石斛属植物生物碱成分研究进展
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摘要
生物碱是药用石斛重要的生理活性成分,是金钗石斛Dendrobiumnobile的特征药效成分。石斛属植物中共获得52个生物碱成分,依据结构分为5种,包括倍半萜类、八氢中氮茚类、酰胺碱类、四氢吡咯类和咪唑类生物碱。倍半萜类生物碱又划分为石斛碱型、石斛星型、石斛酮型等。含有生物碱的石斛共有19种,主要有金钗石斛、束花石斛D. chrysanthum、玫瑰石斛D. crepidatum、棒节石斛D. findleyanum、黄喉石斛D. signatum、铬黄石斛D. friedericksianum等。对石斛属植物中生物碱的结构分类、含生物碱的石斛种类以及石斛属生物碱含量的影响因素研究现状进行综述,以期为石斛属生物碱的深入研究及开发提供参考。
Alkaloids were regarded as important biological activity constituent in medicinal Dendrobium Sw., being characteristic pharmacodynamic components in plants from Dendrobium Sw. A total of 52 constituents of alkaloids were found in plants of Dendrobium Sw. They could be divided into five types, according to different structures. They were sesquiterpenoid alkaloids,octahydroindolizine alkaloids, amides alkaloids, pyrrolidine alkaloids, and imidazole alkaloids etc. Sesquiterpenoid alkaloids could be divided into dendrobine type, dendroxine type, nobiline type, etc. Over 19 Dendrobium species contain alkaloids, and the main species included D. nobile, D. chrysanthum, D. crepidatum, D. findleyanum, D. signatum, D. friedericksianum, etc. This paper reviews the structural classification of alkaloids in Dendrobium, and the species which containing alkaloids and the influencing factors of alkaloids in Dendrobium Sw., in order to provide reference for the in-depth study and the development of alkaloids in plants from Dendrobium Sw.
Alkaloids were regarded as important biological activity constituent in medicinal Dendrobium Sw., being characteristic pharmacodynamic components in plants from Dendrobium Sw. A total of 52 constituents of alkaloids were found in plants of Dendrobium Sw. They could be divided into five types, according to different structures. They were sesquiterpenoid alkaloids,octahydroindolizine alkaloids, amides alkaloids, pyrrolidine alkaloids, and imidazole alkaloids etc. Sesquiterpenoid alkaloids could be divided into dendrobine type, dendroxine type, nobiline type, etc. Over 19 Dendrobium species contain alkaloids, and the main species included D. nobile, D. chrysanthum, D. crepidatum, D. findleyanum, D. signatum, D. friedericksianum, etc. This paper reviews the structural classification of alkaloids in Dendrobium, and the species which containing alkaloids and the influencing factors of alkaloids in Dendrobium Sw., in order to provide reference for the in-depth study and the development of alkaloids in plants from Dendrobium Sw.
引文
[1]Kamemoto H,Amore T D.Breeding Dendrobium Orchids in Hawaii[M].Hawaii:University of Hawaii Press,1999.
[2]王雁,李振坚,彭红明,等.石斛兰资源·生产·应用[M].北京:中国林业出版社,2007.
[3]包雪声,顺庆生,陈立钻.中国药用石斛彩色图谱[M].上海:复旦大学出版社,2001.
[4]中国药典[S].一部.2015.
[5]中国药典[S].一部.2010.
[6]Han X J,Li Q B,Li S L.Chemistry,bioactivity and quality control of Dendrobium,a commonly used tonic herb in traditional Chinese medicine[J].Phytochem Rev,2013,12(2):341-367.
[7]刘宏栋,潘玲玲,周翔,等.兰科植物生物碱类化学成分及药理活性研究进展[J].中草药,2019,50(3):731-744.
[8]叶庆华,赵维民,秦国伟.石斛属植物化学成分及生物活性研究进展[A]//彭司勋.药物化学进展[M].北京:化学工业出版社,2002.
