红绒毛羊蹄甲、五脉绿绒蒿和药用真菌桑黄化学成分研究
摘要
本论文对羊蹄甲属植物(豆科)红绒毛羊蹄甲的醋酸乙酯部位、藏药五脉绿绒蒿(罂粟科)的水溶性部位，以及药用真菌桑黄-针层孔属火木层孔菌正丁醇萃取部位和水相的化学成分和药理活性进行了较系统的研究。
应用各种色谱分离纯化技术和波谱学结构分析鉴定方法(包括1D、2D NMR、IR和MS等)，从红绒毛羊蹄甲90％乙醇提取物的醋酸乙酯萃取部位中分离鉴定了40个化合物，其结构为二聚羊蹄甲素(1)、(2R，3R)-3-O-(3″，5″-二甲氧基)没食子酰表儿茶素(2)、(2R，3R)-3，4′，5，7-四羟基黄酮-3-O-α-L-鼠李糖苷(6→6″)-3″，4′″，5″，7″-四羟基黄酮-3″-O-α-L-鼠李糖苷(3)、白杨素(4)、木犀草素(5)、芹菜素(6)、槲皮素3-O-β-D-半乳糖苷(7)、槲皮素3-O-α-L-鼠李糖苷(8)、3，5，7-三羟基色原酮-3-O-α-L-鼠李糖苷(9)、白杨素7-O-β-D-葡萄糖苷(10)、山奈素3，7-二氧-α-L-双鼠李糖苷(11)、槲皮素3，7-二氧-α-L-双鼠李糖苷(12)、槲皮素3-O-(6″-没食子酰基)-β-D-半乳糖苷(13)、槲皮素3-O-(6″-没食子酰基)-β-D-葡萄糖苷(14)、异黄杞苷(15)、落新妇苷(16)、新落新妇苷(17)、异落新妇苷(18)、新异落新妇苷(19)、(2R，3S)-儿茶素(20)、(2R，3R)-表儿茶素(21)、(2R，3R)-3-O-没食子酰表儿茶素(22)、氰醇[Z]-5α，6β-二羟基-4β-甲氧基-2-环己烯-Δ~(1，α)-乙腈(23)、bauhinilide(24)、bauhinin(25)、羽扇豆-3-醇(26)、羽扇豆-3-酮(27)、豆甾-4-烯-3-酮(28)、β-谷甾醇(29)、胡萝卜苷(30)、3，4-二羟基苯甲酸(31)、4-羟基苯甲酸(32)、3-羟基-4-甲氧基苯甲酸(33)、4-羟基-3-甲氧基苯甲酸(34)、没食子酸(35)、没食子酸甲酯(36)、没食子酸乙酯(37)、(E)-对羟基桂皮酸二十六酯(38)、(E)-咖啡酸二十六酯(39)和(E)-咖啡酸二十四酯(40)；从藏药五脉绿绒蒿的水溶性部位分离鉴定了5个化合物，其结构为：肉桂酸4-O-β-D-吡喃葡萄糖苷(41)、槲皮素3-O-[2′″-O-乙酰基-β-D-吡喃葡萄糖(1→6)-β-D-吡喃葡萄糖苷](42)、槲皮素3-O-[2′″，6′″-O-二乙酰基-β-D-吡喃葡萄糖(1→6)-β-D-吡喃葡萄糖苷](43)、异鼠李黄素3-O-[2′″-O-乙酰基-β-D-吡喃葡萄糖(1→6)-β-D-吡喃葡萄糖苷](44)和槲皮素3-O-[2′″-O-乙酰基-α-L-阿拉伯糖(1→6)-β-D-吡喃葡萄糖苷](45)；从桑黄乙醇提取物的正丁醇萃取相和水相中分离并鉴定了10个化合物，其结构为：桑黄素C(46)、桑黄素D(47)、
This dissertation describes chemical investigations on the EtOAc soluble portion of the ethanolic extract of Bauhinia aurea (Leguminosae), the aq. phase of the ethanolic extract of Meconopsis quintuplinervia Regel (papaverace), and the n-BuOH soluble portion and aq. phase of the ethanolic extract of the medicinal fungus Phellinus igniarius.
