CN111138399A - 一种具有抗氧化作用的总黄酮提取物及制备方法和应用 - Google Patents
一种具有抗氧化作用的总黄酮提取物及制备方法和应用 Download PDFInfo
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- CN111138399A CN111138399A CN202010021719.9A CN202010021719A CN111138399A CN 111138399 A CN111138399 A CN 111138399A CN 202010021719 A CN202010021719 A CN 202010021719A CN 111138399 A CN111138399 A CN 111138399A
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- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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Abstract
本发明属于中药有效部位提取技术领域,具体涉及一种具有抗氧化作用的总黄酮提取物及制备方法和应用;制备方法:干燥黄芫花,回流提取,减压浓缩至无醇,加入蒸馏水进行溶解、沉淀,然后离心,上层液经大孔树脂分离富集,洗脱、浓缩干燥,得到具有抗氧化作用的总黄酮提取物;总黄酮提取物包括但不限于8种黄酮化合物:异荭草苷、荭草苷、牡荆素、异杜荆素、槲皮素3‑氧‑葡萄糖甙、木犀草苷、紫云英苷、木犀草素4’‑氧‑葡萄糖苷,且总黄酮的含量在50%以上。本发明提供的具有抗氧化作用的总黄酮提取物可以制备成胶囊剂、片剂、颗粒剂、凝胶剂、缓释剂、口服液或滴丸剂等剂型用于抗氧化相关的药物或保健食品。
Description
技术领域
本发明属于中药有效部位提取技术领域,具体涉及一种具有抗氧化作用的总黄酮提取物及制备方法和应用。
背景技术
黄芫花是瑞香科荛花属植物河朔荛花(Wikstroemia chamaedaphne Meisn)的干燥花蕾,花小且为黄色,又名绛州芫花、北芫花、黄闷头花、叩皮花、痒眼花。主要分布在中国的山西、甘肃、河南、河北以及陕西,宋代的《图经本草》最先记载该古本草河朔荛花。该药辛、温,有小毒。具泻下逐水、通便功效,它已被用于治疗急慢性传染性肝炎、精神病、癫痫等,还可用于引产。以黄芫花为主要组成的中药复方“芫蒿护肝片”在临床上被用于治疗慢性肝炎。化学成分研究表明黄芫花中主要分离得到的有二萜类、黄酮类、木脂素类、倍半萜类等成分。药理活性研究表明黄芫花在抗早孕、治疗精神疾病以及抗肿瘤方面显示出了一定的毒性,但是对于黄芫花治疗慢性肝病的药理活性研究及药效物质基础研究未见有报道。前期申请人团队从黄芫花中获得大量瑞香烷型和惕各烷型二萜,并对其进行抗HBV活性测试,但其作用都不是很好(张志强等,中草药,2017,48(7),1292-1297;Li Shifei et al,Phytochemistry,2018,151:17-25)。可见,黄芫花在治疗慢性肝炎疾病的药效物质基础是多样的。
黄酮类成分是一类具有C6-C3-C6色原酮类结构,广泛存在于自然界中,在很多中药中黄酮均是药效成分。同时黄酮类成分由于结构存在多样的酚羟基,因此具有普遍的抗氧化作用,如Hu,Jun等研究发现竹菊黄酮在DPPH自由基清除实验中表现出较强的抗氧化能力;白背三七、响铃草、银杏叶等的中药材中均发现具有较强抗氧化能力的黄酮类化合物。众所周知,自由基可以诱导氧化反应,形成脂质过氧化物,破坏细胞结构和功能,导致器官组织受到损伤。