加拿大红枫和美国蓝莓花化学成分及生物活性研究
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摘要
本文对加拿大红枫(Red maple)和美国蓝莓花(Blueberry flower)的化学成分及其清除DPPH自由基和抑制α-葡萄糖苷酶活性进行了研究。根据化合物的理化性质,并采用紫外图谱,红外图谱,NMR(包括二维NMR)和高分辨质谱等多种现代谱学手段鉴定了55个具有不同结构的天然化合物(包括21个没食子酸衍生物,20个黄酮,10个苯丙素类化合物,1个香豆素和3木脂素)。其中新化合物11个。生物活性测试结果表明大部分化合物都具有很强的清除DPPH自由基活性,部分没食子酸衍生物以及黄酮苷类化合物具有很强的抑制α-葡萄糖苷酶活性。对没食子酸衍生物,黄酮和苯丙素类化合物的清除DPPH自由基和抑制α-葡萄糖苷酶活性进行构效关系的探讨。本毕业论文的具体研究内容及结果简述如下：
1)本文利用硅胶,大孔树脂,Sephadex LH-20, ODS及制备HPLC柱层析等多种色谱分离技术,从加拿大红枫树枝(stem)部位分离并鉴定了27个化合物。其中5个为新化合物：maplexin A (2)、maplexin B (3)、maplexin C (5)、 maplexin D(6)和maplexin E (12)。22个为已知化合物：条茶槭丙素(1),条茶槭乙素(4),条茶槭甲素(7),3,6-di-O-galloyl-1,5-anhydro-D-glucitol(8),3-甲氧基-4-羟基苯酚-1-O-β-D-(6'-O-没食子酰)-葡萄糖苷(17),儿茶素(18),表儿茶素(19),表儿茶素-3-O-没食子酸酯(20),原花青素A6(21),原花青素A2(22),槲皮素-3-O-α-L-鼠李糖苷(23),槲皮素-3-O-(3"-没食子酰基)-吡喃鼠李糖苷(24),槲皮素-3-O-(2"-没食子酰基)-吡喃鼠李糖苷(25),去甲络石苷元8'-O-β-D-葡萄糖苷(26),7,8-二羟基-6-甲氧基-香豆素(27),根皮苷(28),没食子酸(29),没食子酸甲酯(30),3,4-二羟基,5-甲氧基-苯甲酸甲酯(31),丁香酸甲酯(32),香草酸甲酯(33)和3,5-二羟基,4-甲氧基-苯甲酸(34)。
2)从加拿大红枫树皮(bark)部位分离并鉴定了12个化合物,其中6个为新化合物：maplexin F (9)、maplexin G (10)、maplexin H (11)、maplexin Ⅰ(13) rubrumosides A(14)和rubrumosides B(16)；1个为已知化合物：nymphaeoside A(15)；以及5个和从树枝(stem)部位分离得到的化合物重复：条茶槭丙素(1),条茶槭乙素(4),条茶槭甲素(7),没食子酸(29),香草酸甲酯(33)。从加拿大红枫树枝(stem)和树皮(bark)部位共分离得到了34个单体化合物,其中11个为新化合物。化合物15,17,21,22,26,28,31和34为首次从槭树科植物中分离得到；化合物1,4,7,8,20,24,25,32和33为首次从该植物中分离得到。
3)对从加拿大红枫中分离得到的化合物进行体外抑制α-葡萄糖苷酶和清除DPPH自由基活性测试,结果表明新化合物Maplexins E-I系列化合物都具有很好的体外抑制α-葡萄糖苷酶活性,其半数抑制浓度(ICso)为7.9-16.1μM。除化合物26,31-34外,其余化合物都具有很强的清除DPPH自由基活性其半数抑制浓度(IC50)为7.7-77.5μM。通过比较分析maplexins(或者ginnalin)化合物(1-13)的抑制α-葡萄糖苷酶活性和结构之间的关系,发现结构中没食子酰基的个数及连接位置对活性都有很大的影响,结构中有三个没食子酰基的化合物活性最强(Maplexins E-I,9-13),一个没食子酰基的活性则最弱(MaplexinsA-B和Ginnalins B-C,1-4);结构中连接有两个没食子酰基的化合物(5-8),其糖的6位羟基连有没食子酰基的化合物(7-8)活性强于6位没有没食子酰基连接的化合物(5-6)。
4)本文对美国蓝莓花进行了化学成分研究,从乙酸乙酯萃取部位分离并鉴定了21个化合物,包括10个苯丙素类化合物和11个黄酮类化合物。它们分别为5-O-咖啡酰莽草酸(35),5-O-咖啡酰奎宁酸(36),5-O-咖啡酰奎宁酸甲酯(37),3,5-二咖啡酰奎宁酸甲酯(38),咖啡酸甲酯(39),5-O-肉桂酰奎宁酸(40),5-O-肉桂酰奎宁酸甲酯(41),肉桂酸甲酯(42),Rosin (43),2'-O-β-D-Glucosylrosine (44),槲皮素-3-O-β-D-葡萄糖苷(45),槲皮素-3-O-β-D-半乳糖苷(46),槲皮素-3-O-α-L-阿拉伯糖苷(47),杨梅素-3-O-β-D-葡萄糖苷(48),杨梅素-3-O-β-D-半乳糖苷(49),槲皮素-3-O-(6"-O-肉桂酰)-β-D-葡萄糖苷(50),槲皮素-3-O-(2"-O-肉桂酰)-β-D-葡萄糖苷(51),山柰酚-3-O-(6"-O-肉桂酰)-β-D-葡萄糖苷(52),另外3个黄酮为苯丙素取代的儿茶素类化合物(53-55)。
5)对从蓝莓花中分离得到的化合物进行体外抑制α-葡萄糖苷酶和清除DPPH自由基活性测试,结果表明黄酮类化合物都具有很好的体外抑制α-葡萄糖苷酶活性,其半数抑制浓度(IC50)为28.9-137.5μM；而苯丙素类化合物活性则很弱,仅3,5-二咖啡酰奎宁酸甲酯(38)表现出活性,其半数抑制浓度(IC50)为99.9μM；除化合物40-44和52外,其余化合物都具有很强的清除DPPH自由基活性,其半数抑制浓度(IC50)为7.8-59.4μM；其抗氧化活性与酚羟基的数目有关。
