CN108997296B - 几种异戊烯基二氢茋和异戊烯基黄酮的结构和用途 - Google Patents
几种异戊烯基二氢茋和异戊烯基黄酮的结构和用途 Download PDFInfo
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- CN108997296B CN108997296B CN201810943697.4A CN201810943697A CN108997296B CN 108997296 B CN108997296 B CN 108997296B CN 201810943697 A CN201810943697 A CN 201810943697A CN 108997296 B CN108997296 B CN 108997296B
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Abstract
本发明涉及几种异戊烯基二氢茋和异戊烯基黄酮的制备、结构及防治肥胖、防治糖尿病和抗肝纤维化活性，特别是新的天然异戊烯基二氢茋化合物—甘草吡喃茋A(glycypytilbene A,1)，甘草二吡喃茋(glycydipytilben,2)，甘草吡喃茋B(glycypytilbene B,3)的制备、结构及生物活性，以及它们在药品、（功能）食品、化妆品、家畜饲料等方面的应用。
Description
技术领域
本发明技术属于化学领域，涉及几种异戊烯基二氢茋和异戊烯基黄酮的制备、结构及防治肥胖、防治糖尿病和抗肝纤维化活性，特别是新的天然异戊烯基二氢茋化合物—甘草吡喃茋A (glycypytilbene A, 1)，甘草二吡喃茋 (glycydipytilben, 2)，甘草吡喃茋B (glycypytilbene B, 3)的制备、结构及生物活性。
背景技术
茋类及黄酮类成分是2类天然产物，最有名的茋类化合物是来自葡萄的白藜芦醇；最有名的黄酮类化合物有卢丁、槲皮素等。发明人之前曾对甘草叶中的1种茋和6种黄酮类化合物进行了富集和鉴定，近期对甘草叶成分进行了进一步研发并比较了其与相关结构化合物的生物活性。甘草(Glycyrrhiza uralensis Fisch)是豆科多年生植物，生长在中国北部的荒漠草原边缘和黄土丘陵区，其根和根茎含有三萜皂苷（以甘草甜素为主）、黄酮和香豆素类等成分，广泛用于传统医药和食品饮料行业（中国药典，2010版，第一卷，80-81页），（张继, 姚健, 丁兰. 甘草的利用研究进展. 草原与草坪2000, 89: 12-17）。甘草地上部分主要用作动物饲料。已知甘草叶中的化学成分主要是黄酮类，尤其是异戊烯基黄酮类成分较多，近年也发现甘草叶中含有茋类化合物。甘草叶黄酮和二氢茋类化合物具有抑菌、抗氧化和抑制α-葡萄糖苷酶等作用。肝硬化是全球性的健康问题，每年导致超过100万人死亡。导致肝硬化的主要途径之一是肝纤维化，而活化的肝星状细胞（hepatic stellatecells, HSC）在肝纤维化形成中起着关键作用，HSC抑制剂具有潜在的抗肝纤维化作用。本发明公开从甘草叶中发现的3种新茋类衍生物的结构、制备方法以及15种甘草成分和3种结构相关化合物对肝星状细胞及α-葡萄糖苷酶的抑制活性。
发明内容
本发明的目的是发现新的活性成分，并提供防治肝纤维化的肝星状细胞抑制剂及防治肥胖和糖尿病的α-葡萄糖苷酶抑制剂。
提供化合物1：甘草吡喃茋A (glycypytilbene A, 1)。
提供化合物2：甘草二吡喃茋 (glycydipytilben, 2)。
提供化合物3：甘草吡喃茋B (glycypytilbene B, 3)。
本发明的另一个方面，提供化合物1-3的组合物。
本发明还提供含有化合物1-3的药物制剂。
本发明的又一个方面，提供化合物1-3用于（功能）食品、化妆品、家畜饲料。
本发明的再一方面，提供化合物1-3或其组合物的制备方法，主要步骤如下：
