银杏叶类脂分离、衍生物合成及其生物活性研究
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摘要
银杏叶类脂主要包括烃类、聚戊烯醇类、萜烯醇类、甾醇类等化合物，聚戊烯醇类脂具有抗病毒、提高免疫功能、肝细胞再生、抑制癌细胞转移等生物活性，是生物体糖蛋白生物合成的重要载体。目前国内有关银杏叶活性物的研究主要集中在黄酮、萜内酯等方面，而具有生理活性的类脂化合物研究与开发很少。本文系统开展银杏叶类脂的化学成分研究，分离和制备聚戊烯醇及其衍生物，进一步评价银杏叶类脂抑菌和抗氧化生物活性，为银杏叶资源生物活性成分的综合利用，为促进银杏叶新产品的开发提供理论应用依据和技术支撑。
通过溶剂提取，皂化等方法制备银杏叶类脂成分，再利用冷冻以及分子蒸馏得到结晶物，轻馏分和重馏分部位，并结合多种色谱技术首次对其各部位进行系统分离；对类脂轻馏分进行Py-GC-MS分析，结果：裂解后化合物中单萜和倍半萜类化合物约为23%；长链醇（酮、酯）及二萜类化合物含量约为47%；烷基酚、甾体类化合物含量约为30%；从银杏叶类脂成分的结晶物、分子蒸馏轻馏分和重馏分部位中分离得到了15个单体化合物，其中β-谷甾醇乙酯、棕榈酸酰胺、三棕榈酸甘油酯、正十一烷、β-石竹烯、异植物醇、橙花叔醇、芳樟醇和松油醇是首次从银杏叶中分离得到。
对聚戊烯醇α-终端单元的-OH基团进行化学结构修饰：通过乙酸酐酯化反应合成得到聚戊烯基乙酸酯（GPA），得率为91%；利用格氏试剂合成正戊基溴化镁作为中间体，与聚戊烯醇偶合反应合成正戊烷基聚戊烯（GAP），得率为90%；利用格氏试剂合成(R)-4-苄氧基-2-甲基-1-丁基溴化镁作为中间体，与聚戊烯醇偶合反应合成聚戊烯基-3-异戊基苄醚（GPB），得率为86%；利用三氯氧磷作为磷酰化剂，在碱性条件下将聚戊烯醇磷酰化为聚戊烯基二氯磷酸酯（GPD），得率为90%；聚戊烯基二氯磷酸酯（GPD）经过碱水解生成聚戊烯基单磷酸酯，继而经过无机碱成盐为聚戊烯基磷酸酯二钠盐（GPP），得率为79%。利用光谱学对以上5种衍生物进行了结构表征。
利用滤纸片法测定样品抑菌圈值，确定MIC、MBC、MFC值和FIC值等指标，首次考察了银杏叶聚戊烯醇和15种类脂成分以及5种聚戊烯醇衍生物对5种不同菌种（沙门氏菌、金黄色葡萄球菌、黑曲霉菌、大肠杆菌和枯草芽孢杆菌）的抑菌及协同作用。橙花叔醇对4种细菌（沙门氏菌、金黄色葡萄球菌、大肠杆菌和枯草芽孢杆菌）的抑菌活性最强，芳樟醇对黑曲霉菌的抑菌活性最强。当β-石竹烯与银杏叶聚戊烯醇质量百分比为43.4:56.58时，抗枯草芽孢杆菌协同作用最佳；当异植物醇与银杏叶聚戊烯醇质量百分比为38.19:61.81时，抗沙门氏菌协同作用最佳。聚戊烯醇衍生物中GPD对5种菌种的抑菌活性最强，银杏叶聚戊烯醇与GPP质量百比为62.59:37.41时，抗沙门氏菌协同作用最佳。
通过柱层析分离，对银杏叶类脂分子蒸馏轻、重集分分别梯度洗脱，得到不同极性集分；利用DPPH、ABTS、超氧阴离子自由基和羟自由基法，结合Sigmoidal拟合曲线法计算不同极性集分的IC_(50)，首次评价了类脂不同极性集分抗氧化性，结果表明轻馏分中集分2（95%石油醚/5%乙酸乙酯部位）在轻馏分各组中对四种自由基抗氧化活性最强，重馏分中集分5（60%石油醚/40%乙酸乙酯部位）清除超氧阴离子和羟自由基抗氧化活性最强。
Ginkgo biloba L. leaves lipids contained alkanes, polyprenols, terpenoids, sterols and soon. Ginkgo biloba polyprenols(GBP) are important lipids components from Ginkgo biloba L.leaves. It was reported on antiviral, improving immune function, hepatoprotective andantitumour effects of GBP. The main content of this paper contains chemical constituentsresearch on Ginkgo biloba leaves lipids, the synthesis of polyprenols derivatives,antibacterial/antifungal activity and antioxidant effects of them. It is provided theoretical basisfor efficient utilization of Ginkgo biloba leaves effective bioactive components, expanding thescope of application in pharmacological effect and the research and development of health careproducts and new drug.
