苄基四氢异喹啉类生物碱的微生物转化
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摘要
苄基四氢异喹啉类生物碱广泛分布于木兰科、防己科、番荔枝科、罂粟科、芸香科、樟科、小檗科等植物中,具有抗肿瘤、镇痛、止咳、降压、抗菌、抗炎、免疫抑制等多种生理活性,吗啡、罗通定、可待因、青藤碱、罂粟碱等多种药物已应用于临床。鉴于其广泛的临床应用,苄基四氢异喹啉类生物碱的结构修饰成为研究的热点,微生物转化由于效率高、手性及立体选择性强、反应条件温和、成本低、反应过程绿色环保等特点,在天然产物的结构修饰中应用越来越广泛。本文综述了微生物转化在苄基四氢异喹啉类生物碱结构修饰中的应用,为更深入的研究苄基四氢异喹啉类生物碱提供一定的依据。
Benzyltetrahydroisoquinolines alkaloids are widely distributed in Magnoliaceae,Menispermaceae,Annonaceae,Papaveraceae,Rutaceae,Lauraceae,Berberidaceae plants. which have varieties of physiological activities,such as anti-tumor,anti-HIV,analgesic,antitussive hypotensive,antibacterial,anti-inflammatory,immunosuppressive and so on. Some of them are widely used in clinical practice,such as morphine,rotundine,codeine,sinomenine,papaverine,etc. In view of its extensive clinical application,the structural modification of benzyltetrahydroisoquinolines alkaloids is a research hotspot. Recently,microbial transformation is more and more widely used in structural modification of natural products. Due to its high efficiency,strong chirality and stereoselectivity,mild reaction conditions,low cost and green environmental protection. In this paper,we have reviewed the application of microbial transformation in the structural modification of benzyltetrahydroisoquinolines alkaloids,which could provide a basis for the further study of benzyltetrahydroisoquinolines alkaloids.
Benzyltetrahydroisoquinolines alkaloids are widely distributed in Magnoliaceae,Menispermaceae,Annonaceae,Papaveraceae,Rutaceae,Lauraceae,Berberidaceae plants. which have varieties of physiological activities,such as anti-tumor,anti-HIV,analgesic,antitussive hypotensive,antibacterial,anti-inflammatory,immunosuppressive and so on. Some of them are widely used in clinical practice,such as morphine,rotundine,codeine,sinomenine,papaverine,etc. In view of its extensive clinical application,the structural modification of benzyltetrahydroisoquinolines alkaloids is a research hotspot. Recently,microbial transformation is more and more widely used in structural modification of natural products. Due to its high efficiency,strong chirality and stereoselectivity,mild reaction conditions,low cost and green environmental protection. In this paper,we have reviewed the application of microbial transformation in the structural modification of benzyltetrahydroisoquinolines alkaloids,which could provide a basis for the further study of benzyltetrahydroisoquinolines alkaloids.
引文
[1]赵娜,高峰,刘彬,等.苄基四氢异喹啉类生物碱的药理作用及其研究进展[J].药学实践杂志,2015,33(4):313-315.
[2]KASHIWADA Y,AOSHIMA A,IKESHIRO Y,et al.Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera,and structure–activity correlations with related alkaloids[J].Bioorganic&Medicinal Chemistry,2005,13(2):443-448.
[3]CHENG Z,WANG K,WEI J,et al.Proteomic analysis of antitumor effects by tetrandrine treatment in Hep G2 cells[J].Phytomedicine,2010,17(13):1000.
[4]JING W,TENG Y,HUANG C,et al.The synthesis and antistaphylococcal activity of 9,13-disubstituted berberine derivatives[J].European Journal of Medicinal Chemistry,2017,127:424.
[5]PUND S,BORADE G,RASVE G.Improvement of anti-inflammatory and anti-angiogenic activity of berberine by novel rapid dissolving nanoemulsifying technique[J].Phytomedicine International Journal of Phytotherapy&Phytopharmacology,2014,21(3):307.
[6]HARTON L R,RICHARDSON J R,ARMENDARIZ A,et al.Dissociation of morphine analgesic effects in the sensory and affective components of formalin-induced spontaneous pain in male and female rats[J].Brain Research,2017,1658:36-41.
[7]UNWIN N,GAN D,WHITING D.The IDF Diabetes Atlas:providing evidence,raising awareness and promoting action[J].Diabetes Research&Clinical Practice,2010,87(1):2-3.
