通关藤的化学成分及其质谱裂解规律的研究
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摘要
本论文由三部分组成,第一和二部分为实验论文,分别报道了摩萝科牛奶菜属植物通关藤的化学成分和通关藤中甾体化合物的电喷雾质谱裂解规律研究结果。第三部分概述了川芎化学成分及药理活性研究进展。
第一部分主要报道云南传统药用植物通关藤的化学成分研究,从中共分离纯化出17个化合物,运用ESI-MS、~1H-NMR、~(13)C-NMR、DEPT、HMBC、HSQC、NOESY等现代波谱技术并结合化学方法,鉴定出17个,其中14个为独特C21甾体环氧孕甾烷:Tenacigenoside I(1),Tenacigenoside K(2),Marsdenoside C(4),Tenacissoside A(5),Marsdenoside A(6),Tenacissoside H(7),Marsdenoside B(8),Marsdenoside H(9),11α-丁烯酰基-12β-乙酰基通关藤苷元B(10),11α-2-甲基丁酰基-12β-乙酰基通关藤苷元B(11),Tenacissoside G(13),Tenacissoside I(14),Tenacissoside B(15),Tenacissoside C(16)。通关藤苷元C-3-O-甲基-6-脱氧-β-D-阿洛糖吡喃糖基-(1→4)-β-D-齐墩果糖吡喃糖苷(3),苦绳双糖苷(12),以及牛弥菜醇(17)。其中(1)为新化合物,(2)为首次从该植物中分离得到, (3)~(17)是已知化合物。
第二部分利用电喷雾串联质谱(ESI-MSn)研究了从云南产通关藤(Marsdenia tenacissima (Roxb.) Wight et Arn)中分离纯化得到的19个甾体化合物的裂解规律,分析了它们从分子离子出发的多级质谱的裂解碎片,总结了Tenacigenoside B,Tenacigenoside G,Tenacigenoside H在ESI正离子模式下[M+Na]~+的裂解途径和碎片离子峰。结果表明:这些甾体化合物主要丢失C-11和C-12位上的取代基,其次是糖苷上的糖的顺序断裂:这样有助于依据此类化合物结构特点和裂解规律来推断其结构,为此类化合物的快速鉴定提供依据。
第三部分综述川芎近年来的研究成果,列举了从该药用植物中分离得到的化合物,同时也对其主要的药理学作用、生物活性和临床应用进行了总结。
This dissertation consists of three parts. The first part elaborated the phytochemical investigation of medicinal plants of Marsdenia tenacissina. The second part analyzed polyoxypregnane glycosides in the stems of Marsdenia tenacissima. The last part reviewed the chemical constituents and bioactive studies of Ligusticum Chuanxiong Hort.
The stems of M. tenacissina, popularly known as‘Tong-guang-teng’, are widely employed to treat inflammation, asthma and cancer in southwest of China. In clinic, the preparations from the aqueous extract of the stems of M. tenacissima, has been used for treatment of gastric carcinoma and liver cancer. First chapter is about the chemical constituents isolated from stems of M. tenacissima. 17 compounds were isolated and their structures were determined by 1D, 2D-NMR analysis and chemical evidence. 14 compounds were elucidated as peculiarity polyoxypregnane: Tenacigenoside I (1), Tenacigenoside K (2), Marsdenoside C (4), Tenacissoside A (5), arsdenoside A (6), Tenacissoside H (7), Marsdenoside B (8), Marsdenoside H (9), 11α-O-Tigloyl-12β-O-acetyltenacigenin B (10), 11α-O-2-Methylbutyryl-12β-O-ace tyltenacigenin B (11), Tenacissoside G (13) , Tenacissoside I (14), Tenacissoside B (15), Tenacissoside C (16). 3-O-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-β-D- oleandropyranosyltenacigenin C (3), methyl-β-D-theveropyranosyl-(1→4)-β-D-cym aropyranoside (12), conduritol (17). Among them, compound 1 was identified as new polyoxypregnanes. Compound 2 was isolated from the title plant for the first time. Compounds 3-17 were known compounds.
The second part was about the results of nineteen polyoxypregnane glycosides which were isolated from the stems of M. tenacissina, and have been investigated by the method based on electrospray ionization tandem mass spectrometry (ESI-MSn). The fragmentation pathways of Tenacigenoside G, Tenacigenoside B, Tenacigenoside H in positive mode have been summarized. The data reveals the first loss position is 11-C and12-C, then glycosides of 3-C. which could save time and material consuming efforts in structure identitification and traditional phytochemistry analyses compound of this species.
