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Coptidis Rhizoma and Its Main Bioactive Meng et al. Chin Med (2018) 13:13 https://doi.org/10.1186/s13020-018-0171-3 Chinese Medicine REVIEW Open Access Coptidis rhizoma and its main bioactive components: recent advances in chemical investigation, quality evaluation and pharmacological activity Fan‑Cheng Meng1, Zheng‑Feng Wu1, Zhi‑Qi Yin2, Li‑Gen Lin1, Ruibing Wang1* and Qing‑Wen Zhang1* Abstract Background: Coptidis rhizoma (CR) is the dried rhizome of Coptis chinensis Franch., C. deltoidea C. Y. Cheng et Hsiao or C. teeta Wall. (Ranunculaceae) and is commonly used in Traditional Chinese Medicine for the treatment of various diseases including bacillary dysentery, typhoid, tuberculosis, epidemic cerebrospinal meningitis, empyrosis, pertussis, and other illnesses. Methods: A literature survey was conducted via SciFinder, ScieneDirect, PubMed, Springer, and Wiley databases. A total of 139 selected references were classifed on the basis of their research scopes, including chemical investigation, quality evaluation and pharmacological studies. Results: Many types of secondary metabolites including alkaloids, lignans, phenylpropanoids, favonoids, phenolic compounds, saccharides, and steroids have been isolated from CR. Among them, protoberberine-type alkaloids, such as berberine, palmatine, coptisine, epiberberine, jatrorrhizine, columamine, are the main components of CR. Quantita‑ tive determination of these alkaloids is a very important aspect in the quality evaluation of CR. In recent years, with the advances in isolation and detection technologies, many new instruments and methods have been developed for the quantitative and qualitative analysis of the main alkaloids from CR. The quality control of CR has provided safety for pharmacological applications. These quality evaluation methods are also frequently employed to screen the active components from CR. Various investigations have shown that CR and its main alkaloids exhibited many powerful pharmacological efects including anti-infammatory, anti-cancer, anti-diabetic, neuroprotective, cardioprotective, hypoglycemic, anti-Alzheimer and hepatoprotective activities. Conclusion: This review summarizes the recent phytochemical investigations, quality evaluation methods, the bio‑ logical studies focusing on CR as well as its main alkaloids. Keywords: Coptidis rhizoma, Coptis genus, Phytochemistry, Quality evaluation, Pharmacological efects Background Makino and C. japonica var. dissecta are also used as CR Coptidis rhizoma (CR) is the dried rhizome of Coptis in Japan. CR has a long history of usage for clearing heat, chinensis Franch., C. deltoidea C. Y. Cheng et Hsiao or C. eliminating dampness, purging fre and detoxifcation teeta Wall. (Ranunculaceae). Te rhizomes of C. japonica in Traditional Chinese Medicine (TCM). CR, also called goldthread, was frequently used for the treatment of bacil- lary dysentery, typhoid, tuberculosis, epidemic cerebrospi- *Correspondence: [email protected]; [email protected] nal meningitis, empyrosis, pertussis, and other diseases. 1 State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macao SAR, People’s Chemical investigations have led to the discovery of Republic of China multiple secondary metabolites including alkaloids, lig- Full list of author information is available at the end of the article nans, phenylpropanoids, favonoids, phenolic acids, © The Author(s) 2018. This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/ publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated. Meng et al. Chin Med (2018) 13:13 Page 2 of 18 saccharides and steroids in CR. Protoberberine-type Alkaloids alkaloids, such as berberine, palmatine, coptisine, epiber- Alkaloids are the main components of CR (Fig. 1 and berine, jatrorrhizine and columamine, are the main bio- Table 1), of which protoberberine alkaloids are most active components of CR. common in plants from the Coptis genus. Most of them Achieving a high degree of quality control is very are isoquinolines and quaternary iminium type alkaloids. important to ensure the safety and efcacy of TCM. So far, the protoberberine alkaloids reported from CR Recent technological advances have made great progress include berberine-type (1–9) [15], oxyberberine-type in the quantitative and qualitative analysis of the main (10–16, 23–24, 30), methyl berberine type (20), and alkaloids extracted from CR. Te applications of High protoberberine-type (21) alkaloids. Benzophenanthri- Performance Liquid Chromatography (HPLC) or Ultra dines (17–19, 22), aporphine (25), benzylisoquinolines Performance Liquid Chromatography (UPLC) combined (26–27), phenethylamines (28–29, 35) and isoquino- with Mass Spectrometry (MS) or MS n [1, 2] and quan- lines (31–34) were also the main alkaloid components of titative 1H-NMR [3] are the most attractive strategies of various species of Coptis genus. Additionally, some other ensuring quality control. Besides, these quality evaluation nitrogen-containing molecules were also isolated from C. methods were also frequently employed to screen the chinensis [16–29]. pharmaceutically active components derived from CR [4, 5]. Lignans Various pharmacological investigations have indicated Lignans (Fig. 2 and Table 2) are also abundant in CR and that CR and its main alkaloids exhibit many biological have a wide variety of structures which can be classifed activities including anti-infammatory, anti-cancer, hypo- into several skeletal types, such as benzofurans (42–48), glycemic, anti-diabetic, neuroprotective and cardiopro- furofurans (49–53), tetrahydrofurans (54–60), arylnaph- tective efects [6–12]. In this paper, we have summarized thanlenes (61–63) and others (64–72) [18, 20, 26, 27, the phytochemical investigations, quality evaluation 30–38]. methods, and biological studies of CR as well as its main alkaloids that have been developed and conducted in Simple phenylpropanoids recent years. Simple phenylpropanoids with a mother-nucleus of phe- nylpropionic acid have been isolated from CR (Fig. 3 and Phytochemical investigation Table 3). Te esterifed derivatives of these phenylpropi- Previous phytochemical investigations on CR have led onic acids bearing methyl, ethyl, n-butyl, quinic acid, etc. to the isolation and identifcation of many types of natu- moieties were also isolated from the plants of CR [18–20, ral products including alkaloids, lignans, phenylpropa- 22, 26–28, 31–35, 37, 39]. noids, favonoids, phenolic compounds, saccharides and steroids. Up to this point, phytochemical investigations Flavonoids have focused on C. chinensis, C. Japonica var. dissecta, C. Plants of the Coptis genus also contain favonoids [33, 34, teeta and the main components of the plants from Coptis 36, 40]. Up to now, 8 favonoids (Fig. 4 and Table 4) have genus were found to be similar while the minor constitu- been isolated from CR. Meng [32] reported a 6,8-dime- ents difered. thyl substituted favonol (98) that was isolated from the Classic column chromatography utilizing silica gel as rhizome of C. teeta. Chen et al. [33] purifed a favonol the stationary phase was widely used for the isolation (99) and a favone (100) from the rhizome of C. chinensis. of constituents from CR. Column chromatography over In earlier chemical studies, a favanone (101) and a dihy- Sephadex LH-20, polyamide and octadecylsilane (ODS) drochalcone (102) were extracted from the seeds of C. was also used as well as preparative HPLC equipped with japonica, and three favonoid glycosides (103–105) were a reversed phase column or a chiral column. In general, isolated from the leaves of C. japonica and rhizomes of C. it has often been difcult to isolate alkaloids from CR. japonica var. dissecta [34, 36, 40]. However, through the application of suitable solvent sys- tems in high-speed countercurrent chromatography, such Others as n-hexane–ethyl-acetate–methanol–water (2:5:2:5) [13] Phenethyl alcohol and its glycosides (106–108), phe- and chloroform–methanol–water (4:3:3, v/v) with HCl nols and organic acids (109–117), hemiterpenoids (60 mM) and triethylamine (5 mM) added into the upper (118–121), dipeptides (122–123), β-sitosterol (124) and aqueous phase and the lower organic phase [14], the polysaccharides were also isolated from CR [18–20, 22, highly pure main alkaloids could be readily separated and 26–28, 32, 34, 37, 39]. Te structures of these compounds obtained in considerable yields. Spectroscopic analyses are shown in Fig. 5, while their corresponding references were employed in structural determination. and sources are summarized in Table 5. Meng et al. Chin Med (2018) 13:13 Page 3 of 18 Fig. 1 Structures of alkaloids isolated from Coptis genus Meng et al. Chin Med (2018) 13:13 Page 4 of 18 Table 1 Alkaloids isolated from Coptis genus No. Compounds Source Rfs. 1 Berberrubine C. chinensis [15, 16] 2 Berberine C. chinensis [16–22] 3 Coptisine C. chinensis [16–18, 21] 4 Palmatine C. chinensis [15, 17, 18, 21] 5 Epiberberine C. chinensis [15–18, 21] 6 Columbamine C. chinensis [15, 17, 18] 7 Tetradehydroscoulerine C. chinensis [17] 8 Jatrorrhizine C. chinensis [15, 17,
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