药蜀葵茎叶化学成分及其体外抑制α-葡萄糖苷酶和5-脂氧合酶活性研究

Chemical constituents from arial part of Althaea officinalis and their inhibition activities in vitro toward α-glucosidase and 5-lipoxygenase

目的对锦葵科蜀葵属植物药蜀葵Althaea officinalis茎叶的化学成分及其体外抑制α-葡萄糖苷酶和5-脂氧合酶活性进行研究。方法运用D101大孔吸附树脂、硅胶柱、MCI凝胶、Sephadex LH-20以及半制备HPLC等多种色谱方法进行分离纯化,根据波谱数据鉴定化合物的结构;通过测定化合物对α-葡萄糖苷酶和5-脂氧合酶体外抑制活性,评价化合物的降血糖和抗炎作用。结果从药蜀葵茎叶中共分离得到24个化合物,分别鉴定为腺苷(1)、4-羟基-2,6二甲氧基苯基-β-D-吡喃葡萄糖苷(2)、苄基-O-β-D-吡喃葡萄糖苷(3)、赤藓醇(4)、5-羟甲基-2-呋喃甲醛(5)、1-[5-(hydroxymethyl)furan-2-yl]ethenone(6)、黑麦草内酯(7)、isololiolide(8)、4-羟基苯甲醛(9)、对羟基苯甲酸甲酯(10)、催吐萝芙木醇(11)、(6S,7Z,9R)-roseoside(12)、二氢芥子醇(13)、3-(3,4,5-trimethoxyphenyl)propan-1-ol(14)、dihydrodehydrodiconifenyl alcohol(15)、齐墩果酸3-O-β-D-吡喃葡萄糖苷(16)、紫云英苷(17)、反式银椴苷(18)、望春花黄酮醇苷(19)、apigenin7-O-(6’’-trans-p-coumaroyl-β-D-glucopyranoside)(20)、香叶木素7-O-β-D-吡喃葡萄糖苷(21)、田蓟苷(22)、芒柄花素7-葡萄糖苷(23)、acacetin 7-O-(6’’-p-coumaroyl)-β-D-glucopyranoside(24)。生物活性测试结果表明,化合物18、19、24对α-葡萄糖苷酶半数抑制浓度(median inhibition concentration,IC_(50))为(12.2±1.3)、(2.8±0.6)、(31.1±3.9)μmol/L;化合物18、24对5-脂氧合酶的IC50为(34.76±4.3)、(25.37±2.4)μmol/L。结论化合物1~16、18~24为首次从该植物中分离获得。发现部分化合物具有较好的体外抑制α-葡萄糖苷酶(18、19、24)和5-脂氧合酶(18、24)作用,表明其具有潜在的降血糖活性和抗炎活性。

Objective To study the chemical constituents from aerial part of Althaea officinalis and their inhibition activities in vitro towardα-glucosidase and 5-lipoxygenas.Methods Chemical constituents were separated and purified by column chromatography on D101 macroporous adsorption resin,silica gel,MCI gel,Sephadex LH-20,and semi-preparative RP-HPLC.The structures were characterized via spectroscopic data analysis.The inhibitory activities of the compounds againstα-glucosidase and 5-lipoxygenase in vitro were measured to evaluate its hypoglycemic and anti-inflammatory effects.Results Twenty-four compounds were isolated and identified as adenosine(1),leonuriside A(2),benzyl-O-β-D-glucopyranoside(3),meso-erythritol(4),5-hydroxymethyl2-furancarboxaldehyde(5),1-[5-(hydroxymethyl)furan-2-yl]ethenone(6),loliolide(7),isololiolide(8),4-hydroxybenzaldehyde(9),methyl 4-hydroxybenzoate(10),vomifoliol(11),(6S,7Z,9R)-roseoside(12),dihydrosyringenin(13),3-(3,4,5-trimethoxyphenyl)propan-1-ol(14),dihydrodehydrodiconifenyl alcohol(15),oleanolic acid 3-O-β-D-glucopyranoside(16),astragalin(17),trans-tiliroside(18),biondnoid I(19),apigenin 7-O-(6''-trans-p-coumaroyl-β-D-glucopyranoside)(20),diosmetin 7-O-β-Dglucopyranoside(21),tilianin(22),formononetin 7-glucoside(23),acacetin 7-O-(6''-p-coumaroyl)-β-D-glucopyranoside(24).The results of the bioactivity test showed that three of the 24 compounds(18,19,24)showed significant enzyme inhibitory activity againstα-glucosidase[IC50 values:(12.2±1.3)μmol/L,(2.8±0.6)μmol/L and(31.1±3.9)μmol/L]and two compounds(18,24)had significant enzyme inhibitory activity against 5-lipoxygenase with IC_(50) values of(34.76±4.3)μmol/L and(25.37±2.4)μmol/L.Conclusion Compounds 1—16,18—24 were isolated from A.officinalis for the first time.Furthermore,it was found that compounds have great inhibitory activities towardα-glucosidase(18,19,24)and 5-lipoxygenase(18,24),which show potential hypoglycemic activity and anti-inflammatory activity.