荔枝核的化学成分及生物活性研究  

Studies on chemical constituents and biological activities from seeds of Litchi chinensis

作　　者：任嘉佳 杨兴 吴石丽 张志毕[2] 李宝晶 李艳平 何红平 左爱学 董发武 REN Jia-jia;YANG Xing;WU Shi-li;ZHANG Zhi-bi;LI Bao-jing;LI Yan-ping;HE Hong-ping;ZUO Ai-xue;DONG Fa-wu(Yunnan Key Laboratory of Sustainable Utilization of Southern Medicine,College of Chinese Materia Medica,Yunnan University of Chinese Medicine,Kunming 650500,China;Yunnan Key Laboratory of Stem Cell and Regenerative Medicine&Biomedical Engineering Research Center,Kunming Medical University,Kunming 650500,China)

机构地区：[1]云南中医药大学中药学院云南省南药可持续利用研究重点实验室,云南昆明650500 [2]昆明医科大学云南省干细胞和再生医学重点实验室&生物医学工程研究中心,云南昆明650500

出　　处：《中草药》2022年第24期7664-7671,共8页Chinese Traditional and Herbal Drugs

基　　金：国家自然科学基金资助项目(82260758);国家自然科学基金资助项目(31860092);云南省高层次人才培养支持计划“青年拔尖人才”专项(YNWR-QNBJ-2020-255);云南省基础研究计划面上项目(202101AT070254);云南省南药可持续利用研究重点实验室开放课题重点项目(202105AG070012ZD2201)。

摘　　要：目的研究荔枝Litchchinensis核正丁醇部位的化学成分及生物活性。方法利用硅胶、D101大孔树脂、MCI、ODS、Sephadex LH-20及半制备型高效液相等色谱技术进行分离纯化,根据理化性质和波谱数据鉴定化合物结构;采用Griess法测定化合物对脂多糖诱导的小鼠巨噬细胞RAW264.7产生一氧化氮(NO)的抑制活性;采用1,1-二苯基-2-三硝基苯肼(1,1-diphenyl-2-trinitrophenylhydrazine,DPPH)方法测定化合物的体外抗氧化活性。结果从荔枝核正丁醇部位分离得到15个化合物,分别鉴定为柚皮素-7-O-(2’’,6’’-二-O-α-L-鼠李糖基)-β-D-吡喃葡萄糖苷(1)、litchioside D(2)、异鼠李素-3-O-(2’’,6’’-二-O-α-L-鼠李糖基)-β-D-吡喃葡萄糖苷(3)、山柰酚-3-O-(6-O-啡酰基)-β-葡萄糖基-(1→3)-α-鼠李糖-7-O-α-鼠李糖苷(4)、5’-O-β-D-葡萄糖苷茉莉酮酸甲酯(5)、5’-O-β-D-葡萄糖苷茉莉酮酸丁酯(6)、5’-O-β-D-葡萄糖苷茉莉酮酸(7)、松脂素-4-O-β-D-葡萄糖苷(8)、表松脂素-4-O-β-D-葡萄糖苷(9)、pyrafortunoside A(10)、苯乙基芸香苷(11)、苯甲醇-O-β-D-吡喃葡萄糖苷(12)、methyl-1-(β-D-ribofuranosyl)-imidazolin-2-one-4-carboxylate(13)、莽草酸甲酯(14)和莽草酸(15)。体外抗炎活性结果表明,化合物13能明显抑制脂多糖诱导的RAW264.7细胞NO释放,其半数抑制浓度(median inhibition concentration,IC50)为(27.9±2.8)μmol/L;化合物15具有一定的抑制活性,其IC50为(62.4±9.7)μmol/L。体外抗氧化活性结果表明,化合物4对DPPH自由基具有一定的清除活性,其IC50为(109.8±1.5)μmol/L。结论化合物1、3~6、9~15为首次从荔枝核中分离得到。化合物13有较强体外抗炎活性,化合物15有一定的体外抗炎活性。化合物4具有一定的体外抗氧化活性。Objective To study the chemical constituents and biological activities from the n-butanol extract of Lizhihe(Litchi Semen).Methods The compounds were systematically isolated and purified by using various chromatographic separation and analysis techniques,including silica gel,D101 macroporous resins,MCI,ODS,Sephadex LH-20 chromatographies and semi-prepative HPLC.The structures were identified on the basis of physicochemical properties and spectral data.The inhibitory effect of the compound on nitirc oxide production in LPS-induced mouse macrophage RAW264.7 cells was evaluated by Griss assay.Moreover,the antioxidant activities in vitro were tested by DPPH assay.Results A total of 15 compounds were isolated and identified as naringenin-7-O-(2’’,6’’-di-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside(1),litchioside D(2),isorhamnetin-3-O-(2’’,6’’-di-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside(3),kaempferol-3-O-[(6-caffeoyl)-β-glucopyranosyl(1 → 3)-α-rhamnopyranoside]-7-O-α-rhamnopyranoside(4),5’-O-β-D-glucopyranosyloxyjasmo-nic methyl ester(5),5’-O-β-Dglucopyranosyloxyjasmonic butyl ester(6),5’-O-β-D-glucopyranosyloxyjasmonic acid(7),pinoresinol-4-O-β-D-glucopyranoside(8),epipinoresinol-4-O-β-D-glucopyranoside(9),pyrafortunoside A(10),phenylethyl-rutinoside(11),benzyl alcohol-O-β-Dglucopyranoside(12),methyl-1-(β-D-ribofuranosyl)-imidazolin-2-one-4-carboxylate(13),methyl shikimate(14),and shikimic acid(15).Amoung them,compound 13 showed strong inhibitory activities against LPS-induced NO production in RAW264.7macrophages,with IC50 value of(27.9±2.8) μmol/L,15 exhibted obvious activities with IC50 value of(62.4±9.7) μmol/L.Additionally,compound 4 displayed a degree of DPPH radical scavenging activities with IC50 value of(109.8±1.5) μmol/L.Conclusion Compounds 1,3—6,9—15 are isolated form Litchi Semen for the first time.Compound 13 had strong anti-inflammatory activity in vitro and 15 possessed moderate anti-inflammatory activity.Moreover,Compound 4 was found to have moderate anti

关 键 词：荔枝核 苷类 抗炎活性 抗氧化活性 山柰酚-3-O-(6-O-啡酰基)-β-葡萄糖基-(1→3)-α-鼠李糖-7-O-α-鼠李糖苷 表松脂素-4-O-β-D-葡萄糖苷 莽草酸 

分 类 号：R284.1[医药卫生—中药学]