无花果果实中新喹啉和新酸酐化合物
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摘要
目的研究无花果Ficus carica果实的化学成分。方法应用天然产物化学分离、纯化技术对无花果果实的化学成分进行分离纯化,通过波谱分析技术(MS、1H-NMR、13C-NMR)、元素分析等方法鉴定化合物的结构。结果从无花果果实的醋酸乙酯部位中共分离得到1个新喹啉和2个新酸酐化合物,分别鉴定为4-羟基-6-甲酰氧基-8α-甲氧基-喹啉-2-酮(1)、5′β,6′α-(双二乙基)-5β,6β-环氧己烷基-环戊酐基-[2,2,1]-2α,3β-环庚烷(2)和5′β,6′β-[双-(11-甲基丁基,11′-甲基丁基)-9,9′]环-8,8′-己二烯基-5α,6α-环氧己烷基-环戊酐基-[2,2,2,1]-2β,3α-环庚烷(3)。结论 3个新化合物分别命名为无花果果素K-1、无花果果素G-1和无花果果素G-2。
Objective To investigate the chemical constituents of the fruits of Ficus carica.Methods The chemical constituents were isolated and purified with silica gel chromatography,Sephdex LH-20 and HPLC,and their structures were elucidated by spectral analysis including MS,NMR,IR spectroscopic analysis,elment analyzer,and chemical evidence.Results One new quinoline and two new anhydride compounds were isolated from ethyl acetate extract of the fruits of F.carica.The structures of the three new compounds were respectively defined as 4-hydroxyl-6-formyl-8α-methoxyl-quinoline-2-one(1),5′β,6′α-[(di-ethyl)-5β,6β-cyclohexyl]-epoxyhexyl,cyclo-pentanhydride-[2,2,1]-2α,3β-cycloheptane(2),and 5′β,6′β-[di-(11-methylbutyl,11′-methylbutyl)-9,9′]-cyclo-8′-hexadiene-5α,6α-epoxyhexyl,cyclo-pentanhydride-[2,2,2,1]-2β,3α-cycloheptane(3).Conclusion These compounds were named figine K-1,figine G-1,and figine G-2,respectively.
Objective To investigate the chemical constituents of the fruits of Ficus carica.Methods The chemical constituents were isolated and purified with silica gel chromatography,Sephdex LH-20 and HPLC,and their structures were elucidated by spectral analysis including MS,NMR,IR spectroscopic analysis,elment analyzer,and chemical evidence.Results One new quinoline and two new anhydride compounds were isolated from ethyl acetate extract of the fruits of F.carica.The structures of the three new compounds were respectively defined as 4-hydroxyl-6-formyl-8α-methoxyl-quinoline-2-one(1),5′β,6′α-[(di-ethyl)-5β,6β-cyclohexyl]-epoxyhexyl,cyclo-pentanhydride-[2,2,1]-2α,3β-cycloheptane(2),and 5′β,6′β-[di-(11-methylbutyl,11′-methylbutyl)-9,9′]-cyclo-8′-hexadiene-5α,6α-epoxyhexyl,cyclo-pentanhydride-[2,2,2,1]-2β,3α-cycloheptane(3).Conclusion These compounds were named figine K-1,figine G-1,and figine G-2,respectively.
引文
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[13]杨峻山.天然有机化合物核磁共振碳谱集(下册)[M].北京:化学工业出版社,2011.
[14]Mahmoudi S,Khali,M,Benkhaled A,et al.Fresh figs(Ficus carica L.)pomological characteristics,nutritional value,and phytochemical properties[J].Eur J Horticul Sci,2018,83(2):104-113.
[15]Takahashi T,Okiura A,Kohno M.Phenylpropanoid composition in fig(Ficus carica L.)leaves[J].J Nat Med,2017,71(4):770-775.
[2]南京中医药大学.中药大辞典[M].第2版.上海:上海科学技术出版社,2006.
[3]国家中医药管理局《中华本草》编委会.中华本草(第5卷)[M].上海:上海科学技术出版社,1999.
[4]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.
[5]王俏先,王业遴.无花果抗癌作用的研究[J].癌症,1990,3(6):223-225.
[6]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):316-320.
[7]尹卫平,陈宏明,阎福林,等.从无花果中提取新的皂苷和糖苷化合物及其活性研究[J].中草药,1998,29(8):505-507.
[8]盂正木,王俏光,纪江,等.无花果叶化学成分研究[J].中国药科大学学报,l996,27(4):202-204.
[9]尹卫平,赵天增,魏谠全.无花果制剂的开发应用研究──康赛康牌无花果营养保健口服液介绍[J].中草药,1997,28(8):512-513.
[10]Pérez C,Domínguez E,Ramiro J M,et al.A study on the glycaemic balance in streptozotocin-diabetic rats treated with an aqueous extract of Ficus carica(fig tree)leaves[J].Phytother Res,2015,10(1):82-83.
[11]Brown N M D,Grundon M F,Harrison D M,et al.Quinoline alkaloids.XXI:The 13C NMR spectra of hemiterpenoid quinoline alkaloids and related prenylquinolines[J].Tetrahedron,1980,36(24):3579-3584.
[12]Brouwer H,Stothers J B,Tan C T.Carbon-13 n.m.r.studies.Part 66-13C spectra of several methyl,hydroxymethyl and carboxylic acid derivatives of bicyclo[2.2.1]heptane and bicyclo[2.2.2]octane[J].Org Mag Res,1977,9(6):360-366.
[13]杨峻山.天然有机化合物核磁共振碳谱集(下册)[M].北京:化学工业出版社,2011.
[14]Mahmoudi S,Khali,M,Benkhaled A,et al.Fresh figs(Ficus carica L.)pomological characteristics,nutritional value,and phytochemical properties[J].Eur J Horticul Sci,2018,83(2):104-113.
[15]Takahashi T,Okiura A,Kohno M.Phenylpropanoid composition in fig(Ficus carica L.)leaves[J].J Nat Med,2017,71(4):770-775.
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