| REVIEW |
|
|
|
|
|
Traditional Chinese medicine Euodiae Fructus: botany, traditional use, phytochemistry, pharmacology, toxicity and quality control |
| Si1, Jia Xiao1, Xi1, Ke Xu2, Wei Chen1, Jia1, Yun Xin1 |
1 Department of Natural Medicinal Chemistry, School of Pharmacy, Naval Medical University, No. 325 Guohe Road, Yangpu District, Shanghai 200433, China;
2 School of Pharmacy, Shandong University of Traditional Chinese Medicine, Jinan 250355, China |
|
|
|
|
Abstract Euodiae Fructus, referred to as “Wuzhuyu” in Chinese, has been used as local and traditional herbal medicines in many regions, especially in China, Japan and Korea, for the treatment of gastrointestinal disorders, headache, emesis, aphtha, dermatophytosis, dysentery, etc. Substantial investigations into their chemical and pharmacological properties have been performed. Recently, interest in this plant has been focused on the different structural types of alkaloids like evodiamine, rutaecarpine, dehydroevodiamine and 1-methyl-2-undecyl-4(1H)-quinolone, which exhibit a wide range of pharmacological activities in preclinical models, such as anticancer, antibacterial, anti-inflammatory, anticardiovascular disease, etc. This review summarizes the up-to-date and comprehensive information concerning the botany, traditional uses, phytochemistry, pharmacology of Euodiae Fructus together with the toxicology and quality control, and discusses the possible direction and scope for future research on this plant.
|
| Keywords
Euodiae Fructus
Traditional uses
Phytochemistry
Pharmacology
Toxicology
|
| Fund:The study was funded by the National Natural Science Foundation of China (82004215, 82173704, 31870327, 82003624, 82004003), the Key Research and Development Program of China (2019YFC1711006, 2017YFC1702002), the National Major Project of China (2018ZX09731016-005), Shanghai Engineering Research Center for the Preparation of Bioactive Natural Products (16DZ2280200), Shanghai Municipal Health Commission Project (20204Y0326), Science and Technology Commission of Shanghai Municipality (20YF1459000, 20YF1458700) and Sailing Program of Naval Medical University. |
|
Corresponding Authors:
Xian-Peng Zu,E-mail:zuxianpeng@163.com;Yun-Heng Shen,E-mail:shenyunheng@hotmail.com
E-mail: zuxianpeng@163.com;shenyunheng@hotmail.com
|
|
Issue Date: 08 March 2023
|
|
|
1. Jiang J, Hu C. Evodiamine:a novel anti-cancer alkaloid from Evodia rutaecarpa. Molecules. 2009;14:1852-9.
2. Gavaraskar K, Dhulap S, Hirwani RR. Therapeutic and cosmetic applications of Evodiamine and its derivatives-a patent review. Fitoterapia. 2015;106:22-35.
3. Jia S, Hu C. Pharmacological effects of rutaecarpine as a cardiovascular protective agent. Molecules. 2010;15:1873-81.
4. Tian KM, Li JJ, Xu SW. Rutaecarpine:a promising cardiovascular protective alkaloid from Evodia rutaecarpa (Wu Zhu Yu). Pharmacol Res. 2019;141:541-50.
5. Fan SM, Zhang CL, Luo T, Wang JQ, Tang Y, Chen ZM, Yu LY. Limonin:A Review of Its Pharmacology, Toxicity, and Pharmacokinetics. Molecules. 2019;24:22.
6. Zhao Z, He X, Han W, Chen X, Liu P, Zhao X, Wang X, Zhang L, Wu S, Zheng X. Genus Tetradium L.:a comprehensive review on traditional uses, phytochemistry, and pharmacological activities. J Ethnopharmacol. 2019;231:337-54.
7. Shan QY, Sang XN, Hui H, Shou QY, Fu HY, Hao M, Liu KH, Zhang QY, Cao G, Qin LP. Processing and polyherbal formulation of Tetradium ruticarpum (A. Juss.) Hartley:phytochemistry, pharmacokinetics, and toxicity. Front Pharmacol. 2020;11:133.
8. Wang T, Yan YF, Yang L, Huang YZ, Duan XH, Su KH, Liu WL. Effects of Zuojin pill on depressive behavior and gastrointestinal function in rats with chronic unpredictable mild stress:role of the brain-gut axis. J Ethnopharmacol. 2020;254:112713.
9. Wang QS, Cui YL, Dong TJ, Zhang XF, Lin KM. Ethanol extract from a Chinese herbal formula, "Zuojin Pill", inhibit the expression of inflammatory mediators in lipopolysaccharide-stimulated RAW 264.7 mouse macrophages. J Ethnopharmacol. 2012;141:377-85.
10. Wang QS, Ding SL, Mao HP, Cui YL, Qi XJ. Antidepressant-like effect of ethanol extract from Zuojin Pill, containing two herbal drugs of Rhizoma Coptidis and Fructus Evodiae, is explained by modulating the monoaminergic neurotransmitter system in mice. J Ethnopharmacol. 2013;148:603-9.
11. Sun MY, Wang DD, Sun J, Zhao XH, Cai S, Wu QX, Jie T, Ni ZH, Sun JY, Tang QF. The Zuo Jin Wan Formula increases chemosensitivity of human primary gastric cancer cells by AKT mediated mitochondrial translocation of cofilin-1. Chin J Nat Med. 2019;17:198-208.
12. Gao L, Jia C, Zhang H, Ma C. Wenjing decoction (herbal medicine) for the treatment of primary dysmenorrhea:a systematic review and metaanalysis. Arch Gynecol Obstet. 2017;296:679-89.
