海南粗榧总碱中化学成分研究
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摘要
目的研究海南粗榧Cephalotaxus hainanensis的生物碱类成分。方法采用硅胶、Sephadex LH-20和ODS等多种柱色谱技术进行分离纯化,根据化合物理化性质及波谱数据鉴定化合物结构。结果从海南粗榧总碱中分离得到13个化合物,分别鉴定为三尖杉碱(1)、异三尖杉酮碱(2)、三尖杉酮碱(3)、三尖杉胺G(4)、(2R,3S,4S,5S)-2,3-二羟基三尖杉碱(5)、乙酰三尖杉碱(6)、脱氧三尖杉酯碱(7)、(R)-丽江三尖杉碱(8)、(S)-丽江三尖杉碱(9)、3-表里哈灭里辛碱异构体(10)、1,4-N-二异丙胺蒽醌(11)、苯甲酸(2-乙基)-正己酯(12)和β-谷甾醇(13)。结论化合物3~6和10~13为首次从海南粗榧中分离得到。
Objective To study the alkaloids constituents from Cephalotaxus hainanensis. Methods The column chromatography Sephadex LH-20 and ODS were used to isolate and purify the compounds of alkaloids part of C. hainanensis. The chemical structures were identified on basis of physicochemical properties and spectral data. Results Thirteen compounds were isolated and identified as cephalotaxine(1), isocephalotaxinone(2), cephalotaxinone(3), cephalezomine G(4),(2 R,3 S,4 S,5 S)-2,3-dihydroxycephalotaxane(5), acetylcephalotaxine(6), deoxyharringtonine(7),(R)-fortunine(8),(S)-fortunine(9), isomer of 3-epi-schellhammericine(10), 1,4(PrINH)2-anthraquinone(11), 2-ethyl-n-hexyl benzoate(12), and β-sitosterol(13). Conclusion Compounds 3—6 and 10—13 are isolated from this plant for the first time.
Objective To study the alkaloids constituents from Cephalotaxus hainanensis. Methods The column chromatography Sephadex LH-20 and ODS were used to isolate and purify the compounds of alkaloids part of C. hainanensis. The chemical structures were identified on basis of physicochemical properties and spectral data. Results Thirteen compounds were isolated and identified as cephalotaxine(1), isocephalotaxinone(2), cephalotaxinone(3), cephalezomine G(4),(2 R,3 S,4 S,5 S)-2,3-dihydroxycephalotaxane(5), acetylcephalotaxine(6), deoxyharringtonine(7),(R)-fortunine(8),(S)-fortunine(9), isomer of 3-epi-schellhammericine(10), 1,4(PrINH)2-anthraquinone(11), 2-ethyl-n-hexyl benzoate(12), and β-sitosterol(13). Conclusion Compounds 3—6 and 10—13 are isolated from this plant for the first time.
引文
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[12]Morita H,Yoshinaga M,Kobayashi J.Cephalezomines G,H,J,K,L,and M,new alkaloids from Cephalotaxus harringtonia var.nana[J].Tetrahedron,2002,58(27):5489-5495.
[13]Taniguchi T,Yokoyama S,Ishibashi H.Asymmetric total synthesis and revised structure of Cephalezomine H[J].J Org Chem,2009,74(19):7592-7594.
[14]马广恩,林隆泽,赵志远,等.三尖杉属植物中生物碱的研究[J].化学学报,1977,35(3):201-208.
[15]Loc T V,Lieu N T,Thao T T P,et al.The alkaloidal constituents of Cephalotaxus Mannii collected in Lam Dong Province,Vietnam[J].Chem Nat Compd,2017,53(6):1122-1126.
[16]张云梅.滇产药用植物贡山三尖杉和西双版纳粗榧的活性成分研究[D].昆明:云南师范大学,2014.
[17]邱明华,陆保平,马昕,等.丽江产三尖杉的生物碱成分[J].云南植物研究,1997,19(1):97-99.
