平榛叶化学成分及其生物活性的研究
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摘要
榛叶为桦木科榛属植物平榛(Corylus heterophylla Fisch)的叶子。《中国长白山药用植物彩色图志》中记载:榛子:益气,开胃,明目,用于病后体虚,食少疲倦。水煎服,用量30-60g。榛的雄花具有消炎、消肿、止痛作用,可用于皮肤炎症、冻伤等,是一味民间沿用历史悠久的药用植物。榛为每年生灌木,采集方便,在我国东北榛资源丰富。本文在综述榛叶研究进展的基础上,对其化学成分和药理活性进行了深入的研究。
本论文创新之处如下:
首次对榛叶85%乙醇总提取物的化学成分进行了研究,利用分步萃取法,正、反向硅胶柱层析及半制备HPLC等色谱手段分离得到32个化合物,通过理化性质及波谱(1HNMR、13CNMR、HMBC、HMQC、HRMS等)解析,鉴定了其中30个单体化合物的结构,分别属于口山酮类、甾醇类、黄酮类、菲类、糖类等。其中化合物3-18和化合物24-30等23个化合物均为首次从该植物中获得;化合物1、2为未见文献报道的新化合物,分别命名为榛子素A和榛子素B。
首次对榛叶乙酸乙酯萃取部分和单体化合物Gartanin(化合物3)的降血脂活性进行了研究。实验结果表明:与模型组比较,乙酸乙酯部分可明显降低高脂模型小鼠血清甘油三酯含量(P<0.05),具有降低血脂的作用;单体化合物Gartanin可明显降低高脂模型小鼠血清总胆固醇含量(P<0.05),具有降低血脂的作用。
首次采用荧光酶标记法对新化合物榛子素B进行了抗金属蛋白酶活性的研究。实验结果表明:榛子素B对金属蛋白酶有显著的抑制作用。由于金属蛋白酶抑制剂具有显著的抗癌作用,故本研究成果为继续开发榛子素B成为抗癌药物提供了科学依据。
本论文不足之处在于未对含量很低的新化合物榛子素A进行生物活性研究。
In this paper, the chemical constituents and pharmacological activities of the leaf of Corylus heterophylla Fisch were studied.
According to the references, a few compounds were isolated and identified as so far, such as steroid, triterpenoid, and so on. Only few references were reported about the chemical constituents from the leaves of Corylus heterophylla Fisch. Modern pharmacyological studies showed that the herb had the effects of benefiting vital energy, promoting appetite and improving eyesight. In order to find out more new chemical constituents furtherly in the leaves of Corylus heterophylla Fisch and develop the accurate pharmacological activites, comprehensive research were carried out in this paper. The research methods and results were showed as follow:
The dried leaves of Corylus heterophylla Fisch, collected in Mt.Changbai, extracted with 85% alcohol. In order to be concentrated, the alcohol solution were evaporated with distillation method at normal pressure.Then the concentrated solution was dissolved with water. Next the water solution was extracted with petroleum ether, chloroform, acetic ether and n-butyl alcohol respectively at room temperature. Finally, thirty two compounds were obtained from chloroform part, acetic ether part and n-butyl alcohol part respectively, which were dealt with silica gel chromatogramphy by using several kinds of solvent systems, HPLC and recrystallizing repeatly. Among of them, thirty compounds' structures were identified on the basis of chemical and spectroscopic evidence (1HNMR, 13CNMR, 2DNMR, HRMS), they are 7,8,10-trimethoxy-4,5-dihydrophenan thro[2,3]dixole ( 1 ), 1,3-dihydroxy-5,8-dimethoxy- 2,4-bis(3-methylbut-2-enyl)-xanthen-9-on(e2),gartanin,(3),kaempferol,(4),2,7-dihydroxy- 3,5-dimethoxy-9, 