乳白香青、珠光香青和翅茎风毛菊化学成分研究
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摘要
本论文对采自青海省互助县的三种菊科植物乳白香青(Anaphalis lacteaMaxim．)、珠光香青(Anaphalis margaritacea Benth et Hook f．)和翅茎风毛菊(Saussurea cauloptera Hand．-Mazz．)进行了系统的化学成分研究。使用硅胶柱层析(CC)，制备薄层层析(prep-TLC)，重结晶等分离方法共分离得到了62个化合物，并利用各种色谱、波谱技术，如EI-MS，HRESIMS，1D NMR(~1HNMR，~(13)CNMR，DEPT)，2D-NMR(COSY，HMQC，HMBC，NOESY)，以及与已知化合物或其文献数据对照，鉴定了这些化合物的结构。
从乳白香青(A．lactea)全草乙醇提取物中分离并鉴定了30个化合物，其中有4个为未见文献报道的新化合物，即：2’，6’-二羟基-3’-(2-羟基-3-甲基-3-丁烯基)-4’-甲氧基查耳酮，4，6-二羟基-7-异丁酰基-5-异戊二烯基-2(3H)-苯并呋喃酮，7-O-(β-D-葡萄糖苷)-5-羟基-1(3H)-异苯并呋喃酮，(2R，3S)-3-甲基-2-(2-异丙烯基-5-己酮)-环戊酮；1个新的天然产物，即：7-methoxyplatypterophthalide。其余化合物分别为黄酮、苯肽、三萜、甾体等。
从珠光香青(A．margaritacea)全草乙醇提取物中分离并鉴定了22个化合物，主要是黄酮(包括4个罕见的A环多取代的黄酮)和三萜类化合物。
从翅茎风毛菊(S．cauloptera)全草乙醇提取物的乙酸乙酯和正丁醇部分分离并鉴定了10个化合物，其中有2个为未见文献报道的新化合物，即：2-(4-羟基亚苄基)-2Z-4-丁二酸正丁酯、(1R~*，2R~*，3S~*，4S~*)-1，3-二(正丁基氧羰甲基)-2，4-二(4-羟基苯基)-环丁烷-1，3-二羧酸。
本论文对从乳白香青和珠光香青中分离得到的黄酮类化合物进行了抗氧化活性研究。
本论文对20年来发现的二聚体倍半萜进行了综述，对研究倍半萜的科技工作者能提供一定的参考。
本论文的研究结果为乳白香青、珠光香青和翅茎风毛菊的化学分类学和开发利用提供了一定的化学依据。
The thesis primarily describes the phytochemical investigation on the plants ofAnaphalis lactea Maxim.,Anaphalis margaritacea Benth et Hook f.and Saussureacauloptera Hand.-Mazz.collected in Huzhu County of Qinghai Province.Sixty-twocompounds were isolated by means of silica gel column chromatography (CC),preparative thin layer chromatography (prep-TLC) and recrystallization etc.Thestructures of these compounds were elucidated on the basis of spectral evidences,including EI-MS,HRESIMS,1D NMR (~1HNMR,~(13)CNMR,DEPT),2D-NMR(COSY,HMQC,HMBC,NOESY),along with comparison to authentic samples orliteratures.
Thirty compounds,including four new ones 2',6'-dihydroxy-3'-(2-hydroxy-3-methyl-3-butenyl)-4'-methoxychalcone,4,6-dihydroxy-7-isobutyryl-5-prenyl-2(3H)-benzo furanone,7-O-(β-D-glucopyranosyloxy)-5-hydroxy-1(3H)-isobenzofuranoneand (2R,3S)-3-methyl-2-(5-oxo-2-isopropenylhexyl)-cyclopentanone and one newnatural product 7-methoxyplatypterophthalide,were isolated from the ethanol extractof the dried whole plant A.lactea.Others were flavonoids,phthalides,triterpenoidsand sterols.
Twenty-two compounds,including four rare flavonoids with multi O-substitutedA-ring,were isolated from the ethanol extract of the dried whole plant A.margaritacea.
Ten compounds,including two new ones,2-(p-hydroxyl benzylidene)-4-butylester-(Z)-succinic acid and (1R~*,2R~*,3S~*,4S~*)-1,3-bis(2-butoxy-2-oxoethyl)-2,4-bis(4-hydroxyphenyl)cyclobutane-1,3-dicarboxylic acid,were isolated from S.cauloptera.
