远志化学成分及其生物活性的研究
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摘要
远志为远志科(Polygalaceae)远志属(Polygala)多年生草本。中国药典收载中药远志的来源为远志科植物细叶远志Polygala tenuifolia Wild.或卵叶远志 Polygala sibirica L.的干燥根。主产于我国西南和华南地区,资源较丰富[1]。通过对该属植物卵叶远志、黄花远志、尾叶远志、细叶远志等的化学成分和药理活性研究发现，远志属植物含有皂苷类、口山酮类、寡糖酯类、挥发油、生物碱等化学成分。具有安神益智、祛痰、镇痛、抗肿瘤、抗菌等多方面生物活性。预示该属植物中含有防治上述疾病的生物活性物质，研究其化学成分及生物活性具有广阔的应用前景。为了更充分地利用这一药用植物资源，在综述了远志属植物近十年的研究进展的基础上，我们对远志水提物的化学成分和药理活性进行了深入地研究。
干燥的远志根，加10倍量水煎煮三次，合并提取液，水提液经大孔吸附树脂柱层析，分别用水、30%乙醇、85%乙醇洗脱，收集85%乙醇洗脱液，减压回收洗脱液至干，得远志总提取物。将远志总提取物经多次硅胶柱层析（干柱、湿柱），选择适当的洗脱剂，洗脱下的各流分经制备薄层层析、活性碳脱色、重结晶等方法进行分离、纯化，得到12个化合物。通过理化性质和波谱(1HNMR、13CNMR、HMBC、HMQC)解析，鉴定了其中8个单体化合物的结构。分别为tenuifoliside A(Ⅰ)[α-D-(6-O-p-hydroxybenzoyl)-glucopyranosyl(1→2)-β-D-(3-O-3,4,5-trimethoxycinnamoyl)-fru-ctofuranose]、α-D-(6-O-白芥子酰基)-吡喃葡萄糖基(1→2)-β-D-(3-O-白芥子酰基)-呋喃果糖[α-D-(6-O-sinapoyl)-glucopyranosyl(1→2)-β-D-(3-O-sinapoyl)-fructofuranose](Ⅱ)、α-D-(6-O-4-甲基-3,5-二甲氧基肉桂酰基)-吡喃葡萄糖基(1→2)-β-D-(3-O-白芥子酰基)-呋喃果糖[α-D-(6-O-4-methyl-3,5-dimethoxycinnamoyl)-glucopyranosyl(1→2)-β-D-(3-O-sinapoyl)-fructofuranose](Ⅲ)、3,4,5-三甲氧基肉
64>
桂酸(3,4,5-trimethoxycinnamylic acid)(Ⅳ)、乙酸苯酯(phenyl acet-ate)(Ⅴ)、苯甲酸丙酯(propyl benzoate)(Ⅵ)、正十二烷(n-dodecane)(Ⅶ)、壬烷(nonane)(Ⅷ)。化合物Ⅲ初步鉴定为新化合物，其余为已知化合物，化合Ⅴ、Ⅵ、Ⅶ、Ⅷ为首次从该植物中获得。
1.化学成分的研究
化合物Ⅰ tenuifoliside A
δC65.16(C-1),104.93(C-2),79.80(C-3),73.17(C-4),84.21(C-5), 63.43(C-6),93.18(C-1′),74.15(C-2′),74.95(C-3′),71.76(C-4′), 72.56(C-5′),65.66(C-6′),131.51(C-1″),106.99(C-2″、6″), 154.81(C-3″、5″),141.41(C-4″),147.28(C-7″),117.81(C-8″), 167.80(C-9″),122.13(C-1’’’),133.03(C-2′″、6′″),116.25(C-3’’’、 5’’’),163.63(C-4’’’),168.20(C-7’’’),56.83(C-3″,5″,2×-OCH3),61.20( C-4″,-OCH3)。
δH3.63(H-1a),3.66(H-1b),5.50(H-3),4.40(H-4,t),3.95(H-5,m),
3.77(H-6a),3.87(H-6b),5.52(H-1′,J=3.5Hz),3.52(H-2′),3.71(H- 3′)，3.48(H-4′)，4.25(H-5′)，4.45(H-6′a),4.68(H-6′b),6.96( H-2″、6″,2H, s),7.74(H-7″,1H,d,J=16.0Hz),6.57(H-8″,J=16.0Hz),7.93(H-2’’’、6’’’,2H,d,J=8.5Hz),6.84(H-3’’’、5’’’,2H,d,J=8.5Hz), 3.89(H-3″、5″,6H,s,2×-OCH3),3.81(H-4″,3H,s,-OCH3)。
化合物Ⅱ α-D-(6-O-白芥子酰基)-吡喃葡萄糖基(1→2)-β-D-(3-O-白芥子酰基)-呋喃果糖
δC65.74(C-1),104.88(C-2),79.37(C-3),74.22(C-4),84.35(C-5), 63.81(C-6),92.69(C-1′),73.13(C-2′),75.11(C-3′),71.98(C-4′),72.53(C-5′),65.62(C-6′),126.58(C-1″),106.97(C-2″、6″), 49.11(C-3″、5″),139.58(C-4″),147.29(C-7″),115.46(C-8″), 168.28(C-9″),126.58(C-1’’’),107.14(C-2’’’、6’’’),149.42(C-3’’’、5’’’),
65>
139.70(C-4’’’),147.95(C-7’’’),115.84(C-8’’’),169.11(C-9’’’),56.89(C-3″、5″,2×-OCH3 ),56.93(C-3’’’、5’’’,2×-OCH3)。
δH3.59(H-1a),3.61(H-1b),5.51(H-3),4.51(H-4,t),3.97(H-5,m),
