三种南方植物中次生代谢物的结构及其生物活性研究
摘要
本文系统研究了三种南方植物,其中包括菊科植物离舌橐吾(Ligularia veitchiana),楝科植物大叶山楝(Aphanamixis grandifolia)的化学成分及部分化合物的生物活性和夹竹桃科仔榄树(Hunteria zeylanica)生物碱成分研究。甘肃文县一带常用离舌橐吾作紫菀入药,用于治疗流行性感冒、咳嗽、溃疡、肺结核等病；大叶山楝在民间具有祛风除湿、舒筋活络、通痹的功效,用于治风寒痹痛,四肢麻木,拘挛及屈伸不利等；据《新华本草纲要》记载,仔榄树的根,味苦、性凉,有消炎止痛的功能,用于毒蛇咬伤、跌打肿痛。
采用常规的萃取、硅胶柱层析(CC)、制备薄层层析(PTLC)、重结晶等手段分离得到了80个化合物。利用各种现代波谱技术(IR、UV、CD、EIMS. ESIMS、HRESIMS、1H NMR、13C NMR、DEPT、NOED、1H-1H COSY、HSQC、HMBC)及X-ray单晶衍射分析法,确定了其中69个化合物的结构,其中9个为新化合物。从离舌橐吾中得到38个化合物,其中3个为新化合物；从大叶山楝中得到35个化合物,其中4个为新化合物；从仔榄树中分离得到7个化合物,其中2个为新化合物。其中我们利用CD和Mosher法确定了化合物Ap6的绝对构型。
此外我们利用micro-broth dilution方法对部分化合物Lvl、Lv2、Lv3、Lv7、Lv9、Lvll、Lv12、Lv15进行了抗菌活性活性实验,利用SRB法对化合物Lvl、Lv7、Lv9、Lvl1、Lv12、Lv15,Apl-Ap7测试了细胞毒活性研究。实验结果表明化合物Lv2对金黄色葡萄球菌(Staphylococcus aureus)有一定的抑制作用,而化合物Lvl1、Lv12和Lv15对人早幼粒白血病细胞(HL-60)、人肝癌细胞(SMMC-7721)和人宫颈癌细胞(HeLa)有中等的抑制活性,它们的IC50≈40gg/mL。化合物Ap3对HL60细胞有强烈的抑制活性,IC50值在5.97μg/mL(阳性对照丝裂霉素的IC50≈0.56μg/mL),化合物Ap2、Ap5、Ap6对HL-60、Hep G2、HeLa三个细胞株有不同程度的中等抑制活性,它们的IC50在40μg/mL附近。这表明具有环尔廷三萜骨架的化合物在抗癌活性开发中具有一定的潜力。
通过比较不同采集地点植物化学成分的异同发现,南方植物与西北植物的化学成分结构类型不同,可能是源于生态环境的差异。
本论文可望为中草药活性成分及其构效关系的研究、药理学、植物化学分类学和新药筛选提供相关的科学依据,为我国天然资源的利用与开发提供帮助。
论文最后从化学分类学的角度出发,系统的总结了近20年来对楝科米仔兰亚族植物,主要是米仔兰属、山楝属和崖摩属植物次生代谢物的研究成果。希望能从化学的角度出发,为该亚族的分类学的进一步发展和完善提供一些参考和帮助。
Three southern plants were researched systematically, including Ligularia veitchiana, Aphanamixis grandifolia and Hunteria zeylanica. L. veitchiana, belonging to the family Compositae, has effects on the treatment of influenza, coughs, ulcers and tuberculosis; A. grandifolia, belonging to the family Meliaceae, is an medicinal plant employed as an astringent for spleen, liver, tumors, abdominal diseases, and applied in treatment of rheumatism in southeast Asia; H. zeylanica, belonging to the family Apocynaceae, is used commonly for smearing on the sores caused by yaws.
Therefore, there are important applicable perspectives for chemical research on these species.80 compounds were isolated from three plants by means of silica gel column chromatography (CC), preparative thin layer chromatography (PTLC), and recrystallization etc. Then various spectroscopic methods including IR, UV, CD, EIMS, FABMS, HRESIMS,1H NMR,13C NMR, DEPT, NOED,'H-'H COSY, HSQC, HMBC, and single-crystal X-ray crystallography were used to elucidate the structures of 69 compounds, among which there were 8 new compounds. The absolute configurations of two carbon stereocenters of compound Ap6 were determined to be 4R,9S by means of CD and auxiliary chiral MTPA derivatives, respectively.
Furthermore the bioactivities of some compounds were also studied. Firstly, micro-broth dilution method was used to evaluate the antimicrobial activity of 8 compounds (Lvl、Lv2、Lv3、Lv7、Lv9、Lv11、Lv12、Lv15) against Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli). Amongst them, compound Lv2 showed modest antibacterial activity against S. aureus. SRB method was used to evaluate the cytotoxicity against selected cancer cell lines of 13 compounds (Lv1、Lv7、Lv9、Lv11、Lv12、Lv15, Apl-Ap7) with mitomycin taken as positive control. The results revealed that compound Ap3 exhibited significant cytotoxicities against HL-60, Hep G2 and HeLa (against HL-60 at 5.97μg/mL). Compounds Lvll, Lv12, and Lv15 exhibited modest cytotoxicities against HL-60, SMMC-7721 and HeLa with IC50≈40μg/mL, and compounds Apl, Ap2, Ap5, Ap6 and Ap7 exhibited modest cytotoxicities against HL-60, Hep G2 and HeLa with IC50≈40μg/mL.
By comparing the chemical constituents of plants collected from different places, the differents of structure isolated from southern and northwestern plants, may be due to different habitats.