The free-radical scavenging activity of flavonoids isolated from A.lactea and A.margaritacea was also studied by DPPH assay.
Dimeric sesquiterpenoids isolated between 1983 and 2006 were reviewed.
The result of this thesis will provide chemical evidences for exploiting thenatural resources and be helpful to plant chemotaxonomy.
从乳白香青(A．lactea)全草乙醇提取物中分离并鉴定了30个化合物，其中有4个为未见文献报道的新化合物，即：2’，6’-二羟基-3’-(2-羟基-3-甲基-3-丁烯基)-4’-甲氧基查耳酮，4，6-二羟基-7-异丁酰基-5-异戊二烯基-2(3H)-苯并呋喃酮，7-O-(β-D-葡萄糖苷)-5-羟基-1(3H)-异苯并呋喃酮，(2R，3S)-3-甲基-2-(2-异丙烯基-5-己酮)-环戊酮；1个新的天然产物，即：7-methoxyplatypterophthalide。其余化合物分别为黄酮、苯肽、三萜、甾体等。
从珠光香青(A．margaritacea)全草乙醇提取物中分离并鉴定了22个化合物，主要是黄酮(包括4个罕见的A环多取代的黄酮)和三萜类化合物。
从翅茎风毛菊(S．cauloptera)全草乙醇提取物的乙酸乙酯和正丁醇部分分离并鉴定了10个化合物，其中有2个为未见文献报道的新化合物，即：2-(4-羟基亚苄基)-2Z-4-丁二酸正丁酯、(1R~*，2R~*，3S~*，4S~*)-1，3-二(正丁基氧羰甲基)-2，4-二(4-羟基苯基)-环丁烷-1，3-二羧酸。
本论文对从乳白香青和珠光香青中分离得到的黄酮类化合物进行了抗氧化活性研究。
本论文对20年来发现的二聚体倍半萜进行了综述，对研究倍半萜的科技工作者能提供一定的参考。
本论文的研究结果为乳白香青、珠光香青和翅茎风毛菊的化学分类学和开发利用提供了一定的化学依据。
The thesis primarily describes the phytochemical investigation on the plants ofAnaphalis lactea Maxim.,Anaphalis margaritacea Benth et Hook f.and Saussureacauloptera Hand.-Mazz.collected in Huzhu County of Qinghai Province.Sixty-twocompounds were isolated by means of silica gel column chromatography (CC),preparative thin layer chromatography (prep-TLC) and recrystallization etc.Thestructures of these compounds were elucidated on the basis of spectral evidences,including EI-MS,HRESIMS,1D NMR (~1HNMR,~(13)CNMR,DEPT),2D-NMR(COSY,HMQC,HMBC,NOESY),along with comparison to authentic samples orliteratures.
Thirty compounds,including four new ones 2',6'-dihydroxy-3'-(2-hydroxy-3-methyl-3-butenyl)-4'-methoxychalcone,4,6-dihydroxy-7-isobutyryl-5-prenyl-2(3H)-benzo furanone,7-O-(β-D-glucopyranosyloxy)-5-hydroxy-1(3H)-isobenzofuranoneand (2R,3S)-3-methyl-2-(5-oxo-2-isopropenylhexyl)-cyclopentanone and one newnatural product 7-methoxyplatypterophthalide,were isolated from the ethanol extractof the dried whole plant A.lactea.Others were flavonoids,phthalides,triterpenoidsand sterols.
Twenty-two compounds,including four rare flavonoids with multi O-substitutedA-ring,were isolated from the ethanol extract of the dried whole plant A.margaritacea.
Ten compounds,including two new ones,2-(p-hydroxyl benzylidene)-4-butylester-(Z)-succinic acid and (1R~*,2R~*,3S~*,4S~*)-1,3-bis(2-butoxy-2-oxoethyl)-2,4-bis(4-hydroxyphenyl)cyclobutane-1,3-dicarboxylic acid,were isolated from S.cauloptera.
The free-radical scavenging activity of flavonoids isolated from A.lactea and A.margaritacea was also studied by DPPH assay.
Dimeric sesquiterpenoids isolated between 1983 and 2006 were reviewed.
The result of this thesis will provide chemical evidences for exploiting thenatural resources and be helpful to plant chemotaxonomy.
引文
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