氧化应激和脂质过氧化在一些肝病特别是酒精性肝损伤中起着重要作用,机体本身存在清除自由基的能力,但是有大量自由基产生(如酒精或化学物品刺激)或者机体清除自由基能力下降的时候,过量的自由基就会进一步氧化生物膜、蛋白质、核酸等生物大分子,从而破坏细胞的完整性和功能性,造成代谢紊乱。由于肝脏是首要的解毒器官,因此首先受到损害的是肝脏。因此,清除体内自由基被认为是一种治疗肝病的机制。前期申请人对黄芫花的化学成分进行了研究,除了发现一系列二萜类成分外,还获得一系列酚类成分,其中主要以黄酮为主(梁雪等,中国中药杂志,2019,44(5),962-967),进一步对这类成分进行富集,通过多种富集方法,从黄芫花中获得一类具有抗氧化作用的总黄酮提取物。该提取物包含但不限于8个已鉴定的黄酮结构,其结构见附图,同时对总黄酮提取物经工艺研究和活性测试,结果表明工艺简便、效果显著、安全可靠、易于工业化生产,且具有抗氧化和清除自由基作用,可能是其发挥治疗慢性肝炎疾病的药效物质基础。目前未见有这类总黄酮提取制备工艺及药理活性应用报道。
发明内容
本发明的目的在于提供一种具有抗氧化作用的总黄酮提取物及制备方法和应用。
为了达到上述目的,本发明采用了下列技术方案:
一种具有抗氧化作用的总黄酮提取物包含但不限于以下八种黄酮化合物,八种黄酮化合物为异荭草苷、荭草苷、牡荆素、异杜荆素、槲皮素3-氧-葡萄糖甙、木犀草苷、紫云英苷和木犀草素4’-O-葡萄糖苷,八种黄酮化合物的结构式如下:
进一步,所述八种黄酮化合物总含量在50%以上。
一种具有抗氧化作用的总黄酮提取物的制备方法,包括以下步骤:干燥黄芫花,回流提取,减压浓缩至无醇,加入蒸馏水进行溶解、沉淀,然后离心,上层液经大孔树脂分离富集,洗脱、浓缩干燥,得到具有抗氧化作用的总黄酮提取物(黄芫花总黄酮提取物)。
进一步,所述步骤中回流提取用体积比为60~90%乙醇,蒸馏水为黄芫花重量的5~10倍,洗脱用体积比为20~50%的乙醇或水。
一种具有抗氧化作用的总黄酮提取物的应用,在制备抗氧化相关的药物或保健食品中的应用。
进一步,所述抗氧化相关的药物为具有抗氧化作用的总黄酮提取物加入药学可接受的辅料制成药剂学可接受的常规剂型。
再进一步,所述常规剂型为胶囊剂、片剂、散剂、颗粒剂、凝胶剂、缓释剂、口服液或滴丸剂。
与现有技术相比本发明具有以下优点:
本发明为首次制备了具有8个不同构型的黄酮物质(结构见图1)的总黄酮提取物,且8个不同构型的黄酮物质总含量为50%以上,为8个不同构型的黄酮物质提取物或者黄芫花黄酮提取物提供重要技术。
本发明发现了黄芫花总黄酮提取物的药用功能,将其用于抗氧化功能方面,并可制备成清除体内自由基或者抗氧化相关的药物,从而为黄芫花总黄酮提取物药用或保健功能的临床应用开拓新的领域。
经典FRAP(铁离子还原/抗氧化能力法)总抗氧化能力和清除DPPH·实验结果表明黄芫花总黄酮提取物具有明显的抗氧化作用。
本发明的黄芫花总黄酮提取物药理作用较强,用于预防、调理和治疗氧化应激产生体内自由基过多症状,其抗氧化功效明显、起效较快、不良反应较小、价格低廉,具有良好的应用前景。
本发明可单独使用黄芫花总黄酮提取物制备预防和治疗抗氧化相关的药物或保健食品。
附图说明
图1为8种黄酮的化学结构式;
图2为黄芫花总黄酮提取物和8个黄酮混合标准品的HPLC图谱(λ=254nm)。
具体实施方式
结合具体实施例,进一步阐述本发明。但这些实施例仅限于说明本发明而不用于限制本发明的范围。
实施例中未注明具体实验条件的实验方法,通常按照常规条件操作,或按照生产厂家推荐的条件操作。
实施例1
