi: 10.1016/j.compbiolchem.2024.108059. Epub ahead of print. PMID: 38608439. 2: Iqbal Andrabi N, Sarkar AR, Assim Haq S, Kumar D, Kour D, Saroch D, Kumar Shukla S, Kumar A, Bhagat A, Ali A, Kour G, Ahmed Z. Site-selective synthesis and pharmacological elucidation of novel semi-synthetic analogues of koenimbine as a potential anti-inflammatory agent. Int Immunopharmacol. 2024 Jan 5;126:111059. doi: 10.1016/j.intimp.2023.111059. Epub 2023 Nov 17. PMID: 37979450. 3: Sadwal S, Bharati S, Dar ZA, Kaur S. Chemopreventive potential of hydroethanolic Murraya koenigii leaves extract against DMBA induced breast carcinogenesis: In-silico and in-vivo study. J Ethnopharmacol. 2024 Jan 30;319(Pt 1):117124. doi: 10.1016/j.jep.2023.117124. Epub 2023 Sep 8. PMID: 37678421. 4: Chatterjee D, Narzish F, Borade P, Singh IP. Simultaneous quantitation of nine carbazole alkaloids from Murraya koenigii (L.) Spreng by 1H qNMR spectroscopy. Nat Prod Res. 2023 Jun 16:1-9. doi: 10.1080/14786419.2023.2219819. Epub ahead of print. PMID: 37322993. 5: Omeershffudin UNM, Kumar S. Antimicrobial resistance in Klebsiella pneumoniae: identification of bacterial DNA adenine methyltransferase as a novel drug target from hypothetical proteins using subtractive genomics. Genomics Inform. 2022 Dec;20(4):e47. doi: 10.5808/gi.22067. Epub 2022 Dec 30. PMID: 36617654; PMCID: PMC9847377. 6: Pakrashy S, Mandal PK, Dey SK, Choudhury SM, Alasmary FA, Almalki AS, Islam MA, Dolai M. Design of a Structurally Novel Multipotent Drug Candidate by the Scaffold Architecture Technique for ACE-II, NSP15, and Mpro Protein Inhibition: Identification and Isolation of a Natural Product to Prevent the Severity of Future Variants of Covid 19 and a Colorectal Anticancer Drug. ACS Omega. 2022 Sep 10;7(37):33408-33422. doi: 10.1021/acsomega.2c04051. PMID: 36157758; PMCID: PMC9494648. 7: Nandan S, Singh SK, Singh P, Bajpai V, Mishra AK, Joshi T, Mahar R, Shukla SK, Mishra DK, Kanojiya S. Quantitative Analysis of Bioactive Carbazole Alkaloids in Murraya koenigii (L.) from Six Different Climatic Zones of India Using UPLC/MS/MS and Their Principal Component Analysis. Chem Biodivers. 2021 Dec;18(12):e2100557. doi: 10.1002/cbdv.202100557. Epub 2021 Oct 27. PMID: 34643999. 8: Astaneh M, Ghafouri-Fard S, Fazeli Z, Taherian-Esfahani Z, Dashti S, Motevaseli E. Assessment of anti-cancer effects of koenimbine on colon cancer cells. Hum Antibodies. 2020;28(3):185-190. doi: 10.3233/HAB-200405. PMID: 32116245. 9: Satyavarapu EM, Sinha PK, Mandal C. Influence of Geographical and Seasonal Variations on Carbazole Alkaloids Distribution in Murraya koenigii: Deciding Factor of Its In Vitro and In Vivo Efficacies against Cancer Cells. Biomed Res Int. 2020 Feb 11;2020:7821913. doi: 10.1155/2020/7821913. PMID: 32104704; PMCID: PMC7036096. 10: Patel OPS, Arun A, Singh PK, Saini D, Karade SS, Chourasia MK, Konwar R, Yadav PP. Pyranocarbazole derivatives as potent anti-cancer agents triggering tubulin polymerization stabilization induced activation of caspase-dependent apoptosis and downregulation of Akt/mTOR in breast cancer cells. Eur J Med Chem. 2019 Apr 1;167:226-244. doi: 10.1016/j.ejmech.2019.02.003. Epub 2019 Feb 7. PMID: 30772606. 