毛酸浆宿萼的化学成分研究
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摘要
毛酸浆Physalis pubescens L.为茄科Solanaceae酸浆属Physalis L.植物的一年生草本,主要分布东北三省,其带萼果实或全草称为灯笼草。始载于《神农本草经》,并列为中品,具有除烦热,清利咽喉等功效。民间用于治疗急性咽炎,疗效显著。近些年来,国内外研究人员对毛酸浆的同属植物酸浆的研究很多,已报道该属植物所含的主要化学成分为甾体类和黄酮类化合物,此外有甾醇类化合物,生物碱类,氨基酸类,萜类以及其他类化合物。现代药理研究表明,酸浆具有抗菌、强心、兴奋子宫、利尿、抗癌、降血脂、降血糖、抗过敏、免疫调节等作用,因此有一定的研究价值。
本文在综述酸浆属植物的化学成分、药理作用及用途的基础上,采用硅胶柱层析、大孔吸附树脂、Sephadex LH-20、中压制备液相、半制备型高效液相等方法,从毛酸浆宿萼的95%乙醇提取物的石油醚萃取物、氯仿萃取物、乙酸乙酯萃取物和正丁醇萃取物部分,分离出34化合物,通过化合物的理化性质和光谱数据以及标准化合物对照或文献数据比较,鉴定了其中的25个化合物,它们分别被确定为:β-谷甾醇(MH-1)、毛酸浆甾醇A(MH-2)、毛酸浆甾醇B(MH-3)、胡萝卜苷(MH-4)、槲皮素(MH-5)、3,7-二甲基槲皮素(MH-6)、商陆素(MH-7)、3,7,3'-三甲基槲皮素(MH-8)、山柰酚(MH-9)、山柰素(MH-10)、3,7-二甲基山柰酚(MH-11)、7-甲基山柰酚(MH-12)、3,7,4'-三甲基杨梅黄酮(MH-13)、羟基阿亚黄酮(MH-14)、毛酸浆黄酮醇A(MH-15)、3,5-二羟基-γ-吡喃酮(MH-16)、毛酸浆呋喃素(MH-17)、3,5-二羟基-2-羟甲基-γ-吡喃酮(MH-18)、2-羟甲基-5-羟基-γ-吡喃酮(MH-19)、5-羟基麦芽酚(MH-20)、顺,顺-己二烯二酸(MH-21)、3-甲氧基-4-羟基苯甲酸(MH-22)、3,4-二羟基苯甲酸(MH-23)、α-D-葡萄糖(MH-24)、α-D-葡萄糖(2-1)β-D-葡萄糖(MH-25);醉茄内酯类成分(MH-26～MH-28);糖酯类成分(MH-29～MH-34)。其中MH-2、MH-3、MH-15、MH-17为新化合物,MH-18、MH-20为新的天然产物,化合物MH-6、MH-8、MH-10、MH-11、MH-12、MH-13、MH-14、MH-15、MH-16、MH-19、MH-21、MH-22、MH-23、MH-24、MH-25为首次从该属植物中分离得到的成分。
?将分离得到的黄酮醇类化合物MH-5、MH-8、MH-9和吡喃酮类化合物MH-19进行了抗菌、抗氧化和抗肿瘤等活性筛选,初步阐明该植物活性作用的物质基础,为天然药物化学和现代中药药理提供研究资料,达到合理用药,拓宽其应用范围的目的。
本论文的研究工作以期为天然资源的开发利用提供重要的理论依据,并对中草药活性成分研究,新药筛选等提供基础的科学依据。
Physalis pubeacens L. has long been a minor fruit of the Northeast region of China and has also been grown in America. The fruit of the Physalis Genus was also extensively used as herb medicine, and had the effects of detoxification and anti-inflammation in traditional Chinese medicine. Currently, the extract of fruits of the Physalis Genus had been reported to have potent antioxidant, anti-inflammatory, and cytotoxic activities. Previous studies on constituents from the Physalis genus led to the isolation of different compounds such as triterpenoids, flavones, alkaloids and steroids.
