目的 研究啤酒花(Humulus lupulus L.)的化学成分,并评价其体外抑制α-葡萄糖苷酶的活性。方法 运用硅胶、十八烷基硅烷键合硅胶(Octadecylsilyl,ODS)、Sephadex LH-20等多种柱色谱及制备高效液相色谱(HPLC)等多种方法对啤酒花雌花序的体积分数95%乙醇提取部位进行分离纯化,利用高分辨质谱(HR-ESI-MS)、核磁共振(NMR)等波谱技术对分离得到的化合物进行结构鉴定,并评价化合物对α-葡萄糖苷酶的抑制活性。结果 从啤酒花中共分离得到14个黄酮类化合物,分别鉴定为furano-[4″,5″:3',4']4,2'-dihydroxy-6'-methoxychalcone (1)、xanthohumol O (2)、xanthohumol (3)、dehydrocycloxanthohumol (4)、xanthohumol L (5)、3'-formyl xanthohumol (6)、2', 6'-dimethoxy-4, 4'-dihydroxychalcone (7)、1-[2,4-Dihydroxy-3-(3-hydroxy-2-methoxy-3-methylbutyl)-6-methoxy-phenyl]-3-(4-hydroxyphenyl)propenone (8)、xanthohumol G (9)、paxiiones A (10)、xanthohumol B (11)、xanthohumol H (12)、8-prenylnaringenin (13)和6-prenylnaringenin(14)。结论 化合物1为新天然产物,化合物10首次从葎草属中分离得到。化合物1,3,4和10体外表现出较好的α-葡萄糖苷酶抑制活性,其半数抑制浓度(half-maximal inhibition concentration,IC50)分别为(124.4±11.7)、(362.3±25.9)、(412.1±46.3)、(239.7±31.5)μmol·L-1,优于阳性药阿卡波糖[IC50=(597.7±8.6) μmol·L-1]。
Abstract
OBJECTIVE To investigate chemical constituents from the flowers of Humulus lupulus L., and to evaluate their in vitro inhibitory activities to α-glucosidase. METHODS The flowers of Humulus lupulus L. were refluxed and extracted by 95% ethanol,then iaolated and purified repeatedly by silica gel column chromatography, ODS column chromatography, Sephadex LH-20 column chromatography and preparative HPLC. The structures of all isolates were mainly elucidated on the basis of spectral technic mainly including HR-ESI-MS and NMR. The in vitro inhibitory activities of the compounds to α-glucosidase were investigated. RESULTS Their structures were identified as furano-[4″, 5″:3', 4']4, 2'-dihydroxy-6'-methoxychalcone (1), xanthohumol O (2), xanthohumol (3), dehydrocycloxanthohumol (4), xanthohumol L (5), 3'-formyl xanthohumol (6), 2', 6'-dimethoxy-4, 4'-dihydroxychalcone (7), 1-[2, 4-dihydroxy-3-(3-hydroxy-2-methoxy-3-methylbutyl)-6-methoxy-phenyl]-3-(4-hydroxyphenyl)propenone (8), xanthohumol G (9), paxiiones A (10), xanthohumol B (11), xanthohumol H (12), 8-prenylnaringenin (13) and 6-prenylnaringenin (14). CONCLUSION Compound 1 is new natural product, compound 10 is isolated from the genus Humulus for the first time. Compounds 1, 3, 4 and 10 displayed the good inhibition against α-glucosidase in vitro with IC50 values of (124.4±11.7), (362.3±25.9), (412.1±46.3), (239.7±31.5) μmol·L-1, respectively. And their inhibitory effect were stronger than that of acarbose with IC50 value of (597.7±8.6) μmol·L-1.
关键词
啤酒花 /
黄酮类化合物 /
结构鉴定 /
α-葡萄糖苷酶
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Key words
Humulus lupulus L. /
flaronoid /
structural identification /
α-glucosidase
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中图分类号：
R284
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参考文献
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脚注
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基金
中央高水平医院临床科研业务费资助(2022-NHLHCRFYNZJ-01);中日友好医院“菁英计划”人才培育工程项目资助(ZRJY2021-BJ06;ZRJY2021-TD06;ZRJY2021-QM16)
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