七种药用植物的化学成分及其生物活性研究
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摘要
本文对七种药用植物川楝Melia toosendan、苦楝Melia azedarach、羌活Notopterygium incisum、海桑Sonneratia caseolaris、卵叶海桑Sonneratia ovata、臭椿Ailanthus altissima和鸦胆子Brucea javanica的化学成分及其生物活性进行了研究。运用波谱学技术(尤其是2D NMR)、化学转化、单晶衍射及相关分子模型理论计算等手段总共鉴定了106个具有不同结构的天然化合物(包括30个三萜、11个柠檬苦素、21个甾体、19个香豆素、10个倍半萜、3个黄酮、6个苯丙素类化合物、4个烯炔类化合物以及联苯类化合物2个)。其中新化合物37个。生物活性测试表明部分化合物具有激活衰老抑制基因klotho启动子的功能；部分化合物显示很好的抗肿瘤细胞增殖作用。对呋哺香豆素类化合物进行构效关系探讨,并用流式细胞仪等手段对它们进行了一定的抗肿瘤细胞增殖作用机理研究。
本毕业论文的具体研究内容简要如下：
1)从楝科楝属植物川楝的果实中分离并鉴定出35个单体化合物(1-35),包括四环三萜16个、柠檬苦素11个、甾体8个。其中新化合物17个,包括12个新的四环三萜(1-12),4个新的柠檬苦素(25-35)和1个新的甾体(13),化合物meliasenins I(1)最终通过X-ray单晶衍射法确定其立体结构。对部分带过氧键的化合物进行了一定的生物合成途径探讨。大部分化合物进行了杀虫活性及体外细胞毒作用等生物活性测试。结果表明：化合物1-10,13-17和22对人骨肉瘤细胞U20S及人乳腺癌细胞MCF-7细胞株均显示较好的抗细胞增殖作用。
2)苦楝为楝科楝属另一植物,本文对其茎皮和树叶分别进行了系统的化学成分研究。从其茎皮中分离得到单体化合物16个(10个甾体和6个三萜),其中新化合物4个,包括2个新的四环三萜和2个新的甾体和1个新的天然来源淄体,化合物21,24-cycloeupha-7-ene-3β,16β,21α,25-tetrol (36)为一个鲜见的侧链带一五元碳环的四环三萜,其相对立体结构最终通过密度函数理论[Density Functional Theory (DET)]计算结合NMR技术来确定。另一新的天然产物2a,3a,20R-trihydroxy-5α-pregnane 16β-methacrylate的波谱数据也首次报导,其相对立体结构也是通过X-ray单晶衍射法来进一步确定。所有化合物进行了生物活性测试,发现化合物14,15,23,37-39,41,43,45,46和48皆具有良好的抗人肺癌细胞(A549,H460)和胃癌(HGC27)细胞的增殖作用。本文还对苦楝树叶的化学成分进行了研究,从中分得6个甾体化合物,其中新化合物3个,部分化合物亦对人肺癌细胞(A549,H460)和神经胶质瘤U251细胞具有中等的抗细胞增殖作用。
3)活性初筛时发现羌活氯仿提取物具有激活衰老抑制因子klotho启动子的作用。本研究从羌活的氯仿提取部分中总共分离鉴定了34个单体化合物,包括17个香豆素,10个倍半萜,1个甾体和6个苯丙素或烯炔类等其它类型化合物。其中新化合物5个,包括3个新的呋哺型香豆素和2个新的愈创木烷型倍半萜。本研究是首次报道从羌活中分离鉴定出倍半萜类化合物。活性跟踪分离得到的化合物77具有激活衰老抑制因子klotho启动子的作用。最新研究报道表明klotho亦可作为一种肿瘤抑制因子,在人类乳腺癌的IGF-1和FGF信号通路中起到重要的调控作用。因此羌活氯仿提取物中所分离得到的化合物均进行了抗细胞增殖作用测试,其中化合物53,54,64和66对人肝癌HepG2细胞,乳腺癌MCF-7细胞及老鼠C6细胞都具有较好的抗细胞增殖作用,并对它们的构效关系(SAR)进行了探讨,发现侧链上具有游离羟基的线型呋喃香豆素具有一定的抗细胞增殖作用。最后,初步探讨了这类化合物的作用机理,化合物notopol(64)及notopterol(66)加药后用流式细胞仪进行了观察,发现大量细胞被阻断在细胞分裂的G2/M期,从而引起癌细胞的凋亡。
4)本研究还对两种海南产的红树林植物海桑及卵叶海桑进行了化学成分研究,从海桑中分离得到9个已知化合物,从卵叶海桑中分离得到7个已知化合物,化合物结构类型包括联苯类化合物、三萜、降木脂素类、苯丙素类、黄酮及其糖苷。其中(-)-(R)-nyasol,(-)-(R)-4'-O-methylnyasol,maslinic acid对大鼠C6细胞具有中等的抗细胞增殖作用。本研究发现降木脂素类化合物和联苯类化合物可作为海桑属植物的标记化合物,此外还对所分得的化合物进行了生源合成途径的探讨研究,并发现海桑与卵卯叶海桑两种植物中体内生物合成及代谢途径的一些区别,对研究该属植物的化学遗传学和生态学提供了一定的理论基础。
5)臭椿和鸦胆子是两种苦木科植物,本论文对它们的化学成分进行了初步的研究。到目前为止,已从臭椿树皮中分得12个化合物(结构包括9个四环三萜,2个香豆素和1个简体),其中含2个新的香豆素和3个新三萜。另外从鸦胆子的种子中分离得到5个已知化合物,包括四个甾体和一个木脂素类化合物。