Lipids from Ginkgo biloba leaves were isolated by extraction with solvent andsaponification. The frozen sediment, the light and heavy distillates were isolated byrefrigerated and molecular distillation. The light Distillates of lipids were analyzed by thePyrolysis-Gas Chromatography-Mass Spectrometry technique and the result showed that therelative content of monoterpene and sesquiterpene compounds is approximately23%, therelative content of chainlike alcohol (ketone, ester) and diterpanes compounds is approximately47%and the relative content of alkylphenol and steroids compounds is approximately30%.Fifteen known compounds were identified by physical and chemical properties andspectroscopic data. The separated and identified compounds: β-sitosterol acetate, palmitamide,glycerol tripalmtate, hendecane, β-caryophyllene, isophytol, nerolidol, linalool and terpineolare reported here for the first time in Ginkgo biloba leaves.
Chemical structure modification of-OH in α-terminal unit of GBP was preparated for fivepolyprenols derivatives that were identified by spectroscopic data. Polyprenyl acetate(GPA)was preparated by esterification using acetic anhydride and the yield was91%. N-amylpolypentylene(GAP) was preparated by coupling reaction using n-amyl magnesium bromide as the grignard reaction intermediate and the yield was90%. Polyprenyl-3-isoamyl benzylether(GPB) was preparated by coupling reaction using (R)-4-benzyloxy-2-methyl-1-butyl-magnesium bromide as the grignard reaction intermediate and the yield was86%. Polyprenyldichlorophosphite(GPD) was preparated by phosphorus acylation reaction using phosphorusoxychloride in alkaline condition and the yield was90%. Polyprenyl phosphate disodiumsalt(GPP) was preparated by basic hydrolysis using GPD and salifing using inorganic salt, theyield was79%.
Antibacterial and antifungal tests of five selected stains (Salmonella enterica,Staphylocococus aureus, Aspergillus niger, Escherichia coli and Bacillus subtilis) were carriedout using a disc-diffusion method by measuring inhibition halos and comparing with MIC,MBC, MFC values and FIC Index of different samples that were polyprenols, other lipids andfive polyprenols derivatives. Nerolidol showed the highest activity against the four tapes ofbacteria(Salmonella enterica, Staphylocococus aureus, Escherichia coli and Bacillus subtilis)among all the tested samples, linalool showed the highest activity against Aspergillus nigeramong all the tested samples and the GBP with β-caryophyllene mixture group had thestrongest synergistic effect against Bacillus subtilis among all mixture groups against the fivetested strains. The proportion of β-caryophyllene and GBP was43.42%:56.58%(wt/wt) thatwas determinated by Mixture Design as the optimal proportion of synergistic effect on GBPwith β-caryophyllene against Bacillus subtilis. The proportion of isophytol and GBP was38.19%:61.81%(wt/wt) that was determinated by Mixture Design as the optimal proportion ofsynergistic effect on GBP with isophytol against Salmonella enterica. GPD showed the highestactivity against all tapes of stains among five polyprenols derivatives. The proportion of GBPand GPP was62.59%:37.41%(wt/wt) that was determinated by Mixture Design as the optimalproportion of synergistic effect on GBP with GPP against Salmonella enterica.
