Research progress on total synthesis and activity of nitidine

ZHAO Zeng; CHEN Hao; YANG Niao; SUN Qingyan; LIU Runhui

doi:10.3969/j.issn.1006-0111.2017.02.002

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2017 > 35(2): 102-107,149

ZHAO Zeng, CHEN Hao, YANG Niao, SUN Qingyan, LIU Runhui. Research progress on total synthesis and activity of nitidine[J]. Journal of Pharmaceutical Practice and Service, 2017, 35(2): 102-107,149. doi: 10.3969/j.issn.1006-0111.2017.02.002

Citation:

ZHAO Zeng, CHEN Hao, YANG Niao, SUN Qingyan, LIU Runhui. Research progress on total synthesis and activity of nitidine[J]. Journal of Pharmaceutical Practice and Service, 2017, 35(2): 102-107,149. doi: 10.3969/j.issn.1006-0111.2017.02.002

Research progress on total synthesis and activity of nitidine

doi: 10.3969/j.issn.1006-0111.2017.02.002

Department of Natural Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2016-03-07
Rev Recd Date: 2016-12-22

Abstract

Nitidine is a benzophenanthridine alkaloid derived from Zanthorulum nitidum (Roxb.) DC root. Research shows that nitidine displays rich biological activities, such as anti-tumor, anti-inflammatory, anti-malaria and etc. This paper reviewed the progress of the total synthesis methods for nitidine and recent research on bioactivities.
- nitidine,
- total synthesis,
- bioactivity,
- mechanism of action