一种具有抗氧化作用的总黄酮提取物的制备方法,包括以下步骤:8种黄酮的分离鉴定:3千克干燥黄芫花,10倍70%乙醇回流提取2次;减压浓缩至无醇;加入5倍蒸馏水进行溶解、沉淀,然后离心;取上层液经大孔树脂分离富集,先用水洗脱,然后用30%乙醇-水洗脱并收集洗脱液,然后浓缩干燥即得具有抗氧化作用的总黄酮提取物(黄芫花总黄酮提取物);取一定量的提取物再经过LH-20凝胶色谱进行层析,用30%乙醇-水洗脱,根据TLC结果进行合并收集;然后用HPLC进行分离,最后分离纯化8个黄酮纯品,8个黄酮化合物进行ESIMS和NMR分析,并与文献数据和标准品比对,8个黄酮化合物(结构见附图)分别鉴定为异荭草苷(1)、荭草苷(2)、牡荆素(3)、异杜荆素(4)、槲皮素3-氧-葡萄糖甙(5)、木犀草苷(6)、紫云英苷(7)和木犀草素4’-氧-葡萄糖苷(8),8个黄酮化合物的ESIMS和NMR的数据如下:
化合物(1):淡黄色粉末,ESI-MS m/z:471[M+Na]+,分子式为C21H20O11,1H-NMR(600MHz,DMSO-d6)δ:12.90(1H,s,5-OH),7.51(1H,d,J=8.4Hz,H-6),7.24(1H,d,J=8.4Hz,H-2′),6.81(1H,s,H-3),4.88(1H,d,J=7.2Hz,H-1),3.73(1H,d,J=11.4Hz,H-6a″);13C-NMR(150MHz,DMSO-d6)δ:164.4(C-2),104.0(C-3),181.8(C-4),157.4(C-5),113.6(C-6),163.2(C-7),94.1(C-8),161.5(C-9),103.8(C-10),124.7(C-1′),113.6(C-2′),147.0(C-3′),148.6(C-4′),116.0(C-5′),118.6(C-6′).该数据与文献(FAN JS,etal.J Food Drug Anal 2015,23(2):821-827)报道数据相一致,故鉴定为异荭草苷。
化合物(2):黄色粉末,ESI-MS m/z:471[M+Na]+,分子式为C21H20O11,1H-NMR(600MHz,DMSO-d6)δ:6.90(1H,d,J=8.4Hz,H-5′),6.27(1H,s,H-6),4.58(1H,s,H-1″),3.89(1H,s,H-6a″),3.59(1H,s,H-6b″),3.17-3.46(3H,m,H-3″,4″,5″);13C-NMR(150MHz,DMSO-d6)δ:177.8(C-4),161.1(C-7),156.4(C-9),121.0(C-1′),119.5(C-2′),115.2(C-5′),120.9(C-6′),107.7(C-8),103.9(C-10),102.3(C-3),98.6(C-6),77.5(C-3″),74.3(C-1″),71.9(C-4″),70.0(C-2″),62.8(C-6″),该数据与文献(Wagner H,etal.Phytochemistry,1971,10(10):2553-2554)报道数据相一致,故确定化合物为荭草苷。
化合物(3):黄色粉末,ESI-MS m/z:433[M+H]+,分子式为C21H20O10,1H-NMR(600MHz,DMSO-d6)δ:13.10(1H,s,OH-5),8.02(1H,d,J=8.7Hz,H-2′,6′),6.89(1H,d,J=8.7Hz,H-3′,5′),6.77(1H,s,H-6),6.25(1H,s,H-3),4.68(1H,d,J=9.9Hz,H-1′);13C-NMR(150MHz,DMSO-d6)δ:164.0(C-2),102.5(C-3),182.2(C-4),156.0(C-5),98.2(C-6),162.7(C-7),104.1(C-8),162.7(C-9),104.6(C-10),121.7(C-1′),129.0(C-2′,6′),115.9(C-3′,5′),160.5(C-4′),78.7(C-1′),73.4(C-2′),70.9(C-3′),70.5(C-4′),81.9(C-5′),该数据与文献(Feng Y,et al.Chem Pharm Bull 2004,52(12):1440-1444)报道数据相一致,故确定化合物为杜荆素。
