骆驼蓬种子中的含氮化合物
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摘要
为研究骆驼蓬Paganum harmala种子中的含氮类活性化合物,该文综合利用硅胶、MCI和ODS柱色谱以及半制备高效液相分离等多种色谱分离技术,从骆驼蓬种子95%乙醇提取物中分离得到14个含氮化合物,并利用波谱学技术鉴定了全部化合物的结构,分别为N-[3-(2-amino-4-methoxyphenyl)-3-oxopropyl]acetamide(1),dehydroharmalacidine(2),harmalacidine(3),harmine N-oxide(4),harmine(5),tetrahydroharmine(6),demethylharmalacidine(7),harmol(8),tetrahydroharmol(9),harmindolβ-D-glucopyranoside(10),tryptophylβ-D-glucopyranoside (11),pegamineβ-D-glucopyranoside (12),vasicol (13)和vasicinone(14)。其中化合物1为新化合物,2和10是2个新天然产物。
To investigate the N-containing compounds in the seeds of Paganum harmala,fourteen compounds were finally isolated from the 95% Et OH extract of P. harmala seeds by using various chromatographic techniques including silica gel,MCI resin,and ODS column chromatography as well as the semi-preparative HPLC. Depending on spectroscopic techniques and comparison with the reported data in the literatures,the structures of all compounds were identified as N-[3-(2-amino-4-methoxyphenyl)-3-oxopropyl]acetamide(1),dehydroharmalacidine(2),harmalacidine(3),harmine N-oxide(4),harmine(5),tetrahydroharmine(6),demethylharmalacidine(7),harmol(8),tetrahydroharmol(9),harmindol β-D-glucopyranoside(10),tryptophyl β-D-glucopyranoside(11),pegamineβ-D-glucopyranoside(12),vasicol(13) and vasicinone(14). Among them,1 was a new compound,and 2 and 10 were obtained as natural products for the first time.
To investigate the N-containing compounds in the seeds of Paganum harmala,fourteen compounds were finally isolated from the 95% Et OH extract of P. harmala seeds by using various chromatographic techniques including silica gel,MCI resin,and ODS column chromatography as well as the semi-preparative HPLC. Depending on spectroscopic techniques and comparison with the reported data in the literatures,the structures of all compounds were identified as N-[3-(2-amino-4-methoxyphenyl)-3-oxopropyl]acetamide(1),dehydroharmalacidine(2),harmalacidine(3),harmine N-oxide(4),harmine(5),tetrahydroharmine(6),demethylharmalacidine(7),harmol(8),tetrahydroharmol(9),harmindol β-D-glucopyranoside(10),tryptophyl β-D-glucopyranoside(11),pegamineβ-D-glucopyranoside(12),vasicol(13) and vasicinone(14). Among them,1 was a new compound,and 2 and 10 were obtained as natural products for the first time.
引文
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[2] Li S P,Cheng X M,Wang C H. A review on traditional uses,phytochemistry,pharmacology,pharmacokinetics and toxicology of the genus Peganum[J]. J Ethnopharmacol,2017,203:127.
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[4] Yang Y D,Cheng X M,Liu W,et al. Potent AChE and BChE inhibitors isolated from seeds of Peganum harmala Linn by a bioassay-guided fractionation[J]. J Ethnopharmacol,2015,168:279.
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[6] Frison G,Favretto D,Zancanaro F,et al. A case ofβ-carboline alkaloid intoxication following ingestion of Peganum harmala seed extract[J]. Forensic Sci Int,2008,179(2/3):37.
[7] Zheng X Y,Zhang Z J,Chou G X,et al. Acetylcholinesterase inhibitive activity guided isolation of two new alkaloids from seeds of Peganum nigellastrum Bunge by an in vitro TLC-bioautographic assay[J]. Arch Pharm Res,2009,32(9):1245.
[8]樊峥嵘,姚新生.骆驼蓬属(Peganum)植物成分及药理作用[J].沈阳药科大学学报,1992,9(2):144.
[9] Yang F,Chen R,Feng L,et al. Two new alkaloids from the aerial part of Peganum nigellastrum[J]. Helv Chim Acta,2011,94(3):514.
[10] Magnus V. Tryptophylβ-D-glucopyranoside:chemical synthesis,metabolism,and growth-promoting activity[J]. Carbohyd Res,1979,76(1):261.
[11] Tekzhenetskaya M V,Tashkhodzhaev B,Yagudaev M R,et al.Structure of vasicol[J]. Chem Nat Compd,1989,25(1):14.
[12] Joshi B S,Bai Y L,Puar M S,et al.1H-and13C-NMR assignments for some pyrrolo[2,1b] quinazoline alkaloids of Adhatoda vasica[J]. J Nat Prod,1994,57(7):953.
[2] Li S P,Cheng X M,Wang C H. A review on traditional uses,phytochemistry,pharmacology,pharmacokinetics and toxicology of the genus Peganum[J]. J Ethnopharmacol,2017,203:127.
[3] Siddiqui S,Khan O Y,Faizi S,et al. Studies in the chemical constituents of the seeds of Peganum harmala:isolation and structure elucidation of twoβ-carboline lactams harmalanine and harmalacidine[J]. Heterocycles,1988,27:1401.
[4] Yang Y D,Cheng X M,Liu W,et al. Potent AChE and BChE inhibitors isolated from seeds of Peganum harmala Linn by a bioassay-guided fractionation[J]. J Ethnopharmacol,2015,168:279.
[5] Al-Shamma A,Drake S,Flynn D L,et al. Antimicrobial agents from higher plants. Antimicrobial agents from Peganum harmala seeds[J]. J Nat Prod,1981,44(6):745.
[6] Frison G,Favretto D,Zancanaro F,et al. A case ofβ-carboline alkaloid intoxication following ingestion of Peganum harmala seed extract[J]. Forensic Sci Int,2008,179(2/3):37.
[7] Zheng X Y,Zhang Z J,Chou G X,et al. Acetylcholinesterase inhibitive activity guided isolation of two new alkaloids from seeds of Peganum nigellastrum Bunge by an in vitro TLC-bioautographic assay[J]. Arch Pharm Res,2009,32(9):1245.
[8]樊峥嵘,姚新生.骆驼蓬属(Peganum)植物成分及药理作用[J].沈阳药科大学学报,1992,9(2):144.
[9] Yang F,Chen R,Feng L,et al. Two new alkaloids from the aerial part of Peganum nigellastrum[J]. Helv Chim Acta,2011,94(3):514.
[10] Magnus V. Tryptophylβ-D-glucopyranoside:chemical synthesis,metabolism,and growth-promoting activity[J]. Carbohyd Res,1979,76(1):261.
[11] Tekzhenetskaya M V,Tashkhodzhaev B,Yagudaev M R,et al.Structure of vasicol[J]. Chem Nat Compd,1989,25(1):14.
[12] Joshi B S,Bai Y L,Puar M S,et al.1H-and13C-NMR assignments for some pyrrolo[2,1b] quinazoline alkaloids of Adhatoda vasica[J]. J Nat Prod,1994,57(7):953.