Seven medicinal plants, Melia toosendan, Melia azedarach, Notopterygium incisum, Sonneratia caseolaris, Sonneratia ovate, Ailanthus altissima and Brucea javanica have been chemically investigated. A total of 106 different compounds were obtained and characterized as thirty triterpenoids, eleven limonoids, twelve-one steroids, nineteen coumarins, ten sesquiterpenoids, three flavonoids, six phenylpropanoids, four polyacetylenes and two diphenyls. Among them,37 compounds were new. Their structures were extensively identified on the basis of spectroscopic methods, chemical transformations, single-crystal X-ray diffraction analysis and molecular modeling studies. Biological activities tests showed that some compounds were klotho (an aging-suppressor gene) promoter activators, while other compounds exhibited significant anti-proliferative effects. For isolated anti-proliferative linear furocoumarins, their structure-activity relationship (SAR) was briefly discussed and the primary mechanism was carried out using flow cytometry (FCM).
1. Thirty-five compounds, including sixteen tetracyclic triterpenoids, eleven limonoids and eight steroids were isolated from Melia toosendan (Meliaceae). Among them, seventeen were new:twelve new tetracyclic triterpenoids (1-12), four new limonoids (25-35) and one new steroid (13). The relative configuration of meliasenins I (1) was determined by its single-crystal X-ray diffraction analysis. The biosynthetic pathway of the isolated peroxylated compounds was briefly discussed. Most compounds were tested for their insecticidal and cytotoxic effects, and compounds 1-10,13-17 and 22 were found to show significantly cytotoxic against U20S human osteosarcoma and MCF-7 human breast cancer cells.
2. The barks and the leaves of the Melia azedarach have been investigated. Two new triterpenoids (36,37), two new steroids (38,39), one new naturally occurring steroid (40) along with eleven related known compounds (14,15,18-21,23,41-44) were isolated from the barks. Among them, compound 36 was a novel triterpenoid bearing a rare 21,24-cyclopentane ring in the side chain, and its relative configuration was determined by density functional theory (DET) calculations together with the NMR analysis. In addition, the NMR data of the steroid 40 was reported for the first time and its relative configuration was confirmed by single-crystal X-ray diffraction analysis. Compounds 14,15,23,37-39,41,43,45,46 and 48 showed significantly cytotoxic effects against A549, H460 and HGC27 cell lines. At the same time, three new (45-47) and several known (48-50) steroids were isolated from the leaves of M. azedarach. Some of the isolates showed moderate cytotoxic effects against A549, H460 and U251 cell lines.
