复叶耳蕨和金星蕨化学成分及生物活性的研究
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摘要
复叶耳蕨Arachniodes exilis(Hance)Ching来源于刺头复叶耳蕨的根茎，具有清热解毒，敛疮的功效。民间主要用于治疗肝炎、痢疾和烧烫伤。目前，国内外有关其化学成分和生物活性的报道很少。为了开发复叶耳蕨潜在的药用价值，并为临床应用提供科学依据，我们对复叶耳蕨的化学成分和生物活性进行了研究，弄清了复叶耳蕨的特征性成分，初步探讨了其保肝作用和相关作用机制，并建立了合理有效的药材质量标准。
通过各种色谱技术从复叶耳蕨根茎中分离得到23个化合物：复叶绵马素BB(1)、复叶耳蕨素A(2)、复叶耳蕨素B(3)、绵马素BB(4)、Methyl-phlor-butyrophenon(5)、绵马酚(6)、圣草素(7)、芒花苷(8)、圣草次苷(9)、圣草素-7-O-β-D-吡喃葡萄糖醛酸苷(10)、木犀草素(11)、木犀草素-4'-O-β-D-吡喃葡萄糖苷(12)、表儿茶素(13)、原花青素B2(14)、(2R，3S)蕨素C-14-O-β-D-吡喃葡萄糖苷(15)、蕨素P-14- O-β-D-吡喃葡萄糖苷(16)、β-谷甾醇(17)、β-谷甾醇乙酸酯(18)、胡萝卜苷(19)、豆甾醇乙酸酯(20)、羽扇豆醇(21)、十六烷酸(22)、十六烷酸甲酯(23)；其中化合物1-3为新化合物，其余均为首次从该种植物中得到。
从复叶耳蕨地上部分分离得到14个成分：柚皮素(1)、柚皮芸香苷(2)、圣草素(3)、芒花苷(4)、圣草次苷(5)、木犀草素-7-O-芸香糖苷(6)、5，7-二羟基色原酮-7-O-α-L-鼠李吡喃糖基-(1→6)-β-D-葡萄吡喃糖苷(7)、5，7-二羟基色原酮(8)、熊果酸(9)、β-谷甾醇(10)、β-谷甾醇乙酸酯(11)、胡萝卜苷(12)、十六烷酸(13)、十六烷酸甲酯(14)。
化学成分研究表明间苯三酚和黄酮类成分是复叶耳蕨的特征性成分。
在生物活性研究中，复叶耳蕨乙醇提取物在体外还原力、脂质过氧化、DPPH自由基清除、ABTS自由基清除、超氧阴离子自由基清除、羟基自由基清除及H_2O_2清除方面均表现出很强的抗氧化能力，且作用效果在一定范围内呈剂量依耐性；在体内CCl_4诱导小鼠肝损伤模型中，复叶耳蕨360、720 mg/kg低、中两个剂量组中均表现出一定的肝保护作用；特别是中等剂量组，能有效逆转CCl_4导致的肝损伤，使各项生化指标趋于正常，且作用效果与水飞蓟素(100 mg/kg)相当。但在高剂量组中，复叶耳蕨则表现出一定的肝脏毒性。复叶耳蕨的保肝作用可能与其良好的抗氧化能力有关。
在复叶耳蕨质量标准的制定中，规定水分不得超过13％，总灰分不得超过6．5％，酸不溶性灰分不得超过2．5％，80％乙醇提取物不得少于20％，总黄酮含量以无水芦丁计不得少于10％，从而有效的对药材质量进行了控制。
金星蕨Parathelypteris glanduligera(Kze.)Ching来源于金星蕨全草。具有清热解毒，利尿，止血功效。目前未见其相关研究报道。为了发掘金星蕨的药用价值，为今后进一步进行生物活性研究以及质量控制提供可靠的物质基础，我们对其化学成分进行了系统研究。从金星蕨甲醇提取物中分离得到16个化合物：金星蕨苷(1)、3，4-二羟基苯甲酸(2)、山奈酚(3)、黄芪苷(4)、三叶豆苷(5)、阿福豆苷(6)、山奈酚-3-O-芸香糖苷(7)、槲皮素(8)、槲皮素-3-O-β-D-吡喃半乳糖苷(9)、芦丁(10)、MyriciatrinⅠ(11)、3′-甲基-4′，6′-二羟基-2′-甲氧基-查儿酮(12)、3′，5′-二甲基-4′，6′-二羟基-2′-甲氧基-查儿酮(13)、β-谷甾醇(14)、胡萝卜苷(15)、β-谷甾醇-3-O-β-D-葡萄糖苷-6′-二十烷酸酯(16)。其中1为新化合物。结果表明黄酮类成分是其特征性成分。
Arachniodes exilis (Hance) Ching is a folk medicine in China to treat hepatitis,inflammation, dysentery and burn scald. Up to now, there was little report about thechemical constituents and bioactivity of A. exilis. We did the investigation on thechemical constituents, antioxidant and hepatoprotective activity and quality standardof A. exilis to explore this folk medicinal resource.
