穿心莲和旱芹的化学成分研究
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摘要
常用中药穿心莲为爵床科穿心莲属植物穿心莲Andrographis paniculata(Burm.f.)Nees.的干燥地上部分。《中华人民共和国药典》(2005版)记载穿心莲具有清热解毒,凉血消肿的功效。临床上主要用于风热感冒,咽喉肿痛,呼吸道感染,细菌性痢疾等疾病的治疗。
利用现代色谱方法从穿心莲的干燥地上部分85%乙醇提取物经萃取后的正丁醇层和水层中分离得到27个化合物,通过理化性质和光谱学方法鉴定了其中25个化合物的结构,它们分别是:14-去氧-11,12-二去氢穿心莲内酯(14-deoxy-11,12-didehydroandrographolide)(1),穿心莲内酯(andrographolide)(2),穿心莲新苷(neoandrographolide)(3),14-去氧穿心莲内酯(14-deoxyandrographolide)(4),14-去氧穿心莲内酯苷(14-deoxyandrographiside)(5),14-去氧-11,12-二去氢穿心莲内酯苷(14-deoxy-11,12-didehydroandrographiside)(6),3-O-β-D-葡萄糖-14-去氧穿心莲内酯苷(3-O-β-D-glucopyranosyl-14-deoxy-andrographiside)(7),3-O-β-D-葡萄糖-14-去氧-11,12-二去氢穿心莲内酯苷(3-O-β-D-glucopyranosyl-14-deoxy-11,12-didenydroandrographiside)(8),异穿心莲内酯(isoandrographolide)(9),穿心莲内酯苷(andrographiside)(10),5,4′-二羟基-7-O-葡萄糖醛酸丁酯(5,4′-dihydroxy-7-O-β-D-pyranglucuronate butyl ester)(11),andrographidine C(12),芹菜素-7-O-β-D-葡萄糖苷(apigenin-7-O-β-D-glucopyranoside)(13),5,4′-二羟基-7-甲氧基-8-O-β-D-吡喃葡萄糖黄酮苷(5,4′-dihydroxy-7-methoxy-8-O-β-D-glucopyranosyloxyflavone)(14),7,8-二甲氧基-2′-羟基-5-O-β-D-吡喃葡萄糖黄酮苷(7,8-dimethoxy-2′-hydroxy-5-O-β-D-glucopyranosyloxyflavone)(15),6-C-β-D-葡萄糖-8-C-β-D-半乳糖芹菜素(6-C-β-D-glucosyl-8-C-β-D-galactosyl-apigenin)(16),6,8-二-C-β-D-葡萄糖白杨素(6,8-di-C-β-D-glucosylchrysin)(17),芹菜素-7-O-β-D-葡萄糖醛酸苷(apigenin-7-O-β-D-glucuronide)(18),8-乙酰基哈帕苷(8-acetyl-harpagide)(19),procumbide(20),teuhircoside(21),2,6-二甲氧基对羟基苯基-1-O-β-D-葡萄糖苷(2,6-dimethoxyl-p-hydroxybenzoyl-1-O-β-D-glucoside)(22),芸香糖苷(roseooside)(23),citroside B(24),草酸(oxalic acid)(25)。这25个化合物中,有10个二萜内酯类化合物,8个黄酮类化合物,3个环烯醚萜类化合物,2个四甲基环己烯苷类化合物,1个酚苷类化合物,1个有机酸类化合物。其中化合物7,8,15为新化合物,11,16,17,18,21,22,23,24,25为首次从穿心莲属植物中分离得到的化合物。本文首次从穿心莲中分离到四甲基环己烯苷类和酚苷类化合物,上述结果是对穿心莲属植物化学成分研究的重要补充。
旱芹(Apium graveolens L.),伞形科芹属植物,以嫩茎、叶(未开花者)供食用和药用,其根也作药用,种子常作为一种调味品,也可入药。茎、叶具有降压、开胃、利尿、调经等功效。作为有良好药理活性的日常食用蔬菜,旱芹中的化学成分引起人们较大的兴趣,但现有文献中,绝大多数是针对芹菜籽所含有效成分进行的研究,而很少有对新鲜旱芹的研究,水溶性部分更不多见。本课题主要针对市售旱芹的食用部分进行研究。
