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MedKoo Cat#: 584666 | Name: Mahanimbine
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Description:

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

Mahanimbine is a major carbazole alkaloid from Murraya koenigii (curry leaves) that may alleviate development of HFD-induced metabolic alterations.

Chemical Structure

Mahanimbine
Mahanimbine
CAS#21104-28-9

Theoretical Analysis

MedKoo Cat#: 584666

Name: Mahanimbine

CAS#: 21104-28-9

Chemical Formula: C23H25NO

Exact Mass: 331.1936

Molecular Weight: 331.46

Elemental Analysis: C, 83.34; H, 7.60; N, 4.23; O, 4.83

Price and Availability

Size Price Availability Quantity
5mg USD 550.00 2 Weeks
10mg USD 950.00 2 weeks
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Related CAS #
No Data
Synonym
Mahanimbine; Mahanimbin
IUPAC/Chemical Name
Pyrano(3,2-a)carbazole, 3,11-dihydro-3,5-dimethyl-3-(4-methyl-3-pentenyl)-, (+)-
InChi Key
HTNVFUBCWIYPJN-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H25NO/c1-15(2)8-7-12-23(4)13-11-18-21-19(14-16(3)22(18)25-23)17-9-5-6-10-20(17)24-21/h5-6,8-11,13-14,24H,7,12H2,1-4H3
SMILES Code
C/C(C)=C/CCC(O1)(C)C=CC2=C1C(C)=CC3=C2NC4=C3C=CC=C4
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).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Mahanimbine is a major carbazole alkaloid from Murraya koenigii (curry leaves) that may alleviate development of HFD-induced metabolic alterations.
In vitro activity:
The results revealed that Mahanimbine could inhibit the proliferation of the all the pancreatic cancer cells with lower cytoxicity against the normal cells. The anticancer activity of Mahanimbine against the Capan-2 and SW119 cells was found to be due to G0/G1 cell cycle arrest and induction of apoptosis. Further, it was observed that Mahanimbine could inhibit the AKT/mTOR and STAT3 signalling pathways in the Capan-2 and SW119 pancreatic cancer cells. Reference: Med Sci Monit. 2018 Oct 1;24:6975-6983. https://pubmed.ncbi.nlm.nih.gov/30273298/
In vivo activity:
This study evaluated the effects of mahanimbine, a major carbazole alkaloid from Murraya koenigii (curry leaves), against progression of high-fat diet (HFD)-induced metabolic complications in mice (male and female). Mahanimbine prevented HFD-induced hyperlipidemia and fat accumulation in adipose tissue and liver along with the restricted progression of systemic inflammation and oxidative stress. Moreover, mahanimbine treatment improved glucose clearance and upregulated the expression of insulin responsive genes in liver and adipose tissue. Reference: Biofactors. 2017 Mar;43(2):220-231. https://pubmed.ncbi.nlm.nih.gov/27663177/
Solvent mg/mL mM
Solubility
DMSO 3.3 10.00
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 331.46 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. Xie H, Zhang T, Yang N, Li Z, Liu Y. Anticancer effects of Mahanimbine alkaloid on the human bladder cancer cells are due to the induction of G0/G1 cell cycle arrest, apoptosis and autophagy. J BUON. 2020 Mar-Apr;25(2):1166-1171. PMID: 32521922. 2. Pei C, He Q, Liang S, Gong X. Mahanimbine Exerts Anticancer Effects on Human Pancreatic Cancer Cells by Triggering Cell Cycle Arrest, Apoptosis, and Modulation of AKT/Mammalian Target of Rapamycin (mTOR) and Signal Transducer and Activator of Transcription 3 (STAT3) Signalling Pathways. Med Sci Monit. 