[9]王锋鹏.生物碱化学[M].北京:化学工业出版社,2008.
[10]Suzuki H,Keimatsu I.Studies on alkaloids in Dendrobium nobile[J].Yakugaku Zasshi,1932,52:1049-1060.
[11]Granelli I,Leander K,Luning B.Studies on orchidaceae alkaloids XVI.A new alkaloid,2-hydroxydendrobine,from Dendrobium findlayanum Par.et Rchb.f.[J].Acta Chem Scand,1970,24(4):1209-1212.
[12]Inubushi Y,Ishii H,Yasui B.Isolation and characterization of alkaloids of the Chinese drug Chin-Shih-Hu[J].Chem Pharm Bull,1964,12(10):1175-1180.
[13]Hedman K,Leander K,Lu N B.Studies on orchidaceae alkaloids XXV.N-isopentenyl derivatives of dendroxine and 6-hydroxydendroxine from Dendrobium friedricksianum Lindl.and Dendrobium hildebrandii Rolfe[J].Acta Chem Scand,1971,25(2):717-720.
[14]Elander M,Leander K.Studies on orchidaceae alkaloids XXI.6-hydroxynobiline,a new alkaloid from Dendrobium hildebrandii Rolfe[J].Acta Chem Scand,1971,25(2):717-720.
[15]Inubushi Y,Nakano J.Structure of dendrine[J].Tetrahedron Lett,1965,6(31):2723-2728.
[16]Wang H K,Zhao T F,Che C T.Dendrobine and3-hydroxy-2-oxodendrobine from Dendrobium nobile[J].J Nat Prod,1985,48(5):796-801.
[17]Zhang S Z,Lin Z H,Chen Z C.Constituents from Dendrobium clavatum var.aurantiacum[J].J Chin Med,2001,12(3):211-218
[18]Hiroshi M,Masako F,Naotoshi Y,et al.New picrotoxinin type and dendrobine type sesquiterpenoids from Dendrobium Snowflake‘Red Star’[J].Tetrahedron Lett,2000,56(32):5801-5805.
[19]Liu Q F,Zhao W M.A new dendrobine-type alkaloid from Dendrobium nobile[J].Chin Chem Lett,2003,14(3):278-279.
[20]Hedman K,Leander K.Studies on Orchidaceae alkaloids XXVII.Quaternary salts of the dendrobine type from Dendrobium nobile Lindl.[J].Acta Chem Scand,1972,26(8):3177-3180.
[21]Toshihiko O,Mitsutaka N,Tadamasa O,et al.The structure of dendroxine,the third alkaloid from Dendrobium nobile[J].Chem Pharm Bull,1966,14(6):672-675.
[22]Toshihiko O,Mitsutaka N,Tadamasa O,et al.The structure of dendramine(6-oxydendrobine)and6-oxydendroxine,the fourth and fifth alkaloid from Dendrobium nobile[J].Chem Pharm Bull,1966,14(6):676-680.
[23]Toshihiko O,Mitsutaka N,Tadamasa O,et al.Further studies on the alkaloidal constituents of Dendrobium nobile(Orchidaceae)-structure determination of4-hydroxy-dendroxine and nobilomethylene[J].Chem Pharm Bull,1972,20(2):418-421.
[24]Yamamura S,Hirata Y.Structures of nobiline and dendrobine[J].Tetrahedron Lett,1964,5(2):79-87.
[25]Liu W H,Hua Y F,Zhan Z J.Moniline,a new alkaloid from Dendrobium moniliforme[J].J Chem Res,2007,48(6):317-318.
[26]Blomqvist L,Brandange S,Gawell L,et al.Studies on Orchidaceae alkaloids XXXVII.Dendrowardine,a quaternary alkaloid from Dendrobium wardianum Warner[J].Acta Chem Scand,1973,27(4):1439-1441.
[27]Yang D,Cheng Z Q,Yang L,et al.Seco-dendrobine-type alkaloids and bioactive phenolics from Dendrobium findlayanum[J].J Nat Prod,2018,81(2):227-235.