References

[1]	Cushman M, Cheng L. Total synthesis of nitidine chloride[J]. J Org Chem, 1978, 43(2):286-288.
[2]	Luo Y, Mei Y, Zhang J, et al. A concise synthesis of nornitidine via nickel-or palladium-catalyzed annulation[J]. Tetrahedron, 2006, 62(39):9131-9134.
[3]	Hanaoka M, Yamagishi H, Marutani M, et al. Chemical transformation of protoberberines. XIII. A novel and efficient synthesis of antitumor benzo[c] phenanthridine alkaloids, nitidine and fagaronine[J]. Chem Pharm Bull, 1987, 35(6):2348-2354.
[4]	Cho WJ, Park MJ, Imanishi T, et al. A novel synthesis of benzo[c] phenanthridine skeleton and biological evaluation of isoquinoline derivatives[J]. Chem Pharm Bull, 1999, 47(6):900-902.
[5]	Watanabe T, Ohashi Y, Yoshino R, et al. Total synthesis of 12-methoxydihydrochelerythrine and anti-tumour activity of its quaternary base:toward an efficient synthetic route for 12-alkoxybenzo[c] phenanthridine bases via naphthoquinone monooxime from 2-benzofuranyl-1-tetralone derivative[J]. Org Biomol Chem, 2003, 1(17):3024-3032.
[6]	Kessar SV, Gupta YP, Balakrishnan P, et al. Benzyne cyclization route to benzo[c] phenanthridine alkaloids. Synthesis of chelerythrine, decarine, and nitidine[J]. J Org Chem, 1988, 53(8):1708-1713.
[7]	Nakanishi T, Suzuki M. Synthesis and cytotoxic activities of a new benzo[c] phenanthridine alkaloid, 7-hydroxynitidine, and some 9-oxygenated benzo[c] phenanthridine derivatives[J]. Org Lett, 1999, 1(7):985-988.
[8]	Harayama T. Synthesis of benzo[c] phenanthridine alkaloids using a palladium-catalyzed aryl-aryl coupling reaction[J]. Heterocycles, 2005, 65(3):697-713.
[9]	Ishikawa T, Saito T, Yoshida M.Triphosgene:A versatile reagent for Bischler-Napieralski reaction[J]. Heterocycles, 2001, 54(1):437-438.
[10]	Blanchot M, Candito DA, Larnaud F, et al. Formal synthesis of nitidine and Nk109 via Palladium-catalyzed domino direct arylation/N-arylation of aryl triflates[J]. Org Lett, 2011, 13(6):1486-1489.
[11]	Lv P, Huang K, Xie L, et al. Palladium-catalyzed tandem reaction to construct benzo[c] phenanthridine:application to the total synthesis of benzo[c] phenanthridine alkaloids[J]. Org Biomol Chem, 2011, 9(9):3133-3135.
[12]	Enomoto T, Girard AL, Yasui Y, et al. Gold (Ⅰ)-catalyzed tandem reactions initiated by hydroamination of alkynyl carbamates:application to the synthesis of nitidine[J]. J Org Chem, 2009, 74(23):9158-9164.
[13]	国家药典委员会. 中华人民共和国药典2015年版一部[S]. 北京:中国医药科技出版社, 2015:232-233.
[14]	黄华来, 李江平, 张进源,等. 抗炎镇痛中药牙膏:201210300349.8[P]. 2012-11-14.
[15]	Hu J, Zhang WD, Liu RH, et al. Benzophenanthridine alkaloids from Zanthoxylum nitidum (Roxb.) DC, and their analgesic and anti-inflammatory activities[J]. Chem Biodivers, 2006, 3(9):990-995.
[16]	Wang Z, Jiang W, Zhang Z, et al. Nitidine chloride inhibits LPS-induced inflammatory cytokines production via MAPK and NF-kappaB pathway in RAW 264.7 cells[J]. J Ethnopharmacol, 2012, 144(1):145-150.
[17]	Lin JM, Shen A, Chen H, et al. Nitidine chloride inhibits hepatic cancer growth via modulation of multiple signaling pathways[J]. BMC Cancer, 2014, 14(1):729.
[18]	Sun M, Zhang N, Wang X, et al. Nitidine chloride induces apoptosis, cell cycle arrest, and synergistic cytotoxicity with doxorubicin in breast cancer cells[J]. Tumour Biol, 2014, 35(10):10201-10212.
[19]	Liu N, Li P, Zang S, et al. Novel agent nitidine chloride induces erythroid differentiation and apoptosis in CML cells through c-Myc-miRNAs axis[J]. PloS one, 2015, 10(2):e0116880.
[20]	Zhai H, Hu S, Liu T, et al. Nitidine chloride inhibits proliferation and induces apoptosis in colorectal cancer cells by suppressing the ERK signaling pathway[J]. Mol Med Rep, 2016, 13(3):2536-2542.
[21]	Jullian V, Bourdy G, Georges S, et al. Validation of use of a traditional antimalarial remedy from French Guiana, Zanthoxylum rhoifolium Lam[J]. J Ethnopharmacol, 2006, 106(3):348-352.
[22]	Muganga R, Angenot L, Tits M, et al. In vitro and in vivo antiplasmodial activity of three rwandan medicinal plants and identification of their active compounds[J]. Planta Med, 2014, 80(6):482-489.
[23]	Bouquet J, Rivaud M, Chevalley S, et al. Biological activities of nitidine, a potential anti-malarial lead compound[J]. Malar J, 2012, 11(1):67-74.
[24]	Egan TJ, Marques HM. The role of haem in the activity of chloroquine and related antimalarial drugs[J]. Coordin Chem Rev, 1999, 190:493-517.
[25]	Nyangulu JM, Hargreaves SL, Sharples SL, et al. Antimalarial benzo[c] phenanthridines[J]. Bioorg Med Chem Lett, 2005, 15(8):2007-2010.
[26]	Rashid MA, Gustafson KR, Kashman Y, et al. Anti-HIV alkaloids from Toddalia asiatica[J]. Nat Prod Lett, 1995, 6(2):153-156.
[27]	Tan GT, Pezzuto JM, Kinghorn AD, et al. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1(HIV-1) reverse transcriptase[J]. J Nat Prod, 1991, 54(1):143-154.
[28]	Tankeo SB, Damen F, Awouafack MD, et al. Antibacterial activities of the methanol extracts, fractions and compounds from Fagara tessmannii[J]. J Ethnopharmacol, 2015, 169:275-279.
[29]	Tavares LdC, Zanon G, Weber AD, et al. Structure-activity relationship of benzophenanthridine alkaloids from Zanthoxylum rhoifolium having antimicrobial activity[J]. PloS one, 2014, 9(5):e97000.
[30]	Del Poeta M, Chen SF, Von Hoff D, et al. Comparison of in vitro activities of camptothecin and nitidine derivatives against fungal and cancer cells[J]. Antimicrob Agents Chemother, 1999, 43(12):2862-2868.
[31]	Addae-Mensah I, Munenge R, Guantai AN. Comparative examination of two Zanthoxylum benzophenanthridine alkaloids for effects in rabbits[J]. Phytother Res, 1989, 3(5):165-169.
[32]	韦锦斌, 龙盛京, 覃少东,等. 氯化两面针碱对大鼠心肌缺血再灌注损伤的保护作用[J]. 中国临床康复, 2006, 10(27):171-174.
[33]	Zhang Y, Luo Z, Wang D, et al. Phytochemical profiles and antioxidant and antimicrobial activities of the leaves of Zanthoxylum bungeanum[J]. Scientific World J, 2014, 2014:181072.

