大风子中木脂素类化学成分研究
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摘要
研究大风子科大风子属植物大风子Hydnocarpus anthelminthica中的木脂素类成分。采用聚酰胺柱色谱、反相硅胶柱色谱、Sephadex LH-20凝胶柱色谱以及制备型HPLC等色谱技术对大风子的95%乙醇提取物进行分离纯化,通过波谱学方法(MS,NMR)进行结构鉴定。从大风子的95%乙醇提取物中分离并鉴定了13个木脂素类化合物,分别为(+)-丁香脂素(1),lirioresinol A(2),(+)-medioresinol(3),(7R,8R,8′R)-4′-guaiacylglyceryl-evofolin B(4), leptolepiso C(5),(-)-(7R,7′R,7″R,8S,8′S,8″S)-4′,4″-dihydroxy-3,3′,3″,5,5′,5″-hexamethoxy-7,9′:7′,9-diepoxy-4,8″-oxy-8,8′-sesquineolignan-7″,9″-diol(6),(-)-(7R,7′R,7″R,8S,8′S,8″S)-4′,4″-dihydroxy-3,3′,3″,5,5′-pentamethoxy-7,9′:7′,9-diepoxy-4,8″-oxy-8,8′ses-quineolignan-7″,9″-diol(7),肥牛木素(8),dydnocarpusol(9),isohydnocarpin(10),(-)-hydnocarpin (11),hydnocarpin (12),hydnocarpin-D(13)。其中,化合物1～8为首次从该属植物中分离得到。
This project is to investigate lignans from the seed of Hydnocarpus anthelminthica. Thirteen lignans were isolated from the 95% ethanol extract of the seed of H. anthelminthica, by polyamide resin, Sephadex LH-20, ODS column chromatography and preparative HPLC. Their structures were elucidated as(+)-syringaresinol(1), lirioresinol A(2),(+)-medioresinol(3),(7R,8R,8′R)-4′-guaiacylglyceryl-evofolin B(4), leptolepisol C(5),(-)-(7R,7′R,7″R,8S,8′S,8″S)-4′,4″-dihydroxy-3,3′,3″,5,5′,5″-hexamethoxy-7,9′:7′,9-diepoxy-4,8″-oxy-8,8′-sesquineolignan-7″,9″-diol(6),(-)-(7R,7′R,7″R,8S,8′S,8″S)-4′,4″-dihydroxy-3,3′,3″,5,5′-pentamethoxy-7,9′:7′,9-diepoxy-4,8″-oxy-8,8′ses-quineolignan-7″,9″-diol(7), ceplignan(8), hydnocarpusol(9), isohydnocarpin(10),(-)-hydnocarpin(11), hydnocarpin(12), and hydnocarpin-D(13) by spectroscopic data analysis. Compounds 1-8 were obtained from the genus Hydnocarpus for the first time.
This project is to investigate lignans from the seed of Hydnocarpus anthelminthica. Thirteen lignans were isolated from the 95% ethanol extract of the seed of H. anthelminthica, by polyamide resin, Sephadex LH-20, ODS column chromatography and preparative HPLC. Their structures were elucidated as(+)-syringaresinol(1), lirioresinol A(2),(+)-medioresinol(3),(7R,8R,8′R)-4′-guaiacylglyceryl-evofolin B(4), leptolepisol C(5),(-)-(7R,7′R,7″R,8S,8′S,8″S)-4′,4″-dihydroxy-3,3′,3″,5,5′,5″-hexamethoxy-7,9′:7′,9-diepoxy-4,8″-oxy-8,8′-sesquineolignan-7″,9″-diol(6),(-)-(7R,7′R,7″R,8S,8′S,8″S)-4′,4″-dihydroxy-3,3′,3″,5,5′-pentamethoxy-7,9′:7′,9-diepoxy-4,8″-oxy-8,8′ses-quineolignan-7″,9″-diol(7), ceplignan(8), hydnocarpusol(9), isohydnocarpin(10),(-)-hydnocarpin(11), hydnocarpin(12), and hydnocarpin-D(13) by spectroscopic data analysis. Compounds 1-8 were obtained from the genus Hydnocarpus for the first time.