3. The chloroform extract of Notopterygium incisum (Qiang-Huo) was preliminarily found to activate the klotho gene promoter. Bioassay-guided isolation and purification led to the identification of thirty-four compounds, including eventeen coumarins, ten sesquiterpenoids and seven other compounds from the dried rhizomes of N. incisum. Among them, compounds 51 and 52 were new linear furocoumarins, while compounds 53 and 54 were new guaiane-type sesquiterpenoids. This is the first time that sesquiterpenoids were isolated and characterized from N. incisum. Compound 77 was found to be a potential klotho gene promoter activator.
Recently, klotho gene was also reported to be a cancer inhibitor gene and has the ability to regulate the IGF-1 and FGF signal pathways of human breast cancer cells. Thus, all isolates from N. incisum were evaluated for their anti-proliterative effect and some compounds showed cytotoxicities against HepG2, MCF-7 and C6 cell lines. The SAR was briefly discussed and revealed that linear furocoumarins bearing a monoterpenyloxyl side chain with a free hydroxyl group were cytotoxic. Notopol (64) and notopterol (66) were selected to study their anti-proliferative mechanism using flow cytometry and found that after treated with these two compounds, MCF-7 cells accumulated in the G2/M phase, and were mostly apoptotic in this phase.
4. Nine known compounds were obtained and determined from Sonneratia caseolaris and seven known compounds were isolated from S. ovate. The structures included diphenyls, triterpenoids, nor-lignans, phenylpropanoids and flavonoids. Compounds 85,86 and 89 were found to show moderate cytotoxic activity against C6 cells. The nor-lignans (85,86) and 6H-benzo[b,d]pyran-6-one derivatives (87,88) may tentatively be considered as taxonomic markers for Sonneratia genus and the biosynthesis of the isolates were discussed herein.
5. Ailanthus altissima and Brucea javanica are two species belonging to Simarubaceae. In this study, twelve compounds were isolated and determined from A. altissima. Among them, compounds 95 and 96 were two new coumarins.97,98 and 99 were three new tetracyclic triterpenoids. Meanwhile, five known compounds, including four steroids and a lignanoids have been so far obtained and determined from B. javanica.
本毕业论文的具体研究内容简要如下：
1)从楝科楝属植物川楝的果实中分离并鉴定出35个单体化合物(1-35),包括四环三萜16个、柠檬苦素11个、甾体8个。其中新化合物17个,包括12个新的四环三萜(1-12),4个新的柠檬苦素(25-35)和1个新的甾体(13),化合物meliasenins I(1)最终通过X-ray单晶衍射法确定其立体结构。对部分带过氧键的化合物进行了一定的生物合成途径探讨。大部分化合物进行了杀虫活性及体外细胞毒作用等生物活性测试。结果表明：化合物1-10,13-17和22对人骨肉瘤细胞U20S及人乳腺癌细胞MCF-7细胞株均显示较好的抗细胞增殖作用。