10-dihydrophe nanthrene, 6-methoxycoelonin,(5),2,3,5,7- tetramethoxy-9, 10-dihydrophenanthrene,(6),kaempferol-3-O-β-D-glucopyranoside,(7),kaempferol-3- qpiofur-anosylglucopyrano side, apioliquiritin,(8),8-deoxygartanin,(9),8-hydroxycudra- xanthone G,(10),7-hydroxy dihydroflavonone-4’-O-β-D-glucopyranoside,(11),7,4’- dehydroxyflavonone,(12),7-hydroxydihydroflavonone-4’-O-β-D-glucopy ranoside, apioli- quiritin,(13),2,4-dihydroxy chalcone-4’-O-β-D-glucopyranoside,(14),2,4-dihydro- xychalcone-4’-O-β-D-glucopyrano side,fructofuranoside ,( 15 ), daucosterol ,( 16 ), 4,4’-dimethoxy-5,5’-bibenzolignin[d] [2,3]dixole,(17),2',6'-diethylbiphenyl-2-ol,(18),β-Sitosterol,(19),2,4,4’- trihydroxychalcone,(20),7,22-dien-3- ergosterol,( 21), ethyl glucopyran oside,( 22),α-D-(6-O-sinapoyl)-glucopy ranosyl-β-D- (3-O-sinapoyl)-fructofuranose,(23),4-hydroxy-3-methoxy benzoic acid, vanillic acid,(24),ρ-hydroxybenzoic acid,(25),pyrocatechol,(26),palmitic acid,(27),2-methyl acrylaldehyde ,( 28 ), phenylacetic acid ,( 29 ), 6,7-dimethoxy-5-hydroxycoumarin ,(30).Among of them, compound 3-18 and 24-30 are all separated from this plant firstly. Both compound 1 and 2 are new chemical compounds.
The effects of ethyl acetate extract of hazel leaves (EEHL) and gartanin on blood lipid metabolism were investigated in experimental hyperlipidemia mice. The results showed that EEHL could decrease the level of TG level and gartanin could decrease the level of TC level in blood serum of experimental hyperlipidemia mice.
The new compound 2 had been carried out anti-metalloproteinase activity with the method of fluorescence enzyme labeling for the first time. The experimental results showed that compound 2 had significant inhibitory effect on Matrix Metalloproteinase (MMP). Because the metalloproteinase inhibitor has the effect of anti-cancer, the results could provide a scientific basis for developing compound 2 as anti-cancer drugs.
本论文创新之处如下:
首次对榛叶85%乙醇总提取物的化学成分进行了研究,利用分步萃取法,正、反向硅胶柱层析及半制备HPLC等色谱手段分离得到32个化合物,通过理化性质及波谱(1HNMR、13CNMR、HMBC、HMQC、HRMS等)解析,鉴定了其中30个单体化合物的结构,分别属于口山酮类、甾醇类、黄酮类、菲类、糖类等。其中化合物3-18和化合物24-30等23个化合物均为首次从该植物中获得;化合物1、2为未见文献报道的新化合物,分别命名为榛子素A和榛子素B。
首次对榛叶乙酸乙酯萃取部分和单体化合物Gartanin(化合物3)的降血脂活性进行了研究。实验结果表明:与模型组比较,乙酸乙酯部分可明显降低高脂模型小鼠血清甘油三酯含量(P<0.05),具有降低血脂的作用;单体化合物Gartanin可明显降低高脂模型小鼠血清总胆固醇含量(P<0.05),具有降低血脂的作用。
首次采用荧光酶标记法对新化合物榛子素B进行了抗金属蛋白酶活性的研究。实验结果表明:榛子素B对金属蛋白酶有显著的抑制作用。由于金属蛋白酶抑制剂具有显著的抗癌作用,故本研究成果为继续开发榛子素B成为抗癌药物提供了科学依据。
本论文不足之处在于未对含量很低的新化合物榛子素A进行生物活性研究。
In this paper, the chemical constituents and pharmacological activities of the leaf of Corylus heterophylla Fisch were studied.