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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

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Research progress on total synthesis and activity of nitidine

Department of Natural Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2016-03-07

Rev Recd Date: 2016-12-22

Key words:

Abstract: Nitidine is a benzophenanthridine alkaloid derived from Zanthorulum nitidum (Roxb.) DC root. Research shows that nitidine displays rich biological activities, such as anti-tumor, anti-inflammatory, anti-malaria and etc. This paper reviewed the progress of the total synthesis methods for nitidine and recent research on bioactivities.

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Reference (33)

[1]	Cushman M, Cheng L. Total synthesis of nitidine chloride[J]. J Org Chem, 1978, 43(2):286-288.
[2]	Luo Y, Mei Y, Zhang J, et al. A concise synthesis of nornitidine via nickel-or palladium-catalyzed annulation[J]. Tetrahedron, 2006, 62(39):9131-9134.
[3]	Hanaoka M, Yamagishi H, Marutani M, et al. Chemical transformation of protoberberines. XIII. A novel and efficient synthesis of antitumor benzo[c] phenanthridine alkaloids, nitidine and fagaronine[J]. Chem Pharm Bull, 1987, 35(6):2348-2354.
[4]	Cho WJ, Park MJ, Imanishi T, et al. A novel synthesis of benzo[c] phenanthridine skeleton and biological evaluation of isoquinoline derivatives[J]. Chem Pharm Bull, 1999, 47(6):900-902.
[5]	Watanabe T, Ohashi Y, Yoshino R, et al. Total synthesis of 12-methoxydihydrochelerythrine and anti-tumour activity of its quaternary base:toward an efficient synthetic route for 12-alkoxybenzo[c] phenanthridine bases via naphthoquinone monooxime from 2-benzofuranyl-1-tetralone derivative[J]. Org Biomol Chem, 2003, 1(17):3024-3032.
[6]	Kessar SV, Gupta YP, Balakrishnan P, et al. Benzyne cyclization route to benzo[c] phenanthridine alkaloids. Synthesis of chelerythrine, decarine, and nitidine[J]. J Org Chem, 1988, 53(8):1708-1713.
[7]	Nakanishi T, Suzuki M. Synthesis and cytotoxic activities of a new benzo[c] phenanthridine alkaloid, 7-hydroxynitidine, and some 9-oxygenated benzo[c] phenanthridine derivatives[J]. Org Lett, 1999, 1(7):985-988.
[8]	Harayama T. Synthesis of benzo[c] phenanthridine alkaloids using a palladium-catalyzed aryl-aryl coupling reaction[J]. Heterocycles, 2005, 65(3):697-713.
[9]	Ishikawa T, Saito T, Yoshida M.Triphosgene:A versatile reagent for Bischler-Napieralski reaction[J]. Heterocycles, 2001, 54(1):437-438.
[10]	Blanchot M, Candito DA, Larnaud F, et al. Formal synthesis of nitidine and Nk109 via Palladium-catalyzed domino direct arylation/N-arylation of aryl triflates[J]. Org Lett, 2011, 13(6):1486-1489.
[11]	Lv P, Huang K, Xie L, et al. Palladium-catalyzed tandem reaction to construct benzo[c] phenanthridine:application to the total synthesis of benzo[c] phenanthridine alkaloids[J]. Org Biomol Chem, 2011, 9(9):3133-3135.
[12]	Enomoto T, Girard AL, Yasui Y, et al. Gold (Ⅰ)-catalyzed tandem reactions initiated by hydroamination of alkynyl carbamates:application to the synthesis of nitidine[J]. J Org Chem, 2009, 74(23):9158-9164.
[13]	国家药典委员会. 中华人民共和国药典2015年版一部[S]. 北京:中国医药科技出版社, 2015:232-233.
[14]	黄华来, 李江平, 张进源,等. 抗炎镇痛中药牙膏:201210300349.8[P]. 2012-11-14.
[15]	Hu J, Zhang WD, Liu RH, et al. Benzophenanthridine alkaloids from Zanthoxylum nitidum (Roxb.) DC, and their analgesic and anti-inflammatory activities[J]. Chem Biodivers, 2006, 3(9):990-995.