By using a variety of chromatographic techniques 40 compounds were isolated from the EtOAc portion of B. aurea. Their structures were identified by IR, MS, 1D NMR, and 2D NMR spectroscopic methods, respectively, as bauhinidimerin (1), (2R,3R)-3-O-(3",5"-dimethoxy) galloylepicatechin (2), 6,6"-bis-(2R,3R)-3,4',5,7-tetrahydroxyflavanone-3-O-α-L-rhamnopyranoside (3), chrysin (4), luteolin (5), apigenin (6), quercetin 3-O-β-D-galacoside (7), quercetin 3-O-α-L-rhamnopyranoside (8), eucryphin (9), chrysin 7-O-β-D-glucopyranoside (10), 3,7-di-O-α-L-rhamno-pyranosyl kaempferol (11), 3,7-di-O-α-L-rhamnopyranosyl quercetin (12), isoquercitrin 6"-O-3'",4'",5'"-trihydroxybenzoyl (13), hyperin 6"-O-3'",4'",5'"-trihydroxybenzoyl (14), isoengeletin (15), astilbin (16), neoastilbin (17), isoastilbin (18), neoisoastilbin (19), (+)-catechin (20), (-)-epicatechin (21), (-)-epicatechin 3-O-gallate (22), [Z]-5a,6p-dihydroxy-4p- methoxy-2-cyclohexene- Δ~(1,α)- acetonitrile (23), bauhinilide (24), bauhinin (25), lupeol (26), lupenone (27), stigmast-4-en-3-one (28), sitosterol (29), daucosterol (30), 3,4-dihydroxybenzoic acid (31), 4-hydroxybenzoic acid (32), 3-hydroxy-4-methoxybenzoic acid (33), 4-hydroxy-3-methoxybenzoic acid (34), gallic acid (35), methyl gallate (36), ethyl gallate (37), hexacosanyl-(E)-p-coumarate (38), caffeic acid hexacosanyl ester (39), caffeic acid hexacosanyl ester (40). From the aq. phase of the the ethanolic extract of Meconopsis quintuplinervia five compounds were isolated and identified respectively as 4-O-β-D-glucopyranosyl-(Z)-p-coumaric acid (41), quercetin 3-O-[2'"-O-acetyl-p-D-glucopyranosyl(1→6)-β-D-glucopyranoside] (42), quercetin 3-O-[2"',6"'-O-diacetyl-P-D-glucopyranosyl-(1→6)-p-D-glucopyranoside (43), isorhamnetin 3-O-[2"'-O-acetyl-p-D-glucopyranosyl-(1→6)-P-D-gIucopyranoside (44), quercetin
应用各种色谱分离纯化技术和波谱学结构分析鉴定方法(包括1D、2D NMR、IR和MS等)，从红绒毛羊蹄甲90％乙醇提取物的醋酸乙酯萃取部位中分离鉴定了40个化合物，其结构为二聚羊蹄甲素(1)、(2R，3R)-3-O-(3″，5″-二甲氧基)没食子酰表儿茶素(2)、(2R，3R)-3，4′，5，7-四羟基黄酮-3-O-α-L-鼠李糖苷(6→6″)-3″，4′″，5″，7″-四羟基黄酮-3″-O-α-L-鼠李糖苷(3)、白杨素(4)、木犀草素(5)、芹菜素(6)、槲皮素3-O-β-D-半乳糖苷(7)、槲皮素3-O-α-L-鼠李糖苷(8)、3，5，7-三羟基色原酮-3-O-α-L-鼠李糖苷(9)、白杨素7-O-β-D-葡萄糖苷(10)、山奈素3，7-二氧-α-L-双鼠李糖苷(11)、槲皮素3，7-二氧-α-L-双鼠李糖苷(12)、槲皮素3-O-(6″-没食子酰基)-β-D-半乳糖苷(13)、槲皮素3-O-(6″-没食子酰基)-β-D-葡萄糖苷(14)、异黄杞苷(15)、落新妇苷(16)、新落新妇苷(17)、异落新妇苷(18)、新异落新妇苷(19)、(2R，3S)-儿茶素(20)、(2R，3R)-表儿茶素(21)、(2R，3R)-3-O-没食子酰表儿茶素(22)、氰醇[Z]-5α，6β-二羟基-4β-甲氧基-2-环己烯-Δ~(1，α)-乙腈(23)、bauhinilide(24)、bauhinin(25)、羽扇豆-3-醇(26)、羽扇豆-3-酮(27)、豆甾-4-烯-3-酮(28)、β-谷甾醇(29)、胡萝卜苷(30)、3，4-二羟基苯甲酸(31)、4-羟基苯甲酸(32)、3-羟基-4-甲氧基苯甲酸(33)、4-羟基-3-甲氧基苯甲酸(34)、没食子酸(35)、没食子酸甲酯(36)、没食子酸乙酯(37)、(E)-对羟基桂皮酸二十六酯(38)、(E)-咖啡酸二十六酯(39)和(E)-咖啡酸二十四酯(40)；从藏药五脉绿绒蒿的水溶性部位分离鉴定了5个化合物，其结构为：肉桂酸4-O-β-D-吡喃葡萄糖苷(41)、槲皮素3-O-[2′″-O-乙酰基-β-D-吡喃葡萄糖(1→6)-β-D-吡喃葡萄糖苷](42)、槲皮素3-O-[2′″，6′″-O-二乙酰基-β-D-吡喃葡萄糖(1→6)-β-D-吡喃葡萄糖苷](43)、异鼠李黄素3-O-[2′″-O-乙酰基-β-D-吡喃葡萄糖(1→6)-β-D-吡喃葡萄糖苷](44)和槲皮素3-O-[2′″-O-乙酰基-α-L-阿拉伯糖(1→6)-β-D-吡喃葡萄糖苷](45)；从桑黄乙醇提取物的正丁醇萃取相和水相中分离并鉴定了10个化合物，其结构为：桑黄素C(46)、桑黄素D(47)、