2018 Oct 1;24:6975-6983. doi: 10.12659/MSM.911013. PMID: 30273298; PMCID: PMC6178883. 3. Jagtap S, Khare P, Mangal P, Kondepudi KK, Bishnoi M, Bhutani KK. Effect of mahanimbine, an alkaloid from curry leaves, on high-fat diet-induced adiposity, insulin resistance, and inflammatory alterations. Biofactors. 2017 Mar;43(2):220-231. doi: 10.1002/biof.1333. Epub 2016 Sep 24. PMID: 27663177. 4. Birari R, Javia V, Bhutani KK. Antiobesity and lipid lowering effects of Murraya koenigii (L.) Spreng leaves extracts and mahanimbine on high fat diet induced obese rats. Fitoterapia. 2010 Dec;81(8):1129-33. doi: 10.1016/j.fitote.2010.07.013. Epub 2010 Jul 23. PMID: 20655993.
In vitro protocol:
1. Xie H, Zhang T, Yang N, Li Z, Liu Y. Anticancer effects of Mahanimbine alkaloid on the human bladder cancer cells are due to the induction of G0/G1 cell cycle arrest, apoptosis and autophagy. J BUON. 2020 Mar-Apr;25(2):1166-1171. PMID: 32521922. 2. Pei C, He Q, Liang S, Gong X. Mahanimbine Exerts Anticancer Effects on Human Pancreatic Cancer Cells by Triggering Cell Cycle Arrest, Apoptosis, and Modulation of AKT/Mammalian Target of Rapamycin (mTOR) and Signal Transducer and Activator of Transcription 3 (STAT3) Signalling Pathways. Med Sci Monit. 2018 Oct 1;24:6975-6983. doi: 10.12659/MSM.911013. PMID: 30273298; PMCID: PMC6178883.
In vivo protocol:
1. Jagtap S, Khare P, Mangal P, Kondepudi KK, Bishnoi M, Bhutani KK. Effect of mahanimbine, an alkaloid from curry leaves, on high-fat diet-induced adiposity, insulin resistance, and inflammatory alterations. Biofactors. 2017 Mar;43(2):220-231. doi: 10.1002/biof.1333. Epub 2016 Sep 24. PMID: 27663177. 2. Birari R, Javia V, Bhutani KK. Antiobesity and lipid lowering effects of Murraya koenigii (L.) Spreng leaves extracts and mahanimbine on high fat diet induced obese rats. Fitoterapia. 2010 Dec;81(8):1129-33. doi: 10.1016/j.fitote.2010.07.013. Epub 2010 Jul 23. PMID: 20655993.
1: Jagtap S, Khare P, Mangal P, Kondepudi KK, Bishnoi M, Bhutani KK. Effect of mahanimbine, an alkaloid from curry leaves, on high-fat diet-induced adiposity, insulin resistance, and inflammatory alterations. Biofactors. 2017 Mar;43(2):220-231. doi: 10.1002/biof.1333. Epub 2016 Sep 24. PubMed PMID: 27663177. 2: Kumar BD, Krishnakumar K, Jaganathan SK, Mandal M. Effect of Mangiferin and Mahanimbine on Glucose Utilization in 3T3-L1 cells. Pharmacogn Mag. 2013 Jan;9(33):72-5. doi: 10.4103/0973-1296.108145. PubMed PMID: 23661997; PubMed Central PMCID: PMC3647398. 3: Dahiya J, Singh J, Kumar A, Sharma A. Isolation, characterization and quantification of an anxiolytic constituent - mahanimbine, from Murraya koenigii Linn. Spreng Leaves. J Ethnopharmacol. 2016 Dec 4;193:706-711. doi: 10.1016/j.jep.2016.10.014. Epub 2016 Oct 11. PubMed PMID: 27737817. 4: Pei C, He Q, Liang S, Gong X. Mahanimbine Exerts Anticancer Effects on Human Pancreatic Cancer Cells by Triggering Cell Cycle Arrest, Apoptosis, and Modulation of AKT/Mammalian Target of Rapamycin (mTOR) and Signal Transducer and Activator of Transcription 3 (STAT3) Signalling Pathways. Med Sci Monit. 2018 Oct 1;24:6975-6983. doi: 10.12659/MSM.911013. PubMed PMID: 30273298; PubMed Central PMCID: PMC6178883. 5: Pandit S, Kumar M, Ponnusankar S, Pal BC, Mukherjee PK. RP-HPLC-DAD for simultaneous estimation of mahanine and mahanimbine in Murraya koenigii. Biomed Chromatogr. 