[18]Chippendale A M,Mathias A,Aujla R S,et al.High-resolution 13C nuclear magnetic resonance spectra of some solid Anthraquinone Dyestuffs and related species[J].J Chem Soc Perkin II,1983,2(9):1357-1361.
[19]Shahzadi T,Abbasi M A,Ur-Rehman A,et al.Characterization of chemical isolates of Caryopteris odorata[J].J Chem Soc Pakistan,2012,34(2):442-447.
[20]刘俐,穆丽华,刘屏.异叶败酱化学成分及其抗肿瘤活性研究[J].现代中药研究与实践,2017,31(5):30-33.
[2]王有生.救救抗癌奇木——海南粗榧[J].植物杂志,1990,17(3):8-9.
[3]梅文莉,吴娇,戴好富.三尖杉属植物化学成分与药理活性研究进展[J].中草药,2006,37(3):452-458.
[4]孙南君,薛智,梁晓天,等.新抗癌有效成分海南粗榧内酯(Hainanolide)结构的研究[J].药学学报,1979,27(14):39-43.
[5]Abdelkafi H,Nay B.Natural products from Cephalotaxus sp.:Chemical diversity and synthetic aspects[J].NatProd Rep,2012,29(8):845-869.
[6]刘胜兰,戴好富,曾艳波,等.海南粗榧中的苯丙素类化合物及其抗氧化活性[J].中国药物化学杂志,2008,19(18):215-218.
[7]刘胜兰,曾艳波,韩壮,等.海南粗榧中的木脂素及其抗氧化活性[J].河南大学学报:医学版,2008,19(27):29-31.
[8]中国医学科学院药物研究所编著.中草药现代研究第二卷[M].北京:北京医科大学中国协和医科大学联合出版社,1996.
[9]Cheng J L,Cui Y X,Li Y,et al.Use of two-dimensional NMR to assign the protons and carbons in cephalotaxine[J].Magn Reson Chem,1988,4(26):1036-1038.
[10]浅田昌三.Alkaloid isolated from the Cephalotaxusdurpacea Sieb.et Zucc.[J].药学杂志,1973,93(7):916-924.
[11]Weisleder D,Powell R G,Smith C R.Carbon-13 nuclear magnetic resonance spectroscopy of Cephalotaxusalkaloids[J].Org Mag Res,1980,13(2):114-115.
[12]Morita H,Yoshinaga M,Kobayashi J.Cephalezomines G,H,J,K,L,and M,new alkaloids from Cephalotaxus harringtonia var.nana[J].Tetrahedron,2002,58(27):5489-5495.
[13]Taniguchi T,Yokoyama S,Ishibashi H.Asymmetric total synthesis and revised structure of Cephalezomine H[J].J Org Chem,2009,74(19):7592-7594.
[14]马广恩,林隆泽,赵志远,等.三尖杉属植物中生物碱的研究[J].化学学报,1977,35(3):201-208.
[15]Loc T V,Lieu N T,Thao T T P,et al.The alkaloidal constituents of Cephalotaxus Mannii collected in Lam Dong Province,Vietnam[J].Chem Nat Compd,2017,53(6):1122-1126.
[16]张云梅.滇产药用植物贡山三尖杉和西双版纳粗榧的活性成分研究[D].昆明:云南师范大学,2014.
[17]邱明华,陆保平,马昕,等.丽江产三尖杉的生物碱成分[J].云南植物研究,1997,19(1):97-99.
[18]Chippendale A M,Mathias A,Aujla R S,et al.High-resolution 13C nuclear magnetic resonance spectra of some solid Anthraquinone Dyestuffs and related species[J].J Chem Soc Perkin II,1983,2(9):1357-1361.
[19]Shahzadi T,Abbasi M A,Ur-Rehman A,et al.Characterization of chemical isolates of Caryopteris odorata[J].J Chem Soc Pakistan,2012,34(2):442-447.
[20]刘俐,穆丽华,刘屏.异叶败酱化学成分及其抗肿瘤活性研究[J].现代中药研究与实践,2017,31(5):30-33.