1）用醇（优选95%乙醇）提取甘草叶，提取液浓缩后用大孔树脂分段，水-乙醇梯度洗脱，得到活性组分（优选80%乙醇洗脱部位），该活性组分经C18反相硅胶色谱分离，60%甲醇洗脱部分用硅胶柱分离，石油醚-乙酸乙酯6:4洗脱部分用Sephadex-LH20色谱分离，甲醇洗脱，并用制备液相色谱纯化68%的甲醇为流动相得化合物1和2；上述硅胶色谱中的石油醚-乙酸乙酯8:2洗脱部分经Sephadex-LH20色谱分离，制备液相色谱纯化69%的甲醇为流动相得化合物3。还分离得到化合物4-15。
2）这些化合物的结构经解析多种光谱数据确定，其中1-3为新化合物，均为异戊烯基二氢茋衍生物。化合物1, 3-4, 6-7, 9-12对肝形状细胞显示出抑制活性；化合物1, 5-11, 14-15化合物对DPPH 自由基有很强的清除作用；化合物2-11, 15对α-葡萄糖苷酶有抑制作用。其中异戊烯基取代的黄酮化合物比对应的无异戊烯基取代的化合物（16-18）表现了更强的抑制α-葡萄糖苷酶和抑制肝形状细胞生长作用。
因此，本发明还涉及化合物1-3的组合物。所述本发明组合物，可按常规方法通过将所述活性组分或化合物1-3的任意一种或几种与药物、食品或化妆品可接受的载体混合来制备。
在本发明---几种异戊烯基二氢茋和异戊烯基黄酮的制备、结构确定和生物活性的一个优选方案中，包括以下步骤：
1）甘草叶用95%乙醇室温提取超声协助。提取物用D-101大孔树脂分段，乙醇-水梯度洗脱，其中80%乙醇洗脱物富含异戊烯基二氢茋和异戊烯基黄酮化合物；
2）上述80%乙醇洗脱物经C18反相硅胶、正相硅胶、Sephadex-LH20凝胶及制备液相分离得到纯成分1-15；
3）化合物4-15通过光谱解析及与文献值（Hayashi H, Zhang S-L, Nakaizumi T,Shimura K, Yamagauchi M, Inoue K, Sarsenbaev K, Ito M, Honda G. Field surveyof Glycyrrhiza plants in central Asia (2).1) Characterization of phenolicsand their variation in the leaves of Glycyrrhizaplants collected inKazakhstan. Chem Pharm Bull 2003, 51: 1147−1152; Ye R, Fan YH, Ma CM,Identification and enrichment of α-glucosidase-inhibiting dihydrostilbene andflavonoids from Glycyrrhiza uralensis leaves. J Agric Food Chem 2017, 65,510–515; Biondi D M, Rocco C, Ruberto G. New dihydrostilbene derivatives fromthe leaves of Glycyrrhiza glabra and evaluation of their antioxidantactivity. J Nat Prod 2003, 66, 477-480.）对照分别确定结构为α,α'-二氢-3,5,4'-三羟基- 4,5'-二异戊烯基茋(α,α'-dihydro-3,5,4'- trihydroxy-4,5'-diisopentenylstilbene，4)，α,α'-二氢-3,5,3′,4′-四羟基- 2,5′-二异戊烯基茋(α,α′-dihydro-3,5,3′,4′-tetrahydroxy- 2,5′- diisopentenylstilbene，5)，6-异戊烯基圣草酚(6-prenyleriodictyol, 6)，5′-异戊烯基圣草酚(5′-prenyleriodictyol, 7)，6-异戊烯基槲皮素-3-甲醚(6-prenylquercetin-3-methyl ether, 8), 5′-异戊烯基槲皮素(5′-prenylquercetin, 9)，6-异戊烯基槲皮素(6-prenylquercetin, 10), 6-异戊烯基柚皮素(6-prenylnaringenin，11)，3′-异戊烯基柚皮素(3′-prenylnaringenin，12)，sigmoidin C(13)，8-[(反)-3-羟甲基-2-丁烯基]-圣草酚{8-[( E)-3-hydroxymethyl-2- butenyl]-eriodictyol, 14}，槲皮素-3-甲醚(quercetin-3-methyl ether, 15)。