利用现代色谱方法从旱芹的70%乙醇提取物中分离得到43个化合物,通过化学和光谱学方法鉴定了其中41个化合物的结构,它们分别是:11,21-二氧-3β,15α-二羟基-乌苏-12-烯-2-O-β-D-葡萄糖苷(11,21-dioxo-3β,15α-dihydroxy-urs-12-en-2 O-β-D-glucoside)(1),11,21-二氧-3β,15α-二羟基-乌苏-12-烯-24-O-β-D-葡萄糖苷(11,21-dioxo-3β,15α-dihydroxy-urs-12-en-24-O-β-D-glucoside)(2),11,21-二氧-3β,15α-二羟基-△~(12)-齐墩果烯-24-O-β-D-葡萄糖苷(11,21-dioxo-3β,15α-dihydroxy-olean-12-en-24-O-β-D-glucoside)(3),芹菜素-7-O-[2″-O-(5′′′-O-阿魏酸)-β-D-呋喃芹糖]-β-D-吡喃葡萄糖苷(apigenin-7-O-(2″-O-(5′′′-O-feruloyl)-β-D-apiofuranosyl)-β-D-glucopyranoside)(4),柯伊利素-7-O-[2″-O-(5′′′-O-阿魏酸)-β-D-呋喃芹糖]-β-D-吡喃葡萄糖苷(chrysoeriol-7-O-[2″-O-(5′′′-O-feruloyl)-β-D-apiofuranosyl]-β-D-glucopyranoside)(5),木犀草素-7-O-[2″-O-(5′′′-O-阿魏酸)-β-D-呋喃芹糖]-β-D-吡喃葡萄糖苷(luteolin-7-O-[2′′-O-(5′′′-O-feruloyl)β-D-apiofuranosyl]-β-D-glucopyranoside)(6),6-C-β-D-葡萄糖-8-C-β-D-半乳糖芹菜素(6-C-β-D-glucosyl-8-C--β-D-galactosyl-apigenin)(7),柚皮素-7-O-(2-O-β-D-呋喃芹糖)-β-D-吡喃葡萄糖苷(naringein-7-O-(2-O-β-D-apiofuranosyl)-β-D-glucopyranoside)(8),芹菜苷(apiin)(9),木犀草素-7-O-β-D-吡喃葡萄糖苷(luteolin-7-O-β-D-glucopyranoside)(10),柯伊利素-7-O-β-D-吡喃葡萄糖苷(chrysoeriol-7-O-β-D-glucopyranoside)(11),芹菜素-7-O-β-D-吡喃葡萄糖苷(apigenin-7-O-β-D-glucopyranoside)(12),柯伊利素(chrysoeriol)(13),木犀草素(luteolin)(14),槲皮素(quercetin)(15),芹菜素(apigenin)(16),(2S)-1-O-(7Z,10Z,13Z-hexadecatrienoyl)-3-O-β-galactopyranosyl-glycerol(17),(2S)-1-O-butanonyl-3-O-β-galactopyranosyl-glycerol(18),4β-O-glucopyranosyl-senkyunolide(19),瑟丹内酯(sedanolide)(20),3-oxo-megastigma-4,8-dien-7-O-β-D-glucoside(21),3-hydroxy-megastigma-5,8-dien-7-one(22),发卡二醇(falcariondiol)(23),(9z)1,9-heptadecadiene-4,6-diyne-3,8,11-triol(24),oplopandiol(25),异芩皮素(isofraxidin)(26),5-甲氧基补骨脂素(5-methoxypsoralen)(27),5,8-二甲氧基补骨脂素(5,8-dimethoxyl psoralen)(28),3—咖啡酰氧基奎宁酸(3-O-caffeoyl-quinic acid)(29),3-反式香豆酰基奎宁酸(3-trans-coumaroylquinicacid)(30),丁香酚(eugnic acid)(31),反式阿魏酸(trans-ferulic acid)(32),反式桂皮酸(trans-cinnamic acid)(33),阿魏酸-对羟基苯乙醇酯(P-hydroxyphenylethanol ferulate)(34),2-(3-甲氧基-4-羟基苯基)-丙烷-1,3-二醇(2-(3-methoxy-4-hydroxy-phenol)-propane-1,3-diol)(35),lunularin(36),lunularic acid(37),D-阿洛糖醇(D-allitol)(38),β-谷甾醇(β-sitosterol)(39),苯甲酸(benzolic acid)(40),丁二酸(succinic acid)(41)。在这41个化合物中,有3个三萜类化合物,13个黄酮类化合物,2个醇苷类化合物,2个苯酞类化合物,2个四甲基环己烯类化合物,3个聚炔类化合物,9个苯丙素类化合物,3个酚酸类化合物,4个其他类化合物。其中化合物1,2,3,4,5,18,19,21共8个化合物为新化合物,6,7,8,17,22,24,25,26,30,34,35,36,37,38共14个化合物为首次从芹属中分离得到的化合物。本文首次从芹属中分离出三萜类、醇苷类、四甲基环己烯类和酚酸类化合物,以上结果丰富了旱芹的化学成分种类,为旱芹相关药效物质研究奠定基础。
论文对三萜类化合物(1-3)、黄酮类化合物(4-16,18)及醇苷类化合物(17)的生物活性进行了测试。采用Griess法考察了以上化合物抑制脂多糖诱导的大鼠RAW264.7巨噬细胞NO释放活性,结果表明有四个黄酮类化合物(化合物13,14,15,16)表现出很强的活性,而黄酮苷和其他两类化合物活性不明显。