During the course of our investigation for bioactive agents from the EtOH extract of calyxs of Physalis pubeacens L., 34 compounds were obtained by using silica gel column chromatography, Sephadex LH-20 chromatography, MPLC, and Semi-HPLC,, and structures of 25 compounds were elucidated through spectroscopic analysis (NMR, MS and IR ). Their structures were identified to beβ-sitosterol (MH-1), physalis pubescensol A (MH-2), physalis pubescensol B (MH-3), daucosterol (MH-4), quercetin (MH-5), 3,7-dimethylquercetin (MH-6), Ombuine (MH-7), 3,7,3'-trimethylquercetin (MH-8), Kaempferol (MH-9), Kaempferide (MH-10), 3,7-dimethylkaempferol (MH-11), 7-methylkaempferol (MH-12), 3,7,4'-trimethyl- myricetin (MH-13), Oxyayanin A (MH-14), physalis pubescens flavones A (MH-15), 3,5-dihydroxy-pyran-4-one(MH-16), physalis pubescens furansu (MH-17), 3,5-dihydroxy-2-hydroxymethyl-pyran-4-one (MH-18), 5-hydroxy-2-hydroxyl- methyl-pyran-4-one (MH-19), 5-hydroxymaltol (MH-20), cis-cis-muconic acid (MH-21), 3-methoxy-4-hydroxy benzoic acid (MH-22), 3,4-dihydroxy benzoic acid (MH-23),α-D-glucose (MH-24),α-D-glucose(2-1)β-D-glucose' (MH-25), withanolides (MH-26～MH-28), sugar esters (MH-29～MH-34). Among them, MH-2, MH-3, MH-15, and MH-17 were new compounds, MH-18 and MH-20 were new natural products, MH-6, MH-8, MH-10, MH-11, MH-12, MH-13, MH-14, MH-15, MH-16, MH-19, MH-21, MH-22, MH-23, MH-24, and MH-25 were isolated from this genus for the first time.
The antibacterial, oxidation and antitumor activitis of compounds MH-5, MH-8, MH-9 and MH-19 were screened, The flavonoids showed some bioactivities, which suggested that flavonoids might be, at least in part, responsible for the proposed therapeutic effect of the calyxs of Physalis pubeacens L.
本文在综述酸浆属植物的化学成分、药理作用及用途的基础上,采用硅胶柱层析、大孔吸附树脂、Sephadex LH-20、中压制备液相、半制备型高效液相等方法,从毛酸浆宿萼的95%乙醇提取物的石油醚萃取物、氯仿萃取物、乙酸乙酯萃取物和正丁醇萃取物部分,分离出34化合物,通过化合物的理化性质和光谱数据以及标准化合物对照或文献数据比较,鉴定了其中的25个化合物,它们分别被确定为:β-谷甾醇(MH-1)、毛酸浆甾醇A(MH-2)、毛酸浆甾醇B(MH-3)、胡萝卜苷(MH-4)、槲皮素(MH-5)、3,7-二甲基槲皮素(MH-6)、商陆素(MH-7)、3,7,3'-三甲基槲皮素(MH-8)、山柰酚(MH-9)、山柰素(MH-10)、3,7-二甲基山柰酚(MH-11)、7-甲基山柰酚(MH-12)、3,7,4'-三甲基杨梅黄酮(MH-13)、羟基阿亚黄酮(MH-14)、毛酸浆黄酮醇A(MH-15)、3,5-二羟基-γ-吡喃酮(MH-16)、毛酸浆呋喃素(MH-17)、3,5-二羟基-2-羟甲基-γ-吡喃酮(MH-18)、2-羟甲基-5-羟基-γ-吡喃酮(MH-19)、5-羟基麦芽酚(MH-20)、顺,顺-己二烯二酸(MH-21)、3-甲氧基-4-羟基苯甲酸(MH-22)、3,4-二羟基苯甲酸(MH-23)、α-D-葡萄糖(MH-24)、α-D-葡萄糖(2-1)β-D-葡萄糖(MH-25);醉茄内酯类成分(MH-26～MH-28);糖酯类成分(MH-29～MH-34)。其中MH-2、MH-3、MH-15、MH-17为新化合物,MH-18、MH-20为新的天然产物,化合物MH-6、MH-8、MH-10、MH-11、MH-12、MH-13、MH-14、MH-15、MH-16、MH-19、MH-21、MH-22、MH-23、MH-24、MH-25为首次从该属植物中分离得到的成分。