Determination of antioxidant effect of different polarity fractions of light, heavy distillatesand polyprenols of ginkgo lipids used4methods (DPPH, ABTS, superoxide anion and hydroxyradical) with Sigmoidal curve fitting method arriving at respective IC50values. The resultsshowed that the light fraction2(95%petroleum ether/5%acetic ether) had the highest antioxidant effect in all tested light fractions. the IC_(50) values of the polyprenols group werelower than all the fractions groups and the positive control groups(Vc and BHT) in usingsuperoxide anion and hydroxy radical methods. The fraction5(60%petroleum ether/40%acetic ether) had the highest antioxidant effect in all tested fractions except the positive controlgroups and the polyprenols group in using the4methods.
通过溶剂提取，皂化等方法制备银杏叶类脂成分，再利用冷冻以及分子蒸馏得到结晶物，轻馏分和重馏分部位，并结合多种色谱技术首次对其各部位进行系统分离；对类脂轻馏分进行Py-GC-MS分析，结果：裂解后化合物中单萜和倍半萜类化合物约为23%；长链醇（酮、酯）及二萜类化合物含量约为47%；烷基酚、甾体类化合物含量约为30%；从银杏叶类脂成分的结晶物、分子蒸馏轻馏分和重馏分部位中分离得到了15个单体化合物，其中β-谷甾醇乙酯、棕榈酸酰胺、三棕榈酸甘油酯、正十一烷、β-石竹烯、异植物醇、橙花叔醇、芳樟醇和松油醇是首次从银杏叶中分离得到。
对聚戊烯醇α-终端单元的-OH基团进行化学结构修饰：通过乙酸酐酯化反应合成得到聚戊烯基乙酸酯（GPA），得率为91%；利用格氏试剂合成正戊基溴化镁作为中间体，与聚戊烯醇偶合反应合成正戊烷基聚戊烯（GAP），得率为90%；利用格氏试剂合成(R)-4-苄氧基-2-甲基-1-丁基溴化镁作为中间体，与聚戊烯醇偶合反应合成聚戊烯基-3-异戊基苄醚（GPB），得率为86%；利用三氯氧磷作为磷酰化剂，在碱性条件下将聚戊烯醇磷酰化为聚戊烯基二氯磷酸酯（GPD），得率为90%；聚戊烯基二氯磷酸酯（GPD）经过碱水解生成聚戊烯基单磷酸酯，继而经过无机碱成盐为聚戊烯基磷酸酯二钠盐（GPP），得率为79%。利用光谱学对以上5种衍生物进行了结构表征。
利用滤纸片法测定样品抑菌圈值，确定MIC、MBC、MFC值和FIC值等指标，首次考察了银杏叶聚戊烯醇和15种类脂成分以及5种聚戊烯醇衍生物对5种不同菌种（沙门氏菌、金黄色葡萄球菌、黑曲霉菌、大肠杆菌和枯草芽孢杆菌）的抑菌及协同作用。橙花叔醇对4种细菌（沙门氏菌、金黄色葡萄球菌、大肠杆菌和枯草芽孢杆菌）的抑菌活性最强，芳樟醇对黑曲霉菌的抑菌活性最强。当β-石竹烯与银杏叶聚戊烯醇质量百分比为43.4:56.58时，抗枯草芽孢杆菌协同作用最佳；当异植物醇与银杏叶聚戊烯醇质量百分比为38.19:61.81时，抗沙门氏菌协同作用最佳。聚戊烯醇衍生物中GPD对5种菌种的抑菌活性最强，银杏叶聚戊烯醇与GPP质量百比为62.59:37.41时，抗沙门氏菌协同作用最佳。
通过柱层析分离，对银杏叶类脂分子蒸馏轻、重集分分别梯度洗脱，得到不同极性集分；利用DPPH、ABTS、超氧阴离子自由基和羟自由基法，结合Sigmoidal拟合曲线法计算不同极性集分的IC_(50)，首次评价了类脂不同极性集分抗氧化性，结果表明轻馏分中集分2（95%石油醚/5%乙酸乙酯部位）在轻馏分各组中对四种自由基抗氧化活性最强，重馏分中集分5（60%石油醚/40%乙酸乙酯部位）清除超氧阴离子和羟自由基抗氧化活性最强。
Ginkgo biloba L. leaves lipids contained alkanes, polyprenols, terpenoids, sterols and soon. Ginkgo biloba polyprenols(GBP) are important lipids components from Ginkgo biloba L.leaves. It was reported on antiviral, improving immune function, hepatoprotective andantitumour effects of GBP. The main content of this paper contains chemical constituentsresearch on Ginkgo biloba leaves lipids, the synthesis of polyprenols derivatives,antibacterial/antifungal activity and antioxidant effects of them. It is provided theoretical basisfor efficient utilization of Ginkgo biloba leaves effective bioactive components, expanding thescope of application in pharmacological effect and the research and development of health careproducts and new drug.
