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Advances in Bio-Active Constituents, Pharmacology and Clinical Cao et al. Chin Med (2017) 12:36 https://doi.org/10.1186/s13020-017-0158-5 Chinese Medicine REVIEW Open Access Advances in bio‑active constituents, pharmacology and clinical applications of rhubarb Yu‑Jie Cao1, Zong‑Jin Pu1, Yu‑Ping Tang1,2* , Juan Shen1, Yan‑Yan Chen2, An Kang1, Gui‑Sheng Zhou1 and Jin‑Ao Duan1 Abstract Rhubarb is one of the most ancient, commonly used and important herbs in Chinese medicine. The modern researches of rhubarb clarifed the efcacies, ingredients and mechanisms in a more scientifc and rigorous way. The main chemical compositions of rhubarb include anthraquinones, anthrones, stilbenes, tannins, polysaccharides etc. These compositions show extensive pharmacological activities including regulating gastrointestinal, anticancer, antimicrobial, hepatoprotective, anti-infammatory, protecting cardiovascular, cerebrovascular and so on. This paper reviews the recent studies on the active ingredients, pharmacological efects, clinical application and functional mechanism. Keywords: Rhubarb, Ingredients, Pharmacological activities, Clinical application, Functional mechanism Background analysis. But there is no article to associate the diferent Rhubarb is a collective name of various perennial plants components of rhubarb with diseases. In this article, we of the genus Rheum L. from Polygonaceae family. Tis not only introduce the active ingredients, pharmacology, plant has important economic value, not only referred applications and mechanism of rhubarb, but also summa- to a few edible rhubarbs [1], but also used as purgative rize the relationship between ingredients and pharmaco- drug in China since the third millennium BC [2], frstly logic action. recorded in Shen Nong’s Herbal Classic. Rhubarb has been suggested to exert eliminating heat, purging fre, Chemical components cooling blood, dispersing blood stasis, dredging collateral Back in the early years of the nineteenth century, the antidotal and purgative efects, used to treat constipation, chemical compositions of ofcinal rhubarb had been diabetic nephropathy, chronic renal failure, acute pan- researched [3]. In recent years, unofcial rhubarbs with creatitis, gastrointestinal bleeding and other diseases [3]. rich resources are also studied. Although they are dif- Tere are articles summarizing the research progresses ferent species, the main composition of these rhubarb of rhubarb on treating acute organophosphorus pesticide species is similar. Scientists and medics isolated various poisoning [4], acute ischemic stroke [5], acute pancreati- types of compounds from rhubarb, containing anth- tis [6], chronic kidney disease [7] in recent years. Zheng raquinones and their glycosides, anthrones and their [8] summarized the researches of rhubarb containing the glycosides, stilbenes, butyrophenones and chromones, isolation, pharmacological activities, and phytochemical tannins, saccharides and so on [9]. Anthraquinones *Correspondence: [email protected] Anthraquinones are the main characteristic as well as 2 College of Pharmacy and Shaanxi Collaborative Innovation Center pharmacodynamic ingredients of rhubarb [10, 11]. Te of Chinese Medicinal Resources Industrialization, Shaanxi University of Chinese Medicine, Xianyang 712046, China proportion of anthraquinones ranges from 3 to 5% in Full list of author information is available at the end of the article diferent species [3]. More than 30 anthraquinones have © The Author(s) 2017. 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. Cao et al. Chin Med (2017) 12:36 Page 2 of 12 been isolated and identifed from rhubarb [12]. Tey are proliferation, inducting apoptosis and blocking cell cycle divided into free type and combination type. Free anth- [24]. raquinones mainly contain rhein, emodin, aloe-emodin, Aloe-emodin, another important active compound of chrysophanol, physcion, isoemodin, chrysaron, isoemo- rhubarb, has attracted much attention, due to its various din, laccaic acid D. Combination anthraquinones are the efects such as cardiovascular protection, hepatoprotective glycosides combined by free anthraquinones and glyco- activities, anti-tumor, antibacterial, antifungal, antiviral, syl. Tere are many kinds of anthraquinone glycosides, anti-infammatory, immune regulation, laxative [17, 25]. containing aloe-emodin-8-glucoside, emodin-8-gluco- Anthraquinone glycosides process the characteristic of side, rhein-8-glucoside, physcion diglucoside, emodin- antioxidant, anticancer, anti-infammatory, laxative