芸薹子中含氮类化学成分分离鉴定
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摘要
目的:芸薹子中含氮类化学成分的分离与鉴定。方法:干燥并经石油醚脱脂后的芸薹子采用75%的乙醇回流提取,减压浓缩后所得浸膏用水悬浮后分别用石油醚、乙酸乙酯萃取为不同极性部位,水部位利用AB-8大孔吸附树脂粗分为30%,60%,95%乙醇极性部位,最后采用硅胶柱色谱,LH-20型羟丙基葡聚糖凝胶(Sephadex LH-20)柱色谱以及半制备HPLC等方法进行分离纯化,根据理化常数和核磁共振谱、质谱等光谱数据对所分离的化学成分进行结构鉴定。结果:从芸薹子75%乙醇提取物中共分离鉴定了13个含氮类化合物,分别鉴定为coixspirolactam C (1),吲哚-3-乙腈(2),2-β-Dglucopyranosylsulfanyl-1H-indole-3-acetonitrile(3),烟酸(4),腺苷(5),吲哚-3-甲醛(6),4-羟基-吲哚-3-甲醛(7),6-羟基-吲哚-3-甲酸(8),ethyl 2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylate(9),5-羟基-4(1H)-喹唑酮(10),4-羟基-2(1H)-喹唑酮(11),2(1H),4(3H)-二羰基-5-羟基喹唑酮(12),5-烯丙基噁唑啉-2-酮(13)。结论:以上所有化合物均为首次从芸薹子植物中分离得到,其中化合物1,3和13为首次从芸薹属植物中分离得到。
Objective: To study nitrogenous chemical constituents from the seeds of Brassica campestris.Method: The aerial parts of nonfat seeds were extracted with 75% ethanol heat refluxing method,then suspended in H_2O and separated with ligarine and ethyl acetate to obtain respective fractions. Chemical constituents were isolated and purified by various chromatographic methods and identified by physicochemical characters and spectroscopic analysis or comparison with standard compounds. Result: Thirteen nitrogenous chemical compounds were isolated and identified as coixspirolactam C( 1),indole-3-acetonitrile( 2),2-β-D-glucopyranosylsulfanyl-1 H-indole-3-acetonitrile( 3),nicotinic acid( 4),adenosine( 5),1 H-indole-3-carbaldehyde( 6),4-hydroxy-1 H-indole-3-carbaldehyde( 7), 6-hydroxy-1 H-indole-3-carboxylic acid( 8), ethyl 2-oxo-1, 2, 3, 4-tetrahydroquinoline-4-carboxylate( 9), 5-hydroxy-4( 1 H)-quinazolinone( 10), 4-hydroxy-2-quinazolinone( 11),5-hydroxy-quinazoline-2( 1 H),4( 3 H)-dione( 12),5-allyloxazolidin-2-one( 13). Conclusion: All of the compounds were isolated from this plant for the first time,and compounds 1,3 and 13 were isolated from Brassica for the first time.
Objective: To study nitrogenous chemical constituents from the seeds of Brassica campestris.Method: The aerial parts of nonfat seeds were extracted with 75% ethanol heat refluxing method,then suspended in H_2O and separated with ligarine and ethyl acetate to obtain respective fractions. Chemical constituents were isolated and purified by various chromatographic methods and identified by physicochemical characters and spectroscopic analysis or comparison with standard compounds. Result: Thirteen nitrogenous chemical compounds were isolated and identified as coixspirolactam C( 1),indole-3-acetonitrile( 2),2-β-D-glucopyranosylsulfanyl-1 H-indole-3-acetonitrile( 3),nicotinic acid( 4),adenosine( 5),1 H-indole-3-carbaldehyde( 6),4-hydroxy-1 H-indole-3-carbaldehyde( 7), 6-hydroxy-1 H-indole-3-carboxylic acid( 8), ethyl 2-oxo-1, 2, 3, 4-tetrahydroquinoline-4-carboxylate( 9), 5-hydroxy-4( 1 H)-quinazolinone( 10), 4-hydroxy-2-quinazolinone( 11),5-hydroxy-quinazoline-2( 1 H),4( 3 H)-dione( 12),5-allyloxazolidin-2-one( 13). Conclusion: All of the compounds were isolated from this plant for the first time,and compounds 1,3 and 13 were isolated from Brassica for the first time.
