title: Nitric oxide inhibitory activity and antioxidant evaluations of 2-benzoyl-6-benzylidenecyclohexanone analogs, a novel series of curcuminoid and diarylpentanoid derivatives.
abstract: A series of twenty-four 2-benzoyl-6-benzylidenecyclohexanone analogs were synthesized and evaluated for their nitric oxide inhibition and antioxidant activity. Six compounds (3, 8, 10, 17, 18 and 19) were found to exhibit significant NO inhibitory activity in LPS/IFN-induced RAW 264.7 macrophages, of which compound 10 demonstrated the highest activity with the IC50 value of 4.2 ± 0.2 μM. Furthermore, two compounds (10 and 17) displayed antioxidant activity upon both the DPPH scavenging and FRAP analyses. However, none of the 2-benzoyl-6-benzylidenecyclohexanone analogs significantly scavenged NO radical. Structure-activity comparison suggested that 3,4-dihydroxylphenyl ring is crucial for bioactivities of the 2-benzoyl-6-benzylidenecyclohexanone analogs. The results from this study and the reports from previous studies indicated that compound 10 could be a candidate for further investigation on its potential as a new anti-inflammatory agent.
authors.affiliation: Laboratory of Natural Products, Institute of Bioscience, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia.
authors.forename: Sze Wei
authors.initials: SW
authors.lastname: Leong
authors.affiliation: Laboratory of Natural Products, Institute of Bioscience, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia; Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia.
authors.forename: Siti Munirah
authors.initials: SM
authors.lastname: Mohd Faudzi
authors.affiliation: Laboratory of Natural Products, Institute of Bioscience, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia; Department of Food Science, Faculty of Food Science and Technology, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia. Electronic address: faridah_abas@upm.edu.my.
authors.forename: Faridah
authors.initials: F
authors.lastname: Abas
authors.affiliation: Drug and Herbal Research Centre Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abd. Aziz, 50300 Kuala Lumpur, Malaysia.
authors.forename: Mohd Fadhlizil Fasihi
authors.initials: MF
authors.lastname: Mohd Aluwi
authors.affiliation: Drug and Herbal Research Centre Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abd. Aziz, 50300 Kuala Lumpur, Malaysia.
authors.forename: Kamal
authors.initials: K
authors.lastname: Rullah
authors.affiliation: Drug and Herbal Research Centre Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abd. Aziz, 50300 Kuala Lumpur, Malaysia.
authors.forename: Kok Wai
authors.initials: KW
authors.lastname: Lam
authors.affiliation: Department of Biochemistry, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia.
authors.forename: Mohd Nazri
authors.initials: MN
authors.lastname: Abdul Bahari
authors.affiliation: Department of Biochemistry, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia.
authors.forename: Syahida
authors.initials: S
authors.lastname: Ahmad
authors.affiliation: Department of Biomedical Science, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia.
authors.forename: Chau Ling
authors.initials: CL
authors.lastname: Tham
authors.affiliation: Laboratory of Natural Products, Institute of Bioscience, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia; Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia.
authors.forename: Khozirah
authors.initials: K
authors.lastname: Shaari
authors.affiliation: Laboratory of Natural Products, Institute of Bioscience, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia. Electronic address: nordinlajis@gmail.com.
authors.forename: Nordin H
authors.initials: NH
authors.lastname: Lajis
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000032:analysis* / Q000737:chemistry; D001597:Benzylidene Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D003474:Curcumin / Q000737:chemistry*; D003512:Cyclohexanones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50; D008264:Macrophages / Q000187:drug effects*; D051379:Mice; D008862:Microsomes, Liver / Q000187:drug effects; D009569:Nitric Oxide / Q000037:antagonists & inhibitors*; D010421:Pentanoic Acids / Q000737:chemistry / Q000494:pharmacology; D000067996:RAW 264.7 Cells; D013329:Structure-Activity Relationship
chemical_list: D000975:Antioxidants; D001597:Benzylidene Compounds; D003512:Cyclohexanones; D010421:Pentanoic Acids; D009569:Nitric Oxide; C036468:cyclohexanone; D003474:Curcumin
keywords: 2-Benzoyl-6-benzylidenecyclohexanone; Anti-inflammatory; Antioxidant; RAW 264.7; Stability