以3,5-二羟基苯甲酸和间苯二酚为原料,分别经酯化、乙酰化、甲氧甲氧基保护或甲基化、酰肼化、氧化、醛酮缩合、环化、Algar-Flynn-Oyamada反应以及脱保护基等步骤,以21%~32%的总收率合成了7,3’,5’-三取代黄烷酮1a^1b和黄酮醇类化合物...以3,5-二羟基苯甲酸和间苯二酚为原料,分别经酯化、乙酰化、甲氧甲氧基保护或甲基化、酰肼化、氧化、醛酮缩合、环化、Algar-Flynn-Oyamada反应以及脱保护基等步骤,以21%~32%的总收率合成了7,3’,5’-三取代黄烷酮1a^1b和黄酮醇类化合物2a^2b,所有合成产物通过1H NMR,IR,MS进行了结构确证.其中黄烷酮1b是从药用植物中间锦鸡儿Caragana intermedia Kang etH.C.Fu中分离得到的新天然有机化合物,此次为首次全合成.展开更多
Pueraria thomsonii has long been used in traditional Chinese medicine.Isoflavonoids are the principle pharmacologically active components,which are primarily observed as glycosyl-conjugates and accumulate in P.thomson...Pueraria thomsonii has long been used in traditional Chinese medicine.Isoflavonoids are the principle pharmacologically active components,which are primarily observed as glycosyl-conjugates and accumulate in P.thomsonii roots.However,the molecular mechanisms underlying the glycosylation processes in(iso)flavonoid biosynthesis have not been thoroughly elucidated.In the current study,an O-glucosyltransferase(PtUGT8)was identified in the medicinal plant P.thomsonii from RNA-seq database.Biochemical assays of the recombinant PtUGT8 showed that it was able to glycosylate chalcone(isoliquiritigenin)at the 4-OH position and glycosylate isoflavones(daidzein,formononetin,and genistein)at the 7-OH or 4′-OH position,exhibiting no enzyme activity to flavonones(liquiritigenin and narigenin)in vitro.The identification of PtUGT8 may provide a useful enzyme catalyst for efficient biotransformation of isoflavones and other natural products for food or pharmacological applications.展开更多
目的：克隆红花中查耳酮异构酶（Chalcone-flavonone isomerase,CHI）基因,进行生物信息学分析、开花1~7 d CHI表达量及羟基红花黄色素A（hydroxysafflor yellow A,HSYA）含量分析,为红花中CHI功能验证、黄酮类成分合成及调控机制研究...目的：克隆红花中查耳酮异构酶（Chalcone-flavonone isomerase,CHI）基因,进行生物信息学分析、开花1~7 d CHI表达量及羟基红花黄色素A（hydroxysafflor yellow A,HSYA）含量分析,为红花中CHI功能验证、黄酮类成分合成及调控机制研究提供基础。方法：克隆CHI序列,通过生物信息学预测CHI特性,使用Real-time PCR检测红花开花1~7 d CHI的相对表达量,HPLC检测HSYA动态累积的百分含量,并进行关联分析。结果：克隆获得红花CHI序列全长,检测得到红花开花1~7 d CHI的相对表达量及HSYA动态累积的百分含量。CHI表达量及HSYA动态累积百分含量呈现相似的变化趋势：均在1~4 d逐渐升高,在第4天达到最高峰,第5~7天急剧降低。结论：此研究可为红花中CHI功能验证、黄酮类成分合成及调控机制研究提供基础。展开更多
文摘以3,5-二羟基苯甲酸和间苯二酚为原料,分别经酯化、乙酰化、甲氧甲氧基保护或甲基化、酰肼化、氧化、醛酮缩合、环化、Algar-Flynn-Oyamada反应以及脱保护基等步骤,以21%~32%的总收率合成了7,3’,5’-三取代黄烷酮1a^1b和黄酮醇类化合物2a^2b,所有合成产物通过1H NMR,IR,MS进行了结构确证.其中黄烷酮1b是从药用植物中间锦鸡儿Caragana intermedia Kang etH.C.Fu中分离得到的新天然有机化合物,此次为首次全合成.
基金supported by the National Key Research and Development Program of China(Nos.2017YFC1702901 and 2017YFC1701601)CAMS Innovation Fund for Medical Sciences(No.2019-I2M-5-065)。
文摘Pueraria thomsonii has long been used in traditional Chinese medicine.Isoflavonoids are the principle pharmacologically active components,which are primarily observed as glycosyl-conjugates and accumulate in P.thomsonii roots.However,the molecular mechanisms underlying the glycosylation processes in(iso)flavonoid biosynthesis have not been thoroughly elucidated.In the current study,an O-glucosyltransferase(PtUGT8)was identified in the medicinal plant P.thomsonii from RNA-seq database.Biochemical assays of the recombinant PtUGT8 showed that it was able to glycosylate chalcone(isoliquiritigenin)at the 4-OH position and glycosylate isoflavones(daidzein,formononetin,and genistein)at the 7-OH or 4′-OH position,exhibiting no enzyme activity to flavonones(liquiritigenin and narigenin)in vitro.The identification of PtUGT8 may provide a useful enzyme catalyst for efficient biotransformation of isoflavones and other natural products for food or pharmacological applications.
文摘目的：克隆红花中查耳酮异构酶（Chalcone-flavonone isomerase,CHI）基因,进行生物信息学分析、开花1~7 d CHI表达量及羟基红花黄色素A（hydroxysafflor yellow A,HSYA）含量分析,为红花中CHI功能验证、黄酮类成分合成及调控机制研究提供基础。方法：克隆CHI序列,通过生物信息学预测CHI特性,使用Real-time PCR检测红花开花1~7 d CHI的相对表达量,HPLC检测HSYA动态累积的百分含量,并进行关联分析。结果：克隆获得红花CHI序列全长,检测得到红花开花1~7 d CHI的相对表达量及HSYA动态累积的百分含量。CHI表达量及HSYA动态累积百分含量呈现相似的变化趋势：均在1~4 d逐渐升高,在第4天达到最高峰,第5~7天急剧降低。结论：此研究可为红花中CHI功能验证、黄酮类成分合成及调控机制研究提供基础。
