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

Message Board

Respected readers, authors and reviewers, you can add comments to this page on any questions about the contribution, review, editing and publication of this journal. We will give you an answer as soon as possible. Thank you for your support!

Name

E-mail

Phone

Title

Content

Verification Code

Volume 35 Issue 2

Turn off MathJax

Article Contents

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.

Proportional views

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Get Citation

PDF

XML

Article Metrics

Article views(3949) PDF downloads(341) Cited by()

Proportional views

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.

HTML

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.

Message Board

Research progress on total synthesis and activity of nitidine

doi: 10.3969/j.issn.1006-0111.2017.02.002

Abstract

References

Proportional views

通讯作者: 陈斌, bchen63@163.com

Article Metrics

Related

Proportional views