Chemical constituents and DPPH free radical scavenging and a-glucosidase inhibition activities of red maple and blueberry flower were investigated in this paper. A total of55different compounds including twenty-one gallic acid derivatives, twenty flavonoids, ten phenylpropanoids, one coumarin and three lignans were isolated and identified. All of their structures were extensively identified by the combination of physicochemical properties, UV spectrum, infrared spectrum, NMR spectrum (including2D NMR) and high-resolution mass spectrum. Among those isolated compounds, eleven were new compounds. Biological activities tests indicated most compounds showed very stronger DPPH free radical scavenging activity, and some gallic acid derivatives and Flavonol glycosides showed powerful a-glucosidase inhibition activity. The structure-activity relationship (SAR) of gallic acid derivatives, flavonoids and phenylpropanoids were briefly discussed. The detailed contents and results of this paper are briefly as follows:
A total of twenty-seven compounds were isolated and purified by the combination of column chromatography of Silica gel coupled with macroporous resin, Sephadex LH-20, RP-ODS and preparative HPLC chromatography from red maple stem. They are five new compounds, including maplexin A (2), maplexin B (3), maplexin C (5), maplexin D (6) and maplexin E (12), respectively. Other twenty-two compounds are known, including Ginnalin C (1), Ginnalin B (4), Ginnalin A (7),3,6-di-O-galloyl-1,5-anhydro-D-glucitol (8),3-Methoxy-4-hydroxyphenol-1-O-P-D-(6'-O-galloyl)-glucopyranoside (17), catechin (18), epicatechin (19), epicatechin-3-O-gallate (20), procyanidins A6(21), procyanidins A2(22), quercetin-3-O-a-L-rhamnoside (23), quercetin-3-O-3"-galloyl-rhamnoside (24), quercetin-3-O-2"-galloyl-rhamnos-ide (25), Nortrachelogenin-8'-O-β-D-glucopyranoside (26),7,8-dihydroxy-6-methoxycoumarin (27), phloridzin (28), gallic acid (29), methyl gallate (30),3,4-dihydroxy-5-methoxybenzoic acid methyl ester (31), methyl syringate (32), methyl vanillate (33) and3,5-dihydroxy-4-methoxybenzoic acid (34).
A total of twelve compounds were isolated and identified from red maple bark. They are six new compounds, including maplexin F (9), maplexin G (10), maplexin H (11), maplexin I (13), rubrumosides A (14) and rubrumosides B (16). Other six compounds are known, including nymphaeoside A (15) and the same five compounds as isolated from red maple stem:Ginnalin C (1), Ginnalin B (4), Ginnalin A (7), gallic acid (29) and methyl vanillate (33), respectively. In short, thirty-four compounds were isolated and identified from red maple and eleven were new compounds. Compounds15,17,21,22,26,28,31and34were isolated from the family of Aceraceae for the first time, and compounds1,4,7,8,20,24,25,32and33were isolated from the plant for the first time.