采用DPPH法对以上三类化合物的清除自由基能力进行了考察,结果表明黄酮类化合物中只有B环为3′,4′二羟基(化合物6,10,13)时,活性最好,其它黄酮类化合物和另外两种化合物则显示弱的或不显示活性。
采用MTT法对以上化合物对人肺癌A549、人宫颈癌Hela,人乳腺癌MCF-7细胞株的体外细胞毒活性进行了考察,结果表明,黄酮类化合物中黄酮苷类和黄酮苷元均不显示活性,仅当接上反式阿魏酸结构单元时(化合物4和5)才显示微弱的细胞毒活性,三萜类和醇苷类不显示活性。
以上测试结果表明了旱芹中黄酮类化合物是其相关生物活性物质。
Chuanxinlian,the dried aerial parts of Andrographis paniculata(Burm.f.)Nees.is a Chinese herbal medicine used as an anti-inflammatory,antiviral and antipyretic drug for treatment of fever,cold,laryngitis and diarrhea.And it was specified in the Pharmacopoeia of the P.R.China(2005)as an anti-virus and anti-bacterial remedy.
The chemical constituents from n-BuOH and water portions of 85%EtOH extract of the aerial parts of this plant was investigated in this thesis and led to the isolation of 27 compounds.On the basis of chemical evidences and spectral analysis,25 compounds of them were identified,and they are 14-deoxy-11,12-didehydroandrographolide(1),andrographolide (2),neoandrographolide(3),14-deoxy andrographolide(4),14-deoxyandrographiside(5), 14-deoxy-11,12-didehydroandrographiside(6),3-O-β-D-glucopyranosyl-14-deoxy-andrographiside (7),3-0-P-D-glucopyranosyl-14-deoxy-11,12-didehydroandrographiside(8), isoandrographolide(9),andrographiside(10),5,4'-dihydroxy-7-O-β-D-pyranglucuronate butyl ester(11),andrographidine C(12),apigenin-7-O-β-D-glucopyranoside(13), 5,4'-dihydroxy-7-methoxy-8-O-β-D-glucopyranosyloxyflavone(14),7,8-dimethoxy-2'-hydroxy-5-O-β-D-glucopyranosyloxyflavone(15),6-C-β-D-glucosyl-8-C-β-D-galactosyl-apigenin (16),6,8-di-C-β-D-glucosyl-chrysin(17),apigenin-7-O-β-D-glucuronide(18), 8-acetyl-harpagide(19),procumbide(20),teuhircoside(21),2,6-dimethoxyl-p-hydroxybenzoyl-1-O-β-D-glucoside(22),roseoside(23),citroside B(24),oxalic acid(25), respectively.Among these twenty-seven compounds,ten are diterpenoid lactones,eight are flavones,three are iridoids,two are megastigamane glycosides,one is a phenol glycoside and one is an organic acid.And among them,7,8 and 15 are new compounds,11,16,17,18,21, 22,23,24 and 25 were isolated for the first time from Andrographis genus.These results revealed the megastigamane glycosides and phenoglycosides were isolated for the first time from Andrographis genus,which were.important supplement to the chemical constituents of Andrographis paniculata.
