Axially chiral biscarbazoles and biological evaluation of the constituents from Murraya koenigii.
Chemical investigation of the fruit pulp of Murraya koenigii resulted in the identification of two new dimeric carbazole alkaloids, bisgerayafoline D (1) and bismahanimbinol (2) along with four known alkaloids, bispyrayafoline (3), O-methyl mahanine (4), O-methyl mukonal (5), and mahanine (6). Structures of 1-6 were determined with the aid of UV, IR, Mass and extensive NMR spectroscopic studies. Absolute configurations of biaryls in 1 and 2 were assigned using a combination of computational Circular Dichroism (CD) and experimental electronic CD spectroscopic data. Compounds 1-6 were evaluated for anti-oxidant, anti-α-glucosidase, DNA binding, protein interactions and cytotoxic activities. Among all the isolates, mahanine (6) was found to exhibit significant radical scavenging and α-glucosidase inhibitory activities. Compound 6 was also found to be active in cytotoxicity assay against three human cancer cell lines HeLa, HCT116, AGS and this compound was weakly active against normal mouse embryonic fibroblasts (NIH3T3).
Department of Chemistry, School of Chemical Sciences, Bharathiar University, Coimbatore 641 046, Tamil Nadu, India; Department of Chemistry, Richardson College for the Environmental and Science Complex, The University of Winnipeg, 599 Portage Avenue, Winnipeg, Manitoba R3B 2G3, Canada.
Chokkalingam
C
Uvarani
Department of Agricultural Microbiology, Tamil Nadu Agricultural University, Coimbatore 641 003, Tamil Nadu, India.
Nanjundan
N
Jaivel
Department of Chemistry, School of Chemical Sciences, Bharathiar University, Coimbatore 641 046, Tamil Nadu, India.
Mathan
M
Sankaran
Department of Chemistry, School of Chemical Sciences, Bharathiar University, Coimbatore 641 046, Tamil Nadu, India.
Kumarasamy
K
Chandraprakash
Department of Chemistry, Richardson College for the Environmental and Science Complex, The University of Winnipeg, 599 Portage Avenue, Winnipeg, Manitoba R3B 2G3, Canada. Electronic address: a.ata@uwinnipeg.ca.
Athar
A
Ata
Department of Chemistry, School of Chemical Sciences, Bharathiar University, Coimbatore 641 046, Tamil Nadu, India. Electronic address: ps_mohan_in@yahoo.com.
Palathurai Subramaniam
PS
Mohan
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002227:Carbazoles / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D005638:Fruit / Q000737:chemistry; D065089:Glycoside Hydrolase Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D032101:Murraya / Q000737:chemistry*; D041681:NIH 3T3 Cells; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D011485:Protein Binding; D000520:alpha-Glucosidases
D000470:Alkaloids; D000975:Antioxidants; D002227:Carbazoles; D065089:Glycoside Hydrolase Inhibitors; D010936:Plant Extracts; C000593499:bisgerayafoline D; C000593500:bismahanimbinol; C465290:mahanine; C041514:carbazole; D000520:alpha-Glucosidases
Antioxidant; Biscarbazoles; Cytotoxicity; DNA and protein binding; Murraya koenigii; α-Glucosidase inhibition