CN114853833B - 一种黄酮醇类衍生物及其制备方法 - Google Patents
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Abstract
本发明属于医药中间体技术领域,公开了一种黄酮醇苷类衍生物及其制备方法。本发明利用现代分离纯化,结构解析等技术,对漆树科漆属漆的天然产物进行了详细分析,获得了一种新型化合物,即一种黄酮醇苷类衍生物。该化合物具有较好的抗肿瘤活性,可以作为抗肿瘤药物的活性成分或医药中间体,具有广泛的医药用途。
Description
技术领域
本发明属于医药中间体技术领域,具体涉及一类黄酮醇类衍生物及其制备方法。
背景技术
漆Toxicodendron vernicifluum(Stokes)F.A.Barkl.是漆树科漆属植物,又称漆树、干漆、大木漆、小木漆、山漆、楂苜或者瞎妮子。属于落叶乔木,除了黑龙江、吉林、内蒙古和新疆外,其他省份均产,生于海拔800-2800米的向阳山坡林内,也有栽培。树干韧皮部割取生漆,漆是一种优良的防腐、防锈的涂料,有不易氧化、耐酸、耐醇和耐高温的性能,用于涂漆建筑物、家俱、电线、广播器材等。种子油可制油墨,肥皂。果皮可取蜡,作蜡烛、蜡纸。叶可提栲胶。叶、根可作土农药。木材供建筑用。干漆在中药上有通经、驱虫、镇咳的功效。
发明内容
鉴于此,本发明的目的是提供一种黄酮醇苷类衍生物及其制备方法,该黄酮醇苷类衍生物可用于作为医药中间体。
本发明提供的黄酮醇苷衍生物为结构式为式Ⅰ的化合物,该化合物B环的羟基被甲基化,与传统黄酮苷类衍生物具有较大的差异,为本发明首次公开的黄酮醇苷新的衍生物。
本发明还提供了上述黄酮醇类衍生物制备方法,包括如下步骤:
1)初步提取:将植物经有机溶剂萃取后,室温下减压浓缩至干,得植物提取物;
2)反相中低压色谱柱纯化:将步骤1)得到的植物提取物溶于适量甲醇,加至装有反相硅胶的色谱柱,依次采用体积浓度为20%的乙醇溶液、体积浓度为30%的乙醇溶液、体积浓度为40%的乙醇溶液、体积浓度为50%的乙醇溶液、体积浓度为60%的乙醇溶液、体积浓度为70%的乙醇溶液、体积浓度为80%的乙醇溶液、体积浓度为100%的乙醇溶液洗脱,取经过体积浓度为20%的乙醇溶液的流份;
3)反相高效液相色谱纯化:将步骤2)得到的流份经反相高效液相色谱分离提纯,得所述黄酮醇苷衍生物。
优选的,上述方法步骤1)植物为漆的木质部;优选采用漆树科漆属植物漆Toxicodendron vernicifluum(Stokes)F.A.Barkl.的新鲜木质部。
优选的,上述方法步骤1)中有机溶剂为无水乙醇。
与现有技术相比,本发明利用现代分离纯化技术,对漆Toxicodendronvernicifluum(Stokes)F.A.Barkl.的新鲜木质部进行了系统分离,获得了一类新的黄酮醇苷类衍生物,该化合物或其药学上可接受的盐具有较好的抗肿瘤活性,可以作为抗肿瘤药物的活性成分,具有广泛的医药用途。
附图说明
图1为本发明实施例1得到的化合物的高效液相分离色谱图;
图2为本发明实施例1得到的化合物的高分辨质谱(HRESIMS)数据图;
图3为本发明实施例1得到的化合物的氢谱数据图;
图4为本发明实施例1得到的化合物的碳谱数据图;
图5为本发明实施例1得到的化合物的二维核磁共振数据图(HSQC);
图6为本发明实施例1得到的化合物的二维核磁共振数据图(HMBC);
图7为本发明实施例1得到的化合物的抗肿瘤活性细胞形态图。
具体实施方式
为了进一步说明本发明,下面结合实施例对本发明提供的黄酮醇苷衍生物及其制备方法进行详细描述。
实施例1、结构式为式I化合物的制备
本发明采用实验室培养条件下常规条件下提取,纯化等步骤,来制备本发明化合物。其中所采用的植物为漆树科漆属植物漆Toxicodendron vernicifluum(Stokes)F.A.Barkl.。
具体化合物的过程如下:
1)提取
采集漆(30kg),阴干后粉碎,用无水乙醇于室温下提取(5L*3),萃取液减压浓缩至干,得到转化物残渣(即漆的提取物)约2kg。
2)反相硅胶色谱柱纯化
将所得残渣溶于适量甲醇,加至装有500g反相硅胶(120埃,30–50目)的色谱柱,用甲醇-水系统梯度洗脱(30%-100%甲醇),收集洗脱组分,取经过体积浓度为20%的乙醇溶液洗脱的流份。
3)反相高效液相色谱纯化
将步骤2)得到的流份用反相高效液相色谱分离提纯。分离条件为:色谱柱HederaC18A-5μm,4.6mm I.D×250mm(江苏汉邦科技),洗脱系统为甲醇–水等度洗脱,具体条件:甲醇–水(30:70,V/V),流速为2.0mL/min。检测波长为254nm,柱温25℃,进样量20μL。得到结构式为式I的化合物,其高效液相分离色谱图、高分辨质谱(HRESIMS)数据、氢谱数据图、碳谱数据图、二维核磁共振数据图(HSQC)、二维核磁共振数据图(HMBC)图如图1-6所示。
化合物I,4′,7-dihydroxy-3′-methoxy-3-O-β-D-glucopyranosyl-flavonoid,黄色无定形粉末。
化合物1的核磁共振氢谱、碳谱以及HMBC相关性数据如表1所示;
化合物1的高分辨ESI质谱数据:(HRESIMS)m/z463.1231[M+H]+(calc.forC22H22O11463.1235).