2)苦楝为楝科楝属另一植物,本文对其茎皮和树叶分别进行了系统的化学成分研究。从其茎皮中分离得到单体化合物16个(10个甾体和6个三萜),其中新化合物4个,包括2个新的四环三萜和2个新的甾体和1个新的天然来源淄体,化合物21,24-cycloeupha-7-ene-3β,16β,21α,25-tetrol (36)为一个鲜见的侧链带一五元碳环的四环三萜,其相对立体结构最终通过密度函数理论[Density Functional Theory (DET)]计算结合NMR技术来确定。另一新的天然产物2a,3a,20R-trihydroxy-5α-pregnane 16β-methacrylate的波谱数据也首次报导,其相对立体结构也是通过X-ray单晶衍射法来进一步确定。所有化合物进行了生物活性测试,发现化合物14,15,23,37-39,41,43,45,46和48皆具有良好的抗人肺癌细胞(A549,H460)和胃癌(HGC27)细胞的增殖作用。本文还对苦楝树叶的化学成分进行了研究,从中分得6个甾体化合物,其中新化合物3个,部分化合物亦对人肺癌细胞(A549,H460)和神经胶质瘤U251细胞具有中等的抗细胞增殖作用。
3)活性初筛时发现羌活氯仿提取物具有激活衰老抑制因子klotho启动子的作用。本研究从羌活的氯仿提取部分中总共分离鉴定了34个单体化合物,包括17个香豆素,10个倍半萜,1个甾体和6个苯丙素或烯炔类等其它类型化合物。其中新化合物5个,包括3个新的呋哺型香豆素和2个新的愈创木烷型倍半萜。本研究是首次报道从羌活中分离鉴定出倍半萜类化合物。活性跟踪分离得到的化合物77具有激活衰老抑制因子klotho启动子的作用。最新研究报道表明klotho亦可作为一种肿瘤抑制因子,在人类乳腺癌的IGF-1和FGF信号通路中起到重要的调控作用。因此羌活氯仿提取物中所分离得到的化合物均进行了抗细胞增殖作用测试,其中化合物53,54,64和66对人肝癌HepG2细胞,乳腺癌MCF-7细胞及老鼠C6细胞都具有较好的抗细胞增殖作用,并对它们的构效关系(SAR)进行了探讨,发现侧链上具有游离羟基的线型呋喃香豆素具有一定的抗细胞增殖作用。最后,初步探讨了这类化合物的作用机理,化合物notopol(64)及notopterol(66)加药后用流式细胞仪进行了观察,发现大量细胞被阻断在细胞分裂的G2/M期,从而引起癌细胞的凋亡。
4)本研究还对两种海南产的红树林植物海桑及卵叶海桑进行了化学成分研究,从海桑中分离得到9个已知化合物,从卵叶海桑中分离得到7个已知化合物,化合物结构类型包括联苯类化合物、三萜、降木脂素类、苯丙素类、黄酮及其糖苷。其中(-)-(R)-nyasol,(-)-(R)-4'-O-methylnyasol,maslinic acid对大鼠C6细胞具有中等的抗细胞增殖作用。本研究发现降木脂素类化合物和联苯类化合物可作为海桑属植物的标记化合物,此外还对所分得的化合物进行了生源合成途径的探讨研究,并发现海桑与卵卯叶海桑两种植物中体内生物合成及代谢途径的一些区别,对研究该属植物的化学遗传学和生态学提供了一定的理论基础。
5)臭椿和鸦胆子是两种苦木科植物,本论文对它们的化学成分进行了初步的研究。到目前为止,已从臭椿树皮中分得12个化合物(结构包括9个四环三萜,2个香豆素和1个简体),其中含2个新的香豆素和3个新三萜。另外从鸦胆子的种子中分离得到5个已知化合物,包括四个甾体和一个木脂素类化合物。
Seven medicinal plants, Melia toosendan, Melia azedarach, Notopterygium incisum, Sonneratia caseolaris, Sonneratia ovate, Ailanthus altissima and Brucea javanica have been chemically investigated. A total of 106 different compounds were obtained and characterized as thirty triterpenoids, eleven limonoids, twelve-one steroids, nineteen coumarins, ten sesquiterpenoids, three flavonoids, six phenylpropanoids, four polyacetylenes and two diphenyls. Among them,37 compounds were new. Their structures were extensively identified on the basis of spectroscopic methods, chemical transformations, single-crystal X-ray diffraction analysis and molecular modeling studies. Biological activities tests showed that some compounds were klotho (an aging-suppressor gene) promoter activators, while other compounds exhibited significant anti-proliferative effects. For isolated anti-proliferative linear furocoumarins, their structure-activity relationship (SAR) was briefly discussed and the primary mechanism was carried out using flow cytometry (FCM).