Apium graveolens L.,the fresh whole plant of Apium graveolens L.in Umbelliferae.,is a normal vegetable to people.It is effective on epilepsy,hyperlipemia,and hypertension;it also can protect the brain cells and enhance memory.As an ordinary vegetable in daily life, celery has a variety of pharmacological activity,and received increased attention on its chemical constituents.Previous studies were focused on celery seeds but not its fresh herb of the whole plant.Therefore,in this thesis,the chemical constituents of the EtOAc,n-BuOH and water extracts from 70%EtOH extract of the fresh herb of Apium graveolens L.were studied.43 constituents were isolated by column chromatographies of silica ge(?)D101., polyamide,Sephadex LH-20,ODS and HPLC.On the basis of the chemical evidence and spectral analysis,the structures of 41 compounds were elucidated,they are 11,21-dioxo-3β,15α-dihydroxy-urs-12-en-2-O-β-D-glucoside(1),11,21-dioxo-3|3,15α-dihydroxy-urs-12-en-24-O-P-D-glucoside(2),11,21-dioxo-3β,15α-dihydroxy-olean-12-en-24-O-β-D-glucoside(3),apigenin-7-O-(2′-O-(5′′′-O-feruloyl)-p-D-apiofuranosyl)-β-D-glucopyranoside(4),chrysoeriol-7-O-[2′′-O-(5′′′-O-feruloyl)-β-D-apiofuranosyl]-β-D-glucopyranoside(5),(luteolin-7-O-[2′′-O-(5′′′-O-feruloyl)-β-D-apiofuranosyl]-p-D-glucopyranoside(6),(6-C-β-D-glucosyl-8-C-P-D-galactosyl-apigenin)(7),naringein-7-O-(2-O-β-D-apiofuran-osyl)-β-D-glucopyranoside(8),apiin(9),luteolin-7-O-β-D-glucopyranoside(10),chrysoeriol-7-O-β-D-glucopyranoside(11),apigenin-7-O-β-D-glucopyranoside(12),chrysoeriol(13),luteolin(14),quercetin(15),apigenin(16), (2S)-1-O-(7Z,10Z,13Z-hexadecatrienoyl)-3-O-β-galactopyanosyl-glycerol(17),(2S)-l-O-butanonyl-3-O-β-galactopyranosyl-glycerol(18),4β-O-glucopyranosyl-senkyunolide(19), sedanolide(20),3-oxo-megastigma-4,8-dien-7-O-β-D-glucoside(21),3-hydroxy-megastigma-5,8-dien-7-one(22),falcariondiol(23),(9z)-l,9-heptadecadiene-4,6-diyne-3,8,11-triol(24), oplopandiol(25),isofraxidin(26),5-methoxy psoralen(27),5,8-dimethoxyl psoralen(28), 3-O-caffeoyl-quinic acid(29),3-trans-coumaroylquinic acid(30),4-allyl-2-methoxyphenol (31),trans-ferulic acid(32),trans-cinnamic acid(33),p-hydroxyphenylethanol ferulate(34), 2-(3-methoxy-4-hydroxy)-propane-l,3-diol(35),lunularin(36),lunularic acid(37),,D-allitol (38),β-sitosterol(39),benzolic acid(40),succinic acid(41),respectively.Among the fourty-one compounds,three are triterpenes,thirteen are flavones,three are alcoholic glycosides,two are pathalides,two are megastigamanes,three are polyalkynes,nine are phenylpropanoids,three are phenol acids and four others.Among them,1,2,3,4,5,18,19 and 21 are new compounds,6,7,8,17,22,24,25,26,30,34,35,36,37 and 38 are isolated from apium genus for the first time.The above mentioned results indicated that triterpenes, alcoholic glycosides,megastigamanes and phenol acids were isolated for the first time from apium genus,which would provide chemical substances for elucidating the bioactive constituents of Apium graveolens.
Bioactivity of three triterpenes(1-3),fourteen flavonoids(4-16,18)and one alcoholic glycoside(17)from Apium graveolens was tested in this thesis.
These compounds were assayed against NO production on LPS activated macrophages by Griess method.Among them,4 flavones(13,14,15 and 16)displayed high inhibitory effects,but flavonoid glycosides and other kinds showed no correlated activity.
The above 18 compounds were evaluated by 1,1-diphenyl-2-picrylhydrazyl(DPPH)free radical scavenging method.The results revealed only flavonoids with 3',4'-dihydroxy in B ring(6,10 and 13)displayed scavenging activity,and the others displayed no scavenging activity.
MTT assay was used to test the cytotoxic activity of these 18 compounds against A549, Hela,and MCF-7 rumor cell lines.Among them,flavonoid aglycones and flavonoid glycosides displayed no cytotoxicity,but only flavonoid glycosides with the unit of trans-ferulic acid(4 and 5)showed cytotoxicity towards different cells.And other compounds displayed no significant cytotoxic activity.