引文
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[3] Wang J F, Yin G F, Zhou X J, et al. Antiinflamatory flavonolignans from Hydnocarpus anthelminthica seeds [J]. J Asian Nat Prod Res, 2010, 13(1): 80.
[4] 蒋欢,廖海兵,梁东,等.中华青牛胆中2个新的木脂素葡萄糖苷[J].中草药, 2018, 49(10): 2336.
[5] 许蒙蒙,姚新生,萧伟,等.接骨木中的木脂素类化学成分及其对UMR106细胞增殖作用的影响[J].中国中药杂志,2014,39(14):2684.
[6] 袁谱龙,王雪萍,贾琦,等.水茄茎化学成分的研究[J].中成药, 2016, 38(1):104.
[7] Xiao H H, Dai Y, Yao X S, et al. New lignans from the bioactive fraction of Sambucus williamsii Hance and proliferation activities on osteoblastic-like UMR106 cells [J]. Fitoterapia, 2014, 94: 29.
[8] Zhu J X, Ren J, Zhang W D, et al. Phenylpropanoids and lignanoids from Euonymus acanthocarpus[J]. Arch Pharm Res, 2012, 35(10): 1739.
[9] Xiong L, Zhu C G, Shi J G, et al. Lignans and neolignans from Sinocalamus affinis and their absolute configurations[J]. J Nat Prod, 2011, 74(5): 1188.
[10] 于洋,高昊,姚新生,等.栀子中的木脂素类成分研究[J].中草药, 2010,41(4):509.
[11] 王俊峰. 两种中药材的化学成分研究[D]. 青岛:青岛科技大学, 2009.
[12] Li P, Young W C, Kinghorn D, et al. Bioactivity-guided isolation of cytotoxic constituents of Brucea javanica collected in Vietnam[J]. Bioorg Med Chem, 2009, 17(6): 2219.
[2] Wang J F, Dai H Q, Wei Y L, et al. Antituberculosis agents and an inhibitor of the paraaminobenzoic acid biosynthetic pathway from Hydnocarpus anthelminthica seeds [J]. Chem Biodivers, 2010, 7: 2046.
[3] Wang J F, Yin G F, Zhou X J, et al. Antiinflamatory flavonolignans from Hydnocarpus anthelminthica seeds [J]. J Asian Nat Prod Res, 2010, 13(1): 80.
[4] 蒋欢,廖海兵,梁东,等.中华青牛胆中2个新的木脂素葡萄糖苷[J].中草药, 2018, 49(10): 2336.
[5] 许蒙蒙,姚新生,萧伟,等.接骨木中的木脂素类化学成分及其对UMR106细胞增殖作用的影响[J].中国中药杂志,2014,39(14):2684.
[6] 袁谱龙,王雪萍,贾琦,等.水茄茎化学成分的研究[J].中成药, 2016, 38(1):104.
[7] Xiao H H, Dai Y, Yao X S, et al. New lignans from the bioactive fraction of Sambucus williamsii Hance and proliferation activities on osteoblastic-like UMR106 cells [J]. Fitoterapia, 2014, 94: 29.
[8] Zhu J X, Ren J, Zhang W D, et al. Phenylpropanoids and lignanoids from Euonymus acanthocarpus[J]. Arch Pharm Res, 2012, 35(10): 1739.
[9] Xiong L, Zhu C G, Shi J G, et al. Lignans and neolignans from Sinocalamus affinis and their absolute configurations[J]. J Nat Prod, 2011, 74(5): 1188.
[10] 于洋,高昊,姚新生,等.栀子中的木脂素类成分研究[J].中草药, 2010,41(4):509.
[11] 王俊峰. 两种中药材的化学成分研究[D]. 青岛:青岛科技大学, 2009.
[12] Li P, Young W C, Kinghorn D, et al. Bioactivity-guided isolation of cytotoxic constituents of Brucea javanica collected in Vietnam[J]. Bioorg Med Chem, 2009, 17(6): 2219.