化合物1-3的结构经过仔细解析多种光谱，特别是二维核磁共振光谱，确定为如图1所示的异戊烯基二氢茋结构，化合物1-3均为新化合物，分别命名为甘草吡喃茋A (glycypytilbene A, 1)，甘草二吡喃茋 (glycydipytilben, 2)，甘草吡喃茋B (glycypytilbene B, 3)。
本发明的新发现和创造性：发现了3个新结构的异戊烯基二氢茋衍生物—甘草吡喃茋A (1)，甘草二吡喃茋 (2)，甘草吡喃茋B (3)。得到的15种成分大多有抑制α-葡萄糖苷酶和抑制肝星状细胞作用，并且联有异戊烯基的化合物比相应的无异戊烯基化合物活性更好。上述结果提示这些异戊烯基二氢茋和异戊烯基黄酮及含有这些化合物的组分有望对糖尿病及肥胖患者有益，还有望对防治肝纤维化和肝硬化起作用。大多数成分还有较好的清除自由基活性。结构中含有异戊烯基的活性成分极性较小，亦可作为低极性食品及化妆品等的抗氧化剂。甘草资源主要利用其地下部分，本发明发现的甘草叶新有效成分为充分开发利用甘草地上部分提供了依据和方法。本发明发现的异戊烯基黄酮比相应的无异戊烯基化合物活性更好的规律，也为进一步合成活性更强化合物提供了线索。
附图说明
图1. 异戊烯基二氢茋和黄酮衍生物1-15及相关化合物16-18的化学结构
图2. 化合物1-3的HMBC主要相关
图3. 化合物1的高分辨ESI-MS(-)
图4. 化合物1的1HNMR图谱
图5. 化合物1的13CNMR图谱
图6. 化合物1的HMBC图谱
图7. 化合物2的高分辨ESI-MS(-)
图8. 化合物2的1HNMR图谱
图9. 化合物2的13CNMR图谱
图10. 化合物2的HMBC图谱
图11. 化合物3的高分辨ESI-MS(-)
图12. 化合物3的1HNMR图谱
图13. 化合物3的13CNMR图谱
图14. 化合物3的HMBC图谱
具体实施方式
具体实施方式是对本发明涉及的异戊烯基二氢茋和异戊烯基黄酮的制备和活性测定方法作详细说明。这些实施例仅用来例证本发明，不应被视为是对本发明保护范围的限制。
实施例1：含异戊烯基二氢茋和黄酮组分的制备
干燥的甘草叶（2公斤）用95%的乙醇（10 L）室温提取，超声协助。提取液浓缩后悬浮于水，用D-101大孔树脂分段，乙醇-水梯度洗脱，其中80%乙醇洗脱物含有化合物1-15。
实施例2：异戊烯基二氢茋和黄酮衍生物的分离纯化
上述大孔树脂80%乙醇洗脱物用反相硅胶C18色谱柱分离，水-甲醇洗脱得组分(O1—O11), 60%甲醇洗脱的前半部分(O6)经Sephadex LH-20纯化得化合物15 (14.5 mg)；60%甲醇洗脱的后半部分(O7)用硅胶分离，石油醚-乙酸乙酯洗脱得流分(OS1—OS12). OS6(石油醚-乙酸乙酯6:4洗脱部分)进一步用Sephadex LH-20分离，甲醇-氯仿6:4洗脱得OS6-1—OS6-6。OS6-2经Sephadex LH-20 (甲醇洗脱)及制备液相(60%甲醇洗脱)得到1 (15.3mg)、2 (5 mg)、14 (19.6 mg)。OS5 (石油醚-乙酸乙酯6:4洗脱部分)进一步用SephadexLH-20分离，甲醇-氯仿6:4洗脱得OS5-1—OS5-6。OS5-4用制备液相纯化78%甲醇为流动相得到6 (7 mg)、7 (9.8 mg)、8 (14.7 mg)。OS5-5经Sephadex LH-20 (甲醇洗脱)及制备液相(58%甲醇洗脱)分离纯化得到9 (20.5 mg)、10 (16 mg)。OS4 (石油醚-乙酸乙酯8:2洗脱部分) 经Sephadex LH-20 (甲醇洗脱)得OS4-1—OS4-14。OS4-3经制备液相(69%甲醇洗脱)分离纯化得到3 (8.5 mg)、4 (6 mg)。OS4-7和OS4-8分别经制备液相(68%甲醇洗脱)分离纯化得到5 (20 mg)、11 (5 mg)。 OS4-10经制备液相(70%甲醇洗脱)分离纯化得到12 (10 mg)、13 (20 mg)。