and 6-glucoside etc. [3, 9]. Main structures of anthraquinones many others biological properties [26], laxative activity (1–11) are as follows (Fig. 1) [3, 8, 12]. strongest among them. Rhein has the ability of protecting kidney [13], inhib- iting the formation of renal fbrosis [14], improving dia- Anthrones and dianthrone betic nephropathy [15] and lipid disorders [16]. Rhein Anthrones and dianthrone, also characteristic compo- also has a strong inhibitory efect on common clinical nents of rhubarb, are related to purgative activity. Mainly anaerobes [17]. these include rheinosides A–D, palmidin A, B, C, rheidin Emodin has a wide range of pharmacological efects, A, B, C, and sennosidin A–F, etc. [9]. 26 anthrones have including anti-tumor [18], anti-microbial [19], antioxi- been isolated from the species of this genus [8]. Senno- dant [20], anti-infammatory [21]. It also can bring high sides have a strong cathartic efects though translating to blood pressure down, decrease blood lipids and improve anthraquinones in vivo. Te main structures of anthrones microcirculation, protect liver and kidney [17]. and dianthrone (12–25) are as follows (Fig. 2) [3, 8, 12]. Chrysophanol has a protective efect on the nervous system, improving the activity of antioxidant enzyme, Stilbenes reducing the damage of oxygen free radicals to cells [22]. Stilbenes are important components of rhubarb, concern- Physcion also has neuroprotective efect, inhibit- ing antihyperlipidemic, antioxidant and hepatoprotective ing the infammatory response after cerebral ischemia efect [3, 27]. So far, there are 31 compounds found in rhu- and reducing the nerve damage caused by reperfusion barb belonging to stilbenes [12], such as rhapontigenin, [23]. Besides, physcion has anti-tumor efects on a vari- isorhapontigenin and rhaponticin. Some representative ety of carcinoma cells, mainly through inhibiting cell R8 O R1 R7 R2 R6 R3 R5 O R4 R1 R2 R3 R4 R5 R6 R7 R8 1 RheinHCOOH HOHOHH HH 2 Emodin HCH3 HOHOHH OH H 3 ChrysophanolHCH3 HOHOHH HH 4 Aloe emodinHCH2OH HOHOHH HH 5 Physcion HCH3 HOHOHH OCH3 H 6 IsoemodinHCH3 OH HOHH HOH 7 Laccaic acid DHOH COOH CH3 OH HOHOH 8 Aloe-emodin-8-oglucoside OH HHHHCH2OH HOGlu 9 Chrysophanol-8-glucoside OH HCH3 HHHHOGlu 10 Physcion-8-glucosideOHH CH3 HHCH3 HOGlu 6 1 11 Physcion diglucosideOHH CH3 HHCH3 H OGlu → Glu Fig. 1 Main structures of rhubarb anthraquinones Cao et al. Chin Med (2017) 12:36 Page 3 of 12 OR1 O OH COOH R2 R3 R1 R2 R3 12 Rheinoside A GluGlu OH 13 Rheinoside BGlu OH Glu 14 Rheinoside C GluGlu H 15 Rheinoside DGlu HGlu OH O OR2 1 R R 1 H H 3 R R 6 1' 4 OR5 O OH R1 R2 R3 R4 R5 R6 16 Palmidin ACH2OH HHOH HCH3 17 Palmidin BCH2OH HHCH3 HH 18 Palmidin C CH3 HHOH HCH3 19 Rheidin AOH HCH3 COOH HH 20 Rheidin BH HCH3 COOH HH 21 Rheidin CH HCH3 COOH HOCH3 22 Sennosidin ACOOH HHCOOH HH 23 Sennosidin CCOOH HHCH2OH HH 24 Sennoside ACOOHGlu 1-1’transH COOH Glu 1-1’transH 25 Sennoside CCOOH Glu 1-1’meso HCOOH Glu 1-1’mesoH Fig. 2 Main structures of rhubarb anthrones and dianthrones structures of stilbenes (26–28) are showed at Fig. 3 [3, 8, in rhubarb generally account for 10–30% [28]. It can be 12]. divided into hydrolytic type and condensation type. Gallic acid and d-cate-chin are the monomers of these tannins. Tannins Studies have discovered that tannins are the active elements Since the 1880s, the discovery that rhubarb tannins owing to the stypticity and constipate activity of rhubarb reduced the content of BUN, sparked great interest and [29]. It has been proved that tannins can adjust genotoxic- attention of scholars both at home and abroad. Tannins ity, oxidative stress, infammation and apoptosis [30]. Total Cao et al. Chin Med (2017) 12:36 Page 4 of 12 OH R4 R3 R5 R2 R1 R1 R2 R3 R4 R5 26 RhaponticinOHH OH OCH3 H 27 Piceatannol 3'-O-glucopyranoside HOHOGluH OH 28 Resveratroloside H OGlu HH OH OH OH HO O HO COOR2 R1 R2 R1 OH OH R1 R2 R1 R2 29 (+)-Catechin HOH 31 Gallic acid OH H 30 (-)-Epicatechin OH H 32 4-O-methyl gallic acid OCH3 H 33 GlucogallinOHGlu HO O O HO O CH CH CCH HO HO 2 2 3 O O HO C O CH OH 2 O O HO O CH2CH2COCH3 HO HO OH OH OH Lindleyin Isolindleyin 34 35 Fig. 3 Main structures of rhubarb stilbenes, tannins, butyrophenones and chromones tannins extract can protect the kidney of K2Cr2O7-injured structures are showed at Fig. 3, have been confrmed pos- rats by treating CrNT as a free radical scavenger [31]. Te sessing anti-infammatory and analgesic activity [32]. basic structures of tannins (29–33) recorded at Fig. 3. Chromones are of expanding coronary vessels, decreas- ing
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