Twenty-three compouds were isolated from the rhizomes of A. exilis by normaland reverse phase silica gel and Sephadex LH-20 gel column chromatography, andidentified as araspidin BB (1), arachniodesin A (2), arachniodesin B (3), aspid in BB(4), Methyl-phlor-butyrophenon (5), aspidinol (6), eriodictyol (7), miscanthoside (8),eriocitrin (9), eriodictyol-7-O-β-D-glucuronide (10), cyanidenon (11), cyanidenon-4'-O-β-D- glucopyranoside (12), epicatechin (13), procyanidin BB (14), pterosin C -14-O-β-D-glucopyranoside (15), pterosin P-14-O-β-D-glucopyranoside (16),β-sitosterol(17),β-sitosterol acetate (18), daucosterol (19), stigmasterol acetate (20),clerodol (21), hexadecanoic acid (22), methyl palmitate (23), respectively, on the basisof physico-chemical properties and spectral analysis. Among these compounds, 1-3were new, and the other were obtained from this species for the first time.
Additionally, fourteen compouds were isolated from the aerial parts of A. exilisand identified as naringenin (1), narirutin (2), eriodictyol (3), miscanthoside (4),eriocitrin (5), luteolin 7-O-rutinoside (6), 5, 7-dihydroxychromone-7-O-rutinoside (7),5, 7-dihydroxychromone (8), ursolic acid (9),β-sitosterol (10),β-sitosterol acetate(11), daucosterol (12), hexadecanoic acid (13), methyl palmitate (14), respectively.
In the bioactivity test, the ethanol extract of A. exilis performed potent in vitroantioxidant activities on reducing power, lipid peroxidation, DPPH radicals, ABTSradicals, superoxide anion radicals, hydroxyl radicals and hydrogen peroxide. And theactivity demonstrated dose-dependent manner. In the in vivo study, the groups with dose 360 and 720 mg/kg treated with extract showed a significant alteration in thelevels of antioxidant and hepatoprotective parameters towards the normal whencompared with the CCl_4 control. Furthermore, the activity exhibited dose-dependentmanner. Especially, the group with dose 720 mg/kg performed similar effect to thepositive control (silybin, 100 mg/kg). Relatedly, the high dose showed hepar damage.The hepatoprotective activity of A. exilis may be related to its antioxidant ability,which need to be confirmed by further study.
In the quality standard study, the moisture content was no more than 13%, thetotal ash content was no more than 6.5%, the acid-insoluble ash content was no morethan 25%, the 80% ethanol extract was no less than 20% and the total flavonoidcontent was no less than 10% with rutin as equivalent.
Parathelypteris glanduligera (Kze.) Ching is another folk med icine, used fortreating dysentery, difficulty in micturition, bleeding wound and scald. Up to now,there was little report on its component. We did study on the chemical constituentsfor the further exploitation. As a result, sixteen compounds were isolated from themethanol extract of P. glanduligera, and identified as parathelypteriside (1), 3, 4-dihydroxyhenzoic acid (2), kaempferol (3), astragaloside (4), trifolioside (5),kaempferol-3-O-α-L-rhamnopyranoside (6), kaempferol-3-O-rutinoside (7),quercetin (8), quercetin-3-O-β-D-galactopyranoside (9), rutin (10), Myriciatrin I(11), 3'-methyl-4', 6'-dihydroxy-2'-methoxy-chalcone (12), 3', 5'-dimethyl-4', 6'-dihydroxy-2'-methoxy-chalcone (13),β-sitosterol (14), daucosterol (15) andβ-sitosterol-3-O-β-D-glucoside-6'-eicosanate (16), respectively. Among thesecompounds, 1 was new, and the others were firstly obtained from this species.