On the basis of chemical and bioactive studies,this thesis confirmed that flavonoids were the major bioactive compounds of fresh celery(Apiun graveolens).
利用现代色谱方法从穿心莲的干燥地上部分85%乙醇提取物经萃取后的正丁醇层和水层中分离得到27个化合物,通过理化性质和光谱学方法鉴定了其中25个化合物的结构,它们分别是:14-去氧-11,12-二去氢穿心莲内酯(14-deoxy-11,12-didehydroandrographolide)(1),穿心莲内酯(andrographolide)(2),穿心莲新苷(neoandrographolide)(3),14-去氧穿心莲内酯(14-deoxyandrographolide)(4),14-去氧穿心莲内酯苷(14-deoxyandrographiside)(5),14-去氧-11,12-二去氢穿心莲内酯苷(14-deoxy-11,12-didehydroandrographiside)(6),3-O-β-D-葡萄糖-14-去氧穿心莲内酯苷(3-O-β-D-glucopyranosyl-14-deoxy-andrographiside)(7),3-O-β-D-葡萄糖-14-去氧-11,12-二去氢穿心莲内酯苷(3-O-β-D-glucopyranosyl-14-deoxy-11,12-didenydroandrographiside)(8),异穿心莲内酯(isoandrographolide)(9),穿心莲内酯苷(andrographiside)(10),5,4′-二羟基-7-O-葡萄糖醛酸丁酯(5,4′-dihydroxy-7-O-β-D-pyranglucuronate butyl ester)(11),andrographidine C(12),芹菜素-7-O-β-D-葡萄糖苷(apigenin-7-O-β-D-glucopyranoside)(13),5,4′-二羟基-7-甲氧基-8-O-β-D-吡喃葡萄糖黄酮苷(5,4′-dihydroxy-7-methoxy-8-O-β-D-glucopyranosyloxyflavone)(14),7,8-二甲氧基-2′-羟基-5-O-β-D-吡喃葡萄糖黄酮苷(7,8-dimethoxy-2′-hydroxy-5-O-β-D-glucopyranosyloxyflavone)(15),6-C-β-D-葡萄糖-8-C-β-D-半乳糖芹菜素(6-C-β-D-glucosyl-8-C-β-D-galactosyl-apigenin)(16),6,8-二-C-β-D-葡萄糖白杨素(6,8-di-C-β-D-glucosylchrysin)(17),芹菜素-7-O-β-D-葡萄糖醛酸苷(apigenin-7-O-β-D-glucuronide)(18),8-乙酰基哈帕苷(8-acetyl-harpagide)(19),procumbide(20),teuhircoside(21),2,6-二甲氧基对羟基苯基-1-O-β-D-葡萄糖苷(2,6-dimethoxyl-p-hydroxybenzoyl-1-O-β-D-glucoside)(22),芸香糖苷(roseooside)(23),citroside B(24),草酸(oxalic acid)(25)。这25个化合物中,有10个二萜内酯类化合物,8个黄酮类化合物,3个环烯醚萜类化合物,2个四甲基环己烯苷类化合物,1个酚苷类化合物,1个有机酸类化合物。其中化合物7,8,15为新化合物,11,16,17,18,21,22,23,24,25为首次从穿心莲属植物中分离得到的化合物。本文首次从穿心莲中分离到四甲基环己烯苷类和酚苷类化合物,上述结果是对穿心莲属植物化学成分研究的重要补充。
旱芹(Apium graveolens L.),伞形科芹属植物,以嫩茎、叶(未开花者)供食用和药用,其根也作药用,种子常作为一种调味品,也可入药。茎、叶具有降压、开胃、利尿、调经等功效。作为有良好药理活性的日常食用蔬菜,旱芹中的化学成分引起人们较大的兴趣,但现有文献中,绝大多数是针对芹菜籽所含有效成分进行的研究,而很少有对新鲜旱芹的研究,水溶性部分更不多见。本课题主要针对市售旱芹的食用部分进行研究。
利用现代色谱方法从旱芹的70%乙醇提取物中分离得到43个化合物,通过化学和光谱学方法鉴定了其中41个化合物的结构,它们分别是:11,21-二氧-3β,15α-二羟基-乌苏-12-烯-2-O-β-D-葡萄糖苷(11,21-dioxo-3β,15α-dihydroxy-urs-12-en-2 