[28]Luning B,Leander K.Studies on Orchidaceae alkaloids III.The alkaloids in Dendrobium primulinum Lindl.and Dendrobium chrysanthum Wall[J].Acta Chem Scand,1965,19(7):1607-1609.
[29]Kierkegaard P,Pilotti A M,Leander K.Studies on Orchidaceae alkaloids XX.The constitution and relative configuration of crepidine,an alkaloid from Dendrobium crepidatum Lindl[J].Acta Chem Scand,1970,24(10):3757-3759.
[30]Elander M,Leander K,Rosenblom J,et al.Studies on Orchidaceae alkaloids XXXII.crepidine,crepidamine and dendrocrepine,three alkaloids from Dendrobium crepidatum Lindl.[J].Acta Chem Scand,1973,27(6):1907-1913.
[31]Hu Y,Zhang C F,Zhao X.(±)-Homocrepidine A,a pair of anti-inflammatory enantiomeric octahydro indolizine alkaloid dimers from Dendrobium crepidatum[J].J Nat Prod,2016,79(1):252-256.
[32]李燕.铁皮石斛化学成分的研究[D].北京:中国协和医科大学,2009.
[33]孟志霞,董海玲,王春兰,等.齿瓣石斛化学成分研究[J].中国药学杂志,2013,48(11):855-859.
[34]梅媛,叶庆华,杨培明,等.报春石斛化学成分研究[J].中国医药工业杂志,2014,45(3):224-228.
[35]汪代芳,侴桂新,赵宁毅,等.金钗石斛茎的化学成分研究[J].中草药,2012,43(8):1492-1495.
[36]张爱莲,于敏,徐宏化,等.齿瓣石斛的化学成分及其抗氧化活性[J].中国中药杂志,2013,38(6):844-847.
[37]管惠娟,张雪,屠凤娟.铁皮石斛化学成分的研究[J].中草药,2009,40(12):1873-1876.
[38]高巍,杨柳,李慧慧,等.杯鞘石斛的化学成分研究[J].中国现代中药,2015,17(4):311-314.
[39]王宪楷,赵同芳.石斛属植物的化学成分与中药石斛[J].药学通报,1986,21(11):666-669.
[40]Yasuo I,Yoshisuke T,Takeshi K,et al.Shihunine:A new phthalide-pyrrolidine alkaloid[J].Chem Pharm Bull,1968,12(6):749-750.
[41]李满飞,平田义正,徐国钧,等.粉花石斛化学成分研究[J].药学学报,1991,26(4):307-310.
[42]Elander M,Leander K,Luning B.Studies on Orchidaceae alkaloids XIV.A phthalide alkaloid from Dendrobium pierardii Roxb.[J].Acta Chem Scand,1969,23(6):2177-2178.
[43]Ekevag U,Elander M,Gawell L,et al.Studies on Orchidaceae alkaloids XXXIII.Two new alkaloids,N-cisand N-trans-cinnamoylnorcuskhygrine from Dendrobium chrysanthum Wall[J].Acta Chem Scand,1973,27(6):1982-1986.
[44]Zhang C F,Nakamura N,Tewtrakul S,Two new alkaloids from Dendrobium chrysanthum[J].Heterocycles,2005,65(3):633-636.
[45]Leander K,Luning B.Studies on orchidaceae alkaloids VIII.An imidazolium salt from Dendrobium anosmum Lindl.and Dendrobium parishii Rchb.F[J].Tetrahedron Lett,1968,9(8):905-908.
[46]Luning B.Studies on Orchidaceae alkaloids IV.:Screening of species for alkaloids 2[J].Phytochemistry,1967,6(6):857-861.
[47]张一新,刘浩,凌蕾,等.金钗石斛生物碱药理作用研究进展[J].上海中医药杂志,2019,53(2):95-97.
[48]Luning B.Studies on Orchidaceae alkaloids I.Screening of species for alkaloids[J].Acta Chem Scand,1964,18(12):1507-1516.