通过各种色谱技术从复叶耳蕨根茎中分离得到23个化合物：复叶绵马素BB(1)、复叶耳蕨素A(2)、复叶耳蕨素B(3)、绵马素BB(4)、Methyl-phlor-butyrophenon(5)、绵马酚(6)、圣草素(7)、芒花苷(8)、圣草次苷(9)、圣草素-7-O-β-D-吡喃葡萄糖醛酸苷(10)、木犀草素(11)、木犀草素-4'-O-β-D-吡喃葡萄糖苷(12)、表儿茶素(13)、原花青素B2(14)、(2R，3S)蕨素C-14-O-β-D-吡喃葡萄糖苷(15)、蕨素P-14- O-β-D-吡喃葡萄糖苷(16)、β-谷甾醇(17)、β-谷甾醇乙酸酯(18)、胡萝卜苷(19)、豆甾醇乙酸酯(20)、羽扇豆醇(21)、十六烷酸(22)、十六烷酸甲酯(23)；其中化合物1-3为新化合物，其余均为首次从该种植物中得到。
从复叶耳蕨地上部分分离得到14个成分：柚皮素(1)、柚皮芸香苷(2)、圣草素(3)、芒花苷(4)、圣草次苷(5)、木犀草素-7-O-芸香糖苷(6)、5，7-二羟基色原酮-7-O-α-L-鼠李吡喃糖基-(1→6)-β-D-葡萄吡喃糖苷(7)、5，7-二羟基色原酮(8)、熊果酸(9)、β-谷甾醇(10)、β-谷甾醇乙酸酯(11)、胡萝卜苷(12)、十六烷酸(13)、十六烷酸甲酯(14)。
化学成分研究表明间苯三酚和黄酮类成分是复叶耳蕨的特征性成分。
在生物活性研究中，复叶耳蕨乙醇提取物在体外还原力、脂质过氧化、DPPH自由基清除、ABTS自由基清除、超氧阴离子自由基清除、羟基自由基清除及H_2O_2清除方面均表现出很强的抗氧化能力，且作用效果在一定范围内呈剂量依耐性；在体内CCl_4诱导小鼠肝损伤模型中，复叶耳蕨360、720 mg/kg低、中两个剂量组中均表现出一定的肝保护作用；特别是中等剂量组，能有效逆转CCl_4导致的肝损伤，使各项生化指标趋于正常，且作用效果与水飞蓟素(100 mg/kg)相当。但在高剂量组中，复叶耳蕨则表现出一定的肝脏毒性。复叶耳蕨的保肝作用可能与其良好的抗氧化能力有关。
在复叶耳蕨质量标准的制定中，规定水分不得超过13％，总灰分不得超过6．5％，酸不溶性灰分不得超过2．5％，80％乙醇提取物不得少于20％，总黄酮含量以无水芦丁计不得少于10％，从而有效的对药材质量进行了控制。
金星蕨Parathelypteris glanduligera(Kze.)Ching来源于金星蕨全草。具有清热解毒，利尿，止血功效。目前未见其相关研究报道。为了发掘金星蕨的药用价值，为今后进一步进行生物活性研究以及质量控制提供可靠的物质基础，我们对其化学成分进行了系统研究。从金星蕨甲醇提取物中分离得到16个化合物：金星蕨苷(1)、3，4-二羟基苯甲酸(2)、山奈酚(3)、黄芪苷(4)、三叶豆苷(5)、阿福豆苷(6)、山奈酚-3-O-芸香糖苷(7)、槲皮素(8)、槲皮素-3-O-β-D-吡喃半乳糖苷(9)、芦丁(10)、MyriciatrinⅠ(11)、3′-甲基-4′，6′-二羟基-2′-甲氧基-查儿酮(12)、3′，5′-二甲基-4′，6′-二羟基-2′-甲氧基-查儿酮(13)、β-谷甾醇(14)、胡萝卜苷(15)、β-谷甾醇-3-O-β-D-葡萄糖苷-6′-二十烷酸酯(16)。其中1为新化合物。结果表明黄酮类成分是其特征性成分。
Arachniodes exilis (Hance) Ching is a folk medicine in China to treat hepatitis,inflammation, dysentery and burn scald. Up to now, there was little report about thechemical constituents and bioactivity of A. exilis. We did the investigation on thechemical constituents, antioxidant and hepatoprotective activity and quality standardof A. exilis to explore this folk medicinal resource.