The paper would be a supplement for the research on bioactivity of chemical constituents as well as structure-activity relationship in traditional Chinese medicine, a helpful reference for pharmacology, chemotaxonomy and screening new medicines, and may benefit utilizing and developing the natural resources of our country.
Finally, there is a summary of phytochemical studies on subtribe Guareinae Harms in chemical opinion, including the genues Aglaia, Amoora and Aphanamixis. The review was hoped to be useful for chemotaxonomy of subtribe Guareinae Harms.
采用常规的萃取、硅胶柱层析(CC)、制备薄层层析(PTLC)、重结晶等手段分离得到了80个化合物。利用各种现代波谱技术(IR、UV、CD、EIMS. ESIMS、HRESIMS、1H NMR、13C NMR、DEPT、NOED、1H-1H COSY、HSQC、HMBC)及X-ray单晶衍射分析法,确定了其中69个化合物的结构,其中9个为新化合物。从离舌橐吾中得到38个化合物,其中3个为新化合物；从大叶山楝中得到35个化合物,其中4个为新化合物；从仔榄树中分离得到7个化合物,其中2个为新化合物。其中我们利用CD和Mosher法确定了化合物Ap6的绝对构型。
此外我们利用micro-broth dilution方法对部分化合物Lvl、Lv2、Lv3、Lv7、Lv9、Lvll、Lv12、Lv15进行了抗菌活性活性实验,利用SRB法对化合物Lvl、Lv7、Lv9、Lvl1、Lv12、Lv15,Apl-Ap7测试了细胞毒活性研究。实验结果表明化合物Lv2对金黄色葡萄球菌(Staphylococcus aureus)有一定的抑制作用,而化合物Lvl1、Lv12和Lv15对人早幼粒白血病细胞(HL-60)、人肝癌细胞(SMMC-7721)和人宫颈癌细胞(HeLa)有中等的抑制活性,它们的IC50≈40gg/mL。化合物Ap3对HL60细胞有强烈的抑制活性,IC50值在5.97μg/mL(阳性对照丝裂霉素的IC50≈0.56μg/mL),化合物Ap2、Ap5、Ap6对HL-60、Hep G2、HeLa三个细胞株有不同程度的中等抑制活性,它们的IC50在40μg/mL附近。这表明具有环尔廷三萜骨架的化合物在抗癌活性开发中具有一定的潜力。
通过比较不同采集地点植物化学成分的异同发现,南方植物与西北植物的化学成分结构类型不同,可能是源于生态环境的差异。
本论文可望为中草药活性成分及其构效关系的研究、药理学、植物化学分类学和新药筛选提供相关的科学依据,为我国天然资源的利用与开发提供帮助。
论文最后从化学分类学的角度出发,系统的总结了近20年来对楝科米仔兰亚族植物,主要是米仔兰属、山楝属和崖摩属植物次生代谢物的研究成果。希望能从化学的角度出发,为该亚族的分类学的进一步发展和完善提供一些参考和帮助。
Three southern plants were researched systematically, including Ligularia veitchiana, Aphanamixis grandifolia and Hunteria zeylanica. L. veitchiana, belonging to the family Compositae, has effects on the treatment of influenza, coughs, ulcers and tuberculosis; A. grandifolia, belonging to the family Meliaceae, is an medicinal plant employed as an astringent for spleen, liver, tumors, abdominal diseases, and applied in treatment of rheumatism in southeast Asia; H. zeylanica, belonging to the family Apocynaceae, is used commonly for smearing on the sores caused by yaws.
Therefore, there are important applicable perspectives for chemical research on these species.80 compounds were isolated from three plants by means of silica gel column chromatography (CC), preparative thin layer chromatography (PTLC), and recrystallization etc. Then various spectroscopic methods including IR, UV, CD, EIMS, FABMS, HRESIMS,1H NMR,13C NMR, DEPT, NOED,'H-'H COSY, HSQC, HMBC, and single-crystal X-ray crystallography were used to elucidate the structures of 69 compounds, among which there were 8 new compounds. The absolute configurations of two carbon stereocenters of compound Ap6 were determined to be 4R,9S by means of CD and auxiliary chiral MTPA derivatives, respectively.
Furthermore the bioactivities of some compounds were also studied. Firstly, micro-broth dilution method was used to evaluate the antimicrobial activity of 8 compounds (Lvl、Lv2、Lv3、Lv7、Lv9、Lv11、Lv12、Lv15) against Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli). Amongst them, compound Lv2 showed modest antibacterial activity against S. aureus. SRB method was used to evaluate the cytotoxicity against selected cancer cell lines of 13 compounds (Lv1、Lv7、Lv9、Lv11、Lv12、Lv15, Apl-Ap7) with mitomycin taken as positive control. The results revealed that compound Ap3 exhibited significant cytotoxicities against HL-60, Hep G2 and HeLa (against HL-60 at 5.97μg/mL). Compounds Lvll, Lv12, and Lv15 exhibited modest cytotoxicities against HL-60, SMMC-7721 and HeLa with IC50≈40μg/mL, and compounds Apl, Ap2, Ap5, Ap6 and Ap7 exhibited modest cytotoxicities against HL-60, Hep G2 and HeLa with IC50≈40μg/mL.
By comparing the chemical constituents of plants collected from different places, the differents of structure isolated from southern and northwestern plants, may be due to different habitats.
The paper would be a supplement for the research on bioactivity of chemical constituents as well as structure-activity relationship in traditional Chinese medicine, a helpful reference for pharmacology, chemotaxonomy and screening new medicines, and may benefit utilizing and developing the natural resources of our country.
Finally, there is a summary of phytochemical studies on subtribe Guareinae Harms in chemical opinion, including the genues Aglaia, Amoora and Aphanamixis. The review was hoped to be useful for chemotaxonomy of subtribe Guareinae Harms.
引文
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