[49]金蓉鸾,孙继军,张远名.11种石斛的总生物碱的测定[J].南京药学院学报,1981,16(1):9-13.
[50]王再花,李杰,章金辉,等.石斛属植物多糖与生物碱含量的比较研究[J].中国农学通报,2015,31(24):242-246.
[51]李泽生,李桂琳,白燕冰,等.金钗石斛组培苗品质评价研究[J].热带农业科技,2017,40(3):17-21.
[52]胡志刚,梁欢,卢金清,等.金钗石斛茎和花中石斛碱的含量比较研究[J].中国药师,2014,17(8):1303-1305.
[53]丁亚平,杨道麒,吴庆生,等.安徽霍山三种石斛总生物碱的测定及其分布规律研究[J].安徽农业大学学报,1994,21(4):503-506.
[54]包英华,白音,陈珺霞,等.金钗石斛生物碱的组织化学定位研究[J].广西植物,2013,33(2):199-202.
[55]何沁嶷.金钗石斛中生物碱积累规律及抗肿瘤活性研究[D].成都:四川农业大学,2016.
[56]赵菊润,孙永玉.不同种植模式对齿瓣石斛生物碱与多糖含量的影响[J].安徽农业科学,2013,41(28):11340-11341.
[57]陈照荣,来平凡,林巧.不同炮制方法对石斛中石斛碱和多糖溶出率的影响[J].浙江中医学院学报,2012,26(4):79-81.
[2]王雁,李振坚,彭红明,等.石斛兰资源·生产·应用[M].北京:中国林业出版社,2007.
[3]包雪声,顺庆生,陈立钻.中国药用石斛彩色图谱[M].上海:复旦大学出版社,2001.
[4]中国药典[S].一部.2015.
[5]中国药典[S].一部.2010.
[6]Han X J,Li Q B,Li S L.Chemistry,bioactivity and quality control of Dendrobium,a commonly used tonic herb in traditional Chinese medicine[J].Phytochem Rev,2013,12(2):341-367.
[7]刘宏栋,潘玲玲,周翔,等.兰科植物生物碱类化学成分及药理活性研究进展[J].中草药,2019,50(3):731-744.
[8]叶庆华,赵维民,秦国伟.石斛属植物化学成分及生物活性研究进展[A]//彭司勋.药物化学进展[M].北京:化学工业出版社,2002.
[9]王锋鹏.生物碱化学[M].北京:化学工业出版社,2008.
[10]Suzuki H,Keimatsu I.Studies on alkaloids in Dendrobium nobile[J].Yakugaku Zasshi,1932,52:1049-1060.
[11]Granelli I,Leander K,Luning B.Studies on orchidaceae alkaloids XVI.A new alkaloid,2-hydroxydendrobine,from Dendrobium findlayanum Par.et Rchb.f.[J].Acta Chem Scand,1970,24(4):1209-1212.
[12]Inubushi Y,Ishii H,Yasui B.Isolation and characterization of alkaloids of the Chinese drug Chin-Shih-Hu[J].Chem Pharm Bull,1964,12(10):1175-1180.
[13]Hedman K,Leander K,Lu N B.Studies on orchidaceae alkaloids XXV.N-isopentenyl derivatives of dendroxine and 6-hydroxydendroxine from Dendrobium friedricksianum Lindl.and Dendrobium hildebrandii Rolfe[J].Acta Chem Scand,1971,25(2):717-720.
[14]Elander M,Leander K.Studies on orchidaceae alkaloids XXI.6-hydroxynobiline,a new alkaloid from Dendrobium hildebrandii Rolfe[J].Acta Chem Scand,1971,25(2):717-720.
[15]Inubushi Y,Nakano J.Structure of dendrine[J].Tetrahedron Lett,1965,6(31):2723-2728.
[16]Wang H K,Zhao T F,Che C T.Dendrobine and3-hydroxy-2-oxodendrobine from Dendrobium nobile[J].J Nat Prod,1985,48(5):796-801.
