啤酒花中1个新的查耳酮类化合物  

A new chalcone from Humulus lupulus

作　　者：王利杰 石妍婧 赫军[4] 丁康 张维库[3] 续洁琨 WANG Lijie;SHI Yanjing;HE Jun;DING Kang;ZHANG Weiku;XU Jiekun(School of Life Sciences,Beijing University of Chinese Medicine,Beijing 100029,China;School of Chinese Materia Medica,Beijing University of Chinese Medicine,Beijing 100029,China;Institute of Clinical Medical Sciences,China-Japan Friendship Hospital,Beijing 100029,China;Department of Pharmacy,China-Japan Friendship Hospital,Beijing 100029,China)

机构地区：[1]北京中医药大学生命科学学院,北京100029 [2]北京中医药大学中药学院,北京100029 [3]中日友好医院临床医学研究所,北京100029 [4]中日友好医院药学部,北京100029

出　　处：《中草药》2024年第12期3943-3948,共6页Chinese Traditional and Herbal Drugs

基　　金：国家自然科学基金项目(82273809);国家自然科学基金项目(82273815);国家自然科学基金项目(82073731);中央高水平医院临床科研业务费&中日友好医院菁英计划(2023-NHLHCRF-CXYW-01,ZRJY2021-BJ06,ZRJY2021-TD06)。

摘　　要：目的研究啤酒花Humulus lupulus的化学成分,并评价其体外抗炎活性。方法采用多种色谱技术进行分离纯化,通过高分辨质谱、核磁共振等方法对化合物进行结构鉴定,并采用脂多糖(lipopolysaccharide,LPS)诱导的RAW264.7细胞炎症模型评价其体外对NO释放的抑制作用。结果从啤酒花带花果穗的95%乙醇提取部位中分离得到6个化合物,分别鉴定为2′,4-二羟基-4′,6′-二甲氧基-3′-(2-羟基-3-甲基-3-丁烯基)查耳酮(1)、tsugafolin(2)、dihydroxanthohumol(3)、4′-O-methylxanthohumol(4)、(2S,2′′S)-4′-hydroxy-5-methoxy-7,8-(2,2-dimethyl-3-hydroxy-2,3-dihydro-4H-pyrano)flavanone(5)和(2R,2′′S)-4′-hydroxy-5-methoxy-7,8-(2,2-dimethyl-3-hydroxy-2,3-dihydro-4H-pyrano)flavanone(6)。体外抗炎实验表明,化合物1和4的半数抑制浓度(median inhibition concentration,IC_(50))分别为(5.83±1.76)和(10.45±2.36)μmol/L。结论化合物1为1个新的查耳酮类化合物,命名为(±)-蛇麻花素A,化合物2为首次从葎草属中分离得到。化合物1和4均具有显著的抗炎活性。Objective To study the chemical constituents of Pijiuhua(Humulus lupulus L.),and to evaluate the isolates against anti-inflammatory activity in vitro.Methods The flowers with fruiting spikes of H.Lupulus were refluxed and extracted by 95%ethanol,then the extract was isolated and purified by use of various chromatographic techniques,and the structure of the compounds were elucidated by HR-ESI-MS and NMR methods.The lipopolysaccharide(LPS)-induced inflammatory model in RAW264.7 cells was used to evaluate inhibitory effect of all compounds on NO release.Results Six compounds were isolated from the extract of H.lupulus and identified as 2′,4′-dihydroxy-4′,6′-dimethoxy-3′-(2-hydroxy-3-methyl-3-butenyl)chalcone(1),tsugafolin(2),dihydroxanthohumol(3),4′-O-methylxanthohumol(4),(2S,2′′S)-4′-hydroxy-5-methoxy-7,8-(2,2-dimethyl-3-hydroxy-2,3-dihydro-4H-pyrano)flavanone(5)and(2R,2′′S)-4′-hydroxy-5-methoxy-7,8-(2,2-dimethyl-3-hydroxy-2,3-dihydro-4H-pyrano)flavanone(6).The results of anti-inflammatory cell assay showed that the median inhibition concentration(IC_(50))of 1 and 4 were(5.83±1.76)and(10.45±2.36)μmol/L,respectively.Conclusion Compound 1 was a new chalcone,named(±)-lupulusone A,and compound 2 was isolated from the Humulus genus for the first time.Compounds 1 and 4 showed significant anti-inflammatory activity.

关 键 词：啤酒花 查耳酮 (±)-蛇麻花素A 抗炎活性 tsugafolin 4′-O-methylxanthohumol 

分 类 号：R284.1[医药卫生—中药学]