[8]HEGAZY M E F,MOHAMED T A,ELHAMY A I,et al.Microbial biotransformation as a tool for drug development based on natural products from mevalonic acid pathway:A review[J].Journal of Advanced Research,2015,6(1):17-33.
[9]贺赐安,余旭亚,孟庆雄,等.生物转化对天然药物进行结构修饰的研究进展[J].天然产物研究与开发,2012,24(6):843-847.
[10]牛红军,王芃,杨官娥.微生物转化技术在中药研究中的应用[J].中国实验方剂学杂志,2013,19(18):346-349.
[11]PETER J S,PETER J H,NEIL C B.Transformation of 2,2'-Bimorphine to the Novel Compounds 10-α-S-Monohydroxy-2,2'-Bimorphine and 10,10'-α,α'-S,S'-Dihydroxy-2,2'-Bimorphine by Cylindrocarpon didymium[J].Applied&Environmental Microbiology,2001,67(8):3716-3719.
[12]AGUSTA A,WULANSARI D,PRAPTIWI,et al.Biotransformation of Protoberberine Alkaloids by the Endophytic Fungus Coelomycetes,AFKR-3 Isolated from Yellow Moonsheed Plant(Archangelisia Flava,(L.)Merr.)[J].Procedia Chemistry,2014,13:38-43.
[13]余伯阳.中药生物技术[M].北京:中国医药科技出版社,2005:274.
[14]徐田,刘吉华,余伯阳,等.微生物转化左旋四氢巴马汀产生左旋紫堇达明高产菌株的紫外诱变选育[J].药物生物技术,2011,18(4):313-316.
[15]CHEN D P,WONG C K,LEUNG P C,et al.Anti-inflammatory activities of Chinese herbal medicine sinomenine and Liang Miao San on tumor necrosis factor-α-activated human fibroblast-like synoviocytes in rheumatoid arthritis[J].Journal of Ethnopharmacology,2011,137(1):457-68.
[16]DENG Z S,ZHAO D,HU Y,et al.Biocatalyzed cross-coupling of sinomenine and 1,2-dihydroxybenzene by Coriolus unicolor[J].中国化学快报(英文版),2012,23(3):321-324.
[17]KYSLIKOVA E,BABIAK P,STEPANEK V,et al.Biotransformation of codeine to 14-OH-codeine derivatives by Rhizobium radiobacter,R89-1[J].Journal of Molecular Catalysis B Enzymatic,2013,87(3):1-5.
[18]VACEK J,PAPOUSKOVA B,KOSINA P,et al.Mass spectrometric investigation of chelerythrine and dihydrochelerythrine biotransformation patterns in human hepatocytes[J].Journal of Chromatography B Analytical Technologies in the Biomedical&Life Sciences,2013,941C(2):17-24.
[19]INGKANINAN K,KHORANA N,SRIPRANG S.Acetylcholinesterase Inhibitor from Stephania suberosa Forman[J].Naresuan University Science Journal,2006,3(1):1-11.
[20]CAI L,DONG J W,ZHAO L X,et al.An improved water-soluble/stereospecific biotransformation of aporphine alkaloids in Stephania epigaea to 4 R-hydroxyaporphine alkaloids by Clonostachys rogersoniana[J].Process Biochemistry 2016,51(8):933-940.
[21]LI L,YE M,BI K,et al.Liquid chromatography–tandem mass spectrometry for the identification of l-tetrahydropalmatine metabolites in Penicillium janthinellum,and rats[J].Biomedical Chromatography,2006,20(1):95-100.
[22]VRBA J,PAPOUSKOVA B,PYSZKOVA M,et al.Metabolism of palmatine by human hepatocytes and recombinant cytochromes P450[J].Journal of Pharmaceutical&Biomedical Analysis,2015,102(102):193-198.
[2]KASHIWADA Y,AOSHIMA A,IKESHIRO Y,et al.Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera,and structure–activity correlations with related alkaloids[J].Bioorganic&Medicinal Chemistry,2005,13(2):443-448.
[3]CHENG Z,WANG K,WEI J,et al.Proteomic analysis of antitumor effects by tetrandrine treatment in Hep G2 cells[J].Phytomedicine,2010,17(13):1000.
[4]JING W,TENG Y,HUANG C,et al.The synthesis and antistaphylococcal activity of 9,13-disubstituted berberine derivatives[J].European Journal of Medicinal Chemistry,2017,127:424.