This dissertation describes chemical investigations on the EtOAc soluble portion of the ethanolic extract of Bauhinia aurea (Leguminosae), the aq. phase of the ethanolic extract of Meconopsis quintuplinervia Regel (papaverace), and the n-BuOH soluble portion and aq. phase of the ethanolic extract of the medicinal fungus Phellinus igniarius.
By using a variety of chromatographic techniques 40 compounds were isolated from the EtOAc portion of B. aurea. Their structures were identified by IR, MS, 1D NMR, and 2D NMR spectroscopic methods, respectively, as bauhinidimerin (1), (2R,3R)-3-O-(3",5"-dimethoxy) galloylepicatechin (2), 6,6"-bis-(2R,3R)-3,4',5,7-tetrahydroxyflavanone-3-O-α-L-rhamnopyranoside (3), chrysin (4), luteolin (5), apigenin (6), quercetin 3-O-β-D-galacoside (7), quercetin 3-O-α-L-rhamnopyranoside (8), eucryphin (9), chrysin 7-O-β-D-glucopyranoside (10), 3,7-di-O-α-L-rhamno-pyranosyl kaempferol (11), 3,7-di-O-α-L-rhamnopyranosyl quercetin (12), isoquercitrin 6"-O-3'",4'",5'"-trihydroxybenzoyl (13), hyperin 6"-O-3'",4'",5'"-trihydroxybenzoyl (14), isoengeletin (15), astilbin (16), neoastilbin (17), isoastilbin (18), neoisoastilbin (19), (+)-catechin (20), (-)-epicatechin (21), (-)-epicatechin 3-O-gallate (22), [Z]-5a,6p-dihydroxy-4p- methoxy-2-cyclohexene- Δ~(1,α)- acetonitrile (23), bauhinilide (24), bauhinin (25), lupeol (26), lupenone (27), stigmast-4-en-3-one (28), sitosterol (29), daucosterol (30), 3,4-dihydroxybenzoic acid (31), 4-hydroxybenzoic acid (32), 3-hydroxy-4-methoxybenzoic acid (33), 4-hydroxy-3-methoxybenzoic acid (34), gallic acid (35), methyl gallate (36), ethyl gallate (37), hexacosanyl-(E)-p-coumarate (38), caffeic acid hexacosanyl ester (39), caffeic acid hexacosanyl ester (40). From the aq. phase of the the ethanolic extract of Meconopsis quintuplinervia five compounds were isolated and identified respectively as 4-O-β-D-glucopyranosyl-(Z)-p-coumaric acid (41), quercetin 3-O-[2'"-O-acetyl-p-D-glucopyranosyl(1→6)-β-D-glucopyranoside] (42), quercetin 3-O-[2"',6"'-O-diacetyl-P-D-glucopyranosyl-(1→6)-p-D-glucopyranoside (43), isorhamnetin 3-O-[2"'-O-acetyl-p-D-glucopyranosyl-(1→6)-P-D-gIucopyranoside (44), quercetin
引文
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