O-β-D-glucoside)(1),11,21-二氧-3β,15α-二羟基-乌苏-12-烯-24-O-β-D-葡萄糖苷(11,21-dioxo-3β,15α-dihydroxy-urs-12-en-24-O-β-D-glucoside)(2),11,21-二氧-3β,15α-二羟基-△~(12)-齐墩果烯-24-O-β-D-葡萄糖苷(11,21-dioxo-3β,15α-dihydroxy-olean-12-en-24-O-β-D-glucoside)(3),芹菜素-7-O-[2″-O-(5′′′-O-阿魏酸)-β-D-呋喃芹糖]-β-D-吡喃葡萄糖苷(apigenin-7-O-(2″-O-(5′′′-O-feruloyl)-β-D-apiofuranosyl)-β-D-glucopyranoside)(4),柯伊利素-7-O-[2″-O-(5′′′-O-阿魏酸)-β-D-呋喃芹糖]-β-D-吡喃葡萄糖苷(chrysoeriol-7-O-[2″-O-(5′′′-O-feruloyl)-β-D-apiofuranosyl]-β-D-glucopyranoside)(5),木犀草素-7-O-[2″-O-(5′′′-O-阿魏酸)-β-D-呋喃芹糖]-β-D-吡喃葡萄糖苷(luteolin-7-O-[2′′-O-(5′′′-O-feruloyl)β-D-apiofuranosyl]-β-D-glucopyranoside)(6),6-C-β-D-葡萄糖-8-C-β-D-半乳糖芹菜素(6-C-β-D-glucosyl-8-C--β-D-galactosyl-apigenin)(7),柚皮素-7-O-(2-O-β-D-呋喃芹糖)-β-D-吡喃葡萄糖苷(naringein-7-O-(2-O-β-D-apiofuranosyl)-β-D-glucopyranoside)(8),芹菜苷(apiin)(9),木犀草素-7-O-β-D-吡喃葡萄糖苷(luteolin-7-O-β-D-glucopyranoside)(10),柯伊利素-7-O-β-D-吡喃葡萄糖苷(chrysoeriol-7-O-β-D-glucopyranoside)(11),芹菜素-7-O-β-D-吡喃葡萄糖苷(apigenin-7-O-β-D-glucopyranoside)(12),柯伊利素(chrysoeriol)(13),木犀草素(luteolin)(14),槲皮素(quercetin)(15),芹菜素(apigenin)(16),(2S)-1-O-(7Z,10Z,13Z-hexadecatrienoyl)-3-O-β-galactopyranosyl-glycerol(17),(2S)-1-O-butanonyl-3-O-β-galactopyranosyl-glycerol(18),4β-O-glucopyranosyl-senkyunolide(19),瑟丹内酯(sedanolide)(20),3-oxo-megastigma-4,8-dien-7-O-β-D-glucoside(21),3-hydroxy-megastigma-5,8-dien-7-one(22),发卡二醇(falcariondiol)(23),(9z)1,9-heptadecadiene-4,6-diyne-3,8,11-triol(24),oplopandiol(25),异芩皮素(isofraxidin)(26),5-甲氧基补骨脂素(5-methoxypsoralen)(27),5,8-二甲氧基补骨脂素(5,8-dimethoxyl psoralen)(28),3—咖啡酰氧基奎宁酸(3-O-caffeoyl-quinic acid)(29),3-反式香豆酰基奎宁酸(3-trans-coumaroylquinicacid)(30),丁香酚(eugnic acid)(31),反式阿魏酸(trans-ferulic acid)(32),反式桂皮酸(trans-cinnamic acid)(33),阿魏酸-对羟基苯乙醇酯(P-hydroxyphenylethanol ferulate)(34),2-(3-甲氧基-4-羟基苯基)-丙烷-1,3-二醇(2-(3-methoxy-4-hydroxy-phenol)-propane-1,3-diol)(35),lunularin(36),lunularic acid(37),D-阿洛糖醇(D-allitol)(38),β-谷甾醇(β-sitosterol)(39),苯甲酸(benzolic acid)(40),丁二酸(succinic acid)(41)。在这41个化合物中,有3个三萜类化合物,13个黄酮类化合物,2个醇苷类化合物,2个苯酞类化合物,2个四甲基环己烯类化合物,3个聚炔类化合物,9个苯丙素类化合物,3个酚酸类化合物,4个其他类化合物。其中化合物1,2,3,4,5,18,19,21共8个化合物为新化合物,6,7,8,17,22,24,25,26,30,34,35,36,37,38共14个化合物为首次从芹属中分离得到的化合物。本文首次从芹属中分离出三萜类、醇苷类、四甲基环己烯类和酚酸类化合物,以上结果丰富了旱芹的化学成分种类,为旱芹相关药效物质研究奠定基础。
论文对三萜类化合物(1-3)、黄酮类化合物(4-16,18)及醇苷类化合物(17)的生物活性进行了测试。采用Griess法考察了以上化合物抑制脂多糖诱导的大鼠RAW264.7巨噬细胞NO释放活性,结果表明有四个黄酮类化合物(化合物13,14,15,16)表现出很强的活性,而黄酮苷和其他两类化合物活性不明显。
采用DPPH法对以上三类化合物的清除自由基能力进行了考察,结果表明黄酮类化合物中只有B环为3′,4′二羟基(化合物6,10,13)时,活性最好,其它黄酮类化合物和另外两种化合物则显示弱的或不显示活性。