13. Nam EY, Kim SA, Kim H, Kim SH, Han JH, Lee JH, Kim DI. Akt activation by Evodiae Fructus extract protects ovary against 4-vinylcyclohexene diepoxide-induced ovotoxicity. J Ethnopharmacol. 2016;194:733-9.
14. Hibino T, Yuzurihara M, Kanno H, Kase Y, Takeda A. Goshuyuto, a traditional Japanese medicine, and aqueous extracts of Evodiae Fructus constrict isolated rat aorta via adrenergic and/or serotonergic receptors. Biol Pharm Bull. 2009;32:237-41.
15. Wu P, Chen Y. Evodiamine ameliorates paclitaxel-induced neuropathic pain by inhibiting inflammation and maintaining mitochondrial antioxidant functions. Hum Cell. 2019;32:251-9.
16. Liang X, Li B, Wu F, Li T, Wang Y, Ma Q, Liang S. Bitterness and antibacterial activities of constituents from Evodia rutaecarpa. BMC Complement Altern Med. 2017;17:180.
17. Zuo GY, He HP, Wang BG, Hong X, Hao XJ. New indoloquinazoline alkaloid from the fruit of Evodia rutaecarpa. Plant Diversity and Resources. 2003;25:103-6.
18. Sugimoto T, Miyase T, Kuroyanagi M, Ueno A. Limonoids and Quinolone Alkaloids from Evodia rutaecarpa BENTHAM. Chem Pharm Bull. 1988;36:4453-61.
19. Wang TY, Wu JB, Hwang TL, Kuo YH, Chen JJ. A new quinolone and other constituents from the fruits of Tetradium ruticarpum effects on neutrophil pro-inflammatory responses. Chem Biodiversity. 2010;7:1828-34.
20. Zhao N, Li ZL, Li DH, Sun YT, Shan DT, Bai J, Pei YH, Jing YK, Hua HM. Quinolone and indole alkaloids from the fruits of Euodia rutaecarpa and their cytotoxicity against two human cancer cell lines. Phytochemistry. 2015;109:133-9.
21. Huang X, Zhang YB, Yang XW. Indoloquinazoline alkaloids from Euodia rutaecarpa and their cytotoxic activities. J Asian Nat Prod Res. 2011;13:977-83.
22. Li DW, Zhang M, Feng L, Huang SS, Zhang BJ, Liu SS, Deng S, Wang C, Ma XC, Leng AJ. Alkaloids from the nearly ripe fruits of Evodia rutaecarpa and their bioactivities. Fitoterapia. 2020;146:104668.
23. Zhang XL, Sun J, Wu HH, Jing YK, Chai X, Wang YF. A new indoloquinazoline alkaloidal glucoside from the nearly ripe fruits of Evodia rutaecarpa. Nat Prod Res. 2013;27:1917-21.
24. Yan Q, Shan Y, Yin M, Xu S, Ma C, Tong HY, Feng X, Wang QZ. Phytochemical and chemotaxonomic study on Evodia rutaecarpa var. officinalis. Biochem Syst Ecol. 2020;88.
25. Zhou Y, Li SH, Jiang RW, Cai M, Liu X, Ding LS, Xu HX, But PP, Shaw PC. Quantitative analyses of indoloquinazoline alkaloids in Fructus Evodiae by high-performance liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry. Rapid Commun Mass Spectrom. 2006;20:3111-8.
26. Xu HY, Zhang TJ, Xiao XF, Zhao P, Liu CX, Xu J. Simultaneous analysis of thirteen bioactive components in Evodia rutaecarpa and its varieties by HPLC-DAD-MS. Chin Herb Med. 2010;2:112-7.
27. Wang QZ, Liang JY, Feng X. Evodiagenine and dievodiamine, two new indole alkaloids from Evodia rutaecarpa. Chin Chem Lett. 2010;21:596-9.
28. Kato A, Yasuko H, Goto H, Hollinshead J, Nash RJ, Adachi I. Inhibitory effect of rhetsinine isolated from Evodia rutaecarpa on aldose reductase activity. Phytomedicine. 2009;16:258-61.
29. Su XL, Xu S, Shan Y, Yin M, Chen Y, Feng X, Wang QZ. Three new quinazolines from Evodia rutaecarpa and their biological activity. Fitoterapia. 2018;127:186-92.
30. Liu QZ, Li HQ, Liu ZL. Nematocidal Constituents from the Ethanol Extract ofEvodia rutaecarpaHort Unripe Fruits. J Chem. 2013;2013:1-5.
31. Liu ZL, Liu QZ, Du SS, Deng ZW. Mosquito larvicidal activity of alkaloids and limonoids derived from Evodia rutaecarpa unripe fruits against Aedes albopictus (Diptera:Culicidae). Parasitol Res. 2012;111:991-6.
32. Zuo GY, Yang XS, Hao XJ. Two New Indole Alkaloids from Evodia rutaecarpa. Chin Chem Lett. 2000;11:127-8.
33. Jin HZ, Du JL, Zhang WD, Chen HS, Lee JH, Lee JJ. A novel alkaloid from the fruits of Evodia officinalis. J Asian Nat Prod Res. 2007;9:685-8.
34. Jin HZ, Du JL, Zhang WD, Yan SK, Chen HS, Lee JH, Lee JJ. A new quinazolinedione alkaloid from the fruits of Evodia officinalis. Fitoterapia. 2008;79:317-8.
35. Teng J, Yang XW. Two new indoloquinazoline alkaloids from the unripe fruits of Evodia rutaecarpa. Heterocycles. 2006;68:1691-8.
