宜昌润楠化学成分和生物活性的研究
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摘要
宜昌润楠(Machilus ichangensis Rehd. et Wils.)是樟科润楠属常绿植物,主要产于湖北省、四川省、陕西省南部、甘肃省西部,资源十分丰富。宜昌润楠在我国传统和民间医药典籍中有应用记载,在三峡区域民间主要应用其治疗各种皮肤炎症、关节肿痛和风湿性疾病,疗效显著,且无明显的毒副作用。宜昌润楠的化学成分及其生物活性的研究国内外未见报道。
本论文对采集自湖北宜昌大老岭的民间药用植物宜昌润楠进行了系统化学分离,根据宜昌润楠民间药用特点和同属植物相关药理学文献报道,在体外细胞毒活性、神经细胞保护和抗炎药理模型上,对已分离鉴定的化学成分和主要提取部位进行了初步的活性评价和筛选,为宜昌润楠的进一步研究和开发提供了科学依据。
主要研究结果如下：
1.通过溶剂提取法和多种色谱方法对宜昌润楠干燥茎枝的95%乙醇提取物进行分离纯化,利用现代波谱技术(IR、UV、MS、1H NMR、13CNMR、DEPT、2D NMR、 CD等)和理化性质进行结构鉴定,一共分离鉴定了52个化合物,分别是润楠香豆素(1),润楠丁内脂A(2),润楠丁内酯B(3),润楠丁内酯C(4),润楠丁内酯D(5),润楠丁内酯E(6),润楠丁内酯F(7),(-)-利卡灵-A(8),(-)-acuminatin (9), odoratisol A (10),(-)-利卡灵-B(11),(+)-松脂醇(12),(+)-丁香树脂酚(13),右旋杜仲树脂酚(14),4-ketopinoresinol (15), iso-4-ketopinoresinol(16),(-)-南烛木树脂酚-3α-O-β-D-吡喃葡萄糖苷(17),(-)-5’-甲氧基异落叶松脂醇-9-O-β-D-吡喃葡萄糖苷(18),(+)-异落叶松脂素-9-O-β-D-吡喃葡萄糖苷(19),樟皮碱B(20), nectandrin A (21), galgravin (22), fragransins B3(23),(-)-开环异落叶松树脂酚(24),楠木脂素A(25),东莨菪素(26),异东莨若素(27),反式香豆酸(28),咖啡酸(29),阿魏酸(30),异阿魏酸(31),榄香脂素(32),胡椒酚-1-O-β-D-吡喃葡萄糖苷(33),(+)-儿茶素(34),(-)-表儿茶素(35),(2R,3R)-4’-羟基-5,7,3’-三甲氧基黄烷-3-醇(36),(2R,3R)-3-羟基-5,7-二甲氧基-3’,4’-亚甲二氧基黄烷(37),柚皮素(38),达维荚蓬苷元(39),胡椒基酸(40),香草酸(41),原儿茶酸(42),丁香酸(43),3,4,5-三甲氧基苯酚-1-O-β-D-吡喃葡萄糖苷(44),phenolphthalein (45),淫羊藿苷B2(46),byzantionosides A (47),(E)-4-(1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl)-but-3-en-2-one (48),脱落酸(49),β-谷甾醇(50),胡萝卜苷(51),软脂酸(52)。包括丁内酯类化合物6个,木脂素类化合物18个,香豆素类化合物3个,苯丙素类化合物6个,黄酮类化合物6个,酚类化合物6个,β-紫罗兰酮类化合物4个,甾体类化合物2个,脂肪酸类化合物1个。其中发现了7个新化合物,1个异香豆素二聚体类化合物(化合物1)和6个丁内酯类化合物(化合物2-7),所有化合物均为首次从该植物中分离得到。
2.体外细胞毒活性研究中,采用MTT法评价了单体化合物的细胞毒活性,结果表明,在供试的7种细胞株中,丁内酯类的6个新化合物(化合物2-7)对肿瘤细胞均表现出一定的细胞毒活性,对正常细胞毒性较小。该类化合物对人乳腺癌细胞MDA-MB-231有选择性细胞毒活性,其中化合物3的细胞毒活性最强,IC50为3.22μM；神经细胞保护活性研究中,建立H202所致人神经母细胞瘤细胞SH-SY5Y的氧化应激损伤模型,通过MTT法检测筛选指标细胞存活率,结果表明,异香豆素二聚体类新化合物(化合物1)在0.625-10.0μg/mL的浓度范围内能显著地保护由H202诱导引起的SH-SY5Y细胞损伤,并具有良好的剂量依赖性：抗炎活性研究中,利用细菌脂多糖(LPS)刺激经佛波酯(PMA)诱导的人单核细胞THP-1建立体外炎症模型,MTT法检测样品的细胞毒性,ELISA方法检测药物干预前后上清液中IL-1β、IL-6、TNF-α和NO的分泌量,综合评价宜昌润楠总苷对炎性细胞因子和介质的抑制作用,结果表明,宜昌润楠总苷极显著的抑制了IL-6和TNF-α以及NO的产生,并且其抑制作用具有时间和剂量依耐性,但对IL-1β没有明显的抑制效果。
Machilus ichangensis Rehd. et Wils.(Lauraceae) belongs to macrophanerophytes, which is widely distributed in the broad-leafed forests in Hubei, Sichuan, southern Shaanxi and Western Gansu Provinces. This plant was recorded in Chinese traditional and folk medicine books, mainly for treatments of various skin inflammations, swelling of the joints and rheumatic diseases in the Three Gorges Region, having significant effects, but no obvious toxic side effects. However, no chemical constituents or biological activities relating to this plant have been reported.
