6′-O-月桂酰京尼平苷的酶法合成及其抗炎活性评价

Enzymatic synthesis and anti-inflammatory activityevaluation of 6′-O-lauroyl genipin

以脂肪酶TLIM为催化剂,以月桂酸乙烯酯为酰基供体,对京尼平苷进行酰基化修饰,通过质谱法(MS)、氢核磁共振(^(1)H NMR)、碳-13核磁共振(^(13)C NMR)、同核位移相关谱(H-H cosy)、多键碳氢关系(HMBC)及异核单量子关系(HSQC)分析,确证其结构为6′-O-月桂酰基京尼平苷(6′-O-LGS)。比较了CaLA、Novozym 435、TLIM和RMIM这4种脂肪酶的催化活性,其中TLIM的活性最高。经优化,在受体/供体的摩尔比1∶8、反应温度40℃、反应时间2 h条件下,6′-O-LGS的转化率达93.26%。以脂多糖诱导的RAW264.7细胞炎症模型验证了6′-O-LGS对5种炎症因子(IL-6、COX2、IL-1β、p-NF-kB、TNF-α)均具有抑制作用,其中对TNF-α的抑制作用最为明显,活性优于相同浓度的京尼平苷。

Acetylation of geniposide with lipase TLIM as catalyst and vinyl laurate as acyl donor,the structure was confirmed to be 6′-O-lauroyl genipin(6′-O-LGS)by mass spectrometry(MS),proton nuclear magnetic resonance(1H NMR),carbon-13 nuclear magnetic resonance(13 C NMR),Chemical shift correlation spectroscopy(H-H cosy),1H detected heteronuclear multiple bond correlation(HMBC)and heteronuclear singular quantum correlation(HSQC)analysis.The catalytic activities of four lipases,CaLA,Novozym 435,TLIM and RMIM,were compared,and TLIM was the most active.After optimization,the conversion rate of 6′-O-LGS was 93.26%at a receptor/donor molar ratio of 1∶8,at 40℃for 2 h.The RAW264.7 cell inflammatory model induced by lipopolysaccharide confirmed that 6′-O-LGS inhibited five inflammatory factors(IL-6,COX2,IL-1β,p-NF-k B,TNF-α).The inhibitory effect on TNF-αwas the most obvious,and the activity was superior to the same concentration of geniposide.