36. Yang XW, Teng J, Wang Y, Xu W. The permeability and the efflux of alkaloids of the Evodiae fructus in the Caco-2 model. Phytother Res. 2009;23:56-60.
37. Li YH, He J, Li Y, Wu XD, Peng LY, Du RN, Cheng X, Zhao QS, Li RT. Evollionines A-C, three new alkaloids isolated from the fruits of Evodia rutaecarpa. Helv Chim Acta. 2014;97:1481-6.
38. Tang YQ, Feng XZ, Huang L. Studies on the chemical constituents of Evodia rutaecarpa[Juss] Benth. J Chin Pharm Sci. 1997;6:65-9.
39. Su XL, Yin M, Xu S, Shan Y, Feng X, Wang QZ. Analysis of chemical constituents in Evodia rutaecarpa by UPLC-Q-TOF-MS. Chin Tradit Patent Med. 2017;39:1223-7.
40. Li YH, Zhang Y, Peng LY, Li XN, Zhao QS, Li RT, Wu XD. (+/-)-Evodiakine, a pair of rearranged rutaecarpine-type alkaloids from Evodia rutaecarpa. Nat Prod Bioprospect. 2016;6:291-6.
41. Wang XX, Gao HY, Jiang Y, Zhao MB, Tu PF. Chemical constituents from fruits of Euodia rutaecarpa. Chin Tradit Herbal Drugs. 2013;44:1241-4.
42. Yu LL, Ho LK, Liao JF, Chen CF. Two 5-HT1A receptor-interactive tryptamine derivatives from the unripe Fruit of Evodia rutaecarpa. J Nat Prod. 1997;60:1196-8.
43. Wang XX, Zan K, Shi SP, Zeng KW, Jiang Y, Guan Y, Xiao CL, Gao HY, Wu LJ, Tu PF. Quinolone alkaloids with antibacterial and cytotoxic activities from the fruits of Evodia rutaecarpa. Fitoterapia. 2013;89:1-7.
44. Zhuang PY, Wang XX, Chen JJ, Zhang DY, Lin XY, Yang YK. Extraction of novel quinolones alkaloid in evodia rutaecarpa useful as neuroprotector patent CN106810495A.2017.
45. Jin HZ, Lee JH, Lee D, Lee HS, Hong YS, Kim YH, Lee JJ. Quinolone alkaloids with inhibitory activity against nuclear factor of activated T cells from the fruits of Evodia rutaecarpa. Biol Pharm Bull. 2004;27:926-8.
46. Adams M, Kunert O, Haslinger E, Bauer R. Inhibition of leukotriene biosynthesis by quinolone alkaloids from the fruits of Evodia rutaecarpa. Planta Med. 2004;70:904-8.
47. Huang X, Li W, Yang XW. New cytotoxic quinolone alkaloids from fruits of Evodia rutaecarpa. Fitoterapia. 2012;83:709-14.
48. Han XH, Hong SS, Lee D, Lee JJ, Lee MS, Moon DC, Han K, Oh KW, Lee MK, Ro JS, Hwang BY. Quinolone alkaloids from evodiae fructus and their inhibitory effects on monoamine oxidase. Arch Pharm Res. 2007;30:397-401.
49. Pan X, Bligh SW, Smith E. Quinolone alkaloids from Fructus Euodiae show activity against methicillin-resistant Staphylococcus aureus. Phytother Res. 2014;28:305-7.
50. Yang XW, Zhang H, Li M, Du LJ, Yang Z, Xiao SY. Studies on the alkaloid constituents of Evodia rutaecarpa (Juss) Benth var. bodinaieri (Dode) Huang and their acute toxicity in mice. J Asian Nat Prod Res. 2006;8:697-703.
51. Lee MK, Hwang BY, Lee SA, Oh GJ, Choi WH, Hong SS, Lee KS, Ro JS. 1-methyl-2-undecyl-4(1H)-quinolone as an irreversible and selective inhibitor of type B monoamine oxidase. Chem Pharm Bull. 2003;51:409-11.
52. Adams M, Mahringer A, Kunert O, Fricker G, Efferth T, Bauer R. Cytotoxicity and p-glycoprotein modulating effects of quinolones and indoloquinazolines from the Chinese herb Evodia rutaecarpa. Planta Med. 2007;73:1554-7.
53. Ma C, Liu X, Shan Y, Xu S, Su XL, Feng X, Wang QZ. A new quinolone alkaloid with cytotoxic activity from the fruits of Euodia Rutaecarpa. Nat Prod Commun. 2018;13:339-41.
54. Shin HK, Do JC, Son JK, Lee CS, Lee CH, Cheong CJ. Quinoline alkaloids from the fruits of Evodia officinalis. Planta Med. 1998;64:764-5.
55. Ko JS, Rho MC, Chung MY, Song HY, Kang JS, Kim K, Lee HS, Kim YK. Quinolone alkaloids, diacylglycerol acyltransferase inhibitors from the fruits of Evodia rutaecarpa. Planta Med. 2002;68:1131-3.
56. Hamasaki N, Ishii E, Tominaga K, Tezuka Y, Nagaoka T, Kadota S, Kuroki T, Yano I. Highly selective antibacterial activity of novel alkyl quinolone alkaloids from a Chinese Herbal Medicine, Gosyuyu (Wu-Chu-Yu), against Helicobacter pylori in vitro. Microbiol Immunol. 2000;44:9-15.