化合物(4):黄色粉末,ESI-MS m/z:433[M+H]+,分子式为C21H20O10,1H-NMR(600MHz,DMSO-d6)δ:13.56(1H,s,5-OH),7.93(2H,d,J=8Hz,H-2′,6′),6.92(2H,d,J=8Hz,H-3′,5′),6.77(1H,s,H-3),6.51(1H,s,H-8),4.58(1H,d,J=9Hz,H-1″),3.10-4.04(5H,m,糖上质子);13C-NMR(150MHz,DMSO-d6)δ:163.5(C-2),102.8(C-3),182.0(C-4),160.6(C-5),108.9(C-6),163.4(C-7),93.6(C-8),156.3(C-9),103.4(C-10),121.1(C-1′),128.5(C-2′,6′),116.0(C-3′,5′),161.2(C-4′),73.1(C-1″),70.6(C-2″),79.0(C-3″),70.2(C-4″),81.6(C-5″),61.6(C-6″),该数据与文献(Pedras MSC,etal.Phytochemistry,2003,64:949–956)报道数据相一致,故确定化合物为异杜荆素。
化合物(5):黄色粉,ESI-MS m/z:465[M+H]+,分子式为C21H20O12,1H-NMR(600MHz,DMSO-d6)δ:6.33(1H,d,J=2.0Hz,H-2′),6.13(1H,dd,J=2.0,8.0Hz,H-2),12.62(2H,d,J=8.0Hz,H-5,5′),5.44(1H,dd,J=8.0,2.0Hz,H-6).13C-NMR(150MHz,DMSO-d6)δ:156.6(C-1),133.2(C-2),177.1(C-3),161.2(C-4),99.3(C-5),161.2(C-6),93.9(C-7),156.6(C-8),101.1(C-9),121.7(C-10),115.3(C-1′),145.0(C-2′),148.8(C-3′),116.0(C-4′),121.7(C-5′),101.1(C-6′),该数据与文献(周志宏,等。云南植物研究,2000,22(1):90-96)报道数据相一致,故确定化合物为槲皮素3-氧-葡萄糖甙。
化合物(6):黄色针晶,ESI-MS m/z:449[M+H]+,分子式为C21H20O11,1H-NMR(600MHz,DMSO-d6)δ:7.51(1H,dd,J=8.4,2.4Hz,H-6'),7.50(1H,d,J=2.4Hz,H-2'),6.82(1H,s,H-3),6.50(1H,d,J=1.8Hz,H-6),5.07(1H,d,J=7.2Hz,H-1″);13C-NMR(150MHz,DMSO-d6)δ:163.2(C-2),104.0(C-3),181.8(C-4),161.4(C-5),99.0(C-6),163.2(C-7),94.1(C-8),157.4(C-9),105.5(C-10),124.7(C-1'),113.6(C-2'),146.9(C-3'),151.9(C-4'),116.0(C-5'),118.5(C-6'),100.1(C-1″),73.2(C-2″),77.3(C-3″),69.8(C-4″),76.1(C-5″),60.0(C-6″),该数据与文献(Markham KR,et al.Tetrahedron,1978,34(9):1389-1397)报道数据相一致,故确定化合物为木犀草苷。
