综述 |
|
|
|
|
微生物异源合成植物异喹啉生物碱的新进展 * |
马雅婷1,刘珍宁1,刘雪1,於洪建2,赵广荣1,**() |
1 天津大学化工学院 教育部合成生物学前沿科学中心 系统生物工程教育部重点实验室 天津 300350 2 天津益倍生物科技集团 天津 300450 |
|
Advances in Production of Plant Isoquinoline Alkaloids in Heterologous Microbes |
MA Ya-ting1,LIU Zhen-ning1,LIU Xue1,YU Hong-jian2,ZHAO Guang-rong1,**() |
1 School of Chemical Engineering and Technology, Tianjin University, Frontier Science Center for Synthetic Biology and Key Laboratory of Systems Bioengineering, Ministry of Education, Tianjin 300350, China 2 Ubasio Biotech Co. , Ltd. , Tianjin 300450, China |
引用本文:
马雅婷,刘珍宁,刘雪,於洪建,赵广荣. 微生物异源合成植物异喹啉生物碱的新进展 *[J]. 中国生物工程杂志, 2019, 39(11): 123-131.
MA Ya-ting,LIU Zhen-ning,LIU Xue,YU Hong-jian,ZHAO Guang-rong. Advances in Production of Plant Isoquinoline Alkaloids in Heterologous Microbes. China Biotechnology, 2019, 39(11): 123-131.
链接本文:
https://manu60.magtech.com.cn/biotech/CN/10.13523/j.cb.20191114
或
https://manu60.magtech.com.cn/biotech/CN/Y2019/V39/I11/123
|
[1] |
Desgagne-Penix I, Hotchandani T . Heterocyclic amaryllidaceae alkaloids: biosynjournal and pharmacological applications. Current Topics in Medicinal Chemistry, 2017,17(4):418-427.
doi: 10.2174/1568026616666160824104052
pmid: 27558679
|
[2] |
He M M, Qu C R, Gao O D , et al. Biological and pharmacological activities of Amaryllidaceae alkaloids. RSC Advances, 2015,5(21):16562-16574.
doi: 10.3390/molecules24234238
pmid: 31766438
|
[3] |
Li L, Dai H J, Ye M , et al. Lycorine induces cell-cycle arrest in the G0G1 phase in K562 cells via HDAC inhibition. Cancer Cell International, 2012,12(1):49-49.
doi: 10.1186/1475-2867-12-49
pmid: 23176676
|
[4] |
Foreman K E, Jesse J N, Kuo P C , et al. Emetine dihydrochloride: a novel therapy for bladder cancer. Journal of Urology, 2014,191(2):502-509.
doi: 10.1016/j.juro.2013.09.014
|
[5] |
Bessi I, Bazzicalupi C, Richter C , et al. Spectroscopic, molecular modeling, and NMR-spectroscopic investigation of the binding mode of the natural alkaloids berberine and sanguinarine to human telomeric G-Quadruplex DNA. ACS Chemical Biology, 2012,7(6):1109-1119.
doi: 10.1021/cb300096g
|
[6] |
Santoshi S, Naik P K . Molecular insight of isotypes specific β-tubulin interaction of tubulin heterodimer with noscapinoids.Journal of Computer- Aided Molecular Design, 2014,28(7):751-763.
doi: 10.1007/s10822-014-9756-9
|
[7] |
Dittbrenner A, Mock H P, Borner A , et al. Variability of alkaloid content in Papaver somniferum L. Journal of Applied Botany and Food Quality-Angewandte Botanik, 2009,82(2):103-107.
|
[8] |
Galanie S, Thodey K, Trenchard I J , et al. Complete biosynjournal of opioids in yeast. Science, 2015,349(6252):1095-1100.
doi: 10.1126/science.aac9373
pmid: 26272907
|
[9] |
Li Y, Li S, Thodey K , et al. Complete biosynjournal of noscapine and halogenated alkaloids in yeast. Proceedings of the National Academy of Sciences, 2018,115(17):3922-3911.
|
[10] |
Singh A, Massicotte M A, Garand A , et al. Cloning and characterization of norbelladine synthase catalyzing the first committed reaction in Amaryllidaceae alkaloid biosynjournal. BMC Plant Biology, 2018,18(1):338.
doi: 10.1186/s12870-018-1570-4
pmid: 30526483
|
[11] |
Kilgore M B, Augustin M M, Starks C M , et al. Cloning and characterization of a norbelladine 4'-O-methyltransferase involved in the biosynjournal of the Alzheimer’s drug galanthamine in Narcissus sp. aff. pseudonarcissus. PLoS One, 2014,9(7):e103223.