引文
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[3] ?pak J. The effect of the glucosinolate sinigrin and of allyl isothiocyanate on the infectivity of turnip mosaic virus[J]. Biologia Plantarum,1988,30(6):465-470.
[4] Kadir H A N,Rossiter J T,Gooderham N J. In vitro toxicity study of synthetic and natural alkenyl glucosinolate hydrolysis products on c Ho1 and MCL5cell lines[J]. Toxicol Lett,2010,196(Suppl):S150.
[5] Bonnesen C,Eggleston I M,Hayes J D. Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines[J]. Cancer Res,2001,61(16):6120-6130.
[6]季宇彬,武晓丹,邹翔.硫代葡萄糖苷的研究[J].哈尔滨商业大学学报:自然科学版,2005,21(5):550-554,562.
[7]孔燕,张璐,房克慧.芸薹子药材薄层色谱鉴别研究[J].海峡药学,2015,27(10):19-21.
[8]孔燕,张璐,房克慧. HPLC法测定芸薹子中芥子碱硫氰酸盐含量[J].天津药学,2015,27(5):15-17.
[9] Yahara S,Nishiyori T,Kohda A,et al. Isolation and characterization of phenolic compounds from Magnoliae Cortex produced in China[J]. Chem Pharm Bull,2008,39(8):2024-2036.
[10] Chung C P,Hsu C Y,LIN J H,et al. Antiproliferative lactams and spiroenone from adlay bran in human breast cancer cell lines[J]. J Agric Food Chem,2011,59(4):1185-1194.
[11]李霞,陈安家,李春.板蓝根水溶性化学成分的研究[J].中国实验方剂学杂志,2010,16(5):64-67.
[12] YANG L,WANG G,WANG M,et al. Indole alkaloids from the roots of Isatis indigotica and their inhibitory effects on nitric oxide production[J]. Fitoterapia,2014,95(2):175-181.
[13]康飞,吕华冲.广西白背叶植物叶的化学成分[J].广东药学院学报,2007,23(2):121-123.
[14]韦玮,王力,梁丽,等.中药药对“都梁丸”化学成分的研究[J].中国现代中药,2017,19(7):944-955.
[15]王晓霞,庄鹏宇,陈金铭,等.党参化学成分的研究[J].中草药,2017,48(9):1719-1723.
[16]朱丹,王帝,王光辉,等.小槐花大极性部位的化学成分研究[J].中国中药杂志,2014,39(16):3112-3116.
[17] Hagemeier J,Schneider B,Oldham N J,et al.Accumulation of soluble and wall-bound indolic metabolites in Arabidopsis thaliana leaves infected with virulent or avirulent Pseudomonas syringae pathovar tomato strains[J]. Proc Natl Acad Sci USA,2001,98(2):753-758.
[18] Kocian O,Ferles M. Reductions of some acids of the quinoline series[J]. Collect Czech Chem Commun,1978,43:1413-1430.
[19] Dempcy R O,Skibo E B. Rational design of quinazolinebased irreversible inhibitors of human erythrocyte purine nucleoside phosphorylase[J]. Biochemistry,1991,30(34):8480-8487.
[20] Kumar M,Sharma K,Rajawat A,et al. Synthesis and evaluation of antioxidant and radical scavenging activities of quinolinobenzothiazinones[J]. Res Chem Intermed,2015,41(4):2265-2276.
[21] Abdel-Razik H H. Synthesis of some quinazoline‐2(1H),4(3H)‐dione derivatives[J]. J Chin Chem Soc,2013,52(1):141-148.
[22] Bartoli G,Bosco M,Carlone A,et al. Direct catalytic synthesis of enantiopure 5-substituted oxazolidinones from racemic terminal epoxides[J]. Org Lett,2005,7(10):1983-1985.