According to the references, a few compounds were isolated and identified as so far, such as steroid, triterpenoid, and so on. Only few references were reported about the chemical constituents from the leaves of Corylus heterophylla Fisch. Modern pharmacyological studies showed that the herb had the effects of benefiting vital energy, promoting appetite and improving eyesight. In order to find out more new chemical constituents furtherly in the leaves of Corylus heterophylla Fisch and develop the accurate pharmacological activites, comprehensive research were carried out in this paper. The research methods and results were showed as follow:
The dried leaves of Corylus heterophylla Fisch, collected in Mt.Changbai, extracted with 85% alcohol. In order to be concentrated, the alcohol solution were evaporated with distillation method at normal pressure.Then the concentrated solution was dissolved with water. Next the water solution was extracted with petroleum ether, chloroform, acetic ether and n-butyl alcohol respectively at room temperature. Finally, thirty two compounds were obtained from chloroform part, acetic ether part and n-butyl alcohol part respectively, which were dealt with silica gel chromatogramphy by using several kinds of solvent systems, HPLC and recrystallizing repeatly. Among of them, thirty compounds' structures were identified on the basis of chemical and spectroscopic evidence (1HNMR, 13CNMR, 2DNMR, HRMS), they are 7,8,10-trimethoxy-4,5-dihydrophenan thro[2,3]dixole ( 1 ), 1,3-dihydroxy-5,8-dimethoxy- 2,4-bis(3-methylbut-2-enyl)-xanthen-9-on(e2),gartanin,(3),kaempferol,(4),2,7-dihydroxy- 3,5-dimethoxy-9, 10-dihydrophe nanthrene, 6-methoxycoelonin,(5),2,3,5,7- tetramethoxy-9, 10-dihydrophenanthrene,(6),kaempferol-3-O-β-D-glucopyranoside,(7),kaempferol-3- qpiofur-anosylglucopyrano side, apioliquiritin,(8),8-deoxygartanin,(9),8-hydroxycudra- xanthone G,(10),7-hydroxy dihydroflavonone-4’-O-β-D-glucopyranoside,(11),7,4’- dehydroxyflavonone,(12),7-hydroxydihydroflavonone-4’-O-β-D-glucopy ranoside, apioli- quiritin,(13),2,4-dihydroxy chalcone-4’-O-β-D-glucopyranoside,(14),2,4-dihydro- xychalcone-4’-O-β-D-glucopyrano side,fructofuranoside ,( 15 ), daucosterol ,( 16 ), 4,4’-dimethoxy-5,5’-bibenzolignin[d] [2,3]dixole,(17),2',6'-diethylbiphenyl-2-ol,(18),β-Sitosterol,(19),2,4,4’- trihydroxychalcone,(20),7,22-dien-3- ergosterol,( 21), ethyl glucopyran oside,( 22),α-D-(6-O-sinapoyl)-glucopy ranosyl-β-D- (3-O-sinapoyl)-fructofuranose,(23),4-hydroxy-3-methoxy benzoic acid, vanillic acid,(24),ρ-hydroxybenzoic acid,(25),pyrocatechol,(26),palmitic acid,(27),2-methyl acrylaldehyde ,( 28 ), phenylacetic acid ,( 29 ), 6,7-dimethoxy-5-hydroxycoumarin ,(30).Among of them, compound 3-18 and 24-30 are all separated from this plant firstly. Both compound 1 and 2 are new chemical compounds.
The effects of ethyl acetate extract of hazel leaves (EEHL) and gartanin on blood lipid metabolism were investigated in experimental hyperlipidemia mice. The results showed that EEHL could decrease the level of TG level and gartanin could decrease the level of TC level in blood serum of experimental hyperlipidemia mice.
The new compound 2 had been carried out anti-metalloproteinase activity with the method of fluorescence enzyme labeling for the first time. The experimental results showed that compound 2 had significant inhibitory effect on Matrix Metalloproteinase (MMP). Because the metalloproteinase inhibitor has the effect of anti-cancer, the results could provide a scientific basis for developing compound 2 as anti-cancer drugs.
引文
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