化合物(7):淡黄色粉末,ESI-MS m/z:471[M+Na]+,分子式C21H20O11,1H-NMR(600MHz,DMSO-d6)δ:3.26(2H,m,H-2″,3″),3.44(1H,m,H-5″),3.71(1H,d,J=10.8Hz,H-6b″),5.07(1H,d,J=7.2Hz,H-1″),6.44(1H,d,J=1.8Hz,H-6),6.78(1H,d,J=1.8Hz,H-8),6.75(1H,s,H-3),6.90(1H,d,J=8.4Hz,H-5′),7.42(1H,d,J=1.8Hz,H-2′),7.45(1H,dd,J=8.4,1.8Hz,H-6′),12.99(1H,s,5-OH).13C-NMR(100MHz,DMSO-d6)δ:164.6(C-2),103.2(C-3),182.0(C-4),163.0(C-5),99.6(C-6),161.3(C-7),94.8(C-8),157.1(C-9),105.4(C-10),121.5(C-1′),113.6(C-2′),145.9(C-3′),150.1(C-4′),116.1(C-5′),119.3(C-6′),99.6(C-1″),73.2(C-2″),76.5(C-3″),69.6(C-4″),77.3(C-5″),60.7(C-6″),该数据与文献(Mourad et al.Phytochemistry,1990,29(7):2295-2297)报道数据相一致,故确定化合物为紫云英苷。
化合物(8):黄色针晶,ESI-MS m/z:471[M+Na]+,分子式为C21H20O11,1H-NMR(600MHz,DMSO-d6)δ:12.90(1H,s,5-OH),7.52(1H,d,J=8.4Hz,H-2'),7.25(1H,d,J=9.0Hz,H-5'),6.82(1H,s,H-3),6.49(1H,d,J=2.4Hz,H-8),6.20(1H,d,J=2.4Hz,H-6),4.88(1H,d,J=7.2Hz,H-1″);13C-NMR(150MHz,DMSO-d6)δ:164.5(C-2),104.0(C-3),181.7(C-4),161.4(C-5),99.0(C-6),163.2(C-7),94.0(C-8),157.4(C-9),104.0(C-10),124.7(C-1'),113.6(C-2'),1476.9(C-3'),148.5(C-4'),116.0(C-5'),118.5(C-6'),101.2(C-1″),73.2(C-2″),77.3(C-3″),69.8(C-4″),75.8(C-5″),60.7(C-6″),该数据与文献(王祝年,等。热带亚热带植物学报,2007,15(4):359-362)报道数据相一致,故确定化合物为木犀草素4'-氧-葡萄糖苷基本一致。
实施例2:
一种具有抗氧化作用的总黄酮提取物的制备方法,包括以下步骤:干燥黄芫花,用体积比为60%的乙醇回流提取,减压浓缩,加入5倍黄芫花重量的蒸馏水进行溶解、沉淀,然后离心,上层液经大孔树脂分离富集,用体积比为20%的乙醇或水洗脱、浓缩干燥即得具有抗氧化作用的总黄酮提取物(黄芫花总黄酮提取物)。经过HPLC分析:黄芫花总黄酮提取物所含的8个总黄酮的总含量达50%以上,详见附图2。
实施例3:
一种具有抗氧化作用的总黄酮提取物的制备方法,包括以下步骤:干燥黄芫花,用体积比为70%的乙醇回流提取,减压浓缩,加入7倍黄芫花重量的蒸馏水进行溶解、沉淀,然后离心,上层液经大孔树脂分离富集,用体积比为30%的乙醇或水洗脱、浓缩干燥即得总黄酮有效部位提取物。
实施例4:
一种具有抗氧化作用的总黄酮提取物的制备方法,包括以下步骤:干燥黄芫花,用体积比为80%的乙醇回流提取,减压浓缩,加入8倍黄芫花重量的蒸馏水进行溶解、沉淀,然后离心,上层液经大孔树脂分离富集,用体积比为40%的乙醇或水洗脱、浓缩干燥即得具有抗氧化作用的总黄酮提取物(黄芫花总黄酮提取物)。
实施例5:
一种具有抗氧化作用的总黄酮提取物的制备方法,包括以下步骤:干燥黄芫花,用体积比为90%乙醇回流提取,减压浓缩,加入10倍黄芫花重量的蒸馏水进行溶解、沉淀,然后离心,上层液经大孔树脂分离富集,50%乙醇或水洗脱、浓缩干燥即得具有抗氧化作用的总黄酮提取物(黄芫花总黄酮提取物)。
