Honmore Varsha S, Kandhare Amit D, Kadam Parag P, Khedkar Vijay M, Sarkar Dhiman, Bodhankar Subhash L, Zanwar Anand A, Rojatkar Supada R, Natu Arun D
Post Graduate and Research Center, Department of Chemistry, MES Abasaheb Garware College, Pune, Maharashtra 411004, India.
Department of Pharmacology, Poona College of Pharmacy, Bharati Vidyapeeth Deemed University, Pune, Maharashtra 411038, India.
Int Immunopharmacol. 2016 Apr;33:8-17. doi: 10.1016/j.intimp.2016.01.024. Epub 2016 Feb 3.
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.
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).
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.
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).
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.
氧化应激引发的炎症可导致多种疾病，如癌症、类风湿性关节炎、哮喘、糖尿病等。在过去几年中，人们对研究黄酮类和二芳基庚烷类等植物成分的抗氧化和抗炎作用重新产生了兴趣。
评估高良姜根茎中分离出的化合物的抗氧化、抗炎活性及总酚含量。此外，进行分子对接以研究这些化合物与环氧合酶-2（COX-2）活性位点的结合模式。
采用甲醇浸渍法提取高良姜根茎。该提取物再用己烷、氯仿和乙酸乙酯进行分配分离，这些馏分进一步纯化后得到5种纯化合物。通过（1）H NMR、（13）C NMR和质谱进行表征。使用角叉菜胶诱导的大鼠足爪肿胀模型进一步评估它们的抗氧化和抗炎活性。使用Schrodinger分子建模软件中集成的Glide模块进行分子对接研究。
这些化合物被鉴定为1,7-二苯基庚-4-烯-3-酮（1）、5-羟基-1,7-二苯基-3-庚酮（2）、3,5,7-三羟基黄酮（高良姜素，3）、3,5,7-三羟基-4'-甲氧基黄酮（山柰酚，4）和5-羟基-7-（4″-羟基-3″-甲氧基苯基）-1-苯基-3-庚酮（5）。化合物3和化合物5（10mg/kg）显示出显著（p<0.001）的抗氧化和抗炎潜力。此外，检测到总酚含量分别为72.96mg和51.18mg没食子酸当量。发现所有5种分离物都是COX-2的良好结合剂（平均对接分数-9.03）。
高良姜素和5-羟基-7-（4″-羟基-3″-甲氧基苯基）-1-苯基-3-庚酮表现出抗炎和体外抗氧化活性，这可能归因于其中存在酚类成分。分子对接研究表明这些化合物对COX-2活性位点具有亲和力，可进一步探索其作为选择性COX-2抑制剂的可能性。本研究所得结果证明高良姜可用于治疗类风湿性关节炎和炎症性肠病等炎症性疾病。