All of the isolated compounds from red maple were tested for their a-glucosidase inhibition and DPPH free radical scavenging activities. New compounds Maplexins E-I all showed powerful a-glucosidase inhibitory activity with range of the IC507.9-16.1μM. All of the compounds except26,31-34showed very strong DPPH free radical scavenging activity with range of the IC507.7-77.5μM. Analysis the relationship of the structure of gallic acid derivatives and the a-glucosidase inhibitory activity, which suggested that the a-glucosidase inhibitory activities of these gallotannins were influenced by both the number and positions of the galloyl groups. Compounds1-4, which possess one galloyl group each, did not show any activity in this assay, while compounds5-8, which possess two galloyl groups each, showed moderate a-glucosidase inhibitory activity. While maplexin E-I (9-13), which contained three galloyl groups, showed powerful a-glucosidase inhibitory activity.
A total of twenty-one compounds including ten phenylpropanoids and eleven flavonoids, were isolated and purified from blueberry flower. The compounds were identified from their nuclear magnetic resonance (NMR) and mass spectral data as5-O-caffeoylshikimic acid (35),5-O-Caffeoylquinic acid (36),5-O-Caffeoylquinic acid methyl ester (37),3,5-dicaffeoylquinic acid methyl ester (38), Methyl caffeate (39),5-O-coumaroylquinic acid (40),5-O-coumaroylquinic methyl ester (41), trans-cinnamic acid methyl ester (42), Rosin (43),2'-O-β-D-Glucosylrosine (44), quercetin-3-O-β-D-glucoside (45), quercetin-3-O-β-D-galactoside (46), quercetin-3-O-α-L-arabinopyranoside (47), myricetin-3-O-β-D-glucoside (48), myricetin-3-O -β-D-galactoside (49), quercetin-3-O-(6"-O-coumaroyl)-β-D-glucoside (50), quercetin-3-O-(2"-O-coumaroyl)-β-D-glucoside (51), kaempferol-3-O-(6"-O-coumaroyl)-β-D-glucoside (52) and other three are phenylpropanoid-substituted catechins (53-55).
All of the isolated compounds from blueberry flower were tested for their α-glucosidase inhibition and DPPH free radical scavenging activities. All of the flavonoids showed powerful a-glucosidase inhibitory activity with range of the IC5028.9-137.5μM, while the phenylpropanoids showed very weak activity, only3,5-dicaffeoylquinic acid methyl ester (38) showed good activity with the IC5099.9μM. All of the compounds except40-44and52showed very strong DPPH free radical scavenging activity with range of the IC507.8-59.4μM. Analysis the relationship of the structure and the DPPH free radical scavenging activity, which suggested that the DPPH free radical scavenging activities were influenced by the number of the hydroxy groups.
1)本文利用硅胶,大孔树脂,Sephadex LH-20, ODS及制备HPLC柱层析等多种色谱分离技术,从加拿大红枫树枝(stem)部位分离并鉴定了27个化合物。其中5个为新化合物：maplexin A (2)、maplexin B (3)、maplexin C (5)、 maplexin D(6)和maplexin E (12)。22个为已知化合物：条茶槭丙素(1),条茶槭乙素(4),条茶槭甲素(7),3,6-di-O-galloyl-1,5-anhydro-D-glucitol(8),3-甲氧基-4-羟基苯酚-1-O-β-D-(6'-O-没食子酰)-葡萄糖苷(17),儿茶素(18),表儿茶素(19),表儿茶素-3-O-没食子酸酯(20),原花青素A6(21),原花青素A2(22),槲皮素-3-O-α-L-鼠李糖苷(23),槲皮素-3-O-(3"-没食子酰基)-吡喃鼠李糖苷(24),槲皮素-3-O-(2"-没食子酰基)-吡喃鼠李糖苷(25),去甲络石苷元8'-O-β-D-葡萄糖苷(26),7,8-二羟基-6-甲氧基-香豆素(27),根皮苷(28),没食子酸(29),没食子酸甲酯(30),3,4-二羟基,5-甲氧基-苯甲酸甲酯(31),丁香酸甲酯(32),香草酸甲酯(33)和3,5-二羟基,4-甲氧基-苯甲酸(34)。
2)从加拿大红枫树皮(bark)部位分离并鉴定了12个化合物,其中6个为新化合物：maplexin F (9)、maplexin G (10)、maplexin H (11)、maplexin Ⅰ(13) rubrumosides A(14)和rubrumosides B(16)；1个为已知化合物：nymphaeoside A(15)；以及5个和从树枝(stem)部位分离得到的化合物重复：条茶槭丙素(1),条茶槭乙素(4),条茶槭甲素(7),没食子酸(29),香草酸甲酯(33)。从加拿大红枫树枝(stem)和树皮(bark)部位共分离得到了34个单体化合物,其中11个为新化合物。化合物15,17,21,22,26,28,31和34为首次从槭树科植物中分离得到；化合物1,4,7,8,20,24,25,32和33为首次从该植物中分离得到。