2011 Sep;25(9):959-62. doi: 10.1002/bmc.1561. Epub 2011 Mar 4. PubMed PMID: 21381062. 6: Birari R, Javia V, Bhutani KK. Antiobesity and lipid lowering effects of Murraya koenigii (L.) Spreng leaves extracts and mahanimbine on high fat diet induced obese rats. Fitoterapia. 2010 Dec;81(8):1129-33. doi: 10.1016/j.fitote.2010.07.013. Epub 2010 Jul 23. PubMed PMID: 20655993. 7: Sharma P, Batra S, Kumar A, Sharma A. In vivo antianxiety and antidepressant activity of Murraya paniculata leaf extracts. J Integr Med. 2017 Jul;15(4):320-325. doi: 10.1016/S2095-4964(17)60352-2. PubMed PMID: 28659237. 8: Kumar NS, Mukherjee PK, Bhadra S, Saha BP, Pal BC. Acetylcholinesterase inhibitory potential of a carbazole alkaloid, mahanimbine, from Murraya koenigii. Phytother Res. 2010 Apr;24(4):629-31. doi: 10.1002/ptr.3023. PubMed PMID: 19943242. 9: Joshi BS, Kamat VN, Gawad DH. On the structures of girinimbine, mahanimbine, isomahanimbine, koenimbidine and murrayacine. Tetrahedron. 1970 Mar;26(6):1475-82. PubMed PMID: 5419188. 10: Nagappan T, Segaran TC, Wahid ME, Ramasamy P, Vairappan CS. Efficacy of carbazole alkaloids, essential oil and extract of Murraya koenigii in enhancing subcutaneous wound healing in rats. Molecules. 2012 Dec 5;17(12):14449-63. doi: 10.3390/molecules171214449. PubMed PMID: 23519245. 11: Narasimhan NS, Paradkar MV, Gokhale AM. Synthesis of girinimbine and (plus or minus) mahanimbine. Tetrahedron Lett. 1970 Apr;(19):1665-8. PubMed PMID: 5430996. 12: Hesse R, Gruner KK, Kataeva O, Schmidt AW, Knölker HJ. Efficient construction of pyrano[3,2-a]carbazoles: application to a biomimetic total synthesis of cyclized monoterpenoid pyrano[3,2-a]carbazole alkaloids. Chemistry. 2013 Oct 11;19(42):14098-111. doi: 10.1002/chem.201301792. Epub 2013 Sep 12. PubMed PMID: 24030919. 13: Nagappan T, Ramasamy P, Wahid ME, Segaran TC, Vairappan CS. Biological activity of carbazole alkaloids and essential oil of Murraya koenigii against antibiotic resistant microbes and cancer cell lines. Molecules. 2011 Nov 21;16(11):9651-64. doi: 10.3390/molecules16119651. PubMed PMID: 22105714. 14: 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. PubMed PMID: 25920265. 15: Wang T, Hoye TR. Hexadehydro-Diels-Alder (HDDA)-Enabled Carbazolyne Chemistry: Single Step, de Novo Construction of the Pyranocarbazole Core of Alkaloids of the Murraya koenigii (Curry Tree) Family. J Am Chem Soc. 2016 Oct 13. [Epub ahead of print] PubMed PMID: 27734671; PubMed Central PMCID: PMC5391310. 16: 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. PubMed PMID: 21972815. 17: Ramsewak RS, Nair MG, Strasburg GM, DeWitt DL, Nitiss JL. Biologically active carbazole alkaloids from Murraya koenigii. J Agric Food Chem. 1999 Feb;47(2):444-7. PubMed PMID: 10563914. 18: Tachibana Y, Kikuzaki H, Lajis NH, Nakatani N. Antioxidative activity of carbazoles from Murraya koenigii leaves. J Agric Food Chem. 2001 Nov;49(11):5589-94. PubMed PMID: 11714364. 19: Meragelman KM, McKee TC, Boyd MR. Siamenol, a new carbazole alkaloid from Murraya siamensis. J Nat Prod. 2000 Mar;63(3):427-8. PubMed PMID: 10757740. 20: Chakraborty M, Saha S, Mukhapadhyay S. Murrayakoeninol--a new carbazole alkaloid from Murraya koenigii (Linn) Spreng. Nat Prod Commun. 2009 Mar;4(3):355-8. PubMed PMID: 19413112.