表1.化合物1的氢谱和碳谱数据(氘代甲醇)
以上结果表明,所得化合物结构正确。
实施例2:本发明化合物I的抗肿瘤活性
(1)实验材料
仪器与试剂:微生物培养箱;酶标仪(Bio-TEK ELx800);LB培养基(上海生物工程有限公司)。测试所用肿瘤细胞系:A549(人非小细胞肺癌细胞系),MDA-MB-231(人乳腺癌细胞),SK-Hep-1(人肝腹水腺癌细胞),SNU638(人胃癌细胞系),HCT116(结肠癌细胞),购于中国医学科学院细胞研究所。
测试样品:漆的活性化合物Ⅰ,纯度在95%以上;同时,选取依托泊苷为阳性对照药物,各化合物均以DMSO溶解后稀释。
(2)实验方法
配置LB培养液,121℃下灭菌25分钟备用,将配置稀释好的菌液加入96孔板中,每孔加入180μl,将化合物1配置为一定浓度的DMSO溶液,以倍数关系逐级稀释加入含有肿瘤株液的微孔中,使其最终浓度依次为0.04,0.2,1,5,25μM,于37℃培养箱中培养24小时,用酶标仪于340nm处读取吸光度,其中采用依托泊苷为阳性对照。实验重复3次。抗肿瘤活性细胞形态图如图7所示。计算各受试样品对人类致病菌的半抑制浓度(IC50值)。
(3)实验结果
实验结果如表2所示。
表2化合物1抗肿瘤活性数据
结果表明,本发明的化合物I具有良好的抗肿瘤活性,可以作为抗肿瘤药物的活性成分或医药中间体。
以上所述仅是本发明的优选实施方式,应当指出,对于本技术领域的普通技术人员来说,在不脱离本发明原理的前提下,还可以做出若干改进和润饰,这些改进和润饰也应视为本发明的保护范围。
Claims (4)
1.一种黄酮醇苷衍生物的制备方法,其特征在于,所述黄酮醇苷衍生物为4′,7-dihydroxy-3′-methoxy-3-O-β-D-glucopyranosyl-flavonoid,具有式Ι结构:
所述制备方法包括如下步骤:
1)初步提取:将植物经有机溶剂萃取后,室温下减压浓缩至干,得植物提取物;
2)反相中低压色谱柱纯化:将步骤1)得到的植物提取物溶于适量甲醇,加至装有反相硅胶的色谱柱,依次采用体积浓度为20%的乙醇溶液、体积浓度为30%的乙醇溶液、体积浓度为40%的乙醇溶液、体积浓度为50%的乙醇溶液、体积浓度为60%的乙醇溶液、体积浓度为70%的乙醇溶液、体积浓度为80%的乙醇溶液、体积浓度为100%的乙醇溶液洗脱,取经过体积浓度为20%的乙醇溶液的流份;
3)反相高效液相色谱纯化:将步骤2)得到的流份经反相高效液相色谱分离提纯,得所述黄酮醇苷衍生物。
2.根据权利要求1所述的制备方法,其特征在于,所述植物为漆的木质部。
3.根据权利要求1所述的制备方法,其特征在于,所述植物为漆树科漆属植物漆的木质部。
4.根据权利要求1所述的制备方法,其特征在于,所述有机溶剂为无水乙醇。
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