采用MTT法对以上化合物对人肺癌A549、人宫颈癌Hela,人乳腺癌MCF-7细胞株的体外细胞毒活性进行了考察,结果表明,黄酮类化合物中黄酮苷类和黄酮苷元均不显示活性,仅当接上反式阿魏酸结构单元时(化合物4和5)才显示微弱的细胞毒活性,三萜类和醇苷类不显示活性。
以上测试结果表明了旱芹中黄酮类化合物是其相关生物活性物质。
Chuanxinlian,the dried aerial parts of Andrographis paniculata(Burm.f.)Nees.is a Chinese herbal medicine used as an anti-inflammatory,antiviral and antipyretic drug for treatment of fever,cold,laryngitis and diarrhea.And it was specified in the Pharmacopoeia of the P.R.China(2005)as an anti-virus and anti-bacterial remedy.
The chemical constituents from n-BuOH and water portions of 85%EtOH extract of the aerial parts of this plant was investigated in this thesis and led to the isolation of 27 compounds.On the basis of chemical evidences and spectral analysis,25 compounds of them were identified,and they are 14-deoxy-11,12-didehydroandrographolide(1),andrographolide (2),neoandrographolide(3),14-deoxy andrographolide(4),14-deoxyandrographiside(5), 14-deoxy-11,12-didehydroandrographiside(6),3-O-β-D-glucopyranosyl-14-deoxy-andrographiside (7),3-0-P-D-glucopyranosyl-14-deoxy-11,12-didehydroandrographiside(8), isoandrographolide(9),andrographiside(10),5,4'-dihydroxy-7-O-β-D-pyranglucuronate butyl ester(11),andrographidine C(12),apigenin-7-O-β-D-glucopyranoside(13), 5,4'-dihydroxy-7-methoxy-8-O-β-D-glucopyranosyloxyflavone(14),7,8-dimethoxy-2'-hydroxy-5-O-β-D-glucopyranosyloxyflavone(15),6-C-β-D-glucosyl-8-C-β-D-galactosyl-apigenin (16),6,8-di-C-β-D-glucosyl-chrysin(17),apigenin-7-O-β-D-glucuronide(18), 8-acetyl-harpagide(19),procumbide(20),teuhircoside(21),2,6-dimethoxyl-p-hydroxybenzoyl-1-O-β-D-glucoside(22),roseoside(23),citroside B(24),oxalic acid(25), respectively.Among these twenty-seven compounds,ten are diterpenoid lactones,eight are flavones,three are iridoids,two are megastigamane glycosides,one is a phenol glycoside and one is an organic acid.And among them,7,8 and 15 are new compounds,11,16,17,18,21, 22,23,24 and 25 were isolated for the first time from Andrographis genus.These results revealed the megastigamane glycosides and phenoglycosides were isolated for the first time from Andrographis genus,which were.important supplement to the chemical constituents of Andrographis paniculata.
