title: 5-Methoxytryptamine reacts with natural food flavour to produce 6-methoxy tetrahydro-β-carbolines: in vitro investigation of their antioxidant and cytotoxicity properties.
abstract: Various 6-methoxytetrahydro-β-carboline derivatives, namely BEN (6-methoxy-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole), ANI (6-methoxy-1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole), ACE (6-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole) and VAN (2-methoxy-4-(6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-l)phenol), were prepared via the Maillard reaction using food flavours and 5-methoxytryptamine in aqueous medium and were investigated for their in vitro antioxidant and cytotoxicity properties. These derivatives were found to exhibit moderate antioxidant properties, based on a combination of DPPH, ABTS and FRAP assays. The results suggested that the Maillard reaction could be used to generate β-carboline antioxidants. It was beneficial that VAN showed the highest antioxidant activity but the least cytotoxic activities on non-tumourous cell lines of NIH/3T3, CCD18-Co and B98-5 using MTT assay. ACE, ANI and BEN showed mild toxicity at effective antioxidative concentrations derived from DPPH and ABTS assays. Furthermore, they are safer compared to 5-fluorouracil, cisplatin and betulinic acid on NIH/3T3, CCD18-Co and B98-5 cells. In conclusion, the antioxidant and cytotoxicity properties of 6-methoxytetrahydro-β-carbolines were demonstrated for the first time.
authors: Centre for Drug Research, Universiti Sains Malaysia, Penang 11800, Malaysia. Electronic address: gohteikbeng@yahoo.com.
authors: Teik Beng
authors: TB
authors: Goh
authors: School of Medicine, International Medical University, No. 126, Jalan Jalil Perkasa 19, Bukit Jalil 57000, Kuala Lumpur, Malaysia.
authors: Rhun Yian
authors: RY
authors: Koh
authors: School of Pharmaceutical Sciences, Universiti Sains Malaysia, Penang 11800, Malaysia.
authors: Mun Fei
authors: MF
authors: Yam
authors: School of Industrial Technology, Food Division, Universiti Sains Malaysia, 11800, Malaysia.
authors: Mat Easa
authors: ME
authors: Azhar
authors: Centre for Drug Research, Universiti Sains Malaysia, Penang 11800, Malaysia.
authors: Mohd Nizam
authors: MN
authors: Mordi
authors: Centre for Drug Research, Universiti Sains Malaysia, Penang 11800, Malaysia. Electronic address: smahsufi@usm.my.
authors: Sharif Mahsufi
authors: SM
authors: Mansor
mesh_terms: D008735:5-Methoxytryptamine / Q000737:chemistry*; D000975:Antioxidants / Q000737:chemistry*; D003602:Cytotoxicity, Immunologic; D005503:Food Additives; D006801:Humans; D066298:In Vitro Techniques; D015416:Maillard Reaction; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry*
chemical_list: D000975:Antioxidants; D005503:Food Additives; D010636:Phenols; D008735:5-Methoxytryptamine
keywords: 6-Methoxytetrahydro-β-carboline; Antioxidant; Cytotoxic properties; Maillard reaction; Thermal stability