实施例3：异戊烯基二氢茋和黄酮衍生物的结构测定
化合物4-15的结构通过光谱解析及与文献值对照光谱数据分别确定为α,α'-二氢-3,5,4'-三羟基- 4,5'-二异戊烯基茋(4)，α,α'-二氢-3,5,3′,4′-四羟基- 2,5′-二异戊烯基茋(5)，6-异戊烯基圣草酚(6)，5′-异戊烯基圣草酚(7)，6-异戊烯基槲皮素-3-甲醚(8), 5′-异戊烯基槲皮素(9)，6-异戊烯基槲皮素(10), 6-异戊烯基柚皮素(11)，3′-异戊烯基柚皮素(12)，sigmoidin C (13)，8-[(反)-3-羟甲基-2-丁烯基]-圣草酚(14)，槲皮素-3-甲醚(15)。化合物1-3的结构经过仔细解析多种光谱，特别是二维核磁共振的HMBC相关(图2)，确定如下：
化合物1：类白色粉末，负离子模式下高分辨ESI-MS测得的准分子离子峰m/z397.2021 (图3)，为分子式C24H30O5的[M-H]-1峰(计算值：m/z 397.2015)。化合物1的1H NMR在δ 1.56 (3H, s, H-10), 1.51 (3H, s, H-11), 1.27 (3H, s, H-11')和1.11 (3H, s,H-10')有2对甲基信号. 在其HMBC谱中，δ 1.56和1.51的1对甲基信号与δ 125.2 (C-8)和129.4 (C-9)的1对双键碳有远程相关，δ 3.13 (2H, d, J=6.8 Hz, H-7)的亚甲基氢也与这对双键碳有远程相关，说明1的结构中有1个异戊烯基存在。在δ 1.27和1.11的另1对甲基信号以及δ 2.80 (1H, dd, J=5.6, 16.6 Hz, H-7'a)和2.53 (1H, overlapped, H-7'b)的亚甲基氢与δ 68.9 (C-8')及77.1 (C-9')的连氧碳有HMBC相关，说明1的结构中还存在1个2,2-二甲基-3-羟基-3,4-二氢吡喃环。在δ 6.13 (1H, br s, H-4), 6.07 (1H, br s,H-6)和6.44 (1H, br s, H-2')，6.32 (1H, br s，H-6')处有2对间位偶合的芳香质子信号，这些信息结合其13C-NMR 数据提示1的结构中有2个苯环存在。在HMBC中，δ 2.56和2.51(CH2-α及CH2-α′)的2个亚甲基信号均与δ 142.0及133.4 (C-1和C-1')的2个芳香碳相关，提示1有二氢茋骨架。根据HMBC中H-7与C-1, C-2和C-3的相关，确定异戊烯基连接在C-2位。根据HMBC 中H-7'与C-4', C-5'及C-6'相关，确定2,2-二甲基-3-羟基-3,4-二氢吡喃环在C-4'和5'。因此，得出化合物1的平面结构，并进一步用详细HMBC相关确证。化合物1在C8'的立体构型通过与文献报道的8-methoxywutaipyranol A的比旋光度对照确定为R（化合物1[α]D 25 = +16.9；8-methoxywutaipyranol A [α]D 24= +26.4) (Huang HY, Ishikawa T,Peng CF, Chen S, Chen IS. Secondary metabolites from the root wood ofZanthoxylum wutaiense and their antitubercular activity. Chem Biodivers.2011,8: 880-886)。化合物1及8-methoxywutaipyranol A 结构中均只有1个手性中心，并且两个化合物手性中心的取代基非常相似，因此通过比较其比旋光度的绝对值可以确定构型。化合物1是新化合物，命名为甘草吡喃茋A (glycypytilbene A, 1)。其1H NMR和13C NMR(图4-5) 的归属经仔细分析其二维NMR特别是HMBC (图6)总结列于表1。