1. Thirty-five compounds, including sixteen tetracyclic triterpenoids, eleven limonoids and eight steroids were isolated from Melia toosendan (Meliaceae). Among them, seventeen were new:twelve new tetracyclic triterpenoids (1-12), four new limonoids (25-35) and one new steroid (13). The relative configuration of meliasenins I (1) was determined by its single-crystal X-ray diffraction analysis. The biosynthetic pathway of the isolated peroxylated compounds was briefly discussed. Most compounds were tested for their insecticidal and cytotoxic effects, and compounds 1-10,13-17 and 22 were found to show significantly cytotoxic against U20S human osteosarcoma and MCF-7 human breast cancer cells.
2. The barks and the leaves of the Melia azedarach have been investigated. Two new triterpenoids (36,37), two new steroids (38,39), one new naturally occurring steroid (40) along with eleven related known compounds (14,15,18-21,23,41-44) were isolated from the barks. Among them, compound 36 was a novel triterpenoid bearing a rare 21,24-cyclopentane ring in the side chain, and its relative configuration was determined by density functional theory (DET) calculations together with the NMR analysis. In addition, the NMR data of the steroid 40 was reported for the first time and its relative configuration was confirmed by single-crystal X-ray diffraction analysis. Compounds 14,15,23,37-39,41,43,45,46 and 48 showed significantly cytotoxic effects against A549, H460 and HGC27 cell lines. At the same time, three new (45-47) and several known (48-50) steroids were isolated from the leaves of M. azedarach. Some of the isolates showed moderate cytotoxic effects against A549, H460 and U251 cell lines.
3. The chloroform extract of Notopterygium incisum (Qiang-Huo) was preliminarily found to activate the klotho gene promoter. Bioassay-guided isolation and purification led to the identification of thirty-four compounds, including eventeen coumarins, ten sesquiterpenoids and seven other compounds from the dried rhizomes of N. incisum. Among them, compounds 51 and 52 were new linear furocoumarins, while compounds 53 and 54 were new guaiane-type sesquiterpenoids. This is the first time that sesquiterpenoids were isolated and characterized from N. incisum. Compound 77 was found to be a potential klotho gene promoter activator.
Recently, klotho gene was also reported to be a cancer inhibitor gene and has the ability to regulate the IGF-1 and FGF signal pathways of human breast cancer cells. Thus, all isolates from N. incisum were evaluated for their anti-proliterative effect and some compounds showed cytotoxicities against HepG2, MCF-7 and C6 cell lines. The SAR was briefly discussed and revealed that linear furocoumarins bearing a monoterpenyloxyl side chain with a free hydroxyl group were cytotoxic. Notopol (64) and notopterol (66) were selected to study their anti-proliferative mechanism using flow cytometry and found that after treated with these two compounds, MCF-7 cells accumulated in the G2/M phase, and were mostly apoptotic in this phase.
4. Nine known compounds were obtained and determined from Sonneratia caseolaris and seven known compounds were isolated from S. ovate. The structures included diphenyls, triterpenoids, nor-lignans, phenylpropanoids and flavonoids. Compounds 85,86 and 89 were found to show moderate cytotoxic activity against C6 cells. The nor-lignans (85,86) and 6H-benzo[b,d]pyran-6-one derivatives (87,88) may tentatively be considered as taxonomic markers for Sonneratia genus and the biosynthesis of the isolates were discussed herein.
5. Ailanthus altissima and Brucea javanica are two species belonging to Simarubaceae. In this study, twelve compounds were isolated and determined from A. altissima. Among them, compounds 95 and 96 were two new coumarins.97,98 and 99 were three new tetracyclic triterpenoids. Meanwhile, five known compounds, including four steroids and a lignanoids have been so far obtained and determined from B. javanica.
引文
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