57. Ling Y, Hu P, Zhang L, Jin H, Chen J, Tao Z, Huang L, Ren R. Identification and structural characterization of acylgluconic acids, flavonol glycosides, limonoids and alkaloids from the fruits of Evodia Rutaecarpa by high performance liquid chromatography coupled to electrospray ionization and quadrupole time-of-flight mass spectrometry. J Chromatogr Sci. 2016;54:1593-604.
58. Tang YQ, Feng XZ, Huang L. Quinolone alkaloids from Evodia Rutaecarpa. Phytochemistry. 1996;43:719-22.
59. Chen M, Liu X, Shan Y, Xu S, Feng X, Wang QZ. A new quinolone alkaloid from the fruits of Tetradium ruticarpum. Nat Prod Res. 2021;35:222-7.
60. Liang J, Chen Y, Ren G, Dong W, Shi M, Xiong L, Li J, Dong J, Li F, Yuan J. Screening hepatotoxic components in Euodia rutaecarpa by UHPLCQTOF/MS based on the spectrum-toxicity relationship. Molecules. 2017;22:1264.
61. Varamini P, Javidnia K, Soltani M, Mehdipour A, Ghaderi A. Cytotoxic activity and cell cycle analysis of quinoline alkaloids isolated from haplophyllum canaliculatum boiss. Planta Med. 2009;75:1509-16.
62. Qiong LI, Tang C, Changqiang KE, Yang YE. A new limonoid from the fruits of Evodia rutaecarpa (Juss.) Benth. J Technol. 2018;18:14-8.
63. Li YH, Liu X, Yin M, Liu F, Wang B, Feng X, Wang QZ. Two new quinolone alkaloids from the nearly ripe fruits of Tetradium ruticarpum. Nat Prod Res. 2019;4:1-6.
64. Zhou X, Zhao Y, Lei P, Cai Z, Liu H. Chromatographic fingerprint study on Evodia rutaecarpa (Juss.) Benth by HPLC/DAD/ESI-MS(n) technique. J Sep Sci. 2010;33:2258-65.
65. Hibino T, Yuzurihara M, Kase Y, Takeda A. Synephrine, a component of Evodiae Fructus, constricts isolated rat aorta via adrenergic and serotonergic receptors. J Pharmacol Sci. 2009;111:73-81.
66. Zhang QH, Gao HY, Wu LJ, Zhang L. Chemical constituents of Evodia rutaecarpa (Juss.) Benth. J Shenyang Pharm Univ. 2005;22:12-4.
67. Zhao N, Li DH, Li ZL, Hua HM. Isolation and identification of the chemical constituents from the fruits of Euoida rutaecarpa. J Shenyang Pharm Univ. 2016;33:103-9.
68. Gong XJ, Zhou X, Cai ZW, Zhang JX, Zhou W. Studies on chemical constituents of Evodia rutaecarpa. China J Chin Mater Med. 2009;34:177-9.
69. Matsuda H, Yoshikawa M, Iinuma M, Kubo M. Antinociceptive and anti-inflammatory activities of limonin isolated from the fruits of Evodia rutaecarpa var. bodinieri. Planta Med. 1998;64:339-42.
70. Shi YS, Xia HM, Wu CH, Li CB, Duan CC, Che C, Zhang XJ, Li HT, Zhang Y, Zhang XF. Novel nortriterpenoids with new skeletons and limonoids from the fruits of Evodia rutaecarpa and their bioactivities. Fitoterapia. 2020;142:104503.
71. Yang ZX, Meng YH, Wang QH, Yang BY, Kuang HX. Substance basis of bitter resolution and composition from Fructus Evodiae. Chin J Exp Tradit Med Formulae. 2011;17:74-7.
72. Ozaki Y, Miyake M, Maeda H, Ifuku Y, Bennett RD, Hasegawa S. Limonoid glucosides in Tetradium Rutaecarpa. Phytochemistry. 1991;30:2365-7.
73. Yang XB, Qian P, Yang XW, Liu JX, Gong NB, Lv Y. Limonoid constituents of Euodia rutaecarpa var. bodinieri and their inhibition on NO production in lipopolysaccharide-activated RAW264.7 macrophages. J Asian Nat Prod Res. 2013;15:1130-8.
74. Wang QZ, Liang JY, Chen J. Chemical constituents of Evodia rutaecarpa. J Chin Pharm Univ. 2005;36:520-2.
75. Hu J, Wu X, Cao G, Chen X. Analysis of the influence of processing of stir-baking with glycyrrhizae on the main components of Euodiae Fructus by high-performance liquid chromatography with diode array detector. Nat Prod Res. 2014;28:1853-8.
76. Hu CQ, Yang XB, Yang XW, Liu JX. Flavonoid glycosides from dried and nearly ripe fruits of Evodia rutaecarpa. China J Chin Mater Med. 2012;37:2571-5.
77. Liu SS, Dai YT, Sui F, Chen LM, Yan LH, Zhang QW, Wang ZM. Flavonol glycosides from the fruits of Evodia rutaecarpa. J Asian Nat Prod Res. 2018;20:867-74.
78. Xu ML, Li G, Moon DC, Lee CS, Woo MH, Lee ES, Jahng Y, Chang HW, Lee SH, Son JK. Cytotoxicity and DNA topoisomerase inhibitory activity of constituents isolated from the fruits of Evodia officinalis. Arch Pharm Res. 2006;29:541-7.
79. Liu AJ, Wang SH, Chen KC, Kuei HP, Shih YL, Hou SY, Chiu WT, Hsiao SH, Shih CM. Evodiamine, a plant alkaloid, induces calcium/JNK-mediated autophagy and calcium/mitochondria-mediated apoptosis in human glioblastoma cells. Chem Biol Interact. 2013;205:20-8.