化合物2：类白色粉末，负离子模式下高分辨ESI-MS测得的准分子离子峰m/z395.1851 [M-H]- (图7)，提示分子式为C24H28O5（计算值：m/z 395.1858)。其1H-NMR(图8)在δ 1.21 (3H, s, H-10), 1.30 (3H, s, H-11)和1.41 (6H, s, H-11', H-10')有2对甲基信号。13C-NMR (图9)确证了这些信息。HMBC中(图10)，δ 1.21及1.30的1对甲基及δ 2.51(1H, dd, J=7.5, 17.0 Hz)和2.87 (1H, dd, J=6.0, 17.0 Hz, ) (H-7)的1个亚甲基与δ69.3 (C-8)及76.1 (C-9)的连氧碳相关，提示有2,2-二甲基-3-羟基-3,4-二氢吡喃环；δ1.41 的另1对甲基及δ 6.28 (1H, d, J=9.5 Hz, H-7')的双键氢信号与δ 130.6 (C-8')及75.9 (C-9')相关，提示有二甲基吡喃基团。δ6.12 (1H, br s, H-2)，6.19 (1H, br s,H-6)及6.51 (1H, br s, H-2')和6.34 (1H, br s，H-6')的两对间位取代的芳环信号及13C-NMR信息提示化合物2结构中有2个苯环存在。在其HMBC谱中，δ 2.67 (2H, CH2-α)和2.67 (2H, CH2-α')的两个亚甲基信号均与δ 141.2 (C-1)及134.3 (C-1')的两个芳香碳相关，提示化合物2有二氢茋骨架。2,2-二甲基-3-羟基-3,4-二氢吡喃及二甲基吡喃基的位置通过HMBC中的H-7与C-3, C-4及C-5相关，以及H-7'与C-4', C-5'及C-6'相关确定(图2)。C8的立体结构通过其比旋光度( [α]D 25 = +10.2)与8-methoxywutaipyranol A比较确定为R。化合物2为新化合物，命名为甘草二吡喃茋 (glycydipytilben, 2)。
化合物3：类白色粉末，负离子模式下高分辨ESI-MS测得的准分子离子峰m/z379.1907 [M-H]- (图11)，提示分子式为C24 H28O4（计算值：m/z 379.1909); 1H-NMR(图12)在δ 1.67 (3H, s, H-10), 1.58 (3H, s, H-11),以及1.33 (3H, s,H-11'), 1.33(3H,s, H-10')处有对甲基信号。13C-NMR (图13)及HMBC(图14)相关提示其结构中存在1个异戊烯基和1个二甲基吡喃基。通过仔细解析其2D NMR确定其结构为如图2所示的为二氢茋衍生物。化合物3为新化合物，命名为甘草吡喃茋B (glycypytilbene B, 3)。
表1 化合物1-3的1H 及13C NMR数据
*: 重叠信号
实施例4：清除1,1-二苯基苦基苯肼（DPPH）自由基实验
清除DPPH实验参考文献方法 (Ma JN, Wang SL, Zhang K, Wu ZG, Hattori M,Chen G L. Chemical components and antioxidant activity of the peels ofcommercial apple-shaped pear (fruit of pyrus pyrifolia cv. pingguoli). J Food Sci, 2012, 10: 1097−1102)在96孔板上测定4个浓度的清除率。以浓度为横坐标，清除率为纵坐标作曲线求出清除率为50%时的浓度（EC50）。