In this paper, chemical constituents of Machilus ichangensis, collected from Dalaoling in Hubei Province, was investigated, in order to provide a scientific basis for the further research and development of this genus. According to its folk application characteristics and pharmacology literature, we evaluated the pharmacological activities of its extracts and compounds, using in vitro cytotoxicity, neuroprotective and anti-inflammatory models.
The main results can be described as follows:
1. Various chromatographic methods were used for the isolation of the compounds, and their structures were identified by modern spectral technologies (including IR, UV, MS,'H NMR,13C NMR, DEPT,2D NMR and CD) with physicochemical properties. Fifty-two compounds were isolated from the95%ethanol extract of the stems of Machilus ichangensis, and the structures of them were identified as follows:machilusmarin (1), machilusolide A (2), machilusolide B (3), machilusolide C (4), machilusolide D (5), machilusolide E (6), machilusolide F (7),(-)-licarin A (8),(-)-acuminatin (9), odoratisol A (10),(-)-licarin B (11),(+)-pinoresinol (12),(+)-syringaresinol (13),(+)-medioresinol (14),4-ketopinoresinol (15),iso-4-ketopinoresinol (16),(-)-lyoniresinol-3α-O-β-D-glucopyranoside (17), (-)-5'-methoxyisolariciresinol-3α-O-β-D-glucopyran-oside(18), isolariciresinol-9-O-β-D-glucopyranoside (19), nectandrin B (20), nectandrin A (21), galgravin (22), fragransins B3(23),(-)-secoisolariciresinol (24), machilin A (25), scopoletin (26), isoscopoletin (27), E-p-coumaric acid (28), caffeic acid (29), ferulic acid (30), isoerulic acid (31), elemicin (32), chavico-l-O-β-D-glucopyranoside (33),(+)-catechin (34),(-)-epicatechin (35),(2R,3R)-4'-hydroxy-5,7,3'-trimethoxyflavan-3-ol (36),(2R,3R)-3-hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan (37), naringenin (38), davidigenin (39), piperonylic acid (40), vanillic acid (41), protocatechuic acid (42), syringic acid (43),3,4,5-trimethoxyphenol-l-O-β-D-glucopyranoside (44), phenolphthalein (45), icariside B2(46), byzantionosides A (47),(E)-4-(1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl)-but-3-en-2-one (48), abscisic acid (49),β-sitosterol (50), daucosterol (51), and palmitic acid (52), including six butanolides, eighteen lignans, three coumarins, six phenylpropanoids, six flavonoids, six phenols, four β-ionones, two steroids and one fatty acids. Among them, seven compounds were new, which included one dimeric isocoumarin derivate (1) and six butanolides (2-7). All those compounds were isolated from this plant for the first time.
2. In vitro cytotoxicity of compounds was determined by MTT assay. Six new butanolides showed selective cytotoxicity against MDA-MB-231, compound3had the best cytotoxicity, with IC503.22μM; The neuroprotective activity of all the compounds was evaluated by SH-SY5Y human neuroblastoma cells apoptosis induced by hydrogen peroxide. Compound1showed significant neuroprotective activity against SH-SY5Y human neuroblastoma cells apoptosis induced by hydrogen peroxide, its concentrations ranging from0.625μg/mL to10.0μg/mL; Inflammation model in vitro was established by stimulating human acute monocytic leukemia cell line with lipopolysaccharide, after which were differentiated into macrophages by phorbol ester. Cytotoxicity of total glucoside of Machilus ichangensis was determined by MTT assay, the anti-inflammatory potential of total glucoside of Machilus ichangensis was evaluated by monitoring its effects on the modulation of cytokines and mediators of inflammation, such as interleukin1β, interleukin6, tumor necrosis factor-a and nitric oxide in cell culture medium, using ELISA methods. Total glucoside of Machilus ichangensis showed great significant dose-and time-dependent inhibitory activities on IL-6, TNF-a and NO synthesis, but slight effect on IL-1β.
