摘要
鸡血藤是一味沿用千年的活血化瘀中药,古代多篇本草论著中都记载了其“祛瘀血,生新血”的功效,称之为“血分之圣药”。文献记载的鸡血藤植物来源复杂,为了澄清鸡血藤品种并开发药源,本论文前期对鸡血藤四种基源植物密花豆藤、白花油麻藤、香花崖豆藤、皱果崖豆藤的50%、95%乙醇提取物进行了60Coγ射线辐射小鼠外周血象影响的研究,发现四种植物对辐射所致的小鼠造血功能损伤均表现一定保护作用,其中密花豆藤及白花油麻藤作用较显著。前期他人已对密花豆藤的乙醇提取物进行了系统的化学成分研究,并从中发现一个活性单体—儿茶素。为了进一步研究其他鸡血藤的化学成分及其之间异同,且更深入发掘活性更好成分,本论文运用多种色谱和波谱技术,并结合化学方法,对以上另外两种基源植物白花油麻藤及香花崖豆藤的藤茎乙醇提取物分别进行了系统的化学成分研究,并对其中的单体化合物进行了生物活性筛选。
白花油麻藤Mucuna birdwoodianaTutch为豆科油麻藤属植物,主要分布于我国广东、广西、云南等省。本论文对采自广西金秀县的白花油麻藤藤茎的50%乙醇提取物进行分离鉴定,共得26个化合物,其中6个化合物(Mu-1-Mu-6)为新化合物,且除化合物Mu-11, Mu-12, Mu-24, Mu-25外,其余均为首次从该属植物中分离得到。其中包括1个3-苯基香豆素类化合物,7个2-苯基苯并呋喃类衍生物,12个异黄酮及其苷类化合物,1个紫檀烯类化合物,1个蒽醌类化合物,1个木脂素,2个三萜类化合物,1个长链类化合物,分别为：mucodianins A-F (Mu-1 Mu-6),6-demethylvignafuran (Mu-7), eryvarin L (Mu-8), isopterofuran (Mu-9), lespeflorin F1 (Mu-10),芒柄花素(formononetin, Mu-11),染料木素(genisten, Mu-12),8-甲雷杜辛(8-O-methylreyusin, Mu-13),7,3'-二羟基-5′-甲氧基异黄酮(7,3'-dihydroxy-5'-methoxyisoflavone, Mu-14), formononetin 7-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside(Mu-15), ononin (Mu-16),7-hydroxy-4,8-dimethoxyisof-lavone 7-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (Mu-17),7-hydroxy-4',8-dimethoxyisoflavone 7-O-β-D-glucopyranoside (Mu-18),染料木素苷(genistin, Mu-19), retusin 7-O-β-D-glucopyranoside (Mu-20),3'-methoxycoumestrol (Mu-21),大黄酚(chrysophanol, Mu-22),(一)丁香脂素[(-)syringaresinol, Mu-23],表木栓醇(epifriedelanol, Mu-24),羽扇豆醇(lupeol, Mu-25),正二十烷酸甘油单酯(glyceryl a-monoeicosa, Mu-26)。
筛选了其中13个化合物(化合物Mu-2, Mu-4, Mu-7, Mu-8, Mu-10-Mu-14, Mu-21, Mu-22, Mu-24, Mu-25)在血清诱导血管平滑肌细胞增殖的抑制活性筛选模型上的药理活性,其浓度为10-5M时,化合物Mu-12及Mu-22表现出较强活性,抑制率达到50%以上。香花崖豆藤Millettia dielsiana Harms为豆科崖豆藤属植物,分布在我国华南、西南、华中等地区。本论文研究的香花崖豆藤采自云南勐腊曼变,对其藤茎的95%乙醇提取物进行分离鉴定,共得37个化合物,其中8个化合物(Mi-1～Mi-6,Mi-23,Mi-24)为新化合物。所分得化合物包括1个二苯基二酮类化合物,30个异黄酮及其苷类化合物,1个黄酮类化合物,1个酚苷类化合物,1个生物碱类化合物,1个长链化合物,2个其他。分别为：dielsianone (Mi-1), millesianins A-E (Mi-2-Mi-6),6-methoxycalpogonium isoflavone A (Mi-7), durmillone (Mi-8), ichthy-none (Mi-9), jamaicin (Mi-10), toxicarol isoflavone (Mi-11), barbigerone (Mi-12),阿弗洛莫生(afromosin, Mi-13), caviunin (Mi-14), cladrastin (Mi-15),大豆黄素(daidzein, Mi-16),染料木素(genisten, Mi-17),芒柄花素(formononetin, Mi-18), hernancorizin (Mi-19),正二十六碳酸(hexacosendioic acid, Mi-20),谷甾醇(β-sitosterol, Mi-21),胡萝卜苷(daucosterol, Mi-22), millesianin F (Mi-23), millesi-anin G (Mi-24),大豆苷(daidzin, Mi-25), claclrastin 7-O-β-D-glucopyranoside (Mi-26),7-hydroxy-4',6-dimethoxyisoflavone 