蔓性千斤拔化学成分与质量控制研究
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摘要
千斤拔药材为豆科千斤拔属多年生草本植物蔓性千斤拔Flemingiaphilippinensis Merr.et Rolfe的干燥根,在我国主要分布于西南、中南和东南部地区。该药材性味甘,微涩,平,具有祛风除湿和治疗一些妇科疾病的功效。有关蔓性千斤拔化学成分和药理活性的研究较少,对质量标准控制方面的研究更为鲜有。因此本研究以蔓性千斤拔为对象,对其化学成分和质量控制等方面进行了系统的研究,并对其粗提物和部分单体成分进行了药理活性筛选。另外对千斤拔属植物的分布、生存环境、药用功效、化学成分和药理作用的研究现状进行了综述。本研究取得了一定的进展,现归纳总结如下。
利用现代色谱分离方法对广西道地药材蔓性千斤拔根的75%乙醇提取物进行了系统的分离工作,共分得46个化合物,并根据其理化性质和现代波谱学技术(包括UV、IR、~1H-NMR、~(13)C-NMR、HMQC、HMBC、NOESY、COSY、EI-MS、FAB-MS和HR-EI-MS)鉴定了其中43个化合物的结构(FP-1～FP-43),包括28个黄酮类成分,4个蒽醌类成分,4个有机酸及其酯类成分,3个甾醇类成分,1个多异戊烯基取代的多酮类成分,1个香豆素类成分,1个核苷类成分,还有1个烷烃类成分。
这些化合物分别为大黄酚(FP-1)、大黄素甲醚(FP-2)、eriosematin(FP-3)、滨蒿内酯(FP-4)、羽扇豆醇(FP-5)、白桦酸(FP-6)、咖啡酸二十八烷酯(FP-7)、β-谷甾醇(FP-8)、蔓性千斤拔酮A(FP-9)、单棕榈酸甘油酯(FP-10)、大黄素(FP-11)、islandicin(FP-12)、水杨酸(FP-13)、对甲氧基苯丙酸(FP-14)、十三烷-1,4-二烯烃(FP-15)、lupinifolin(FP-16)、千斤拔素D(FP-17)、蔓性千斤拔素A(FP-18)、auriculasin(FP-19)、erythrinin B(FP-20)、6-C-异戊烯基木犀草素(FP-21)、8-(1,1-二甲烯丙基)-染料木黄酮(FP-22)、蔓性千斤拔素E(FP-23)、蔓性千斤拔素F(FP-24)、5,7,3′,4′-四羟基-6,8-双异戊烯基异黄酮(FP-25)、蔓性千斤拔素D(FP-26)、dorsmaninsⅠ(FP-27)、osajin(FP-28)、6,8-双异戊烯基圣草素(FP-29)、lupinalbin A(FP-30)、染料木黄酮(FP-31)、3'-O-甲基香豌豆苷元(FP-32)、奥洛醇(FP-33)、5,7,2′,3′,4′-五羟基黄酮(FP-34)、鹰嘴豆素甲和樱黄素的混合物(FP-35和FP-36)、染料木苷(FP-37)、槐属苷(FP-38)、7-葡萄糖基-3'-O-甲基香豌豆苷(FP-39)、印度黄檀苷和樱黄素4′-O-β-D-葡萄糖苷的混合物(FP-40和FP-41)、腺嘌呤核苷(FP-42)和木犀草苷(FP-43,混合物)。其中,化合物FP-9为新的异戊烯基取代的多酮骨架,FP-23和FP-24为新化合物,FP-34为新天然产物,21个首次从该属植物中提取分离得到,4个为首次从该植物中分离得到。
另外,蔓性千斤拔的粗提物及部分单体化合物进行抗氧化和抗肿瘤活性筛选实验发现,咖啡酸二十八烷酯、蔓性千斤拔素A、5,7,3′,4′-四羟基-6,8-双异戊烯基异黄酮、auriculasin和dorsmaninsⅠ具有中等的清除DPPH自由基的能力,同时蔓性千斤拔素A呈现比较明显的细胞毒活性。
此外,对千斤拔药材的质量控制标准进行了研究:(1)根据蔓性千斤拔中所含的化学成分及其药效分析,采用紫外—可见分光光度法,对药材的总黄酮进行了含量测定;(2)采用反相HPLC-DAD法,根据19批不同产地的样品建立了蔓性千斤拔药材的指纹图谱;(3)在建立指纹图谱的同时,对药材中具有多种生理活性的染料木苷、染料木黄酮和5,7,3′,4′-四羟基-6,8-双异戊烯基异黄酮3个异黄酮成分进行了定量分析。在以上工作的基础上,起草了蔓性千斤拔药材的质量标准(草案),为鉴别该药材的真伪和评价其质量优劣提供了科学的方法。
综上,本文主要系统地研究了千斤拔药材化学成分,药理活性,指纹图谱和成分定量分析等方面的研究,建立了千斤拔药材的质量控制标准,为进一步的开发和利用该药材提供了物质基础和理论依据。
Qianjinba,known as "I-Tiao-Gung",is the dried root of perennial herbage Flemingia philippinensis Merr.et Rolfe which belongs to the genus Flemingia of family Leguminosea.It distributes in the south-west,middle-south and east-south China.It is sweet and astringent taste according to the record of Chinese Materia Medica,and it has the functions of dipelling wind and eliminating dampness and treatment for the gynecological diseases.There are little studies about the chemical constituents and pharmacological action of the crude drug,and no method was established to evaluate the quality at the present time.In order to use and develop this drug further,the chemical constituents and quality control were studied systematically,and the pharmacological activities of the crude extract and partial compounds were screened.In addition,the distribution,living environment,medical efficacy,chemical constituent and pharmacological action about the genus Flemingia plants were summarized.Our research results are as follows.
