无花果果实水溶性成分的分离与鉴定
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摘要
通过各种柱色谱分离纯化技术,对无花果果实的水溶性成分进行了提取和分离,然后借助现代波谱学手段(UV、IR、HRMS、~1H NMR及~(13)C NMR)鉴定并推断了化合物的结构。从无花果果浆的乙醇提取物中分离得到7个单体化合物,分别为:无花果多糖(F-1),乳糖(1)、阿拉伯糖基表乳糖(2)、鼠李糖基纤维二糖(3)、维生素C(4)、二十二碳六烯酸(DHA,5)和β-胡萝卜素(6)。化合物2和3为首次报道的新寡糖类化合物,化合物1～5均为首次从无花果的果实中分离得到,化合物5是植物源DHA的重要发现。
Several water-soluble components from fig(Ficus carica Linn.) fruit were isolated and identified by column chromatography separation and purification techniques, and the structures were verified by modern spectroscopic methods(UV, IR, HRMS, ~1H NMR and ~(13)C NMR). Seven monomer compounds were isolated from the ethanol extract of F. carica pulp, as F. carica polysaccharide(F-1), lactose(1), arabinosyl epilactose(2), rhamnosyl cellobiose(3), vitamin C(4), docosahexaenoic acid(DHA, 5) and β-carotene(6). Compounds 2 and 3 were new oligosaccharides reported for the first time. Compounds 1-5 were isolated from F. carica fruit for the first time.
Several water-soluble components from fig(Ficus carica Linn.) fruit were isolated and identified by column chromatography separation and purification techniques, and the structures were verified by modern spectroscopic methods(UV, IR, HRMS, ~1H NMR and ~(13)C NMR). Seven monomer compounds were isolated from the ethanol extract of F. carica pulp, as F. carica polysaccharide(F-1), lactose(1), arabinosyl epilactose(2), rhamnosyl cellobiose(3), vitamin C(4), docosahexaenoic acid(DHA, 5) and β-carotene(6). Compounds 2 and 3 were new oligosaccharides reported for the first time. Compounds 1-5 were isolated from F. carica fruit for the first time.
引文
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[3]SOLOMON A,GOLUBOWICZ S,YABLOWICZ Z,et al.Antioxidant activities and anthocyanin content of fresh fruits of common fig (Ficus carica L.)[J].Journal of Agricultural and Food Chemistry,2006,54(20):7717-7723.
[4]曹尚银.无花果高效栽培与加工利用[M].北京:中国农业出版社,2002.CAO S Y.High-efficiency cultivation and processing of figs[M].Beijing:China Agriculture Press,2002.
[5]于磊.无花果栽培技术研究[J].中国林副特产,2015(5):53-54.YU L.Study on fig cultivation technology[J].Forest by-Product and Speciality in China,2015(5):53-54.
[6]曹尚银,杨福兰.无花果主要优良品种简介[J].果农之友,2002 (4):10-13.CAO S Y,YANG F L.Brief introduction of the main varieties of figs[J].Fruit Grower's Friend,2002 (4):10-13.
[7]RUBNOV S,KASHMAN Y,RABINOWITZ R,et al.Suppressors of cancer cell proliferation from fig (Ficus carica) resin:Isolation and structure elucidation[J].Journal of natural products,2001,64(7):993-996.
[8]尹卫平,陈宏明,王天欣,等.无花果抽提物抗肿瘤成分的分析[J].新乡医学院学报,1995,12(4):316-319.YIN W P,CHEN H M,WANG T X,et al.Analysis of antineoplastic consittuents of figs extract[J].Journal of Xinxiang Medical College,1995,12(4):316-319.
[9]YIN W P,ZHAO T Z,ZHANG H Y.A novel oligosaccharide ester from Syringa pubescens[J].Journal of Asian Natural Products Research,2008,10(1):95-100.
[10]赵天增.核磁共振氢谱[M].北京:北京大学出版社,1981:217.ZHAO T Z.Nuclear magnetic resonance hydrogen spectrum[M].Beijing:Peking University Press,1981:217.
[11]KOCHETKOWOV N K,TORGOV V I,MALYSHEVA N N,et al.Synthesis of the tetrasaccharide repeating unit of the o-specific polysaccharide from salmonella muenster and salmonella minneapolis[J].Tetrohedron,1980,36(9):1227-1230.
[12]吴亚林,黄静,潘远红.无花果多糖的分离、纯化和鉴定[J].浙江大学学报(理学版),2004,31(2):177-179.WU Y L,HUANG J,PAN Y H.Isolation,purification and identification of figs polysaccharide[J].Journal of Zhejiang University(Science Edition),2004,31(2):177-179.
[13]VOELTER W,BILIK V,BREITMAIER E.Konfigurationsund mutarotationseinflüsse auf die 13C-NMR spektren einiger disaccharide [J].Collection of Czechoslovak Chemical Communications,1973,38:2054-2059.
[14]BOCK K,PEDERSEN C.Advances in Carbonhydrate Chemistry and Biochemistry[M].New York:Acadmic Press,1983,41:275.
[15]BACKINOWSKY L V,BALAN N F,SHASHKOV A S,et al.A new and improved synthesis of p-nitrophenyl β-D-mannopyranoside[J].Carbohydrate Research,1978,64(1):279-282.
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[18]杨阳,蔡飞,杨琦,等.头花蓼化学成分的研究(I)[J].第二军医大学学报,2009,30(8):937-940.YANG Y,CAI F,YANG Y,etal.Study on chemical constituents of Polygonum capitaltum Buch.-Ham.Ex D.Don(I)[J].Journal of the second military Medical University,2009,30(8):937-940.
[19]RUCHMANN A,LAUTERWEIN J,BCKER T,et al.17O NMR of L-ascorbic acid:New spectroscopy of an old molecule[J].Magnetic Resonance in Chemistry,2015,34(2):116-122.
[20]NORD?Y A ,MARCHIOLI R,ARNESEN H,et al.n-3 Polyunsaturated fatty acids and cardiovascular diseases:To whom,how much,preparations[J].Lipids,2001,36(1):127-129.
[21]曹万新,孟橘,田玉霞.DHA的生理功能及应用研究进展[J].中国油脂,2011,36(3):1-4.CAO W X,MENG J,TIAN Y X.Research progress on physiological function and application of DHA[J].Chinese Oil,2011,36(3):1-4.
[22]NECATTIN C I,OMER S T,SALIH K,et al.Microencapsulation of fig seed oil rich in polyunsaturated fatty acids by spray drying[J].Journal of Food Measurement and Characterization,2017,11(1):50-57.
[23]KOLESNIK A A,KAKHNIASHVILI T A,ZHEREBIN Y L,et al.Lipids of the fruit of Ficus carica[J].Chemistry of Natural Compounds,1986,22(4):394-397.
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