doi: 10.1371/journal.pone.0103223
pmid: 25061748
|
[12] |
Kilgore M B, Augustin M M, May G D , et al. CYP96T1 of Narcissus sp. aff. pseudonarcissus catalyzes formation of the para-para’ C-C phenol couple in the amaryllidaceae alkaloids. Frontiers in Plant Science, 2016,7:225.
doi: 10.3389/fpls.2016.00225
pmid: 26941773
|
[13] |
Kilgore M B, Holland C K, Jez J M , et al. Identification of a noroxomaritidine reductase with amaryllidaceae alkaloid biosynjournal related activities. Journal of Biological Chemistry, 2016,291(32):16740-16752.
doi: 10.1074/jbc.M116.717827
pmid: 27252378
|
[14] |
Nomura T, Quesada A L, Kutchan T M . The new-D-glucosidase in terpenoid-isoquinoline alkaloid biosynjournal in Psychotria ipecacuanha. Journal of Biological Chemistry, 2008,283(50):34650-34659.
doi: 10.1074/jbc.M806953200
pmid: 18927081
|
[15] |
Nomura T, Kutchan T M . Three new O-methyltransferases are sufficient for all O-methylation reactions of ipecac alkaloid biosynjournal in root culture of Psychotria ipecacuanha. Journal of Biological Chemistry, 2010,285(7):7722-7738.
doi: 10.1074/jbc.M109.086157
pmid: 20061395
|
[16] |
Cheong B E, Takemura T, Yoshimatsu K , et al. Molecular cloning of an O-methyltransferase from adventitious roots of Carapichea ipecacuanha. Journal of the Agricultural Chemical Society of Japan, 2011,75(1):107-113.
doi: 10.1271/bbb.100605
pmid: 21228475
|
[17] |
Guo L, Winzer T, Yang X F , et al. The Opium poppy genome and morphinan production. Science, 2018,362(6412):343-347.
doi: 10.1126/science.aat4096
pmid: 30166436
|
[18] |
Winzer T, Gazda V, He Z , et al. A Papaver somniferum 10-gene cluster for synjournal of the anticancer alkaloid noscapine. Science, 2012,336(6089):1704-1708.
doi: 10.1126/science.1220757
pmid: 22653730
|
[19] |
Dang T T, Chen X, Facchini P J . Acetylation serves as a protective group in noscapine biosynjournal in Opium poppy. Nature Chemical Biology, 2015,11(2):104-106.
doi: 10.1038/nchembio.1717
pmid: 25485687
|
[20] |
Li Y, Smolke C D . Engineering biosynjournal of the anticancer alkaloid noscapine in yeast. Nature Communications, 2016,7:12137.
doi: 10.1038/ncomms12137
pmid: 27378283
|
[21] |
Winzer T, Kern M, King A J , et al. Morphinan biosynjournal in Opium poppy requires a P450-oxidoreductase fusion protein. Science, 2015,349(6245):309-312.
doi: 10.1126/science.aab1852
pmid: 26113639
|
[22] |
Farrow S C, Hagel J M ,Beaudoin G A W, et al. Stereochemical inversion of(S)-reticuline by a cytochrome P450 fusion in Opium poppy. Nature Chemical Biology, 2015,11(9):728-732.
doi: 10.1038/nchembio.1879
pmid: 26147354
|
[23] |
Chen X, Hagel J M, Chang L , et al. A pathogenesis-related 10 protein catalyzes the final step in thebaine biosynjournal. Nature Chemical Biology, 2018,14(7):738-743.
doi: 10.1038/s41589-018-0059-7
pmid: 29807982
|
[24] |
刘金凤, 黄鹏, 卿志星 , 等. 苄基异喹啉类生物碱生物合成与代谢工程研究进展. 基因组学与应用生物学, 2016,35(8):2194-2200.
|
|
Liu J F, Huang P, Qing Z X , et al. Advances in the biosynjournal and metabolic engineering research of benzylisoquinoline alkaloids. Genomics and Applied Biology, 2016,35(8):2194-2200.
|
[25] |
Trenchard I J, Siddiqui M S, Thodey K , et al. De novo production of the key branch point benzylisoquinoline alkaloid reticuline in yeast. Metabolic Engineering, 2015,31:74-83.