[17]Zhang S Z,Lin Z H,Chen Z C.Constituents from Dendrobium clavatum var.aurantiacum[J].J Chin Med,2001,12(3):211-218
[18]Hiroshi M,Masako F,Naotoshi Y,et al.New picrotoxinin type and dendrobine type sesquiterpenoids from Dendrobium Snowflake‘Red Star’[J].Tetrahedron Lett,2000,56(32):5801-5805.
[19]Liu Q F,Zhao W M.A new dendrobine-type alkaloid from Dendrobium nobile[J].Chin Chem Lett,2003,14(3):278-279.
[20]Hedman K,Leander K.Studies on Orchidaceae alkaloids XXVII.Quaternary salts of the dendrobine type from Dendrobium nobile Lindl.[J].Acta Chem Scand,1972,26(8):3177-3180.
[21]Toshihiko O,Mitsutaka N,Tadamasa O,et al.The structure of dendroxine,the third alkaloid from Dendrobium nobile[J].Chem Pharm Bull,1966,14(6):672-675.
[22]Toshihiko O,Mitsutaka N,Tadamasa O,et al.The structure of dendramine(6-oxydendrobine)and6-oxydendroxine,the fourth and fifth alkaloid from Dendrobium nobile[J].Chem Pharm Bull,1966,14(6):676-680.
[23]Toshihiko O,Mitsutaka N,Tadamasa O,et al.Further studies on the alkaloidal constituents of Dendrobium nobile(Orchidaceae)-structure determination of4-hydroxy-dendroxine and nobilomethylene[J].Chem Pharm Bull,1972,20(2):418-421.
[24]Yamamura S,Hirata Y.Structures of nobiline and dendrobine[J].Tetrahedron Lett,1964,5(2):79-87.
[25]Liu W H,Hua Y F,Zhan Z J.Moniline,a new alkaloid from Dendrobium moniliforme[J].J Chem Res,2007,48(6):317-318.
[26]Blomqvist L,Brandange S,Gawell L,et al.Studies on Orchidaceae alkaloids XXXVII.Dendrowardine,a quaternary alkaloid from Dendrobium wardianum Warner[J].Acta Chem Scand,1973,27(4):1439-1441.
[27]Yang D,Cheng Z Q,Yang L,et al.Seco-dendrobine-type alkaloids and bioactive phenolics from Dendrobium findlayanum[J].J Nat Prod,2018,81(2):227-235.
[28]Luning B,Leander K.Studies on Orchidaceae alkaloids III.The alkaloids in Dendrobium primulinum Lindl.and Dendrobium chrysanthum Wall[J].Acta Chem Scand,1965,19(7):1607-1609.
[29]Kierkegaard P,Pilotti A M,Leander K.Studies on Orchidaceae alkaloids XX.The constitution and relative configuration of crepidine,an alkaloid from Dendrobium crepidatum Lindl[J].Acta Chem Scand,1970,24(10):3757-3759.
[30]Elander M,Leander K,Rosenblom J,et al.Studies on Orchidaceae alkaloids XXXII.crepidine,crepidamine and dendrocrepine,three alkaloids from Dendrobium crepidatum Lindl.[J].Acta Chem Scand,1973,27(6):1907-1913.
[31]Hu Y,Zhang C F,Zhao X.(±)-Homocrepidine A,a pair of anti-inflammatory enantiomeric octahydro indolizine alkaloid dimers from Dendrobium crepidatum[J].J Nat Prod,2016,79(1):252-256.
[32]李燕.铁皮石斛化学成分的研究[D].北京:中国协和医科大学,2009.
[33]孟志霞,董海玲,王春兰,等.齿瓣石斛化学成分研究[J].中国药学杂志,2013,48(11):855-859.
[34]梅媛,叶庆华,杨培明,等.报春石斛化学成分研究[J].中国医药工业杂志,2014,45(3):224-228.