?将分离得到的黄酮醇类化合物MH-5、MH-8、MH-9和吡喃酮类化合物MH-19进行了抗菌、抗氧化和抗肿瘤等活性筛选,初步阐明该植物活性作用的物质基础,为天然药物化学和现代中药药理提供研究资料,达到合理用药,拓宽其应用范围的目的。
本论文的研究工作以期为天然资源的开发利用提供重要的理论依据,并对中草药活性成分研究,新药筛选等提供基础的科学依据。
Physalis pubeacens L. has long been a minor fruit of the Northeast region of China and has also been grown in America. The fruit of the Physalis Genus was also extensively used as herb medicine, and had the effects of detoxification and anti-inflammation in traditional Chinese medicine. Currently, the extract of fruits of the Physalis Genus had been reported to have potent antioxidant, anti-inflammatory, and cytotoxic activities. Previous studies on constituents from the Physalis genus led to the isolation of different compounds such as triterpenoids, flavones, alkaloids and steroids.
During the course of our investigation for bioactive agents from the EtOH extract of calyxs of Physalis pubeacens L., 34 compounds were obtained by using silica gel column chromatography, Sephadex LH-20 chromatography, MPLC, and Semi-HPLC,, and structures of 25 compounds were elucidated through spectroscopic analysis (NMR, MS and IR ). Their structures were identified to beβ-sitosterol (MH-1), physalis pubescensol A (MH-2), physalis pubescensol B (MH-3), daucosterol (MH-4), quercetin (MH-5), 3,7-dimethylquercetin (MH-6), Ombuine (MH-7), 3,7,3'-trimethylquercetin (MH-8), Kaempferol (MH-9), Kaempferide (MH-10), 3,7-dimethylkaempferol (MH-11), 7-methylkaempferol (MH-12), 3,7,4'-trimethyl- myricetin (MH-13), Oxyayanin A (MH-14), physalis pubescens flavones A (MH-15), 3,5-dihydroxy-pyran-4-one(MH-16), physalis pubescens furansu (MH-17), 3,5-dihydroxy-2-hydroxymethyl-pyran-4-one (MH-18), 5-hydroxy-2-hydroxyl- methyl-pyran-4-one (MH-19), 5-hydroxymaltol (MH-20), cis-cis-muconic acid (MH-21), 3-methoxy-4-hydroxy benzoic acid (MH-22), 3,4-dihydroxy benzoic acid (MH-23),α-D-glucose (MH-24),α-D-glucose(2-1)β-D-glucose' (MH-25), withanolides (MH-26～MH-28), sugar esters (MH-29～MH-34). Among them, MH-2, MH-3, MH-15, and MH-17 were new compounds, MH-18 and MH-20 were new natural products, MH-6, MH-8, MH-10, MH-11, MH-12, MH-13, MH-14, MH-15, MH-16, MH-19, MH-21, MH-22, MH-23, MH-24, and MH-25 were isolated from this genus for the first time.
The antibacterial, oxidation and antitumor activitis of compounds MH-5, MH-8, MH-9 and MH-19 were screened, The flavonoids showed some bioactivities, which suggested that flavonoids might be, at least in part, responsible for the proposed therapeutic effect of the calyxs of Physalis pubeacens L.
引文
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