微花藤和瑶山润楠的化学成分研究
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摘要
本学位论文对药用植物微花藤(Iodes cirrhosa Turcz．)和瑶山润楠(Machilusyaoshansis S．Lee et F．N．Wei)的化学成分进行了研究，并对分离得到的化合物在多种药理模型上进行了生物活性筛选。同时，通过对微花藤中分离鉴定的天然8-4′氧木脂素和苯丙三醇类化合物及其衍生物在不同溶剂中~((1))H和~((13))C NMR谱数据的测定和分析研究，较系统和深入地探讨了J_((7,8))和△δ_((C8-C7))与相关化合物构型的关联性及其在相关化合物构型确定应用中存在的问题、应用范围和适用条件。并且通过苯丙三醇衍生物的不对称合成，验证了其绝对构型与旋光符号之间的关系。
首次对微花藤属植物的化学成分进行了较系统的研究。利用多种色谱学手段和波谱学技术从微花藤根和瑶山润楠根的95％乙醇提取物中分别分离并鉴定了58个化合物(I1~((*))—158)和17个化合物(M1~((*))—M17)，化合物编号、名称与结构如Table 1和Figure 1所示。从微花藤根中发现新化合物10个(I1~((*))—I4~((*))，I7~((*))—I10~((*))，I12~((*))，I14~((*)))，新天然产物1个(I13~((^)))，并首次确定了3个化合物(I5~((#))，I6~((#))，I11~((#)))的绝对构型，其中I1~((*))—I3~((*))为少见的8-4′氧木脂素3′-糖苷；从瑶山润楠中发现新化合物5个(M1~((*))—M5~((*)))，其中，M1~((*))和M2~((*))为首次发现的苷元部分具有通过两个半缩酮形成呋喃[3，2-b]骈吡喃结构单元的葫芦烷三萜皂苷，化合物M3~((*))为首次发现侧链降三碳的葫芦烷三萜皂苷。
在多种药理模型上对分离鉴定的部分化合物进行了活性筛选，发现在10~((-5))M浓度水平，I4~((*))和I56对谷氨酸损伤的鼠嗜铬细胞瘤(PC12)细胞显示出保护活性；在10~((-6))M浓度条件下，I3~((*))、I11~((#))、I12~((*))和I13~((^))对去血清造成的PC12细胞损伤具有保护活性；在10~((-6))M浓度下，化合物I16、I17、I19、I23、I24、I27、I30、I32和I35对去血清后JNK3转染人神经母细胞瘤细胞(SH-SY5Y-JNK3)稳定表达株具有保护作用；在10~((-5))M浓度下，化合物I28显示出钟通道阻断作用；在10~((-6))M浓度下，化合物I35有抑制脂质过氧化产物丙二醛生成的抗氧化活性；在10~((-5))M时，化合物I35对小鼠腹腔巨噬细胞的TNFα分泌有抑制作用；化合物I35对人结肠癌细胞(HCT-8)、肺腺癌细胞(A549)和卵巢癌细胞(A2780)，I37对HCT-8细胞以及M6对人胃癌细胞(BGC-823)和A549细胞显示选择性细胞毒活性；化合物M6显示抗H5N1型高致病性禽流感病毒的活性。在10~((-5))M浓度下，化合物M2、M4和M9对蛋白酪氨酸酶具有抑制活性。
Table 1．化合物编号与名称一览表
注：化合物I1~((*))—I58为从微花藤中分离得剑，化合物M1~((*))—M17为从瑶山润楠中分离得到，标*者为新化合物，~((#))为新确定绝对构型的化合物，~((^))为新天然产物。
This dessertation investigated chemical constituents of ethanolic extracts of the rootsof Iodes cirrhosa and Machilus yaoshansis and their bioactivities on severalpharmacological models.In addition, based on a systematic analysis of NMR data ofthreo and erythro 8-4′-oxyneolignans and arylglycerols in different solvents, thevalidity, existing problems and application conditions of the coupling constant of thebenzyl proton (~((3))J_((7,8))) and the chemical shift difference between C-8 and C-7 (△δ_((C8-C7)))values to distinguish threo and erythro derivatives were discussed in detail, as well asthe relationship between the absolute configuration of arylglycerols and their opticalrotations were confirmed through a chiral synthesis of and arylglycerol aglycone.