[16]	Wang Z, Jiang W, Zhang Z, et al. Nitidine chloride inhibits LPS-induced inflammatory cytokines production via MAPK and NF-kappaB pathway in RAW 264.7 cells[J]. J Ethnopharmacol, 2012, 144(1):145-150.
[17]	Lin JM, Shen A, Chen H, et al. Nitidine chloride inhibits hepatic cancer growth via modulation of multiple signaling pathways[J]. BMC Cancer, 2014, 14(1):729.
[18]	Sun M, Zhang N, Wang X, et al. Nitidine chloride induces apoptosis, cell cycle arrest, and synergistic cytotoxicity with doxorubicin in breast cancer cells[J]. Tumour Biol, 2014, 35(10):10201-10212.
[19]	Liu N, Li P, Zang S, et al. Novel agent nitidine chloride induces erythroid differentiation and apoptosis in CML cells through c-Myc-miRNAs axis[J]. PloS one, 2015, 10(2):e0116880.
[20]	Zhai H, Hu S, Liu T, et al. Nitidine chloride inhibits proliferation and induces apoptosis in colorectal cancer cells by suppressing the ERK signaling pathway[J]. Mol Med Rep, 2016, 13(3):2536-2542.
[21]	Jullian V, Bourdy G, Georges S, et al. Validation of use of a traditional antimalarial remedy from French Guiana, Zanthoxylum rhoifolium Lam[J]. J Ethnopharmacol, 2006, 106(3):348-352.
[22]	Muganga R, Angenot L, Tits M, et al. In vitro and in vivo antiplasmodial activity of three rwandan medicinal plants and identification of their active compounds[J]. Planta Med, 2014, 80(6):482-489.
[23]	Bouquet J, Rivaud M, Chevalley S, et al. Biological activities of nitidine, a potential anti-malarial lead compound[J]. Malar J, 2012, 11(1):67-74.
[24]	Egan TJ, Marques HM. The role of haem in the activity of chloroquine and related antimalarial drugs[J]. Coordin Chem Rev, 1999, 190:493-517.
[25]	Nyangulu JM, Hargreaves SL, Sharples SL, et al. Antimalarial benzo[c] phenanthridines[J]. Bioorg Med Chem Lett, 2005, 15(8):2007-2010.
[26]	Rashid MA, Gustafson KR, Kashman Y, et al. Anti-HIV alkaloids from Toddalia asiatica[J]. Nat Prod Lett, 1995, 6(2):153-156.
[27]	Tan GT, Pezzuto JM, Kinghorn AD, et al. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1(HIV-1) reverse transcriptase[J]. J Nat Prod, 1991, 54(1):143-154.
[28]	Tankeo SB, Damen F, Awouafack MD, et al. Antibacterial activities of the methanol extracts, fractions and compounds from Fagara tessmannii[J]. J Ethnopharmacol, 2015, 169:275-279.
[29]	Tavares LdC, Zanon G, Weber AD, et al. Structure-activity relationship of benzophenanthridine alkaloids from Zanthoxylum rhoifolium having antimicrobial activity[J]. PloS one, 2014, 9(5):e97000.
[30]	Del Poeta M, Chen SF, Von Hoff D, et al. Comparison of in vitro activities of camptothecin and nitidine derivatives against fungal and cancer cells[J]. Antimicrob Agents Chemother, 1999, 43(12):2862-2868.
[31]	Addae-Mensah I, Munenge R, Guantai AN. Comparative examination of two Zanthoxylum benzophenanthridine alkaloids for effects in rabbits[J]. Phytother Res, 1989, 3(5):165-169.
[32]	韦锦斌, 龙盛京, 覃少东,等. 氯化两面针碱对大鼠心肌缺血再灌注损伤的保护作用[J]. 中国临床康复, 2006, 10(27):171-174.
[33]	Zhang Y, Luo Z, Wang D, et al. Phytochemical profiles and antioxidant and antimicrobial activities of the leaves of Zanthoxylum bungeanum[J]. Scientific World J, 2014, 2014:181072.

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Research progress on total synthesis and activity of nitidine

doi: 10.3969/j.issn.1006-0111.2017.02.002

Abstract

References

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通讯作者: 陈斌, bchen63@163.com

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