The last part is a review of previous studies of Ligusticum Chuanxiong Hort.. Their biological activities and Clinical Application were also summed up.
第一部分主要报道云南传统药用植物通关藤的化学成分研究,从中共分离纯化出17个化合物,运用ESI-MS、~1H-NMR、~(13)C-NMR、DEPT、HMBC、HSQC、NOESY等现代波谱技术并结合化学方法,鉴定出17个,其中14个为独特C21甾体环氧孕甾烷:Tenacigenoside I(1),Tenacigenoside K(2),Marsdenoside C(4),Tenacissoside A(5),Marsdenoside A(6),Tenacissoside H(7),Marsdenoside B(8),Marsdenoside H(9),11α-丁烯酰基-12β-乙酰基通关藤苷元B(10),11α-2-甲基丁酰基-12β-乙酰基通关藤苷元B(11),Tenacissoside G(13),Tenacissoside I(14),Tenacissoside B(15),Tenacissoside C(16)。通关藤苷元C-3-O-甲基-6-脱氧-β-D-阿洛糖吡喃糖基-(1→4)-β-D-齐墩果糖吡喃糖苷(3),苦绳双糖苷(12),以及牛弥菜醇(17)。其中(1)为新化合物,(2)为首次从该植物中分离得到, (3)~(17)是已知化合物。
第二部分利用电喷雾串联质谱(ESI-MSn)研究了从云南产通关藤(Marsdenia tenacissima (Roxb.) Wight et Arn)中分离纯化得到的19个甾体化合物的裂解规律,分析了它们从分子离子出发的多级质谱的裂解碎片,总结了Tenacigenoside B,Tenacigenoside G,Tenacigenoside H在ESI正离子模式下[M+Na]~+的裂解途径和碎片离子峰。结果表明:这些甾体化合物主要丢失C-11和C-12位上的取代基,其次是糖苷上的糖的顺序断裂:这样有助于依据此类化合物结构特点和裂解规律来推断其结构,为此类化合物的快速鉴定提供依据。
第三部分综述川芎近年来的研究成果,列举了从该药用植物中分离得到的化合物,同时也对其主要的药理学作用、生物活性和临床应用进行了总结。
This dissertation consists of three parts. The first part elaborated the phytochemical investigation of medicinal plants of Marsdenia tenacissina. The second part analyzed polyoxypregnane glycosides in the stems of Marsdenia tenacissima. The last part reviewed the chemical constituents and bioactive studies of Ligusticum Chuanxiong Hort.
The stems of M. tenacissina, popularly known as‘Tong-guang-teng’, are widely employed to treat inflammation, asthma and cancer in southwest of China. In clinic, the preparations from the aqueous extract of the stems of M. tenacissima, has been used for treatment of gastric carcinoma and liver cancer. First chapter is about the chemical constituents isolated from stems of M. tenacissima. 17 compounds were isolated and their structures were determined by 1D, 2D-NMR analysis and chemical evidence. 14 compounds were elucidated as peculiarity polyoxypregnane: Tenacigenoside I (1), Tenacigenoside K (2), Marsdenoside C (4), Tenacissoside A (5), arsdenoside A (6), Tenacissoside H (7), Marsdenoside B (8), Marsdenoside H (9), 11α-O-Tigloyl-12β-O-acetyltenacigenin B (10), 11α-O-2-Methylbutyryl-12β-O-ace tyltenacigenin B (11), Tenacissoside G (13) , Tenacissoside I (14), Tenacissoside B (15), Tenacissoside C (16). 3-O-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-β-D- oleandropyranosyltenacigenin C (3), methyl-β-D-theveropyranosyl-(1→4)-β-D-cym aropyranoside (12), conduritol (17). Among them, compound 1 was identified as new polyoxypregnanes. Compound 2 was isolated from the title plant for the first time. Compounds 3-17 were known compounds.
The second part was about the results of nineteen polyoxypregnane glycosides which were isolated from the stems of M. tenacissina, and have been investigated by the method based on electrospray ionization tandem mass spectrometry (ESI-MSn). The fragmentation pathways of Tenacigenoside G, Tenacigenoside B, Tenacigenoside H in positive mode have been summarized. The data reveals the first loss position is 11-C and12-C, then glycosides of 3-C. which could save time and material consuming efforts in structure identitification and traditional phytochemistry analyses compound of this species.
The last part is a review of previous studies of Ligusticum Chuanxiong Hort.. Their biological activities and Clinical Application were also summed up.
引文
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