The chemical constituents of the plants of the genus Iodes were investigated forthe first time. By using a variety of chromatographic techniques and spectroscopicmethods, 58 (I1~((*))-I58) and 17 (M1~((*))-M17) compounds were isolated and determinedfrom the 95% ethanol extracts of the roots of I.cirrhosa and M. yaoshansis,respectively. Chemical names and structures of purified compounds are listed in Table1 and Figure 1. Among them, I1~((*))-I4~((*)), I7~((*))-I10~((*)), I12~((*)), I14~((*)) and M1~((*))-M5~((*)) are newwhile I13~((^)) was obtained from nature and the absolute configurations of I5~((#)), I6~((#)), andI11~((#)) were determined, for the first time. I1~((*))-I3~((*)) are unsual 8-4′oxyneoliganglycosides with a glycosyoxyl group at C-3′. M1~((*)) and M2~((*)) are two cucurbitanetritepenoids with an unusual furo[3,2-b]pyran ring consisiting of two hemiacetals, andM3~((*)) is the first example of the trinorcucurbitane tritepenoid losing a three carbon unitat the side chain. I4~((*)) and I56 exhibited nuroprotective activity againstglutamate-induced PC12 cell damage at 10~((-5)) M while I3~((*)), I11~((#)), I12~((*)), and I13~((^)) wereactive against serum deprivation-induced PC12 cell apoptosis at 10~((-6)) M. I16, I17, I19,I23, I24, I27, I30, I32, and I35 were active against serum deprivation-inducedSH-SY5Y-JNK3 apoptosis at a concentration of 10~((-6)) M. 128 showed inhibitory effectagainst potassium channels in both non-specific and specific K~((+)) channel-regulatorscreening models. I35 showed antioxidant activities inhibiting Fe~((+2))-cystine-induced rat liver microsomal lipid peroxidation at a concentration of 10~((-6)) M. I35 was active toTNFαsecretion of mouse peritoneal macrophages with an inhibition rate of 33.4% at aconcentration of 10~((-5)) M. I35 showed selective cytotoxicity against several humancancer cell lines including colon (HCT-8), lung (A549) and ovarian (A2780) cancercells, while I37 exhibited cytotoxicity against HCT-8 and M6 against BGC-823 andA549 cells. M6 was also active against H5N1 avian influenza virus, M2, M4 and M9inhibited the protein tyrosine phosphatase 1B at a concentration of 10~((-5)) M.
Table 1. Compounds isolated from lodes cirrhosa (I1~((*))-I58) and Machilus yaoshansis(MI~((*))-M17)
~((*)) New compounds.~((#)) The absolute configuration of which was determined for the first time.~((^)) New natural compound.
首次对微花藤属植物的化学成分进行了较系统的研究。利用多种色谱学手段和波谱学技术从微花藤根和瑶山润楠根的95％乙醇提取物中分别分离并鉴定了58个化合物(I1~((*))—158)和17个化合物(M1~((*))—M17)，化合物编号、名称与结构如Table 1和Figure 1所示。从微花藤根中发现新化合物10个(I1~((*))—I4~((*))，I7~((*))—I10~((*))，I12~((*))，I14~((*)))，新天然产物1个(I13~((^)))，并首次确定了3个化合物(I5~((#))，I6~((#))，I11~((#)))的绝对构型，其中I1~((*))—I3~((*))为少见的8-4′氧木脂素3′-糖苷；从瑶山润楠中发现新化合物5个(M1~((*))—M5~((*)))，其中，M1~((*))和M2~((*))为首次发现的苷元部分具有通过两个半缩酮形成呋喃[3，2-b]骈吡喃结构单元的葫芦烷三萜皂苷，化合物M3~((*))为首次发现侧链降三碳的葫芦烷三萜皂苷。
在多种药理模型上对分离鉴定的部分化合物进行了活性筛选，发现在10~((-5))M浓度水平，I4~((*))和I56对谷氨酸损伤的鼠嗜铬细胞瘤(PC12)细胞显示出保护活性；在10~((-6))M浓度条件下，I3~((*))、I11~((#))、I12~((*))和I13~((^))对去血清造成的PC12细胞损伤具有保护活性；在10~((-6))M浓度下，化合物I16、I17、I19、I23、I24、I27、I30、I32和I35对去血清后JNK3转染人神经母细胞瘤细胞(SH-SY5Y-JNK3)稳定表达株具有保护作用；在10~((-5))M浓度下，化合物I28显示出钟通道阻断作用；在10~((-6))M浓度下，化合物I35有抑制脂质过氧化产物丙二醛生成的抗氧化活性；在10~((-5))M时，化合物I35对小鼠腹腔巨噬细胞的TNFα分泌有抑制作用；化合物I35对人结肠癌细胞(HCT-8)、肺腺癌细胞(A549)和卵巢癌细胞(A2780)，I37对HCT-8细胞以及M6对人胃癌细胞(BGC-823)和A549细胞显示选择性细胞毒活性；化合物M6显示抗H5N1型高致病性禽流感病毒的活性。在10~((-5))M浓度下，化合物M2、M4和M9对蛋白酪氨酸酶具有抑制活性。