3)对从加拿大红枫中分离得到的化合物进行体外抑制α-葡萄糖苷酶和清除DPPH自由基活性测试,结果表明新化合物Maplexins E-I系列化合物都具有很好的体外抑制α-葡萄糖苷酶活性,其半数抑制浓度(ICso)为7.9-16.1μM。除化合物26,31-34外,其余化合物都具有很强的清除DPPH自由基活性其半数抑制浓度(IC50)为7.7-77.5μM。通过比较分析maplexins(或者ginnalin)化合物(1-13)的抑制α-葡萄糖苷酶活性和结构之间的关系,发现结构中没食子酰基的个数及连接位置对活性都有很大的影响,结构中有三个没食子酰基的化合物活性最强(Maplexins E-I,9-13),一个没食子酰基的活性则最弱(MaplexinsA-B和Ginnalins B-C,1-4);结构中连接有两个没食子酰基的化合物(5-8),其糖的6位羟基连有没食子酰基的化合物(7-8)活性强于6位没有没食子酰基连接的化合物(5-6)。
4)本文对美国蓝莓花进行了化学成分研究,从乙酸乙酯萃取部位分离并鉴定了21个化合物,包括10个苯丙素类化合物和11个黄酮类化合物。它们分别为5-O-咖啡酰莽草酸(35),5-O-咖啡酰奎宁酸(36),5-O-咖啡酰奎宁酸甲酯(37),3,5-二咖啡酰奎宁酸甲酯(38),咖啡酸甲酯(39),5-O-肉桂酰奎宁酸(40),5-O-肉桂酰奎宁酸甲酯(41),肉桂酸甲酯(42),Rosin (43),2'-O-β-D-Glucosylrosine (44),槲皮素-3-O-β-D-葡萄糖苷(45),槲皮素-3-O-β-D-半乳糖苷(46),槲皮素-3-O-α-L-阿拉伯糖苷(47),杨梅素-3-O-β-D-葡萄糖苷(48),杨梅素-3-O-β-D-半乳糖苷(49),槲皮素-3-O-(6"-O-肉桂酰)-β-D-葡萄糖苷(50),槲皮素-3-O-(2"-O-肉桂酰)-β-D-葡萄糖苷(51),山柰酚-3-O-(6"-O-肉桂酰)-β-D-葡萄糖苷(52),另外3个黄酮为苯丙素取代的儿茶素类化合物(53-55)。
5)对从蓝莓花中分离得到的化合物进行体外抑制α-葡萄糖苷酶和清除DPPH自由基活性测试,结果表明黄酮类化合物都具有很好的体外抑制α-葡萄糖苷酶活性,其半数抑制浓度(IC50)为28.9-137.5μM；而苯丙素类化合物活性则很弱,仅3,5-二咖啡酰奎宁酸甲酯(38)表现出活性,其半数抑制浓度(IC50)为99.9μM；除化合物40-44和52外,其余化合物都具有很强的清除DPPH自由基活性,其半数抑制浓度(IC50)为7.8-59.4μM；其抗氧化活性与酚羟基的数目有关。
Chemical constituents and DPPH free radical scavenging and a-glucosidase inhibition activities of red maple and blueberry flower were investigated in this paper. A total of55different compounds including twenty-one gallic acid derivatives, twenty flavonoids, ten phenylpropanoids, one coumarin and three lignans were isolated and identified. All of their structures were extensively identified by the combination of physicochemical properties, UV spectrum, infrared spectrum, NMR spectrum (including2D NMR) and high-resolution mass spectrum. Among those isolated compounds, eleven were new compounds. Biological activities tests indicated most compounds showed very stronger DPPH free radical scavenging activity, and some gallic acid derivatives and Flavonol glycosides showed powerful a-glucosidase inhibition activity. The structure-activity relationship (SAR) of gallic acid derivatives, flavonoids and phenylpropanoids were briefly discussed. The detailed contents and results of this paper are briefly as follows:
A total of twenty-seven compounds were isolated and purified by the combination of column chromatography of Silica gel coupled with macroporous resin, Sephadex LH-20, RP-ODS and preparative HPLC chromatography from red maple stem. They are five new compounds, including maplexin A (2), maplexin B (3), maplexin C (5), maplexin D (6) and maplexin E (12), respectively. Other twenty-two compounds are known, including Ginnalin C (1), Ginnalin B (4), Ginnalin A (7),3,6-di-O-galloyl-1,5-anhydro-D-glucitol (8),3-Methoxy-4-hydroxyphenol-1-O-P-D-(6'-O-galloyl)-glucopyranoside (17), catechin (18), epicatechin (19), epicatechin-3-O-gallate (20), procyanidins A6(21), procyanidins A2(22), quercetin-3-O-a-L-rhamnoside (23), quercetin-3-O-3"-galloyl-rhamnoside (24), quercetin-3-O-2"-galloyl-rhamnos-ide (25), Nortrachelogenin-8'-O-β-D-glucopyranoside (26),7,8-dihydroxy-6-methoxycoumarin (27), phloridzin (28), gallic acid (29), methyl gallate (30),3,4-dihydroxy-5-methoxybenzoic acid methyl ester (31), methyl syringate (32), methyl vanillate (33) and3,5-dihydroxy-4-methoxybenzoic acid (34).