7-O-β-D-apiofuranosyl-(1→6)-β-D-glucop-yranoside (Mi-27), wistin (Mi-28),7-hydroxy-4',8-dimethoxyisoflavone 7-O-β-D-g-lucopyranoside (Mi-29),7-hydroxy-4',8-dimethoxyisoflavone 7-O-β-D-apiofuranos-yl-(1→6)-β-D-glucopyr-anoside (Mi-30), glycitin (Mi-31), odoratin-7-O-β-D-glucop-yranoside (Mi-32), dalpatin (Mi-33),染料木素苷(genistin, Mi-34),5,7,4'-trihy-droxyisoflavone 7-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (Mi-35),2,4,6-trimethoxyphenol-1-O-β-D-glucopyranoside (Mi-36),3H-imidazo[4,5-c] pyridine( Mi-37)。
对其中10个化合物(化合物Mi-2,Mi-4,Mi-7,Mi-8,Mi-11-Mi-17)进行了活性筛选,浓度为10-5M时,在抑制PAF刺激的多形核白细胞β-葡萄糖苷酸酶释放的模型上,3个化合物(化合物Mi-2,Mi-12,Mi-17)具有抗炎活性(抑制率大于50%,P<0.05)。采用MTT法测定了12个化合物(化合物Mi-2-Mi-4, Mi-6-Mi-8, Mi-11-Mi-14, Mi-16, Mi-17)对五种人肿瘤细胞(A549：人肺腺癌细胞；Bel-7402人肝癌细胞；BGC-823：人胃癌细胞；HCT-8：人结肠癌细胞；A2780：人卵巢癌细胞)的抑制作用。结果显示化合物Mi-4对BGC-823人胃癌细胞有抑制作用,IC50=0.74μM,其余部分化合物表现出对部分细胞株的一般活性。
Traditional Chinese medicine "ji-xue-teng" has been used to invigorate the circulation of blood and enrich the blood for thousands of years, named as "Imperial Medicine of blood" in many old herbal treatises. But the source of traditional Chinese medicine "ji-xue-teng" was complicated, and in order to investigate the effect of these plants and develop more active compounds, the 50% and 95% EtOH extracts of stem bark of four kinds of "ji-xue-teng" plants (Spatholobus suberectu, Mucuna birdwoodiana, Millettia dielsiana, and Millettia oosperma) were tested on peripheral blood cell counts of mice with bone marrow suppresion induced by 60Co y ray irradiation. All the four kinds of plant extracts can accelerate the recovery of WBC, RBC and PLT counts in peripheral blood of mice with bone marrow suppression, while the effects of Spatholobus suberectu and Mucuna birdwoodiana are relative good. The 95% EtOH extract of stem bark of Spatholobus suberectu was investigated on their chemical constituents systematically and one bioactive compound - catechin had been found out. However, for the more active compounds from the plants of "ji-xue-teng", the EtOH extracts of stem bark of Mucuna birdwoodiana and Millettia dielsiana had been investigated respectively on their chemical constituents systematically by various kinds of chromatographic methods. The structures of the compounds were elucidated on the basis of spectroscopic analysis and chemical methods as well. Some of them in sufficient amount were assayed for their bioactivities.