3.82(H-6a),3.91(H-6b),5.53(H-1′,J=3.5Hz),3.49(H-2′),3.68(H- 3′),3.32(H-4′),4.29(H-5′),4.22(H-6′a),4.67(H-6′b),6.93(H- 2″、6″,2H,s),7.68(H-7″,1H,d,J=16.0Hz),6.48(H-8″,1H,d,J=16.0Hz), 6.89(H-2’’’、6’’’,2H,s),7.59(H-7’’’,1H,d,J=16.0Hz), 6.45(H-8’’’,1H,d,J=16.0Hz),3.88(H-3″、5″,6H,s,2×-OCH3),3.83(H-3’’’、5’’’,3H,s,-OCH3)。
化合物Ⅲ α-D-(6-O-4-甲基-3,5-二甲氧基肉桂酰基)-吡喃葡萄糖基(1→2)-β-D-(3-O-白芥子酰基)-呋喃果糖
δC65.67(C-1),104.90(C-2),79.39(C-3),74.25(C-4),84.39(C-5),
63.85(C-6),92.72(C-1′),73.18(C-2′),75.15(C-3′),72.03(C-4′), 72.56(C-5′),65.67(C-6′),126.63(C-1″),107.01(C-2″、6″), 149.47(C-3″、5″),139.75(C-4″),147.29(C-7″),115.51(C-8″), 168.26(C-9″),116.26(C-1’’’),107.18(C-2’’’、6’’’),149.47(C-3’’’、5’’’), 132.99(C-4’’’),147.93(C-7’’’),115
In order to find out more chemical constituents and its pharmacological activities in Polygala tenuifolia Wild. In this paper, we had a comprehensive research on it. The methods and results as follow：
The dried roots of Polygala tenuifolia Wild. were extracted three times with boiling water. The extracted solution was passed through macroporous resin column and the adsorbed material eluted successively with H2O, 30%EtOH aq. and 85% EtOH aq. The 85% alcohol solution were collected and concentrated with reduced press and the general extraction were obtained. Twelve pure compounds were isolated from the general extraction by using silica gel chromatography, prep.TLC, active carbon decoloration, crystallization et al.
The structures of the compounds had been identified on
the basis of chemical and spectroscopic evidence(1HNMR,
13CNMR, HMBC, HMQC et al.). They are tenuifoliside A(Ⅰ),
α-D-(6-O-sinapoyl)-glucopyranosyl(1→2)-β-D-(3-O-sinapoyl)-
fructofuranose(Ⅱ),α-D-(6-O-4-methyl-3,5-dimethoxycinnamoyl)-
69>
glucopyranosyl(1→2)-β-D-(3-O-sinapoyl)-fructofuranose(Ⅲ),
3,4,5-trimethoxycinnamylic acid(Ⅳ),phenyl acetate(Ⅴ),nonane(Ⅷ)
ethyl benzoate(Ⅵ),n-dodecane(Ⅶ). In which compound Ⅲ is a new constituent, other compounds but for compoundsⅠ,Ⅱ,Ⅳ were isolated from Polygala tenuifolia Wild. for the first time.
At the same time, the chemical constituents in volatile oil from Polygala tenuifolia Wild. was analyzed by GC-MS-Computer technology. The results showed that the volatile oil contained at least 55 compounds, in which 18 compounds were identified with the computer standard MS spectra. The major compounds were Hexanoic acid, Phenylethy Alcohol, n-Hexadecanoic acid,
Octadecanoic acid, 2-Methoxy-4-vinylphenol, Hexadecanoic acid and 2-hydroxy-(1-hydroxy methyl)-ethyl ester. In which their relatively quantities are 21.52%, 6.19%, 4.00%, 3.09%, 1.94% and 1.40% respectively.