Lipids from Ginkgo biloba leaves were isolated by extraction with solvent andsaponification. The frozen sediment, the light and heavy distillates were isolated byrefrigerated and molecular distillation. The light Distillates of lipids were analyzed by thePyrolysis-Gas Chromatography-Mass Spectrometry technique and the result showed that therelative content of monoterpene and sesquiterpene compounds is approximately23%, therelative content of chainlike alcohol (ketone, ester) and diterpanes compounds is approximately47%and the relative content of alkylphenol and steroids compounds is approximately30%.Fifteen known compounds were identified by physical and chemical properties andspectroscopic data. The separated and identified compounds: β-sitosterol acetate, palmitamide,glycerol tripalmtate, hendecane, β-caryophyllene, isophytol, nerolidol, linalool and terpineolare reported here for the first time in Ginkgo biloba leaves.
Chemical structure modification of-OH in α-terminal unit of GBP was preparated for fivepolyprenols derivatives that were identified by spectroscopic data. Polyprenyl acetate(GPA)was preparated by esterification using acetic anhydride and the yield was91%. N-amylpolypentylene(GAP) was preparated by coupling reaction using n-amyl magnesium bromide as the grignard reaction intermediate and the yield was90%. Polyprenyl-3-isoamyl benzylether(GPB) was preparated by coupling reaction using (R)-4-benzyloxy-2-methyl-1-butyl-magnesium bromide as the grignard reaction intermediate and the yield was86%. Polyprenyldichlorophosphite(GPD) was preparated by phosphorus acylation reaction using phosphorusoxychloride in alkaline condition and the yield was90%. Polyprenyl phosphate disodiumsalt(GPP) was preparated by basic hydrolysis using GPD and salifing using inorganic salt, theyield was79%.
Antibacterial and antifungal tests of five selected stains (Salmonella enterica,Staphylocococus aureus, Aspergillus niger, Escherichia coli and Bacillus subtilis) were carriedout using a disc-diffusion method by measuring inhibition halos and comparing with MIC,MBC, MFC values and FIC Index of different samples that were polyprenols, other lipids andfive polyprenols derivatives. Nerolidol showed the highest activity against the four tapes ofbacteria(Salmonella enterica, Staphylocococus aureus, Escherichia coli and Bacillus subtilis)among all the tested samples, linalool showed the highest activity against Aspergillus nigeramong all the tested samples and the GBP with β-caryophyllene mixture group had thestrongest synergistic effect against Bacillus subtilis among all mixture groups against the fivetested strains. The proportion of β-caryophyllene and GBP was43.42%:56.58%(wt/wt) thatwas determinated by Mixture Design as the optimal proportion of synergistic effect on GBPwith β-caryophyllene against Bacillus subtilis. The proportion of isophytol and GBP was38.19%:61.81%(wt/wt) that was determinated by Mixture Design as the optimal proportion ofsynergistic effect on GBP with isophytol against Salmonella enterica. GPD showed the highestactivity against all tapes of stains among five polyprenols derivatives. The proportion of GBPand GPP was62.59%:37.41%(wt/wt) that was determinated by Mixture Design as the optimalproportion of synergistic effect on GBP with GPP against Salmonella enterica.
Determination of antioxidant effect of different polarity fractions of light, heavy distillatesand polyprenols of ginkgo lipids used4methods (DPPH, ABTS, superoxide anion and hydroxyradical) with Sigmoidal curve fitting method arriving at respective IC50values. The resultsshowed that the light fraction2(95%petroleum ether/5%acetic ether) had the highest antioxidant effect in all tested light fractions. the IC_(50) values of the polyprenols group werelower than all the fractions groups and the positive control groups(Vc and BHT) in usingsuperoxide anion and hydroxy radical methods. The fraction5(60%petroleum ether/40%acetic ether) had the highest antioxidant effect in all tested fractions except the positive controlgroups and the polyprenols group in using the4methods.
引文
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