本论文对采集自湖北宜昌大老岭的民间药用植物宜昌润楠进行了系统化学分离,根据宜昌润楠民间药用特点和同属植物相关药理学文献报道,在体外细胞毒活性、神经细胞保护和抗炎药理模型上,对已分离鉴定的化学成分和主要提取部位进行了初步的活性评价和筛选,为宜昌润楠的进一步研究和开发提供了科学依据。
主要研究结果如下：
1.通过溶剂提取法和多种色谱方法对宜昌润楠干燥茎枝的95%乙醇提取物进行分离纯化,利用现代波谱技术(IR、UV、MS、1H NMR、13CNMR、DEPT、2D NMR、 CD等)和理化性质进行结构鉴定,一共分离鉴定了52个化合物,分别是润楠香豆素(1),润楠丁内脂A(2),润楠丁内酯B(3),润楠丁内酯C(4),润楠丁内酯D(5),润楠丁内酯E(6),润楠丁内酯F(7),(-)-利卡灵-A(8),(-)-acuminatin (9), odoratisol A (10),(-)-利卡灵-B(11),(+)-松脂醇(12),(+)-丁香树脂酚(13),右旋杜仲树脂酚(14),4-ketopinoresinol (15), iso-4-ketopinoresinol(16),(-)-南烛木树脂酚-3α-O-β-D-吡喃葡萄糖苷(17),(-)-5’-甲氧基异落叶松脂醇-9-O-β-D-吡喃葡萄糖苷(18),(+)-异落叶松脂素-9-O-β-D-吡喃葡萄糖苷(19),樟皮碱B(20), nectandrin A (21), galgravin (22), fragransins B3(23),(-)-开环异落叶松树脂酚(24),楠木脂素A(25),东莨菪素(26),异东莨若素(27),反式香豆酸(28),咖啡酸(29),阿魏酸(30),异阿魏酸(31),榄香脂素(32),胡椒酚-1-O-β-D-吡喃葡萄糖苷(33),(+)-儿茶素(34),(-)-表儿茶素(35),(2R,3R)-4’-羟基-5,7,3’-三甲氧基黄烷-3-醇(36),(2R,3R)-3-羟基-5,7-二甲氧基-3’,4’-亚甲二氧基黄烷(37),柚皮素(38),达维荚蓬苷元(39),胡椒基酸(40),香草酸(41),原儿茶酸(42),丁香酸(43),3,4,5-三甲氧基苯酚-1-O-β-D-吡喃葡萄糖苷(44),phenolphthalein (45),淫羊藿苷B2(46),byzantionosides A (47),(E)-4-(1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl)-but-3-en-2-one (48),脱落酸(49),β-谷甾醇(50),胡萝卜苷(51),软脂酸(52)。包括丁内酯类化合物6个,木脂素类化合物18个,香豆素类化合物3个,苯丙素类化合物6个,黄酮类化合物6个,酚类化合物6个,β-紫罗兰酮类化合物4个,甾体类化合物2个,脂肪酸类化合物1个。其中发现了7个新化合物,1个异香豆素二聚体类化合物(化合物1)和6个丁内酯类化合物(化合物2-7),所有化合物均为首次从该植物中分离得到。
2.体外细胞毒活性研究中,采用MTT法评价了单体化合物的细胞毒活性,结果表明,在供试的7种细胞株中,丁内酯类的6个新化合物(化合物2-7)对肿瘤细胞均表现出一定的细胞毒活性,对正常细胞毒性较小。该类化合物对人乳腺癌细胞MDA-MB-231有选择性细胞毒活性,其中化合物3的细胞毒活性最强,IC50为3.22μM；神经细胞保护活性研究中,建立H202所致人神经母细胞瘤细胞SH-SY5Y的氧化应激损伤模型,通过MTT法检测筛选指标细胞存活率,结果表明,异香豆素二聚体类新化合物(化合物1)在0.625-10.0μg/mL的浓度范围内能显著地保护由H202诱导引起的SH-SY5Y细胞损伤,并具有良好的剂量依赖性：抗炎活性研究中,利用细菌脂多糖(LPS)刺激经佛波酯(PMA)诱导的人单核细胞THP-1建立体外炎症模型,MTT法检测样品的细胞毒性,ELISA方法检测药物干预前后上清液中IL-1β、IL-6、TNF-α和NO的分泌量,综合评价宜昌润楠总苷对炎性细胞因子和介质的抑制作用,结果表明,宜昌润楠总苷极显著的抑制了IL-6和TNF-α以及NO的产生,并且其抑制作用具有时间和剂量依耐性,但对IL-1β没有明显的抑制效果。
Machilus ichangensis Rehd. et Wils.(Lauraceae) belongs to macrophanerophytes, which is widely distributed in the broad-leafed forests in Hubei, Sichuan, southern Shaanxi and Western Gansu Provinces. This plant was recorded in Chinese traditional and folk medicine books, mainly for treatments of various skin inflammations, swelling of the joints and rheumatic diseases in the Three Gorges Region, having significant effects, but no obvious toxic side effects. However, no chemical constituents or biological activities relating to this plant have been reported.