doi: 10.1016/j.ymben.2015.06.010
pmid: 26166409
|
[26] |
Galanie S, Smolke C D . Optimization of yeast-based production of medicinal protoberberine alkaloids. Microbial Cell Factories, 2015,14(1):144.
doi: 10.1186/s12934-015-0332-3
pmid: 26376732
|
[27] |
Nakagawa A, Minami H, Kim J S , et al. A bacterial platform for fermentative production of plant alkaloids. Nature Communications, 2011,2(2):8.
doi: 10.1038/ncomms1327
pmid: 22179145
|
[28] |
DeLoache W C, Russ Z N, Narcross L , et al. An enzyme-coupled biosensor enables (S)-reticuline production in yeast from glucose. Nature Chemical Biology, 2015,11(7):465-471.
doi: 10.1038/nchembio.1816
pmid: 25984720
|
[29] |
Fossati E, Narcross L, Ekins A , et al. Synjournal of morphinan alkaloids in Saccharomyces cerevisiae. PLoS One, 2015,10(4):15
doi: 10.1097/PAF.0000000000000508
pmid: 31688050
|
[30] |
Thodey K, Galanie S, Smolke C D . A microbial biomanufacturing platform for natural and semisynthetic opioids. Nature Chemical Biology, 2014,10(10):837-844.
doi: 10.1038/NCHEMBIO.1613
|
[31] |
Nakagawa A, Matsumura E, Koyanagi T , et al. Total biosynjournal of opiates by stepwise fermentation using engineered Escherichia coli. Nature Communications, 2016,7:10390.
doi: 10.1038/ncomms10390
pmid: 26847395
|
[32] |
Brown S, Clastre M, Courdavault V , et al. De novo production of the plant-derived alkaloid strictosidine in yeast. Proceedings of the National Academy of Sciences, 2015,112(11):3205-3210.
|
[33] |
Caputi L, Franke J, Farrow S C , et al. Missing enzymes in the biosynjournal of the anticancer drug vinblastine in Madagascar periwinkle. Science, 2018,360(6394):1235-1238.
doi: 10.1126/science.aat4100
pmid: 29724909
|
[34] |
Minami H, Kim J S, Ikezawa N , et al. Microbial production of plant benzylisoquinoline alkaloids. Proceedings of the National Academy of Sciences, 2008,105(21):7393-7398.
|
[35] |
Trenchard I J, Smolke C D . Engineering strategies for the fermentative production of plant alkaloids in yeast. Metabolic Engineering, 2015,30:96-104.
doi: 10.1016/j.ymben.2015.05.001
pmid: 25981946
|
[36] |
Minami H, Dubouzet E, Iwasa K , et al. Functional analysis of norcoclaurine synthase in Coptis japonica. Journal of Biological Chemistry, 2007,282(9):6274-6282.
doi: 10.1074/jbc.M608933200
pmid: 17204481
|
[37] |
Hawkins K M, Smolke C D . Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae. Nature Chemical Biology, 2008,4(9):564-573.
doi: 10.1038/nchembio.105
pmid: 18690217
|
[38] |
Matsumura E, Nakagawa A, Tomabechi Y , et al. Microbial production of novel sulphated alkaloids for drug discovery. Scientific Reports, 2018,8(1):7980.
doi: 10.1038/s41598-018-26306-7
pmid: 29789647
|
[39] |
Chen W, Yao J, Meng J , et al. Promiscuous enzymatic activity-aided multiple-pathway network design for metabolic flux rearrangement in hydroxytyrosol biosynjournal. Nature Communications, 2019,10:12.
doi: 10.1038/s41467-018-07943-y
pmid: 30602727
|
[40] |
Fossati E, Ekins A, Narcross L , et al. Reconstitution of a 10-gene pathway for synjournal of the plant alkaloid dihydrosanguinarine in Saccharomyces cerevisiae. Nature Communications, 2014,5:3283.
doi: 10.1038/ncomms4283
pmid: 24513861
|
[41] |
Lee H, Deloache W C, Dueber J E . Spatial organization of enzymes for metabolic engineering. Metabolic Engineering, 2012,14(3):242-251.
doi: 10.1016/j.ymben.2011.09.003
|
[42] |
Biggs B W, Paepe B D , Santos C N S , et al. Multivariate modular metabolic engineering for pathway and strain optimization .Current Opinion in Biotechnology. 2014,29(1):156-162.
doi: 10.1016/j.tibtech.2018.07.003
pmid: 30064888
|
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
|
Shared |
|
|
|
|
|
Discussed |
|
|
|
|