Forty-six compounds were isolated from the 75%ethanol extract of the root of famous-region drug Flemingia philippinensis Merr.et Rolfe by using the modern chromatographic techniques.The structures of forty-three ones(FP-1～FP-43) were identified by the physico-chemical properties and modern spectral techniques,including UV,IR,~1H-NMR,~(13)C-NMR,HMQC,HMBC,NOESY,COSY,EI-MS,FAB-MS and HR-EI-MS.They contained twenty-eight flavonoids,four anthraquinones,four organic acids and ester,three sterols,one prenylated ketone,one coumarin,one nucleoside and one diolefine compound.These compounds were identified as follows:chrysophanol (FP-1),physcion(FP-2),eriosematin(FP-3),scoparone(FP-4),lupeol(FP-5),betulinic acid(FP-6),3',4'-Dihydroxy-trans-cinamic acid octacosyl ester(FP-7),β-sitosterol (FP-8),flemiphilippinone A(FP-9),monopalmitin(FP-10),emodin(FP-11),islandicin (FP-12),salicylic acid(FP-13),p-methoxyphenylpropionic acid(FP-14),trideca-1, 3-diene(FP-15),lupinifolin(FP-16),flemichin D(FP-17),flemiphilippinin A(FP-18), auriculasin(FP-19),erythrinin B(FP-20),6-C-prenylluteolin(FP-21), 8-(1,1-dimethylallyl) genistein(FP-22),flemiphilippinin E(FP-23),flemiphilippinin F (FP-24),5,7,3',4'-tetrahydroxy-6,8-diprenylisoflavone(FP-25),flemiphilippinin D (FP-26),dorsmaninsⅠ(FP-27),osajin(FP-28),6,8-diprenyleriodictyol(FP-29), lupinalbin A(FP-30),genistein(FP-31),3'-O-methylorobol(FP-32),orobol(FP-33), 5,7,2',3',4'-pentahrdroxyflavone(FP-34),the mixture of biochanin A and prunetin (FP-35 and 36),genistin(FP-37),sophororicoside(FP-38),3'-O-methylorobol-7-glucoside(FP-39),the mixture of sissotrin and prunetin 4'-O-β-D-glucoside(FP-40 and 41),adenosine(FP-42) and luteoloside(FP-43,mixture).Among these compounds,FP-9 was a novel skeleton of prenylated ketone,FP-23 and FP-24 were new compounds, FP-34 was a novel natural product,twenty-one were isolated from the Flemingia genus for the first time,and four were isolated from the F.philippinensis for the first time.
In addition,anti-oxidative and antitumor activities of seventeen compounds and four crude extract parts were researched.The results indicated that 3',4'-dihydroxy-trans-cinamic acid octacosyl ester,flemiphilippinin A,5,7,3',4'-tetrahydroxy-6,8-diprenylisoflavone,auriculasin and dorsmaninsⅠshowed strong activity in free radical-scavenging activity determined with the scavenging effect on DPPH free radical,while flemiphilippinin A showed strong cytotoxicity activity studied with MTT method.
At last,the method to control the quality of F.philippinensis was established for the first time.The studies contained:(1) Acorrding to the chemical character and pharmacodynamic analysis of this drug,the quantitative determination of total flavoniod was studied using UV-VIS;(2) The fingerprint of was established using RP-HPLC-DAD comparing 19 samples from different distributing regions;(3) The quantitative analysis of three active isoflavones,genistin,genistein and 5,7,3',4'-tetrahydroxy-6,8-diprenylisoflavone in F.philippinensis was researched using a HPLC-DAD method. Based on above results,a quality standard of Qianjinba was drafted to provide the scientific method for identification and evaluation of the crude drug.