In this paper, chemical constituents of Machilus ichangensis, collected from Dalaoling in Hubei Province, was investigated, in order to provide a scientific basis for the further research and development of this genus. According to its folk application characteristics and pharmacology literature, we evaluated the pharmacological activities of its extracts and compounds, using in vitro cytotoxicity, neuroprotective and anti-inflammatory models.
The main results can be described as follows:
1. Various chromatographic methods were used for the isolation of the compounds, and their structures were identified by modern spectral technologies (including IR, UV, MS,'H NMR,13C NMR, DEPT,2D NMR and CD) with physicochemical properties. Fifty-two compounds were isolated from the95%ethanol extract of the stems of Machilus ichangensis, and the structures of them were identified as follows:machilusmarin (1), machilusolide A (2), machilusolide B (3), machilusolide C (4), machilusolide D (5), machilusolide E (6), machilusolide F (7),(-)-licarin A (8),(-)-acuminatin (9), odoratisol A (10),(-)-licarin B (11),(+)-pinoresinol (12),(+)-syringaresinol (13),(+)-medioresinol (14),4-ketopinoresinol (15),iso-4-ketopinoresinol (16),(-)-lyoniresinol-3α-O-β-D-glucopyranoside (17), (-)-5'-methoxyisolariciresinol-3α-O-β-D-glucopyran-oside(18), isolariciresinol-9-O-β-D-glucopyranoside (19), nectandrin B (20), nectandrin A (21), galgravin (22), fragransins B3(23),(-)-secoisolariciresinol (24), machilin A (25), scopoletin (26), isoscopoletin (27), E-p-coumaric acid (28), caffeic acid (29), ferulic acid (30), isoerulic acid (31), elemicin (32), chavico-l-O-β-D-glucopyranoside (33),(+)-catechin (34),(-)-epicatechin (35),(2R,3R)-4'-hydroxy-5,7,3'-trimethoxyflavan-3-ol (36),(2R,3R)-3-hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan (37), naringenin (38), davidigenin (39), piperonylic acid (40), vanillic acid (41), protocatechuic acid (42), syringic acid (43),3,4,5-trimethoxyphenol-l-O-β-D-glucopyranoside (44), phenolphthalein (45), icariside B2(46), byzantionosides A (47),(E)-4-(1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl)-but-3-en-2-one (48), abscisic acid (49),β-sitosterol (50), daucosterol (51), and palmitic acid (52), including six butanolides, eighteen lignans, three coumarins, six phenylpropanoids, six flavonoids, six phenols, four β-ionones, two steroids and one fatty acids. Among them, seven compounds were new, which included one dimeric isocoumarin derivate (1) and six butanolides (2-7). All those compounds were isolated from this plant for the first time.
2. In vitro cytotoxicity of compounds was determined by MTT assay. Six new butanolides showed selective cytotoxicity against MDA-MB-231, compound3had the best cytotoxicity, with IC503.22μM; The neuroprotective activity of all the compounds was evaluated by SH-SY5Y human neuroblastoma cells apoptosis induced by hydrogen peroxide. Compound1showed significant neuroprotective activity against SH-SY5Y human neuroblastoma cells apoptosis induced by hydrogen peroxide, its concentrations ranging from0.625μg/mL to10.0μg/mL; Inflammation model in vitro was established by stimulating human acute monocytic leukemia cell line with lipopolysaccharide, after which were differentiated into macrophages by phorbol ester. Cytotoxicity of total glucoside of Machilus ichangensis was determined by MTT assay, the anti-inflammatory potential of total glucoside of Machilus ichangensis was evaluated by monitoring its effects on the modulation of cytokines and mediators of inflammation, such as interleukin1β, interleukin6, tumor necrosis factor-a and nitric oxide in cell culture medium, using ELISA methods. Total glucoside of Machilus ichangensis showed great significant dose-and time-dependent inhibitory activities on IL-6, TNF-a and NO synthesis, but slight effect on IL-1β.
引文
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