A total of twelve compounds were isolated and identified from red maple bark. They are six new compounds, including maplexin F (9), maplexin G (10), maplexin H (11), maplexin I (13), rubrumosides A (14) and rubrumosides B (16). Other six compounds are known, including nymphaeoside A (15) and the same five compounds as isolated from red maple stem:Ginnalin C (1), Ginnalin B (4), Ginnalin A (7), gallic acid (29) and methyl vanillate (33), respectively. In short, thirty-four compounds were isolated and identified from red maple and eleven were new compounds. Compounds15,17,21,22,26,28,31and34were isolated from the family of Aceraceae for the first time, and compounds1,4,7,8,20,24,25,32and33were isolated from the plant for the first time.
All of the isolated compounds from red maple were tested for their a-glucosidase inhibition and DPPH free radical scavenging activities. New compounds Maplexins E-I all showed powerful a-glucosidase inhibitory activity with range of the IC507.9-16.1μM. All of the compounds except26,31-34showed very strong DPPH free radical scavenging activity with range of the IC507.7-77.5μM. Analysis the relationship of the structure of gallic acid derivatives and the a-glucosidase inhibitory activity, which suggested that the a-glucosidase inhibitory activities of these gallotannins were influenced by both the number and positions of the galloyl groups. Compounds1-4, which possess one galloyl group each, did not show any activity in this assay, while compounds5-8, which possess two galloyl groups each, showed moderate a-glucosidase inhibitory activity. While maplexin E-I (9-13), which contained three galloyl groups, showed powerful a-glucosidase inhibitory activity.
A total of twenty-one compounds including ten phenylpropanoids and eleven flavonoids, were isolated and purified from blueberry flower. The compounds were identified from their nuclear magnetic resonance (NMR) and mass spectral data as5-O-caffeoylshikimic acid (35),5-O-Caffeoylquinic acid (36),5-O-Caffeoylquinic acid methyl ester (37),3,5-dicaffeoylquinic acid methyl ester (38), Methyl caffeate (39),5-O-coumaroylquinic acid (40),5-O-coumaroylquinic methyl ester (41), trans-cinnamic acid methyl ester (42), Rosin (43),2'-O-β-D-Glucosylrosine (44), quercetin-3-O-β-D-glucoside (45), quercetin-3-O-β-D-galactoside (46), quercetin-3-O-α-L-arabinopyranoside (47), myricetin-3-O-β-D-glucoside (48), myricetin-3-O -β-D-galactoside (49), quercetin-3-O-(6"-O-coumaroyl)-β-D-glucoside (50), quercetin-3-O-(2"-O-coumaroyl)-β-D-glucoside (51), kaempferol-3-O-(6"-O-coumaroyl)-β-D-glucoside (52) and other three are phenylpropanoid-substituted catechins (53-55).
All of the isolated compounds from blueberry flower were tested for their α-glucosidase inhibition and DPPH free radical scavenging activities. All of the flavonoids showed powerful a-glucosidase inhibitory activity with range of the IC5028.9-137.5μM, while the phenylpropanoids showed very weak activity, only3,5-dicaffeoylquinic acid methyl ester (38) showed good activity with the IC5099.9μM. All of the compounds except40-44and52showed very strong DPPH free radical scavenging activity with range of the IC507.8-59.4μM. Analysis the relationship of the structure and the DPPH free radical scavenging activity, which suggested that the DPPH free radical scavenging activities were influenced by the number of the hydroxy groups.
引文
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