80. Chuang WC, Cheng CM, Chang HC, Chen YP, Sheu SJ. Contents of constituents in mature and immature fruits of Evodia species. Planta Med. 1999;65:567-71.
81. Zhang XL, Jing YK, Peng SW, Li SS, Chai X, Wang YF. Chemical constituents from the nearly ripe fruits of Evodia rutaecarpa (Juss.) Benth. Nat Prod Res Dev. 2013;25:470-4.
82. Gai L, Rao GX, Song CQ, Hu ZB. Studies on the chemical constituents of Evodia rutaecarpa (Juss.) Benth. var. officinalis (Dode) Huang. Acta Pharm Sin. 2001;36:743-5.
83. Wang L, Wang DJ, Guo W, Sun KB, Huang NN, Sun R. Four new caffeoylgluconic acid positional isomers from the fruits of Evodia rutaecarpa. J Asian Nat Prod Res. 2019;21:1104-11.
84. Zhao N, Li ZL, Li DH, Hua HM. A new phenylpropanoid glycoside from Euodia rutaecarpa. Chin Tradit Herbal Drugs. 2015;46:15-8.
85. He W, Jiang Y, Zhao MB, Zeng KW, Tu PF. Ruticarpsides A-C, three new ester glycosides from the fruits of Tetradium ruticarpum. J Asian Nat Prod Res. 2017;19:659-65.
86. Xin X, Shao B, Li Y, Liu S, Li D, Wang C, Chen L, Jin L, Ma X, Wu G. New chemical constituents from the fruits of Tetradium ruticarpum. Nat Prod Res. 2022;36:1673-8.
87. Zhao MY, Yang XW. Two new acylgluconic acids from the nearly ripe fruits of Evodia rutaecarpa. J Asian Nat Prod Res. 2008;10:759-63.
88. Seya K, Furukawa K, Chiyoya M, Yu Z, Kikuchi H, Daitoku K, Motomura S, Murakami M, Oshima Y, Fukuda I. 1-Methyl-2-undecyl-4(1H)- quinolone, a derivative of quinolone alkaloid evocarpine, attenuates high phosphate-induced calcification of human aortic valve interstitial cells by inhibiting phosphate cotransporter PiT-1. J Pharmacol Sci. 2016;131:51-7.
89. Survay NS, Upadhyaya CP, Kumar B, Young KE, Yoon DY, Park SW. New genera of flavonols and flavonol derivatives as therapeutic molecules. J Korean Soc Appl Biol Chem. 2011;54:1-18.
90. Carullo G, Cappello AR, Frattaruolo L, Badolato M, Armentano B, Aiello F. Quercetin and derivatives:useful tools in inflammation and pain management. Future Med Chem. 2017;9:79-93.
91. Liu SS, Liu ZX, Wei H, Yin YY, Zhang QW, Yan LH, Wang ZM, Yang LX. Chemical compositions, yield variations and antimicrobial activities of essential oils from three species of Euodiae Fructus in China. Ind Crop Prod. 2019;138:7.
92. Lou FM, Li QF, Huang XN, Qiu WW. Analysis of the essential oil from Evodia rutaecarpa (Juss.) Benth. by SPME-GC-MS. Chin J Pharm Anal. 2010;30:1248-53.
93. Liu ZL, Du SS. Fumigant components from the essential oil of Evodia rutaecarpa Hort unripe fruits. E-J Chem. 2011;8:1937-43.
94. Fu J, Zhao H. Analysis of volatile oil constituents in Evodia rutaecarpa Benth. and E. lenticellata Huang by GC-MS. Lishizhen Med Mater Med Res. 2010;21:60-4.
95. Yin LS, Sun R. Research progress on pharmacology and toxicology of the Volatile Oil components from Evodia Fructus. Chin J Pharmacovigilance. 2016;13:162-4.
96. Park SY, Park C, Park SH, Hong SH, Kim GY, Hong SH, Choi YH. Induction of apoptosis by ethanol extract of Evodia rutaecarpa in HeLa human cervical cancer cells via activation of AMP-activated protein kinase. Biosci Trends. 2017;10:467-76.
97. Park E, Lee MY, Seo CS, Jang JH, Kim YU, Shin HK. Ethanol extract of Evodia rutaecarpa attenuates cell growth through caspase-dependent apoptosis in benign prostatic hyperplasia-1 cells. Nutrients. 2018;10:523.
98. Thuille N, Fille M, Nagl M. Bactericidal activity of herbal extracts. Int J Hyg Environ Health. 2003;206:217-21.
99. Chang CP, Chang JY, Wang FY, Tseng YM, Chang JG. The effect of Evodia rutaecarpa extract on cytokine secretion by human mononuclear cells in vitro. Am J Chin Med. 1995;23:173-80.
100. Chiou WF, Ko HC, Wei BL. Evodia rutaecarpa and three major alkaloids abrogate influenza A virus (H1N1)-induced chemokines production and cell migration. J Evid-Based Complement Altern Med. 2011;2011:1-10.
101. Matsuda H, Wu JX, Tanaka T, Iinuma M, Kubo M. Antinociceptive activities of 70% methanol extract of evodiae fructus (fruit of Evodia rutaecarpa var. bodinieri) and its alkaloidal components. Biol Pharm Bull. 1997;20:243-8.
102. Yu LL, Liao JF, Chen CE. Anti-diarrheal effect of water extract of Evodiae fructus in mice. J Ethnopharmacol. 2000;73:39-45.