11: Cianciosi D, Varela-Lopez A, Forbes-Hernandez TY, Gasparrini M, Afrin S, Reboredo-Rodriguez P, Zhang J, Quiles JL, Nabavi SF, Battino M, Giampieri F. Targeting molecular pathways in cancer stem cells by natural bioactive compounds. Pharmacol Res. 2018 Sep;135:150-165. doi: 10.1016/j.phrs.2018.08.006. Epub 2018 Aug 10. PMID: 30103002. 12: Kamalidehghan B, Ghafouri-Fard S, Motevaseli E, Ahmadipour F. Inhibition of human prostate cancer (PC-3) cells and targeting of PC-3-derived prostate cancer stem cells with koenimbin, a natural dietary compound from Murraya koenigii (L) Spreng. Drug Des Devel Ther. 2018 May 4;12:1119-1133. doi: 10.2147/DDDT.S156826. PMID: 29765202; PMCID: PMC5942175. 13: Hobani YH. The Role of Oxidative Stress in Koenimbine-Induced DNA Damage and Heat Shock Protein Modulation in HepG2 Cells. Integr Cancer Ther. 2017 Dec;16(4):563-571. doi: 10.1177/1534735416678982. Epub 2016 Nov 22. PMID: 27879375; PMCID: PMC5739142. 14: Dandawate PR, Subramaniam D, Jensen RA, Anant S. Targeting cancer stem cells and signaling pathways by phytochemicals: Novel approach for breast cancer therapy. Semin Cancer Biol. 2016 Oct;40-41:192-208. doi: 10.1016/j.semcancer.2016.09.001. Epub 2016 Sep 5. PMID: 27609747; PMCID: PMC5565737. 15: Nalli Y, Khajuria V, Gupta S, Arora P, Riyaz-Ul-Hassan S, Ahmed Z, Ali A. Four new carbazole alkaloids from Murraya koenigii that display anti- inflammatory and anti-microbial activities. Org Biomol Chem. 2016 Mar 28;14(12):3322-32. doi: 10.1039/c6ob00267f. Erratum in: Org Biomol Chem. 2018 Mar 14;16(11):1994. PMID: 26947457. 16: Joshi T, Mahar R, Singh SK, Srivastava P, Shukla SK, Mishra DK, Bhatta RS, Kanojiya S. Quantitative analysis of bioactive carbazole alkaloids in Murraya koenigii. Nat Prod Commun. 2015 Feb;10(2):293-5. PMID: 25920265. 17: Ahmadipour F, Noordin MI, Mohan S, Arya A, Paydar M, Looi CY, Keong YS, Siyamak EN, Fani S, Firoozi M, Yong CL, Sukari MA, Kamalidehghan B. Koenimbin, a natural dietary compound of Murraya koenigii (L) Spreng: inhibition of MCF7 breast cancer cells and targeting of derived MCF7 breast cancer stem cells (CD44(+)/CD24(-/low)): an in vitro study. Drug Des Devel Ther. 2015 Feb 24;9:1193-208. doi: 10.2147/DDDT.S72127. PMID: 25759564; PMCID: PMC4346015. 18: Sim KM, Teh HM. A new carbazole alkaloid from the leaves of Malayan Murraya koenigii. J Asian Nat Prod Res. 2011 Oct;13(10):972-5. doi: 10.1080/10286020.2011.602970. PMID: 21972815. 19: Uvarani C, Ramesh P, Ravichandran K, Mohan PS, Ponnuswamy MN. 8-Meth- oxy-3,3,5-trimethyl-3,11-dihydro-pyrano[3,2-a]carbazole. Acta Crystallogr Sect E Struct Rep Online. 2010 Jun 5;66(Pt 7):o1581. doi: 10.1107/S160053681002074X. PMID: 21587821; PMCID: PMC3006796. 20: Birari R, Roy SK, Singh A, Bhutani KK. Pancreatic lipase inhibitory alkaloids of Murraya koenigii leaves. Nat Prod Commun. 2009 Aug;4(8):1089-92. PMID: 19768989.