In summary,the chemical contituents,pharmacological activities,fingerprint and quantitative analysis were systematical studied in this thesis.Moreover,the method for quality control of Qianjinba was established.These provided the theoretical basis and scientific reference for further study,development and application of Flemingia philippinensis Merr.et Rolfe.
利用现代色谱分离方法对广西道地药材蔓性千斤拔根的75%乙醇提取物进行了系统的分离工作,共分得46个化合物,并根据其理化性质和现代波谱学技术(包括UV、IR、~1H-NMR、~(13)C-NMR、HMQC、HMBC、NOESY、COSY、EI-MS、FAB-MS和HR-EI-MS)鉴定了其中43个化合物的结构(FP-1～FP-43),包括28个黄酮类成分,4个蒽醌类成分,4个有机酸及其酯类成分,3个甾醇类成分,1个多异戊烯基取代的多酮类成分,1个香豆素类成分,1个核苷类成分,还有1个烷烃类成分。
这些化合物分别为大黄酚(FP-1)、大黄素甲醚(FP-2)、eriosematin(FP-3)、滨蒿内酯(FP-4)、羽扇豆醇(FP-5)、白桦酸(FP-6)、咖啡酸二十八烷酯(FP-7)、β-谷甾醇(FP-8)、蔓性千斤拔酮A(FP-9)、单棕榈酸甘油酯(FP-10)、大黄素(FP-11)、islandicin(FP-12)、水杨酸(FP-13)、对甲氧基苯丙酸(FP-14)、十三烷-1,4-二烯烃(FP-15)、lupinifolin(FP-16)、千斤拔素D(FP-17)、蔓性千斤拔素A(FP-18)、auriculasin(FP-19)、erythrinin B(FP-20)、6-C-异戊烯基木犀草素(FP-21)、8-(1,1-二甲烯丙基)-染料木黄酮(FP-22)、蔓性千斤拔素E(FP-23)、蔓性千斤拔素F(FP-24)、5,7,3′,4′-四羟基-6,8-双异戊烯基异黄酮(FP-25)、蔓性千斤拔素D(FP-26)、dorsmaninsⅠ(FP-27)、osajin(FP-28)、6,8-双异戊烯基圣草素(FP-29)、lupinalbin A(FP-30)、染料木黄酮(FP-31)、3'-O-甲基香豌豆苷元(FP-32)、奥洛醇(FP-33)、5,7,2′,3′,4′-五羟基黄酮(FP-34)、鹰嘴豆素甲和樱黄素的混合物(FP-35和FP-36)、染料木苷(FP-37)、槐属苷(FP-38)、7-葡萄糖基-3'-O-甲基香豌豆苷(FP-39)、印度黄檀苷和樱黄素4′-O-β-D-葡萄糖苷的混合物(FP-40和FP-41)、腺嘌呤核苷(FP-42)和木犀草苷(FP-43,混合物)。其中,化合物FP-9为新的异戊烯基取代的多酮骨架,FP-23和FP-24为新化合物,FP-34为新天然产物,21个首次从该属植物中提取分离得到,4个为首次从该植物中分离得到。
另外,蔓性千斤拔的粗提物及部分单体化合物进行抗氧化和抗肿瘤活性筛选实验发现,咖啡酸二十八烷酯、蔓性千斤拔素A、5,7,3′,4′-四羟基-6,8-双异戊烯基异黄酮、auriculasin和dorsmaninsⅠ具有中等的清除DPPH自由基的能力,同时蔓性千斤拔素A呈现比较明显的细胞毒活性。
此外,对千斤拔药材的质量控制标准进行了研究:(1)根据蔓性千斤拔中所含的化学成分及其药效分析,采用紫外—可见分光光度法,对药材的总黄酮进行了含量测定;(2)采用反相HPLC-DAD法,根据19批不同产地的样品建立了蔓性千斤拔药材的指纹图谱;(3)在建立指纹图谱的同时,对药材中具有多种生理活性的染料木苷、染料木黄酮和5,7,3′,4′-四羟基-6,8-双异戊烯基异黄酮3个异黄酮成分进行了定量分析。在以上工作的基础上,起草了蔓性千斤拔药材的质量标准(草案),为鉴别该药材的真伪和评价其质量优劣提供了科学的方法。
综上,本文主要系统地研究了千斤拔药材化学成分,药理活性,指纹图谱和成分定量分析等方面的研究,建立了千斤拔药材的质量控制标准,为进一步的开发和利用该药材提供了物质基础和理论依据。
Qianjinba,known as "I-Tiao-Gung",is the dried root of perennial herbage Flemingia philippinensis Merr.et Rolfe which belongs to the genus Flemingia of family Leguminosea.It distributes in the south-west,middle-south and east-south China.It is sweet and astringent taste according to the record of Chinese Materia Medica,and it has the functions of dipelling wind and eliminating dampness and treatment for the gynecological diseases.There are little studies about the chemical constituents and pharmacological action of the crude drug,and no method was established to evaluate the quality at the present time.In order to use and develop this drug further,the chemical constituents and quality control were studied systematically,and the pharmacological activities of the crude extract and partial compounds were screened.In addition,the distribution,living environment,medical efficacy,chemical constituent and pharmacological action about the genus Flemingia plants were summarized.Our research results are as follows.