103. Chao DC, Lin LJ, Hsiang CY, Li CC, Lo HY, Liang JA, Kao ST, Wu SL, Ho TY. Evodiamine inhibits 12-O-tetradecanoylphorbol-13-acetate-induced activator protein 1 transactivation and cell transformation in human hepatocytes. Phytother Res. 2011;25:1018-23.
104. Guo W, Huang JH, Wang N, Tan HY, Cheung F, Chen FY, Feng YB. Integrating network pharmacology and pharmacological evaluation for deciphering the action mechanism of herbal formula zuojin pill in suppressing hepatocellular carcinoma. Front Pharmacol. 2019;10:1185.
105. Cai A, Xiao L, Zhou YP, Zhang ZG, Yang QW. Effect of Evodia rutaecarpa (Juss) Benth extract on Alzheimer disease in mice. Trop J Pharm Res. 2020;19:823-8.
106. Lim DK, Lee YB, Kim HS. Effects of dehydroevodiamine exposure on glutamate release and uptake in the cultured cerebellar cells. Neurochem Res. 2004;29:407-11.
107. Park CH, Kim SH, Choi W, Lee YJ, Kim JS, Kang SS, Suh YH. Novel anticholinesterase and antiamnesic activities of dehydroevodiamine, a constituent of Evodia rutaecarpa. Planta Med. 1996;62:405-9.
108. Fang J, Liu R, Tian Q, Hong XP, Wang SH, Cao FY, Pan XP, Wang JZ. Dehydroevodiamine attenuates calyculin A-induced tau hyperphosphorylation in rat brain slices. Acta Pharmacol Sin. 2007;28:1717-23.
109. Peng JH, Zhang CE, Wei W, Hong XP, Pan XP, Wang JZ. Dehydroevodiamine attenuates tau hyperphosphorylation and spatial memory deficit induced by activation of glycogen synthase kinase-3 in rats. Neuropharmacology. 2007;52:1521-7.
110. Shin KY, Kim KY, Suh YH. Dehydroevodiamine. HCl enhances cognitive function in memory-impaired rat models. Korean J Physiol Pharmacol. 2017;21:55-64.
111. Wang D, Wang C, Liu L, Li S. Protective effects of evodiamine in experimental paradigm of Alzheimer's disease. Cogn Neurodyn. 2018;12:303-13.
112. Yuan SM, Gao K, Wang DM, Quan XZ, Liu JN, Ma CM, Qin C, Zhang LF. Evodiamine improves congnitive abilities in SAMP8 and APP(swe)/PS1(DeltaE9) transgenic mouse models of Alzheimer's disease. Acta Pharmacol Sin. 2011;32:295-302.
113. Zhang Y, Wang J, Wang C, Li Z, Liu X, Zhang J, Lu J, Wang D. Pharmacological basis for the use of Evodiamine in Alzheimer's Disease:antioxidation and antiapoptosis. Int J Mol Sci. 2018;19:1527.
114. Lee B, Choi EJ, Lee EJ, Han SM, Hahm DH, Lee HJ, Shim I. The neuroprotective effect of methanol extract of gagamjungjihwan and fructus "euodiae on ischemia-induced neuronal and cognitive impairment in the rat. J Evid-Based Complement Altern Med. 2011;2011:685254.
115. Zhang YN, Yang YF, Yang XW. Blood-brain barrier permeability and neuroprotective effects of three main alkaloids from the fruits of Euodia rutaecarpa with MDCK-pHaMDR cell monolayer and PC12 cell line. Biomed Pharmacother. 2018;98:82-7.
116. Zhang WD, Chen XY, Wu C, Lian YN, Wang YJ, Wang JH, Yang F, Liu CH, Li XY. Evodiamine reduced peripheral hypersensitivity on the mouse with nerve injury or inflammation. Mol Pain. 2020;16:1744806920902563.
117. Han M, Hu L, Chen Y. Rutaecarpine may improve neuronal injury, inhibits apoptosis, inflammation and oxidative stress by regulating the expression of ERK1/2 and Nrf2/HO-1 pathway in rats with cerebral ischemia-reperfusion injury. Drug Des Devel Ther. 2019;13:2923-31.
118. Ko HC, Wang YH, Liou KT, Chen CM, Chen CH, Wang WY, Chang S, Hou YC, Chen KT, Chen CF, Shen YC. Anti-inflammatory effects and mechanisms of the ethanol extract of Evodia rutaecarpa and its bioactive components on neutrophils and microglial cells. Eur J Pharmacol. 2007;555:211-7.
119. Woo HG, Lee CH, Noh MS, Lee JJ, Jung YS, Baik EJ, Moon CH, Lee SH. Rutaecarpine, a quinazolinocarboline alkaloid, inhibits prostaglandin production in RAW264.7 macrophages. Planta Med. 2001;67:505-9.
120. Li Z, Yang M, Peng Y, Gao M, Yang B. Rutaecarpine ameliorated sepsisinduced peritoneal resident macrophages apoptosis and inflammation responses. Life Sci. 2019;228:11-20.
121. Moon TC, Murakami M, Kudo I, Son KH, Kim HP, Kang SS, Chang HW. A new class of COX-2 inhibitor, rutaecarpine from Evodia rutaecarpa. Inflamm Res. 1999;48:621-5.
122. Zhang YB, Yan TT, Sun DX, Xie C, Wang TX, Liu XY, Wang J, Wang Q, Luo YH, Wang P, Yagai T, Krausz KW, Yang XW, Gonzalez FJ. Rutaecarpine inhibits KEAP1-NRF2 interaction to activate NRF2 and ameliorate dextran sulfate sodium-induced colitis. Free Radic Bio Med. 2020;148:33-41.