The pharmacological activities of the general extraction from Polygala tenuifolia Wild. were studied. The results showed that the general extraction have the function of removing phlegm and accelerating gastrointestinal peristalsis.
干燥的远志根，加10倍量水煎煮三次，合并提取液，水提液经大孔吸附树脂柱层析，分别用水、30%乙醇、85%乙醇洗脱，收集85%乙醇洗脱液，减压回收洗脱液至干，得远志总提取物。将远志总提取物经多次硅胶柱层析（干柱、湿柱），选择适当的洗脱剂，洗脱下的各流分经制备薄层层析、活性碳脱色、重结晶等方法进行分离、纯化，得到12个化合物。通过理化性质和波谱(1HNMR、13CNMR、HMBC、HMQC)解析，鉴定了其中8个单体化合物的结构。分别为tenuifoliside A(Ⅰ)[α-D-(6-O-p-hydroxybenzoyl)-glucopyranosyl(1→2)-β-D-(3-O-3,4,5-trimethoxycinnamoyl)-fru-ctofuranose]、α-D-(6-O-白芥子酰基)-吡喃葡萄糖基(1→2)-β-D-(3-O-白芥子酰基)-呋喃果糖[α-D-(6-O-sinapoyl)-glucopyranosyl(1→2)-β-D-(3-O-sinapoyl)-fructofuranose](Ⅱ)、α-D-(6-O-4-甲基-3,5-二甲氧基肉桂酰基)-吡喃葡萄糖基(1→2)-β-D-(3-O-白芥子酰基)-呋喃果糖[α-D-(6-O-4-methyl-3,5-dimethoxycinnamoyl)-glucopyranosyl(1→2)-β-D-(3-O-sinapoyl)-fructofuranose](Ⅲ)、3,4,5-三甲氧基肉
桂酸(3,4,5-trimethoxycinnamylic acid)(Ⅳ)、乙酸苯酯(phenyl acet-ate)(Ⅴ)、苯甲酸丙酯(propyl benzoate)(Ⅵ)、正十二烷(n-dodecane)(Ⅶ)、壬烷(nonane)(Ⅷ)。化合物Ⅲ初步鉴定为新化合物，其余为已知化合物，化合Ⅴ、Ⅵ、Ⅶ、Ⅷ为首次从该植物中获得。
1.化学成分的研究
化合物Ⅰ tenuifoliside A
δC65.16(C-1),104.93(C-2),79.80(C-3),73.17(C-4),84.21(C-5), 63.43(C-6),93.18(C-1′),74.15(C-2′),74.95(C-3′),71.76(C-4′), 72.56(C-5′),65.66(C-6′),131.51(C-1″),106.99(C-2″、6″), 154.81(C-3″、5″),141.41(C-4″),147.28(C-7″),117.81(C-8″), 167.80(C-9″),122.13(C-1’’’),133.03(C-2′″、6′″),116.25(C-3’’’、 5’’’),163.63(C-4’’’),168.20(C-7’’’),56.83(C-3″,5″,2×-OCH3),61.20( C-4″,-OCH3)。
δH3.63(H-1a),3.66(H-1b),5.50(H-3),4.40(H-4,t),3.95(H-5,m),
3.77(H-6a),3.87(H-6b),5.52(H-1′,J=3.5Hz),3.52(H-2′),3.71(H- 3′)，3.48(H-4′)，4.25(H-5′)，4.45(H-6′a),4.68(H-6′b),6.96( H-2″、6″,2H, s),7.74(H-7″,1H,d,J=16.0Hz),6.57(H-8″,J=16.0Hz),7.93(H-2’’’、6’’’,2H,d,J=8.5Hz),6.84(H-3’’’、5’’’,2H,d,J=8.5Hz), 3.89(H-3″、5″,6H,s,2×-OCH3),3.81(H-4″,3H,s,-OCH3)。
化合物Ⅱ α-D-(6-O-白芥子酰基)-吡喃葡萄糖基(1→2)-β-D-(3-O-白芥子酰基)-呋喃果糖
δC65.74(C-1),104.88(C-2),79.37(C-3),74.22(C-4),84.35(C-5), 63.81(C-6),92.69(C-1′),73.13(C-2′),75.11(C-3′),71.98(C-4′),72.53(C-5′),65.62(C-6′),126.58(C-1″),106.97(C-2″、6″), 49.11(C-3″、5″),139.58(C-4″),147.29(C-7″),115.46(C-8″), 168.28(C-9″),126.58(C-1’’’),107.14(C-2’’’、6’’’),149.42(C-3’’’、5’’’),
139.70(C-4’’’),147.95(C-7’’’),115.84(C-8’’’),169.11(C-9’’’),56.89(C-3″、5″,2×-OCH3 ),56.93(C-3’’’、5’’’,2×-OCH3)。
δH3.59(H-1a),3.61(H-1b),5.51(H-3),4.51(H-4,t),3.97(H-5,m),
3.82(H-6a),3.91(H-6b),5.53(H-1′,J=3.5Hz),3.49(H-2′),3.68(H- 3′),3.32(H-4′),4.29(H-5′),4.22(H-6′a),4.67(H-6′b),6.93(H- 2″、6″,2H,s),7.68(H-7″,1H,d,J=16.0Hz),6.48(H-8″,1H,d,J=16.0Hz), 6.89(H-2’’’、6’’’,2H,s),7.59(H-7’’’,1H,d,J=16.0Hz), 6.45(H-8’’’,1H,d,J=16.0Hz),3.88(H-3″、5″,6H,s,2×-OCH3),3.83(H-3’’’、5’’’,3H,s,-OCH3)。
