伊犁贝母的化学成分研究
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摘要
目的研究伊犁贝母Fritillariapallidiflora中的化学成分。方法运用柱色谱方法进行分离纯化,结合波谱技术与理化常数鉴定化合物结构。结果从伊犁贝母95%乙醇提取物中分离得到了16个化合物,包括酚酸类、酯类、生物碱类等,分别鉴定为1,4-联苯基丁烷(1)、顺式肉桂酸(2)、4-羟基-3-甲氧基苯甲醛(3)、香草乙酮(4)、油酸甲酯(5)、阿魏酸甲酯(6)、1-O-阿魏酸甘油(7)、反式异阿魏酸(8)、丁香脂素(9)、松脂醇(10)、2,3-O-二阿魏酸甘油(11)、1,3-O-二阿魏酸甘油(12)、环(L-脯-L-丙)二肽(13)、环(L-亮-L-缬)二肽(14)、双(二乙二醇)邻苯二甲酸酯(15)、环(苯丙-缬)二肽(16)。结论所有化合物均为首次从伊犁贝母中分离得到,其中化合物1、3～8、10～13、15、16为该属植物中首次分离得到。
Objective To study the chemical constituents from Fritillaria pallidiflora. Methods The constituents were isolated from F. pallidiflora and purified by column chromatography, and the structures were identified by spectra analysis and chemical methods.Results Sixteen compounds were isolated from F. pallidiflora, including phenolic acids, esters, alkaloids, and the structures were identified as 1,4-diphenylbutane(1), cis-cinnamic acid(2), 4-hydroxy-3-methoxybenzaldehyde(3), acetovanillone(4),9-octadecenoicacidmethylester(5), methyl ferulate(6), 1-O-feruloylglycerol(7), trans-isoferulic acid(8), syringaresinol(9),pinoresinol(10), 2,3-O-diferuloylglycerol(11), 1,3-O-diferuloyl-glycerol(12), cyclo(L-Pro-L-Ala)(13), cyclo(L-Leu-L-Val)(14), bis(diethylene glycol)phthalate(15), and cyclo-(Phe-Val)(16). Conclusion All compounds are isolated from F. pallidiflora for the first time, and componds 1, 3—8, 10—13, 15, and 16 are isolated from the genus of Fritillaria for the first time.
Objective To study the chemical constituents from Fritillaria pallidiflora. Methods The constituents were isolated from F. pallidiflora and purified by column chromatography, and the structures were identified by spectra analysis and chemical methods.Results Sixteen compounds were isolated from F. pallidiflora, including phenolic acids, esters, alkaloids, and the structures were identified as 1,4-diphenylbutane(1), cis-cinnamic acid(2), 4-hydroxy-3-methoxybenzaldehyde(3), acetovanillone(4),9-octadecenoicacidmethylester(5), methyl ferulate(6), 1-O-feruloylglycerol(7), trans-isoferulic acid(8), syringaresinol(9),pinoresinol(10), 2,3-O-diferuloylglycerol(11), 1,3-O-diferuloyl-glycerol(12), cyclo(L-Pro-L-Ala)(13), cyclo(L-Leu-L-Val)(14), bis(diethylene glycol)phthalate(15), and cyclo-(Phe-Val)(16). Conclusion All compounds are isolated from F. pallidiflora for the first time, and componds 1, 3—8, 10—13, 15, and 16 are isolated from the genus of Fritillaria for the first time.
引文
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[2]陈梅花,王慧春,朱艳媚,等.贝母的药理研究[J].安徽农学通报,2007,13(1):103-105.
[3]中国药典[S].一部.2010.
[4]Songlin L,Li P,Lin G,et al.Simultaneous determination of seven major isosteroidal alkaloids in bulbs of Fritillaria by gas chromatography[J].J Chromatogr A,2000,873(2):221-228.
[5]伊江兰,麦迪尼亚提.伊贝母总生物碱的研究概述[J].新疆中医药,2002,20(4):77-79.
[6]徐惠波,杨晓波,温富春,等.伊犁贝母和梭砂贝母生理活性的初步比较[J].中国中药杂志,2000,25(7):391-393.
[7]Fleck M,Walter M.1,4-Diphenylbutane[J].Acta Crystallogr,2005,61(12):4099-4100.
[8]尹田鹏,陈阳,舒燕,等.玉龙乌头的化学成分研究[J].云南大学学报:自然科学版,2018,40(1):148-153.
[9]岳文静,罗素琴,刘乐乐,等.4-羟基-3-甲氧基苯甲醛木糖苷的合成[J].内蒙古医科大学学报,2009,31(6):632-634.
[10]段洁,李巍,胡旭佳,等.九子参化学成分研究[J].中草药,2009,40(4):528-530.
[11]Chibber V K,Chaudhary R B,Tyagi O S,et al.Anti wear and anti friction characteristics of tribochemical films of alkyl octa-decenoates and their derivatives[J].Lubrication Sci,2010,18(1):63-76.
[12]陈雯,唐生安,秦楠,等.牛尾菜抗氧化活性成分研究[J].中国中药杂志,2012,37(6):806-810.
[13]Luo J,Li L,Kong L.Preparative separation of phenylpropenoid glycerides from the bulbs of Lilium lancifolium by high-speed counter-current chromatography and evaluation of their antioxidant activities[J].Food Chem,2012,131(3):1056-1062.
[14]Yoshimura M,Ochi K,Sekiya H,et al.Identification of characteristic phenolic constituents in mousouchiku extract used as food additives[J].Chem Pharm Bull,2017,65(9):878-882.
[15]毛士龙,桑圣民,劳爱娜,等.山海螺的化学成分研究[J].天然产物研究与开发,2000,12(1):1-3.
[16]Milder I E,Arts I C,Van d P B,et al.Lignan contents of dutch plant foods:A database including lariciresinol,pinoresinol,secoisolariciresinol and matairesinol[J].Br JNutr,2005,93(3):393-402.
[17]Luo J,Li L,Kong L.Preparative separation of phenylpropenoid glycerides from the bulbs of Lilium lancifolium by high-speed counter-current chromatography and evaluation of their antioxidant activities[J].Food Chem,2012,131(3):1056-1062.
[18]Sun S,Hu B,Song F,et al.Ionic liquids improve the selective synthesis of hydrophilic glyceryl ferulates by the enzymatic transesterification of ethyl ferulate with monostearin:Comparison with organic solvents[J].Eur JLipid Sci Technol,2015,117(8):1171-1178.
[19]张晓晓,黄龙江,滕大为.光活环二肽环(L-脯-L-丙)和环(L-脯-L-缬)的合成[J].化学与生物工程,2013,30(3):61-63.
[20]刘海滨,高昊,王乃利,等.红树林真菌草酸青霉(092007)的环二肽类成分[J].沈阳药科大学学报,2007,24(8):474-478.
[21]Jayakumar R,Radhakrishnan S,Nanjundan S.Studies on poly(urethane-urea)s based on zinc salt of mono[hydroxyethoxyethyl]phthalate[J].React Funct Polymers,2003,57(1):23-31.