123. Zhao Z, Gong S, Wang S, Ma C. Effect and mechanism of evodiamine against ethanol-induced gastric ulcer in mice by suppressing Rho/NFsmall ka, CyrillicB pathway. Int Immunopharmacol. 2015;28:588-95.
124. Fan X, Zhu JY, Sun Y, Luo L, Yan J, Yang X, Yu J, Tang WQ, Ma W, Liang HP. Evodiamine inhibits zymosan-induced inflammation in vitro and in vivo:inactivation of NF-kappaB by inhibiting IkappaBalpha phosphorylation. Inflammation. 2017;40:1012-27.
125. Zhang H, Yin L, Lu M, Wang J, Li YT, Gao WL, Yin ZS. Evodiamine attenuates adjuvant-induced arthritis in rats by inhibiting synovial inflammation and restoring the Th17/Treg balance. J Pharm Pharmacol. 2020;72:798-806.
126. Lin J, Zhang X, Li C, Zhang Y, Lu H, Chen J, Li Z, Yang X, Wu Z. Evodiamine via targeting nNOS and AMPA receptor GluA1 inhibits nitroglycerin-induced migraine-like response. J Ethnopharmacol. 2020;254:112727.
127. Kobayashi Y. The nociceptive and anti-nociceptive effects of Evodiamine from fruits of Evodia rutaecarpa in mice. Planta Med. 2003;69:425-8.
128. Liu S, Zhang S, Lv X, Lu J, Ren C, Zeng Z, Zheng L, Zhou X, Fu H, Zhou D, Chen Y. Limonin ameliorates ulcerative colitis by regulating STAT3/miR- 214 signaling pathway. Int Immunopharmacol. 2019;75:105768.
129. Du J, Wang XF, Zhou QM, Zhang TL, Lu YY, Zhang H, Su SB. Evodiamine induces apoptosis and inhibits metastasis in MDAMB-231 human breast cancer cells in vitro and in vivo. Oncol Rep. 2013;30:685-94.
130. Wang KL, Hsia SM, Yeh JY, Cheng SC, Wang PS, Wang SW. Anti-proliferative effects of evodiamine on human breast cancer cells. PLoS ONE. 2013;8:e67297.
131. Hong Z, Wang Z, Zhou B, Wang J, Tong H, Liao Y, Zheng P, Jamshed MB, Zhang Q, Chen H. Effects of evodiamine on PI3K/Akt and MAPK/ERK signaling pathways in pancreatic cancer cells. Int J Oncol. 2020;56:783-93.
132. Su Z, Wang C, Chang D, Zhu X, Sai C, Pei J. Limonin attenuates the stemness of breast cancer cells via suppressing MIR216A methylation. Biomed Pharmacother. 2019;112:108699.
133. Yang ZG, Chen AQ, Liu B. Antiproliferation and apoptosis induced by evodiamine in human colorectal carcinoma cells (COLO-205). Chem Biodivers. 2009;6:924-33.
134. Li FS, Huang J, Cui MZ, Zeng JR, Li PP, Li L, Deng Y, Hu Y, He BC, Shu DZ. BMP9 mediates the anticancer activity of evodiamine through HIF1alpha/p53 in human colon cancer cells. Oncol Rep. 2020;43:415-26.
135. Huang J, Chen ZH, Ren CM, Wang DX, Yuan SX, Wu QX, Chen QZ, Zeng YH, Shao Y, Li Y, Wu K, Yu Y, Sun WJ, He BC. Antiproliferation effect of evodiamine in human colon cancer cells is associated with IGF-1/HIF- 1alpha downregulation. Oncol Rep. 2015;34:3203-11.
136. Ogasawara M, Matsunaga T, Takahashi S, Saiki I, Suzuki H. Antiinvasive and metastatic activities of evodiamine. Biol Pharm Bull. 2002;25:1491-3.
137. Zhou P, Li XP, Jiang R, Chen Y, Lv XT, Guo XX, Tian K, Yuan DZ, Lv YW, Ran JH, Li J, Chen DL. Evodiamine inhibits migration and invasion by Sirt1-mediated post-translational modulations in colorectal cancer. Anticancer Drugs. 2019;30:611-7.
138. Hong JY, Park SH, Min HY, Park HJ, Lee SK. Anti-proliferative effects of evodiamine in human lung cancer cells. J Cancer Prev. 2014;19:7-13.
139. Su T, Yang X, Deng JH, Huang QJ, Huang SC, Zhang YM, Zheng HM, Wang Y, Lu LL, Liu ZQ. Evodiamine, a novel NOTCH3 methylation stimulator, significantly suppresses lung carcinogenesis in vitro and in vivo. Front Pharmacol. 2018;9:434.
140. Yang X, Zhang Y, Huang Y, Wang Y, Qi X, Su T, Lu L. Evodiamine suppresses Notch3 signaling in lung tumorigenesis via direct binding to gamma-secretases. Phytomedicine. 2020;68:153176.
141. Gong C, Qi L, Huo Y, Zhang S, Ning X, Bai L, Wang Z. Anticancer effect of Limonin against benzo(a)pyrene-induced lung carcinogenesis in Swiss albino mice and the inhibition of A549 cell proliferation through apoptotic pathway. J Biochem Mol Toxicol. 2019;33:e22374.
142. Hu CY, Wu HT, Su YC, Lin CH, Chang CJ, Wu CL. Evodiamine exerts an anti-hepatocellular carcinoma activity through a WWOX-dependent pathway. Molecules. 2017;22:1175.