实施例6:
黄芫花总黄酮提取物的抗氧化作用测试。
1、总抗氧化能力的测定:将300mmol/L醋酸-醋酸钠缓冲液(pH=3.6)、10mmol/LTPTZ溶液与20mmol/L FeCl3溶液以10:1:1比例混匀,制成FRAP工作液。吸取20μL系列浓度(0.07μmol/L、0.16μmol/L、0.33μmol/L、0.49μmol/L、0.66μmol/L、1.32μmol/L)的FeSO4溶液于96孔酶标板中,再分别加入150μL的FRAP工作液,37℃静置10min,于593nm读取吸光度值,以FRAP值(即FeSO4溶液的浓度)为纵坐标,吸光度值(OD)为横坐标绘制标准曲线。取浓度为100μg/mL的Vc、总黄酮及黄酮化合物部分按同样方法进行实验,得到相应总抗氧化能力(FRAP)值。
2、DPPH·清除率的测定:用无水乙醇配制0.1mmol/L DPPH·溶液备用。配制浓度梯度为1μg/mL、5μg/mL、10μg/mL、15μg/mL、25μg/mL、50μg/mL、75μg/mL、100μg/mL、200μg/mL的Vc溶液、总黄酮溶液、黄酮化合物溶液适量。分别吸取100μL Vc溶液于96孔酶标板中,再分别加入100μL DPPH·溶液,室温避光反应10min,于517nm读取吸光度值。同时用蒸馏水和无水乙醇做空白。以DPPH·清除率为纵坐标,溶液浓度(mg/mL)为横坐标绘制清除率曲线,用Vc做标准对照。
DPPH·清除率(%)=1-(A1-A2)/(A3-A4)×100%,用EC50来表示清除率为50%时样品的浓度。其中,A1为样品组的吸光度值;A2为样品对照组的吸光度值;A3为对照组的吸光度值;A4为空白组的吸光度值。
3.实验结果。
黄芫花总黄酮提取物及8个黄酮单体成分的总抗氧化能力和清除DPPH·的能力结果见下表。
黄芫花总黄酮提取物抗氧化实验结果表
由实验结果可知,黄芫花总黄酮提取物及各个黄酮均表现出了较强的抗氧化和清除DPPH·的能力,其中牡荆素、异杜荆素、紫云英苷、木犀草素4’-氧-葡萄糖苷和总黄酮提取物的抗氧化能力远高于阳性药物Vc;木犀草苷清除DPPH·的能力也要好于Vc,异荭草苷、荭草苷、槲皮素3-氧-葡萄糖甙和总黄酮提取物清除DPPH·的能力与Vc相一致。可见,黄芫花中黄酮类成分表现出了较好的抗氧化能力,极有可能是其发挥抗肝炎作用的药效物质基础。因此,本发明的黄芫花总黄酮提取物可用于预防和治疗抗氧化相关的药物或保健食品。
Claims (7)
2.根据权利要求1所述的一种具有抗氧化作用的总黄酮提取物,其特征在于,所述八种黄酮化合物总含量在50%以上。
3.一种具有抗氧化作用的总黄酮提取物的制备方法,其特征在于,包括以下步骤:干燥黄芫花,回流提取,减压浓缩至无醇,加入蒸馏水进行溶解、沉淀,然后离心,上层液经大孔树脂分离富集,洗脱、浓缩干燥,得到具有抗氧化作用的总黄酮提取物。
4.根据权利要求3所述的一种具有抗氧化作用的总黄酮提取物的制备方法,其特征在于,所述步骤中回流提取用体积比为60~90%乙醇,蒸馏水为黄芫花重量的5~10倍,洗脱用体积比为20~50%乙醇或水。
5.一种具有抗氧化作用的总黄酮提取物的应用,其特征在于,所述具有抗氧化作用的总黄酮提取物在制备抗氧化相关的药物或保健食品中的应用。
6.根据权利要求5所述的一种具有抗氧化作用的总黄酮提取物的应用,其特征在于,所述抗氧化相关的药物为具有抗氧化作用的总黄酮提取物加入药学可接受的辅料制成药剂学可接受的常规剂型。
7.根据根据权利要求6所述的一种具有抗氧化作用的总黄酮提取物的应用,其特征在于,所述常规剂型为胶囊剂、片剂、散剂、颗粒剂、凝胶剂、缓释剂、口服液或滴丸剂。
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