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Int Immunopharmacol. 2016 Apr;33:8-17. doi: 10.1016/j.intimp.2016.01.024. Epub 2016 Feb 3.

Isolates of Alpinia officinarum Hance as COX-2 inhibitors: Evidence from anti-inflammatory, antioxidant and molecular docking studies.

Author information

1
Post Graduate and Research Center, Department of Chemistry, MES Abasaheb Garware College, Pune, Maharashtra 411004, India.
2
Department of Pharmacology, Poona College of Pharmacy, Bharati Vidyapeeth Deemed University, Pune, Maharashtra 411038, India.
3
Combichem-Bioresource Center, Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr Homi Bhabha Road, Pashan, Pune, Maharashtra 411008, India.
4
Department of Pharmacology, Poona College of Pharmacy, Bharati Vidyapeeth Deemed University, Pune, Maharashtra 411038, India. Electronic address: drslbodh@gmail.com.
5
Center for Innovation in Nutrition Health Disease, IRSHA, BVDU, Dhankawadi, Pune, Maharashtra 411043, India.
6
R&D Centre in Pharmaceutical Sciences and Applied Chemistry, Poona College of Pharmacy, Bharati Vidyapeeth Deemed University, Pune, Maharashtra 411038, India. Electronic address: srojatkar@yahoo.com.
7
Post Graduate and Research Center, Department of Chemistry, MES Abasaheb Garware College, Pune, Maharashtra 411004, India. Electronic address: arun.natu@gmail.com.

Abstract

BACKGROUND:

Inflammation triggered by oxidative stress can cause various ailments, such as cancer, rheumatoid arthritis, asthma, diabetes etc. In the last few years, there has been a renewed interest in studying the antioxidant and anti-inflammatory action of plant constituents such as flavonoids and diarylheptanoids.

AIM:

To evaluate the antioxidant, anti-inflammatory activity and the total phenolic content of isolated compounds from Alpinia officinarum rhizomes. Furthermore, molecular docking was performed to study the binding mode of these compounds into the active site of cyclooxygenase-2 (COX-2).

METHODS:

A. officinarum rhizomes were extracted by maceration, using methanol. This extract was further fractionated by partitioning with hexane, chloroform and ethyl acetate and these fractions on further purification resulted in isolation of five pure compounds. Characterization was carried out by using (1)H NMR, (13)C NMR and MS. They were further evaluated for antioxidant and anti-inflammatory activity using carrageenan-induced paw edema model in rats. Molecular docking study was performed using Glide module integrated in Schrodinger molecular modeling software.

RESULTS:

The compounds were identified as 1,7-diphenylhept-4-en-3-one (1), 5-hydroxy-1,7-diphenyl-3-heptanone (2), 3,5,7-trihydroxyflavone (Galangin, 3), 3,5,7-trihydroxy-4'-methoxyflavone (Kaempferide, 4) and 5-hydroxy-7-(4″-hydroxy-3″-methoxyphenyl)-1-phenyl-3-heptanone (5). The compound-3 and compound-5 (10mg/kg) showed significant (p<0.001) antioxidant and anti-inflammatory potential. Moreover, total phenolic content was detected as 72.96 mg and 51.18 mg gallic acid equivalent respectively. All the five isolates were found to be good binders with COX-2 (average docking score -9.03).

CONCLUSIONS:

Galangin and 5-hydroxy-7-(4″-hydroxy-3″-methoxyphenyl)-1-phenyl-3-heptanone exhibited anti-inflammatory and in-vitro antioxidant activity which may be due to presence of phenolic content in it. The molecular docking study revealed that these compounds have affinity towards COX-2 active site which can further be explored as selective COX-2 inhibitors. The results obtained in this work justify the use of A. officinarum in the treatment of inflammatory disorders like rheumatoid arthritis and inflammatory bowel diseases.

KEYWORDS:

5-Hydroxy-7-(4″-hydroxy-3″-methoxyphenyl)-1-phenyl-3-heptanone; Alpinia officinarum; Anti-inflammatory; Antioxidant; COX-2 inhibitors; Galangin

PMID:
26849772
DOI:
10.1016/j.intimp.2016.01.024
[Indexed for MEDLINE]

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