Apium graveolens L.,the fresh whole plant of Apium graveolens L.in Umbelliferae.,is a normal vegetable to people.It is effective on epilepsy,hyperlipemia,and hypertension;it also can protect the brain cells and enhance memory.As an ordinary vegetable in daily life, celery has a variety of pharmacological activity,and received increased attention on its chemical constituents.Previous studies were focused on celery seeds but not its fresh herb of the whole plant.Therefore,in this thesis,the chemical constituents of the EtOAc,n-BuOH and water extracts from 70%EtOH extract of the fresh herb of Apium graveolens L.were studied.43 constituents were isolated by column chromatographies of silica ge(?)D101., polyamide,Sephadex LH-20,ODS and HPLC.On the basis of the chemical evidence and spectral analysis,the structures of 41 compounds were elucidated,they are 11,21-dioxo-3β,15α-dihydroxy-urs-12-en-2-O-β-D-glucoside(1),11,21-dioxo-3|3,15α-dihydroxy-urs-12-en-24-O-P-D-glucoside(2),11,21-dioxo-3β,15α-dihydroxy-olean-12-en-24-O-β-D-glucoside(3),apigenin-7-O-(2′-O-(5′′′-O-feruloyl)-p-D-apiofuranosyl)-β-D-glucopyranoside(4),chrysoeriol-7-O-[2′′-O-(5′′′-O-feruloyl)-β-D-apiofuranosyl]-β-D-glucopyranoside(5),(luteolin-7-O-[2′′-O-(5′′′-O-feruloyl)-β-D-apiofuranosyl]-p-D-glucopyranoside(6),(6-C-β-D-glucosyl-8-C-P-D-galactosyl-apigenin)(7),naringein-7-O-(2-O-β-D-apiofuran-osyl)-β-D-glucopyranoside(8),apiin(9),luteolin-7-O-β-D-glucopyranoside(10),chrysoeriol-7-O-β-D-glucopyranoside(11),apigenin-7-O-β-D-glucopyranoside(12),chrysoeriol(13),luteolin(14),quercetin(15),apigenin(16), (2S)-1-O-(7Z,10Z,13Z-hexadecatrienoyl)-3-O-β-galactopyanosyl-glycerol(17),(2S)-l-O-butanonyl-3-O-β-galactopyranosyl-glycerol(18),4β-O-glucopyranosyl-senkyunolide(19), sedanolide(20),3-oxo-megastigma-4,8-dien-7-O-β-D-glucoside(21),3-hydroxy-megastigma-5,8-dien-7-one(22),falcariondiol(23),(9z)-l,9-heptadecadiene-4,6-diyne-3,8,11-triol(24), oplopandiol(25),isofraxidin(26),5-methoxy psoralen(27),5,8-dimethoxyl psoralen(28), 3-O-caffeoyl-quinic acid(29),3-trans-coumaroylquinic acid(30),4-allyl-2-methoxyphenol (31),trans-ferulic acid(32),trans-cinnamic acid(33),p-hydroxyphenylethanol ferulate(34), 2-(3-methoxy-4-hydroxy)-propane-l,3-diol(35),lunularin(36),lunularic acid(37),,D-allitol (38),β-sitosterol(39),benzolic acid(40),succinic acid(41),respectively.Among the fourty-one compounds,three are triterpenes,thirteen are flavones,three are alcoholic glycosides,two are pathalides,two are megastigamanes,three are polyalkynes,nine are phenylpropanoids,three are phenol acids and four others.Among them,1,2,3,4,5,18,19 and 21 are new compounds,6,7,8,17,22,24,25,26,30,34,35,36,37 and 38 are isolated from apium genus for the first time.The above mentioned results indicated that triterpenes, alcoholic glycosides,megastigamanes and phenol acids were isolated for the first time from apium genus,which would provide chemical substances for elucidating the bioactive constituents of Apium graveolens.
Bioactivity of three triterpenes(1-3),fourteen flavonoids(4-16,18)and one alcoholic glycoside(17)from Apium graveolens was tested in this thesis.
These compounds were assayed against NO production on LPS activated macrophages by Griess method.Among them,4 flavones(13,14,15 and 16)displayed high inhibitory effects,but flavonoid glycosides and other kinds showed no correlated activity.
The above 18 compounds were evaluated by 1,1-diphenyl-2-picrylhydrazyl(DPPH)free radical scavenging method.The results revealed only flavonoids with 3',4'-dihydroxy in B ring(6,10 and 13)displayed scavenging activity,and the others displayed no scavenging activity.
MTT assay was used to test the cytotoxic activity of these 18 compounds against A549, Hela,and MCF-7 rumor cell lines.Among them,flavonoid aglycones and flavonoid glycosides displayed no cytotoxicity,but only flavonoid glycosides with the unit of trans-ferulic acid(4 and 5)showed cytotoxicity towards different cells.And other compounds displayed no significant cytotoxic activity.
On the basis of chemical and bioactive studies,this thesis confirmed that flavonoids were the major bioactive compounds of fresh celery(Apiun graveolens).
引文
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