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

MedKoo CAT#: 406297

CAS#: 28360-49-8

Description: Mahanine, a carbazole alkaloid (occurs in the edible part of Micromelum minutum, Murraya koenigii and related species), is a DNA minor groove binding agent with potent anticancer activity. Mahanine down regulates cell survival factors by activation of caspase-3 through mitochondrial dependent pathway. Mahanine was found to inhibit growth of PC3 and LNCaP prostate cancer cells in a dose and time-dependent manner. Mechanistically, mahanine inhibited cell-survival pathway by dephosphorylation of PIP3 dependent kinase 1 (PDK1) thereby deactivation of Akt and downregulation of Bcl-xL. In addition, mahanine activated caspase pathway (caspases 9 and 3) and eventually cleavage of DNA repair enzyme, PARP resulting DNA fragmentation and apoptosis.

Chemical Structure

CAS# 28360-49-8

Theoretical Analysis

MedKoo Cat#: 406297
Name: Mahanine
CAS#: 28360-49-8
Chemical Formula: C23H25NO2
Exact Mass: 347.18853
Molecular Weight: 347.45
Elemental Analysis: C, 79.51; H, 7.25; N, 4.03; O, 9.21

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Synonym: Mahanine.

IUPAC/Chemical Name: (R)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-3,11-dihydropyrano[3,2-a]carbazol-9-ol


InChi Code: InChI=1S/C23H25NO2/c1-14(2)6-5-10-23(4)11-9-18-21-19(12-15(3)22(18)26-23)17-8-7-16(25)13-20(17)24-21/h6-9,11-13,24-25H,5,10H2,1-4H3/t23-/m1/s1

SMILES Code: OC1=CC2=C(C=C1)C3=C(C(C=C[C@](CC/C=C(C)/C)(C)O4)=C4C(C)=C3)N2.

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, not in water

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

Preparing Stock Solutions

The following data is based on the product molecular weight 347.45 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

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1: Samanta SK, Dutta D, Roy S, Bhattacharya K, Sarkar S, Dasgupta AK, Pal BC, Mandal C, Mandal C. Mahanine, A DNA Minor Groove Binding Agent Exerts Cellular Cytotoxicity with Involvement of C-7-OH and -NH Functional Groups. J Med Chem. 2013 Jul 5. [Epub ahead of print] PubMed PMID: 23829449.

2: 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.

3: Biswas A, Bhattacharya S, Dasgupta S, Kundu R, Roy SS, Pal BC, Bhattacharya S. Insulin resistance due to lipid-induced signaling defects could be prevented by mahanine. Mol Cell Biochem. 2010 Mar;336(1-2):97-107. doi: 10.1007/s11010-009-0257-4. Epub 2009 Oct 14. PubMed PMID: 19826769.

4: Bhattacharya K, Samanta SK, Tripathi R, Mallick A, Chandra S, Pal BC, Shaha C, Mandal C. Apoptotic effects of mahanine on human leukemic cells are mediated through crosstalk between Apo-1/Fas signaling and the Bid protein and via mitochondrial pathways. Biochem Pharmacol. 2010 Feb 1;79(3):361-72. doi: 10.1016/j.bcp.2009.09.007. Epub 2009 Sep 12. PubMed PMID: 19751707.

5: Jagadeesh S, Sinha S, Pal BC, Bhattacharya S, Banerjee PP. Mahanine reverses an epigenetically silenced tumor suppressor gene RASSF1A in human prostate cancer cells. Biochem Biophys Res Commun. 2007 Oct 12;362(1):212-7. Epub 2007 Aug 9. PubMed PMID: 17698033.

6: Sinha S, Pal BC, Jagadeesh S, Banerjee PP, Bandyopadhaya A, Bhattacharya S. Mahanine inhibits growth and induces apoptosis in prostate cancer cells through the deactivation of Akt and activation of caspases. Prostate. 2006 Sep 1;66(12):1257-65. PubMed PMID: 16683271.

7: Roy MK, Thalang VN, Trakoontivakorn G, Nakahara K. Mahanine, a carbazole alkaloid from Micromelum minutum, inhibits cell growth and induces apoptosis in U937 cells through a mitochondrial dependent pathway. Br J Pharmacol. 2005 May;145(2):145-55. PubMed PMID: 15753952; PubMed Central PMCID: PMC1576126.

8: Roy MK, Thalang VN, Trakoontivakorn G, Nakahara K. Mechanism of mahanine-induced apoptosis in human leukemia cells (HL-60). Biochem Pharmacol. 2004 Jan 1;67(1):41-51. PubMed PMID: 14667927.

9: Nakahara K, Trakoontivakorn G, Alzoreky NS, Ono H, Onishi-Kameyama M, Yoshida M. Antimutagenicity of some edible Thai plants, and a bioactive carbazole alkaloid, mahanine, isolated from Micromelum minutum. J Agric Food Chem. 2002 Aug 14;50(17):4796-802. PubMed PMID: 12166962.

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