化合物Ⅲ α-D-(6-O-4-甲基-3,5-二甲氧基肉桂酰基)-吡喃葡萄糖基(1→2)-β-D-(3-O-白芥子酰基)-呋喃果糖
δC65.67(C-1),104.90(C-2),79.39(C-3),74.25(C-4),84.39(C-5),
63.85(C-6),92.72(C-1′),73.18(C-2′),75.15(C-3′),72.03(C-4′), 72.56(C-5′),65.67(C-6′),126.63(C-1″),107.01(C-2″、6″), 149.47(C-3″、5″),139.75(C-4″),147.29(C-7″),115.51(C-8″), 168.26(C-9″),116.26(C-1’’’),107.18(C-2’’’、6’’’),149.47(C-3’’’、5’’’), 132.99(C-4’’’),147.93(C-7’’’),115
In order to find out more chemical constituents and its pharmacological activities in Polygala tenuifolia Wild. In this paper, we had a comprehensive research on it. The methods and results as follow：
The dried roots of Polygala tenuifolia Wild. were extracted three times with boiling water. The extracted solution was passed through macroporous resin column and the adsorbed material eluted successively with H2O, 30%EtOH aq. and 85% EtOH aq. The 85% alcohol solution were collected and concentrated with reduced press and the general extraction were obtained. Twelve pure compounds were isolated from the general extraction by using silica gel chromatography, prep.TLC, active carbon decoloration, crystallization et al.
The structures of the compounds had been identified on
the basis of chemical and spectroscopic evidence(1HNMR,
13CNMR, HMBC, HMQC et al.). They are tenuifoliside A(Ⅰ),
α-D-(6-O-sinapoyl)-glucopyranosyl(1→2)-β-D-(3-O-sinapoyl)-
fructofuranose(Ⅱ),α-D-(6-O-4-methyl-3,5-dimethoxycinnamoyl)-
glucopyranosyl(1→2)-β-D-(3-O-sinapoyl)-fructofuranose(Ⅲ),
3,4,5-trimethoxycinnamylic acid(Ⅳ),phenyl acetate(Ⅴ),nonane(Ⅷ)
ethyl benzoate(Ⅵ),n-dodecane(Ⅶ). In which compound Ⅲ is a new constituent, other compounds but for compoundsⅠ,Ⅱ,Ⅳ were isolated from Polygala tenuifolia Wild. for the first time.
At the same time, the chemical constituents in volatile oil from Polygala tenuifolia Wild. was analyzed by GC-MS-Computer technology. The results showed that the volatile oil contained at least 55 compounds, in which 18 compounds were identified with the computer standard MS spectra. The major compounds were Hexanoic acid, Phenylethy Alcohol, n-Hexadecanoic acid,
Octadecanoic acid, 2-Methoxy-4-vinylphenol, Hexadecanoic acid and 2-hydroxy-(1-hydroxy methyl)-ethyl ester. In which their relatively quantities are 21.52%, 6.19%, 4.00%, 3.09%, 1.94% and 1.40% respectively.
The pharmacological activities of the general extraction from Polygala tenuifolia Wild. were studied. The results showed that the general extraction have the function of removing phlegm and accelerating gastrointestinal peristalsis.
引文
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