[5]PUND S,BORADE G,RASVE G.Improvement of anti-inflammatory and anti-angiogenic activity of berberine by novel rapid dissolving nanoemulsifying technique[J].Phytomedicine International Journal of Phytotherapy&Phytopharmacology,2014,21(3):307.
[6]HARTON L R,RICHARDSON J R,ARMENDARIZ A,et al.Dissociation of morphine analgesic effects in the sensory and affective components of formalin-induced spontaneous pain in male and female rats[J].Brain Research,2017,1658:36-41.
[7]UNWIN N,GAN D,WHITING D.The IDF Diabetes Atlas:providing evidence,raising awareness and promoting action[J].Diabetes Research&Clinical Practice,2010,87(1):2-3.
[8]HEGAZY M E F,MOHAMED T A,ELHAMY A I,et al.Microbial biotransformation as a tool for drug development based on natural products from mevalonic acid pathway:A review[J].Journal of Advanced Research,2015,6(1):17-33.
[9]贺赐安,余旭亚,孟庆雄,等.生物转化对天然药物进行结构修饰的研究进展[J].天然产物研究与开发,2012,24(6):843-847.
[10]牛红军,王芃,杨官娥.微生物转化技术在中药研究中的应用[J].中国实验方剂学杂志,2013,19(18):346-349.
[11]PETER J S,PETER J H,NEIL C B.Transformation of 2,2'-Bimorphine to the Novel Compounds 10-α-S-Monohydroxy-2,2'-Bimorphine and 10,10'-α,α'-S,S'-Dihydroxy-2,2'-Bimorphine by Cylindrocarpon didymium[J].Applied&Environmental Microbiology,2001,67(8):3716-3719.
[12]AGUSTA A,WULANSARI D,PRAPTIWI,et al.Biotransformation of Protoberberine Alkaloids by the Endophytic Fungus Coelomycetes,AFKR-3 Isolated from Yellow Moonsheed Plant(Archangelisia Flava,(L.)Merr.)[J].Procedia Chemistry,2014,13:38-43.
[13]余伯阳.中药生物技术[M].北京:中国医药科技出版社,2005:274.
[14]徐田,刘吉华,余伯阳,等.微生物转化左旋四氢巴马汀产生左旋紫堇达明高产菌株的紫外诱变选育[J].药物生物技术,2011,18(4):313-316.
[15]CHEN D P,WONG C K,LEUNG P C,et al.Anti-inflammatory activities of Chinese herbal medicine sinomenine and Liang Miao San on tumor necrosis factor-α-activated human fibroblast-like synoviocytes in rheumatoid arthritis[J].Journal of Ethnopharmacology,2011,137(1):457-68.
[16]DENG Z S,ZHAO D,HU Y,et al.Biocatalyzed cross-coupling of sinomenine and 1,2-dihydroxybenzene by Coriolus unicolor[J].中国化学快报(英文版),2012,23(3):321-324.
[17]KYSLIKOVA E,BABIAK P,STEPANEK V,et al.Biotransformation of codeine to 14-OH-codeine derivatives by Rhizobium radiobacter,R89-1[J].Journal of Molecular Catalysis B Enzymatic,2013,87(3):1-5.
[18]VACEK J,PAPOUSKOVA B,KOSINA P,et al.Mass spectrometric investigation of chelerythrine and dihydrochelerythrine biotransformation patterns in human hepatocytes[J].Journal of Chromatography B Analytical Technologies in the Biomedical&Life Sciences,2013,941C(2):17-24.
[19]INGKANINAN K,KHORANA N,SRIPRANG S.Acetylcholinesterase Inhibitor from Stephania suberosa Forman[J].Naresuan University Science Journal,2006,3(1):1-11.
[20]CAI L,DONG J W,ZHAO L X,et al.An improved water-soluble/stereospecific biotransformation of aporphine alkaloids in Stephania epigaea to 4 R-hydroxyaporphine alkaloids by Clonostachys rogersoniana[J].Process Biochemistry 2016,51(8):933-940.
[21]LI L,YE M,BI K,et al.Liquid chromatography–tandem mass spectrometry for the identification of l-tetrahydropalmatine metabolites in Penicillium janthinellum,and rats[J].Biomedical Chromatography,2006,20(1):95-100.
[22]VRBA J,PAPOUSKOVA B,PYSZKOVA M,et al.Metabolism of palmatine by human hepatocytes and recombinant cytochromes P450[J].Journal of Pharmaceutical&Biomedical Analysis,2015,102(102):193-198.