Forty-six compounds were isolated from the 75%ethanol extract of the root of famous-region drug Flemingia philippinensis Merr.et Rolfe by using the modern chromatographic techniques.The structures of forty-three ones(FP-1～FP-43) were identified by the physico-chemical properties and modern spectral techniques,including UV,IR,~1H-NMR,~(13)C-NMR,HMQC,HMBC,NOESY,COSY,EI-MS,FAB-MS and HR-EI-MS.They contained twenty-eight flavonoids,four anthraquinones,four organic acids and ester,three sterols,one prenylated ketone,one coumarin,one nucleoside and one diolefine compound.These compounds were identified as follows:chrysophanol (FP-1),physcion(FP-2),eriosematin(FP-3),scoparone(FP-4),lupeol(FP-5),betulinic acid(FP-6),3',4'-Dihydroxy-trans-cinamic acid octacosyl ester(FP-7),β-sitosterol (FP-8),flemiphilippinone A(FP-9),monopalmitin(FP-10),emodin(FP-11),islandicin (FP-12),salicylic acid(FP-13),p-methoxyphenylpropionic acid(FP-14),trideca-1, 3-diene(FP-15),lupinifolin(FP-16),flemichin D(FP-17),flemiphilippinin A(FP-18), auriculasin(FP-19),erythrinin B(FP-20),6-C-prenylluteolin(FP-21), 8-(1,1-dimethylallyl) genistein(FP-22),flemiphilippinin E(FP-23),flemiphilippinin F (FP-24),5,7,3',4'-tetrahydroxy-6,8-diprenylisoflavone(FP-25),flemiphilippinin D (FP-26),dorsmaninsⅠ(FP-27),osajin(FP-28),6,8-diprenyleriodictyol(FP-29), lupinalbin A(FP-30),genistein(FP-31),3'-O-methylorobol(FP-32),orobol(FP-33), 5,7,2',3',4'-pentahrdroxyflavone(FP-34),the mixture of biochanin A and prunetin (FP-35 and 36),genistin(FP-37),sophororicoside(FP-38),3'-O-methylorobol-7-glucoside(FP-39),the mixture of sissotrin and prunetin 4'-O-β-D-glucoside(FP-40 and 41),adenosine(FP-42) and luteoloside(FP-43,mixture).Among these compounds,FP-9 was a novel skeleton of prenylated ketone,FP-23 and FP-24 were new compounds, FP-34 was a novel natural product,twenty-one were isolated from the Flemingia genus for the first time,and four were isolated from the F.philippinensis for the first time.
In addition,anti-oxidative and antitumor activities of seventeen compounds and four crude extract parts were researched.The results indicated that 3',4'-dihydroxy-trans-cinamic acid octacosyl ester,flemiphilippinin A,5,7,3',4'-tetrahydroxy-6,8-diprenylisoflavone,auriculasin and dorsmaninsⅠshowed strong activity in free radical-scavenging activity determined with the scavenging effect on DPPH free radical,while flemiphilippinin A showed strong cytotoxicity activity studied with MTT method.
At last,the method to control the quality of F.philippinensis was established for the first time.The studies contained:(1) Acorrding to the chemical character and pharmacodynamic analysis of this drug,the quantitative determination of total flavoniod was studied using UV-VIS;(2) The fingerprint of was established using RP-HPLC-DAD comparing 19 samples from different distributing regions;(3) The quantitative analysis of three active isoflavones,genistin,genistein and 5,7,3',4'-tetrahydroxy-6,8-diprenylisoflavone in F.philippinensis was researched using a HPLC-DAD method. Based on above results,a quality standard of Qianjinba was drafted to provide the scientific method for identification and evaluation of the crude drug.
In summary,the chemical contituents,pharmacological activities,fingerprint and quantitative analysis were systematical studied in this thesis.Moreover,the method for quality control of Qianjinba was established.These provided the theoretical basis and scientific reference for further study,development and application of Flemingia philippinensis Merr.et Rolfe.
引文
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