Mucuna birdwoodiana is the species belonging to the genus Mucuna of Leguminosae, it mostly distributes in Province Guangdong, Guangxi, and Yunnan etc. The stem bark of M. birdwoodiana in our study were collected from Jinxiu County of Guangxi Province. Twenty-six compounds had been isolated from the 50% EtOH extracts of stem bark of M. birdwoodiana, among which six ones ( Mu-1-Mu-6) were new compounds, and except for the compounds Mu-11, Mu-12, Mu-24, Mu-25, the rest were isolated from this genus for the first time. These compounds included one 3-arylcoumarin, seven 2-arylbenzofurans, twelve isoflavone aglycons or glycosides, one pterocarpene, one anthraquinone, one lignan, two triterpenes, one long chain compounds, list as follows:mucodianins A-F (Mu-1-Mu-6),6-demethylvignafuran (Mu-7), eryvarin L (Mu-8), isopterofuran (Mu-9), lespeflorin F1 (Mu-10), formononetin (Mu-11), genisten (Mu-12),8-O-me-thylreyusin (Mu-13),7,3'-dihydroxy-5'-methoxyisoflavone (Mu-14), formononetin 7-O- β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (Mu-15), ononin (Mu-16),7-hydroxy-4',8-dimethoxyisoflavone 7-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (Mu-1 7),7-hydroxy-4',8-dimethoxyisoflavone 7-O-β-D-glucopyranoside (Mu-18), genistin (Mu-19), retusin 7-O-β-D-glucopyranoside (Mu-20),3'-methoxycoumestrol (Mu-21), chrysophanol (Mu-22), (-)syringaresinol (Mu-23), epifriedelanol (Mu-24), lupeol (Mu-25), glyceryl a-monoeicosa (Mu-26).
Thirteen compounds (Mu-2, Mu-4, Mu-7, Mu-8, Mu-10-Mu-14, Mu-21, Mu-22, Mu-24, Mu-25) were tested by the assay to inhibitory action of smooth muscle cell proliferation induced by blood serum, Mu-12 and Mu-22 displayed moderate activities with the inhibitory rates more than 50% at a concentration of 10-5 M.
Millettia dielsiana belongs to the genus Millettia of the family Leguminosae, distributed in the southern, southwestern, middle region of China. The stem bark of M. dielsiana in our study were collected in County of Manbian, Yunnan Province. Thirty-seven compounds had been isolated from the 95% EtOH extracts of stem bark of M. dielsiana, among which eight ones (Mi-1-Mi-6, Mi-23, Mi-24) were new compounds. These compounds included one benzil, thirty isoflavone aglycons or glycosides, one flavone, one phenolic glycoside, one alkloid, one long chain compounds, list as follows:dielsianone (Mi-1), millesianins A-E (Mi-2-Mi-6),6-methoxycalpogonium isoflavone A (Mi-7), durmillone (Mi-8), ichthynone (Mi-9), jamaicin (Mi-10), toxicarol isoflavone (Mi-11), barbigerone (Mi-12), afro-mosin (Mi-13), caviunin (Mi-14), cladrastin (Mi-15), daidzein (Mi-16), genisten (Mi-17), formononetin (Mi-18), hernancorizin (Mi-19), hexacosendioic acid (Mi-20),β-sitosterol (Mi-21), daucosterol (Mi-22), millesianin F (Mi-23), millesianin G (Mi-24), daidzin (Mi-25), claclrastin 7-O-β-D-glucopyranoside (Mi-26),7-hydroxy-4',6-dimethoxyisoflavone 7-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (Mi-27), wistin (Mi-28),7-hydroxy-4',8-dimethoxyisoflavone 7-O-β-D-glucopyranoside (Mi-29),7-hydroxy-4',8-dimethoxyisoflavone7-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyra-noside (Mi-30), glycitin (Mi-31), odoratin-7-O-β-D-glucopyranoside (Mi-32), dalpa-tin (Mi-33), genistin (Mi-34),5,7,4'-trihydroxyisoflavone 7-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (Mi-35),2,4,6-trimethoxyphenol-l-O-β-D-glucopyran-oside (Mi-36),3H-imidazo[4,5-c] pyridine(Mi-37).
Ten compounds (Mi-2, Mi-4, Mi-7, Mi-8, Mi-11-Mi-17) were tested for their anti-inflammatory activities in vitro by an assay to release ofβ-glucuronidase from rat PMNs induced by PAR Compounds Mi-2, Mi-12 and Mi-17 showed significant activities with the inhibitiory ratios more than 50%(P< 0.05) at concentration of 10-5 M.
Twelve compounds (compounds Mi-2-Mi-4, Mi-6-Mi-8, Mi-11-Mi-14, Mi-16, Mi-17) were evaluated for cytotoxicity test against five human tumor cell lines (A549, Bel-7402, BGC-823, HCT-8 and A2780). Compound Mi-4 showed obvious activity against BGC823 (IC50= 0.74μM). The other compounds displayed moderate activities against five human tumor cells.
引文
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