核桃青皮化学成分及其抗肿瘤活性研究
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摘要
采用柱色谱、重结晶等方法从核桃青皮Walnut green husk进行分离得到13个化合物,利用现代波谱学方法鉴定了它们的结构,分别鉴定为3,5-二甲氧基-4-羟基-苯甲酸-7-O-β-D-葡萄糖苷(1)、myricananin F(2)、β-谷甾醇(3)、齐墩果酸(4)、核桃酮(5)、积雪草酸(6)、常春藤皂苷元(7)、β-胡萝卜苷(8)、(4R)-4,8-二羟基-α-四氢萘酮-4-O-β-D-吡喃葡萄糖苷(9)、3β,23-二羟基-12-烯-28-乌苏酸(10)、熊果酸(11)、丁香酸(12)、Juglanoside B(13)。其中,化合物1、2、6、7、9、10均为首次从该属植物中分离得到。经体外抗肿瘤活性筛选,发现化合物4对人肝癌细胞(Hep G-2)的增殖显示了较强的生长抑制活性,化合物9对人乳腺癌细胞(MCF-7)的增殖具有一定的生长抑制活性。
The experiment aimed to investigate the chemical compositions of Walnut green husk and the antitumor activities of the isolated compounds. The chemical constituents were isolated and purified by column chromatography and recrystallization,and their structures have been elucidated on the basis of spectral data analysis. As a result,thirteen compounds were isolated and identified as 3,5-dimethoxy-4-hydroxy benzene carbonic-7-O-β-D-pyranglucose( 1),myricanain F(2),β-stitosterol(3),oleanolic acid(4),regiolone(5),asiatic acid(6),hederagenin(7),β-daucosterin(8),(R)-8-hydroxy-α-tetralone-O-β-D-glucopyranoside(9),3β,23-dihydroxy-urs-12-en-28-oic acid(10),ursolic acid(11),syringc acid(12),Juglanoside B(13). Compounds 1,2,6,7,9 and 10 are all separated from the genus for the first time. Furthermore,compound 4 showed strong inhibitory activity towards human carcinoma( Hep G-2),and compound 9 showed moderate inhibitory activity towards human breast cancer cells( MCF-7).
The experiment aimed to investigate the chemical compositions of Walnut green husk and the antitumor activities of the isolated compounds. The chemical constituents were isolated and purified by column chromatography and recrystallization,and their structures have been elucidated on the basis of spectral data analysis. As a result,thirteen compounds were isolated and identified as 3,5-dimethoxy-4-hydroxy benzene carbonic-7-O-β-D-pyranglucose( 1),myricanain F(2),β-stitosterol(3),oleanolic acid(4),regiolone(5),asiatic acid(6),hederagenin(7),β-daucosterin(8),(R)-8-hydroxy-α-tetralone-O-β-D-glucopyranoside(9),3β,23-dihydroxy-urs-12-en-28-oic acid(10),ursolic acid(11),syringc acid(12),Juglanoside B(13). Compounds 1,2,6,7,9 and 10 are all separated from the genus for the first time. Furthermore,compound 4 showed strong inhibitory activity towards human carcinoma( Hep G-2),and compound 9 showed moderate inhibitory activity towards human breast cancer cells( MCF-7).
引文
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2 Gao XN(高小宁),Sun XF(孙晓飞),Huang GX(黄国兴). New tetralone from Juglans mandshurica Maxim[J].Chin Tradit Pat Med(中成药),2013,35:1487-1489.
3 Zhang JB(张建斌),Liu JX(柳军玺),Cha F(查飞),et al.Chemical constituents in green walunt husks of Juglans regia[J]. China Tradit Herb Drugs(中草药),2009,40:847-849.
4 Su DM(苏东敏),Tang WZ(唐文照),Yu SS(庾石山),et al. Water-soluble constituents from roots of Capparis tenera[J]. Chin J Nat Med(中国中药杂志),2008,33:1021-1023.
5 Wang JF,Zhang CL,Lu Q,et al. Three new diarylheptanoids from Myrica nana[J]. Helvetica Chimica Acta,2009,92:1594-1599.
6 Wei XH,Yang SJ,Liang N,et al. Chemical constituents of caesalpinia decapetala(Roth)alston[J]. Molecules,2013,18:1325-1336.
7 Liu SX(刘书霞),Li ZL(李振麟),Lan TJ(兰太进),et al.Chemical constituents from leaves of Adinandra nitida[J].China Tradit Herb Drugs(中草药),2016,47:2436-2440.
8 Liu JX,Di DL,Li C,et al. Regiolone from the pericarps of Juglans regia L.[J]. Acta Cryst(E),2007,63:2713-2714.
9 He WN,Dai JG,Ye M,et al. Microbial transformation of asiatic acid by Alternaria longipes[J]. J Asian Nat Prod Res,2010,12:760-764.
10 Wei Q(卫强),Qiu Z(邱振),Xu F(徐飞),et al. Chemical components from leaves of Futsia japonica and their antitumor activities in vitro[J]. Chin Med Matl(中药材),2015,38:745-750.
11 Tang WX(唐万侠),Wu XF(吴晓峰),Zhao M(赵明),et al. Chemical constituents from inflorescence bracts of Arctii Fructus[J]. China Tradit Herb Drugs(中草药),2015,46:958-961.
12 Wang YF,Cao J,Thomas E,et al. Cytotoxic and new tetralone derivatives from Berchemia floribunda(WALL.)BRONGN[J]. Chemistry&Biodiversity,2006,3:646-653.
13 Shu JC(舒积成),Chou GX(侴桂新),Wang ZT(王铮涛).Triterpenoids constituents in fruits of Psidium guajava Linn[J]. Chin J Nat Med(中国中药杂志),2009,34:3047-3050.
14 Liu JX,Di DL,Shi YP,et al. Diversity of chemical constituents from Saxifraga montana H[J]. J Chin Chem Soc,2008,55:863-870.
15 Li HY(李火云),Jiao K(焦珂),Zhang P(张鹏),et al.Chemical constituents from Isodon excisoides[J]. China Tradit Herb Drugs(中草药),2014,45:154-160.
16 Wang CW(王呈文),Chen GY(陈光英),Song XP(宋小平),et al. Chemical constituents from roots of Millettia speciosa[J]. China Tradit Herb Drugs(中草药),2014,45:1515-1520.
17 Liu LJ,Li W,Kazuo Koike,et al. Newɑ-Tetralonly Glucosides from the fruit of Juglans mandshurica[J]. Chem Pharm Bull,2004,52:566-569.