结果如表2所示，所有化合物均显示清除DPPH活性，其中结构中有邻位酚羟基的化合物比相应的无邻位酚羟基化合物显示了更强的清除DPPH活性(5 vs 4; 6 vs 11; 7 vs12; 17 vs 16)。
实施例5：对α-葡萄糖苷酶抑制活性测试
参考文献报道方法(Ma CM, Sato N, Li XY, Nakamura N, Hattori M. Flavan-3-ol contents, anti-oxidative and α-glucosidase inhibitory activities ofCynomorium songaricum. Food Chem, 2010, 118: 116−119) 在96孔板上测定4个浓度的抑制率。以浓度为横坐标，抑制率为纵坐标作曲线求出抑制率50%时的浓度（IC50）。
结果如表2所示，除化合物1, 12-14以外，从甘草中得到的其他二氢茋成分和黄酮衍生物均有较强的抑制α-葡萄糖苷酶活性，其中活性最强的是2个槲皮素衍生物—5′-异戊烯基槲皮素(9, IC50: 3.9 μg/mL)，6-异戊烯基槲皮素(10, IC50: 3.7 μg/mL)。与对应的无异戊烯基黄酮相比，异戊烯基黄酮显示了更强的α-葡萄糖苷酶抑制活性 (9, 10vs 18;6, 7vs17; 11, 12vs 16)。
实施例6：对肝星状细胞(Hepatic Stellate Cells, HSCs)抑制活性测试
HSCs购自武汉普诺赛生命科技有限公司。将HSCs以每孔5000个细胞的浓度接种于96孔板上，用含10%胎牛血清、00 U/mL青霉素及100 μg/L链霉素的DMEM培养基，37 °C下5%CO2培养箱中培养24 h后用不同浓度 (11.25, 22.5, 45, 90 μg/ml)的化合物处理，继续培养24 h，用倒置显微镜(Olympus, Tokyo, Japan)观察细胞形态。用下述MTT法测定细胞活力：弃去培养基后每孔加入20 μL MTT (5 mg/mL)，继续培养4 h，弃去培养基加入150 μLDMSO室温轻摇10 min 后在570 nm测定吸光度。通过与没有加药的对照孔的吸光度比较计算抑制率。以浓度为横坐标，抑制率为纵坐标作曲线求出抑制率50%时的浓度（IC50）。
化合物1-18对HSCs抑制活性如表2所示。化合物1, 3-4, 6-7, 9-12, 15 抑制了HSCs增殖，IC50小于90 μg/ml。阳性对照绿原酸对HSC增殖有一定抑制作用，但IC50 >90 μg/ml。在5个二氢茋衍生物中，3个化合物抑制HSCs增殖的IC50小于90 μg/ml。化合物4在这18个化合物中活性最强。异戊烯基柚皮素(9, 10)，异戊烯基槲皮素(9, 10)，异戊烯基圣草酚(6, 7)比柚皮素(16)，槲皮素(18)和圣草酚(17)有更强的抑制了HSCs增殖作用。该结果显示了异戊烯基黄酮及异戊烯基二氢茋作为抗肝纤维化试剂的潜力。
表2化合物1-18的清除DPPH自由基、抑制α-葡萄糖苷酶和抑制肝星状细胞活性
注: 结果为三次测定的平均值；acarbose用作α-葡萄糖苷酶抑制活性的阳性对照；CA (绿原酸)为抑制肝星状细胞增殖测试的阳性对照；n.t.：没有测试。
综上，我们分离鉴定到5个异戊烯基二氢茋及10 个黄酮类化合物。其中3个异戊烯基二氢茋—甘草吡喃茋A (1)，甘草二吡喃茋 (2)，甘草吡喃茋B (3)为新化合物。除化合物1及12-14以外，分离鉴定出的其他异戊烯基二氢茋及黄酮衍生物有抑制α-葡萄糖酶作用，预期有益于防治肥胖及糖尿病。异戊烯基二氢茋衍生物—1, 3-4以及黄酮衍生物6-7, 9-12, 15能够抑制肝星状细胞的增殖，IC50均低于阳性对照—绿原酸，因此，这些异戊烯基二氢茋及黄酮衍生物预期有益于防治肝纤维化和肝硬化。
Claims (2)
1.一种异戊烯基二氢茋衍生物，其特征在于，所述衍生物为甘草吡喃茋A，结构式为：
2.一种异戊烯基二氢茋衍生物，其特征在于，所述衍生物为甘草二吡喃茋，结构式为：
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