143. Yang F, Shi L, Liang T, Ji L, Zhang G, Shen Y, Zhu F, Xu L. Anti-tumor effect of evodiamine by inducing Akt-mediated apoptosis in hepatocellular carcinoma. Biochem Biophys Res Commun. 2017;485:54-61.
144. Guo XX, Li XP, Zhou P, Li DY, Lyu XT, Chen Y, Lyu YW, Tian K, Yuan DZ, Ran JH, Chen DL, Jiang R, Li J. Evodiamine induces apoptosis in SMMC-7721 and HepG2 cells by suppressing NOD1 signal pathway. Int J Mol Sci. 2018;19:3419.
145. Zhao S, Xu K, Jiang R, Li DY, Guo XX, Zhou P, Tang JF, Li LS, Zeng D, Hu L, Ran JH, Li J, Chen DL. Evodiamine inhibits proliferation and promotes apoptosis of hepatocellular carcinoma cells via the Hippo- Yes-Associated Protein signaling pathway. Life Sci. 2020;251:117424.
146. Tang Z, Tang Y, Li L, Liu T, Yang J. Limonin provokes hepatocellular carcinoma cells with stemness entry into cycle via activating PI3K/Akt signaling. Biomed Pharmacother. 2019;117:109051.
147. Wen Z, Feng S, Wei L, Wang Z, Hong D, Wang Q. Evodiamine, a novel inhibitor of the Wnt pathway, inhibits the self-renewal of gastric cancer stem cells. Int J Mol Med. 2015;36:1657-63.
148. Hu C, Gao X, Han Y, Guo Q, Zhang K, Liu M, Wang Y, Wang J. Evodiamine sensitizes BGC-823 gastric cancer cells to radiotherapy in vitro and in vivo. Mol Med Rep. 2016;14:413-9.
149. Wu WS, Chien CC, Liu KH, Chen YC, Chiu WT. Evodiamine prevents glioma growth, induces glioblastoma cell apoptosis and cell cycle arrest through JNK activation. Am J Chin Med. 2017;45:879-99.
150. Zhang T, Qu S, Shi Q, He D, Jin X. Evodiamine induces apoptosis and enhances TRAIL-induced apoptosis in human bladder cancer cells through mTOR/S6K1-mediated downregulation of Mcl-1. Int J Mol Sci. 2014;15:3154-71.
151. Shi CS, Li JM, Chin CC, Kuo YH, Lee YR, Huang YC. Evodiamine induces cell growth arrest, apoptosis and suppresses tumorigenesis in human urothelial cell carcinoma cells. Anticancer Res. 2017;37:1149-59.
152. Bae JR, Park WH, Suh DH, No JH, Kim YB, Kim K. Role of limonin in anticancer effects of Evodia rutaecarpa on ovarian cancer cells. BMC Complement Med Ther. 2020;20:94.
153. Chen TC, Chien CC, Wu MS, Chen YC. Evodiamine from Evodia rutaecarpa induces apoptosis via activation of JNK and PERK in human ovarian cancer cells. Phytomedicine. 2016;23:68-78.
154. Wei LJ, Jin XY, Cao ZP, Li WL. Evodiamine induces extrinsic and intrinsic apoptosis of ovarian cancer cells via the mitogen-activated protein kinase phosphatidylinositol-3-kinaseprotein kinase B signaling pathways. J Tradit Chin Med. 2016;36:353-9.
155. Yuan XL, Zhang P, Liu XM, Du YM, Hou XD, Cheng S, Zhang ZF. Cytological assessments and transcriptome profiling demonstrate that evodiamine inhibits growth and induces apoptosis in a renal carcinoma cell line. Sci Rep. 2017;7:12572.
156. Wu WS, Chien CC, Chen YC, Chiu WT. Protein kinase RNA-like endoplasmic reticulum kinase-mediated Bcl-2 protein phosphorylation contributes to evodiamine-induced apoptosis of human renal cell carcinoma cells. PLoS ONE. 2016;11:e0160484.
157. Wang C, Li S, Wang MW. Evodiamine-induced human melanoma A375-S2 cell death was mediated by PI3K/Akt/caspase and Fas-L/NF-kappaB signaling pathways and augmented by ubiquitin-proteasome inhibition. Toxicol In Vitro. 2010;24:898-904.
158. Zhang Y, Zhang QH, Wu LJ, Tashiro S, Onodera S, Ikejima T. Atypical apoptosis in L929 cells induced by evodiamine isolated from Evodia rutaecarpa. J Asian Nat Prod Res. 2004;6:19-27.
159. Meng ZJ, Wu N, Liu Y, Shu KJ, Zou X, Zhang RX, Pi CJ, He BC, Ke ZY, Chen L, Deng ZL, Yin LJ. Evodiamine inhibits the proliferation of human osteosarcoma cells by blocking PI3K/Akt signaling. Oncol Rep. 2015;34:1388-96.
160. Zhou Y, Hu J. Evodiamine induces apoptosis, G2/M cell cycle arrest, and inhibition of cell migration and invasion in Human Osteosarcoma Cells via Raf/MEK/ERK signalling pathway. Med Sci Monit. 2018;24:5874-80.
161. Zhu B, Zhao L, Liu Y, Jin Y, Feng J, Zhao F, Sun J, Geng R, Wei Y. Induction of phosphatase shatterproof 2 by evodiamine suppresses the proliferation and invasion of human cholangiocarcinoma. Int J Biochem Cell Biol. 2019;108:98-110. |
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
| |
Shared |
|
|
|
|
| |
Discussed |
|
|
|
|