Twenty-three compouds were isolated from the rhizomes of A. exilis by normaland reverse phase silica gel and Sephadex LH-20 gel column chromatography, andidentified as araspidin BB (1), arachniodesin A (2), arachniodesin B (3), aspid in BB(4), Methyl-phlor-butyrophenon (5), aspidinol (6), eriodictyol (7), miscanthoside (8),eriocitrin (9), eriodictyol-7-O-β-D-glucuronide (10), cyanidenon (11), cyanidenon-4'-O-β-D- glucopyranoside (12), epicatechin (13), procyanidin BB (14), pterosin C -14-O-β-D-glucopyranoside (15), pterosin P-14-O-β-D-glucopyranoside (16),β-sitosterol(17),β-sitosterol acetate (18), daucosterol (19), stigmasterol acetate (20),clerodol (21), hexadecanoic acid (22), methyl palmitate (23), respectively, on the basisof physico-chemical properties and spectral analysis. Among these compounds, 1-3were new, and the other were obtained from this species for the first time.
Additionally, fourteen compouds were isolated from the aerial parts of A. exilisand identified as naringenin (1), narirutin (2), eriodictyol (3), miscanthoside (4),eriocitrin (5), luteolin 7-O-rutinoside (6), 5, 7-dihydroxychromone-7-O-rutinoside (7),5, 7-dihydroxychromone (8), ursolic acid (9),β-sitosterol (10),β-sitosterol acetate(11), daucosterol (12), hexadecanoic acid (13), methyl palmitate (14), respectively.
In the bioactivity test, the ethanol extract of A. exilis performed potent in vitroantioxidant activities on reducing power, lipid peroxidation, DPPH radicals, ABTSradicals, superoxide anion radicals, hydroxyl radicals and hydrogen peroxide. And theactivity demonstrated dose-dependent manner. In the in vivo study, the groups with dose 360 and 720 mg/kg treated with extract showed a significant alteration in thelevels of antioxidant and hepatoprotective parameters towards the normal whencompared with the CCl_4 control. Furthermore, the activity exhibited dose-dependentmanner. Especially, the group with dose 720 mg/kg performed similar effect to thepositive control (silybin, 100 mg/kg). Relatedly, the high dose showed hepar damage.The hepatoprotective activity of A. exilis may be related to its antioxidant ability,which need to be confirmed by further study.
In the quality standard study, the moisture content was no more than 13%, thetotal ash content was no more than 6.5%, the acid-insoluble ash content was no morethan 25%, the 80% ethanol extract was no less than 20% and the total flavonoidcontent was no less than 10% with rutin as equivalent.
Parathelypteris glanduligera (Kze.) Ching is another folk med icine, used fortreating dysentery, difficulty in micturition, bleeding wound and scald. Up to now,there was little report on its component. We did study on the chemical constituentsfor the further exploitation. As a result, sixteen compounds were isolated from themethanol extract of P. glanduligera, and identified as parathelypteriside (1), 3, 4-dihydroxyhenzoic acid (2), kaempferol (3), astragaloside (4), trifolioside (5),kaempferol-3-O-α-L-rhamnopyranoside (6), kaempferol-3-O-rutinoside (7),quercetin (8), quercetin-3-O-β-D-galactopyranoside (9), rutin (10), Myriciatrin I(11), 3'-methyl-4', 6'-dihydroxy-2'-methoxy-chalcone (12), 3', 5'-dimethyl-4', 6'-dihydroxy-2'-methoxy-chalcone (13),β-sitosterol (14), daucosterol (15) andβ-sitosterol-3-O-β-D-glucoside-6'-eicosanate (16), respectively. Among thesecompounds, 1 was new, and the others were firstly obtained from this species.
引文
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