Table 1．化合物编号与名称一览表
注：化合物I1~((*))—I58为从微花藤中分离得剑，化合物M1~((*))—M17为从瑶山润楠中分离得到，标*者为新化合物，~((#))为新确定绝对构型的化合物，~((^))为新天然产物。
This dessertation investigated chemical constituents of ethanolic extracts of the rootsof Iodes cirrhosa and Machilus yaoshansis and their bioactivities on severalpharmacological models.In addition, based on a systematic analysis of NMR data ofthreo and erythro 8-4′-oxyneolignans and arylglycerols in different solvents, thevalidity, existing problems and application conditions of the coupling constant of thebenzyl proton (~((3))J_((7,8))) and the chemical shift difference between C-8 and C-7 (△δ_((C8-C7)))values to distinguish threo and erythro derivatives were discussed in detail, as well asthe relationship between the absolute configuration of arylglycerols and their opticalrotations were confirmed through a chiral synthesis of and arylglycerol aglycone.
The chemical constituents of the plants of the genus Iodes were investigated forthe first time. By using a variety of chromatographic techniques and spectroscopicmethods, 58 (I1~((*))-I58) and 17 (M1~((*))-M17) compounds were isolated and determinedfrom the 95% ethanol extracts of the roots of I.cirrhosa and M. yaoshansis,respectively. Chemical names and structures of purified compounds are listed in Table1 and Figure 1. Among them, I1~((*))-I4~((*)), I7~((*))-I10~((*)), I12~((*)), I14~((*)) and M1~((*))-M5~((*)) are newwhile I13~((^)) was obtained from nature and the absolute configurations of I5~((#)), I6~((#)), andI11~((#)) were determined, for the first time. I1~((*))-I3~((*)) are unsual 8-4′oxyneoliganglycosides with a glycosyoxyl group at C-3′. M1~((*)) and M2~((*)) are two cucurbitanetritepenoids with an unusual furo[3,2-b]pyran ring consisiting of two hemiacetals, andM3~((*)) is the first example of the trinorcucurbitane tritepenoid losing a three carbon unitat the side chain. I4~((*)) and I56 exhibited nuroprotective activity againstglutamate-induced PC12 cell damage at 10~((-5)) M while I3~((*)), I11~((#)), I12~((*)), and I13~((^)) wereactive against serum deprivation-induced PC12 cell apoptosis at 10~((-6)) M. I16, I17, I19,I23, I24, I27, I30, I32, and I35 were active against serum deprivation-inducedSH-SY5Y-JNK3 apoptosis at a concentration of 10~((-6)) M. 128 showed inhibitory effectagainst potassium channels in both non-specific and specific K~((+)) channel-regulatorscreening models. I35 showed antioxidant activities inhibiting Fe~((+2))-cystine-induced rat liver microsomal lipid peroxidation at a concentration of 10~((-6)) M. I35 was active toTNFαsecretion of mouse peritoneal macrophages with an inhibition rate of 33.4% at aconcentration of 10~((-5)) M. I35 showed selective cytotoxicity against several humancancer cell lines including colon (HCT-8), lung (A549) and ovarian (A2780) cancercells, while I37 exhibited cytotoxicity against HCT-8 and M6 against BGC-823 andA549 cells. M6 was also active against H5N1 avian influenza virus, M2, M4 and M9inhibited the protein tyrosine phosphatase 1B at a concentration of 10~((-5)) M.
Table 1. Compounds isolated from lodes cirrhosa (I1~((*))-I58) and Machilus yaoshansis(MI~((*))-M17)
~((*)) New compounds.~((#)) The absolute configuration of which was determined for the first time.~((^)) New natural compound.
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