[35]汪代芳,侴桂新,赵宁毅,等.金钗石斛茎的化学成分研究[J].中草药,2012,43(8):1492-1495.
[36]张爱莲,于敏,徐宏化,等.齿瓣石斛的化学成分及其抗氧化活性[J].中国中药杂志,2013,38(6):844-847.
[37]管惠娟,张雪,屠凤娟.铁皮石斛化学成分的研究[J].中草药,2009,40(12):1873-1876.
[38]高巍,杨柳,李慧慧,等.杯鞘石斛的化学成分研究[J].中国现代中药,2015,17(4):311-314.
[39]王宪楷,赵同芳.石斛属植物的化学成分与中药石斛[J].药学通报,1986,21(11):666-669.
[40]Yasuo I,Yoshisuke T,Takeshi K,et al.Shihunine:A new phthalide-pyrrolidine alkaloid[J].Chem Pharm Bull,1968,12(6):749-750.
[41]李满飞,平田义正,徐国钧,等.粉花石斛化学成分研究[J].药学学报,1991,26(4):307-310.
[42]Elander M,Leander K,Luning B.Studies on Orchidaceae alkaloids XIV.A phthalide alkaloid from Dendrobium pierardii Roxb.[J].Acta Chem Scand,1969,23(6):2177-2178.
[43]Ekevag U,Elander M,Gawell L,et al.Studies on Orchidaceae alkaloids XXXIII.Two new alkaloids,N-cisand N-trans-cinnamoylnorcuskhygrine from Dendrobium chrysanthum Wall[J].Acta Chem Scand,1973,27(6):1982-1986.
[44]Zhang C F,Nakamura N,Tewtrakul S,Two new alkaloids from Dendrobium chrysanthum[J].Heterocycles,2005,65(3):633-636.
[45]Leander K,Luning B.Studies on orchidaceae alkaloids VIII.An imidazolium salt from Dendrobium anosmum Lindl.and Dendrobium parishii Rchb.F[J].Tetrahedron Lett,1968,9(8):905-908.
[46]Luning B.Studies on Orchidaceae alkaloids IV.:Screening of species for alkaloids 2[J].Phytochemistry,1967,6(6):857-861.
[47]张一新,刘浩,凌蕾,等.金钗石斛生物碱药理作用研究进展[J].上海中医药杂志,2019,53(2):95-97.
[48]Luning B.Studies on Orchidaceae alkaloids I.Screening of species for alkaloids[J].Acta Chem Scand,1964,18(12):1507-1516.
[49]金蓉鸾,孙继军,张远名.11种石斛的总生物碱的测定[J].南京药学院学报,1981,16(1):9-13.
[50]王再花,李杰,章金辉,等.石斛属植物多糖与生物碱含量的比较研究[J].中国农学通报,2015,31(24):242-246.
[51]李泽生,李桂琳,白燕冰,等.金钗石斛组培苗品质评价研究[J].热带农业科技,2017,40(3):17-21.
[52]胡志刚,梁欢,卢金清,等.金钗石斛茎和花中石斛碱的含量比较研究[J].中国药师,2014,17(8):1303-1305.
[53]丁亚平,杨道麒,吴庆生,等.安徽霍山三种石斛总生物碱的测定及其分布规律研究[J].安徽农业大学学报,1994,21(4):503-506.
[54]包英华,白音,陈珺霞,等.金钗石斛生物碱的组织化学定位研究[J].广西植物,2013,33(2):199-202.
[55]何沁嶷.金钗石斛中生物碱积累规律及抗肿瘤活性研究[D].成都:四川农业大学,2016.
[56]赵菊润,孙永玉.不同种植模式对齿瓣石斛生物碱与多糖含量的影响[J].安徽农业科学,2013,41(28):11340-11341.
[57]陈照荣,来平凡,林巧.不同炮制方法对石斛中石斛碱和多糖溶出率的影响[J].浙江中医学院学报,2012,26(4):79-81.