1. School of Pharmacy, Harbin University of Commerce, Harbin 150076, China; 2. Key Laboratory for Drug Research on Prevention and Treatment of Geriatric Diseases of Heilongjiang Province, Harbin 150076, China; 3. School of Pharmacy, Harbin Medical University, Harbin 150081, China
Abstract:In recent years, in order to improve the bioavailability and bioactivity of emodin, researchers have modified its structure to obtain many emodin derivatives.In this paper, the bioactivities of 79 emodin derivatives including quaternary ammonium salts, quaternary phosphonium salts, methylated salts, glycosides and metal complexes were reviewed by referring to and sorting out relevant literatures domestic and overseas in recent years.The biological activities of most of the derivatives revolve around antitumor activity in vitro, and the other derivatives involve anti-mosquito activities, free radical scavenging, anti-Staphylococcus aureus and anti-tobacco mosaic virus, etc.This review provides reference for the research on the structure-activity relationship of emodin and the development of emodin drugs.
GAO X H, ZHOU J H. Advances in research on antiinflamatory activity and related mechanisms of emodin[J]. J Jining Med Univ(济宁医学院学报), 2016,39(5):348-352.
[2]
CAI Q Y, XU L J.Regulation of emodin on exosome level andoxidative stress of pancreatic acinar cells in acute pancreatitis[J]. J Zhengzhou Univ(郑州大学学报), 2020, 55(3):373-376.
[3]
YAO J Y, YUAN X M, XU Y, et al. Bacteriostatic test of emodin on hydromildew in vitro[J]. Sci Fish Farming(科学养鱼), 2018,(2):61-63.doi:10.14184/j.cnki.issn1004-843x.2018.02.037.
[4]
SHRIMALI D, SHANMUGAM M K, KUMAR A P,et al. Targeted abrogation of diverse signal transduction cascades by emodin for the treatment of inflammatory disorders and cancer[J].Cancer Lett, 2013, 341(2):139-149.
[5]
SHU Z H,WANG H L, LIU Y Y, et al.Research progress on the mechanism of emodin in the treatment of hepatic carcinoma[J].Jilin J Chin Med (吉林中医药),2020,40(2):278-280.
[6]
LI M, ZHANG X Y. Synergistic effect of free radical scavenging in emodin and vitamin C [J]. Appl Chem Ind (应用化工), 2013, 42(10):1823-1825.
[7]
CAO J, LIU Z Q, YANG D W. Effects of emodin on apoptosis,oxidative stress and expressions of AMPK signaling pathway proteins in cardiomyocytes with hypoxia-reoxygenation[J]. J Zhengzhou Univ (郑州大学学报), 2020, 55(1):74-77.
[8]
HUANG D Y, XUE X T, ZHANG K. Research on emodin bioactivities[J]. J Guangdong Ind Polytech(广东轻工职业技术学院学报), 2016, 15(4):13-18.
[9]
LI G P, CUI H R, GUO W B, et al. Protective effects of emodin on L02 cells iniury[J]. Northwest Pharm J (西北药学杂志),2020, 35(3):383-386.
[10]
WANG Q Q, ZHANG H, CAO H Q, et al. Mechanism of emodin inhibiting proliferation and migration of sorafenib-resistant hepatocellular carcinoma cells[J]. Zhejiang Med J (浙江医学),2019, 41(17):1836-1839,1844,1915.
[11]
LIU W, QIAN F, YE L, et al. Coupling of UDP-glucuronosyltransferases and multidrug resistance-associated proteins is responsible for the intestinal disposition and poor bioavailability of emodin[J].Toxicol Appl Pharmacol, 2012,265(3):316-324.
[12]
MA M X, HUANG H, LI M J, et al. Progress of anti-tumor effects of emodin new preparation[J]. J Anhui Agric Sci (安徽农业科学),2016,44(27):144-146.
[13]
LIU W W, WANG Y X, LIU S H, et al.Research progress on structural modification of emodin[J]. J Xuzhou Instit Technol (徐州工程学院学报), 2019, 34(3):27-33.
[14]
TU J J. Study on antitumor effect and mechanism of emodin derivative HXX-37 [D]. Fuzhou: Fujian Medical University, 2018.
[15]
ATWELL G J, CAIN B F, BAGULEY B C,et al. Potentialantitumor agents. Part 43. Synthesis and biological activityof Dibasic 9-aminoacridine-4-carboxamides,a new class of antitumor agent[J].J Med Chem,1984,27(11):1481-1485.
[16]
HUANG Y L, WANG W F, HU J D, et al. Effect of emodin de rivative E11 on T lymphocytic leukemia cell line molt-4 and its possible mechanisms [J]. J Exp Hematol(中国实验血液学杂志),2016, 24(1):8-13.
[17]
ZHANG L. Effects of E35-induced autophagy and apoptosis in acute myeloid leukemia HL-60 and Kasumi cells [D]. Fuzhou:Fujian Medical University, 2016.
[18]
WANG C H, ZHANG F S, DU H D, et al.Synthesis of double long-chain quaternary ammonium salt derivatives of emodin and research of anticancer activity[J]. J Fuzhou Univ (福州大学学报), 2011, 39(3):455-459.
[19]
WANG X N. Effects of ZYY48-induced autophagy and apoptosis in Burkitt′s lymphoma CA46 and acute myeloid leukemia HL-60 cell lines [D].Fuzhou: Fujian Medical University, 2017.
[20]
LI B J. The effect of emodin derivative on proliferation inhibition and apoptosis induction in chronic myelogenous leukemia cell K562 and imatinib-resistant K562/G01[D]. Fuzhou: Fujian Medical University,2013.
[21]
ZHU Y H. Design, synthesis and biological evaluation of water-solubleI emodin derivatives[D]. Fuzhou: Fuzhou University, 2015.
[22]
JIN D T, ZHONG L, LIU B Z, et al.Synthesis of trimethoxy derivatives of emdoin and its anti-tumor activities test in vitro[J].Chin Hosp Pham J (中国医院药学杂志),2010, 30(5):360-362.
[23]
XING J Y,SONG G P,DENG J P,et al.Antitumor effects and mechanism of novel emodin rhamnosidederivatives against human cancer cellsin vitro[J].PLoS One, 2015, 10(12): 1-26,doi:10.1371/journal.pone.0144781
[24]
WEN H R, YAN Y J, SONG J, et al.Study on in viro and in vivo genotoxicity of emodin-8-O-β-D-glucoside[J]. J China Pharm(中国药房), 2020, 31(1):18-23.
[25]
LI Y Q, LIANG H X, LIU C Z, et al. Effects of emodin-8-O-β-D-glucopyranoside on tumor cell migration and metastasis in vitro and in vivo[J]. Chin J Pharmacov(中国药物警戒), 2019, 16(12):705-710.
[26]
CHEN H, WANG Y,LENG L, et al.A new series of emodin derivatives with bone affinity[J].Chin Chem Lett,2007, 18(2):141-144.
[27]
ZHAO L M,ZHANG L M,LIU J J,et al. Synthesis and antitumor activity of conjugates of 5-fluorouracil and emodin[J]. Eur J Med Chem,2012,47(1):255-260.
[28]
ZHANG X M, ZHENG G, WANG J J.Synthesis of 10-osition Schiff base derivatives of emodin and preliminary investigation of anti-tumor activity in vitro[J].China Pharm(中国药师),2015,18(2):194-196.
[29]
LI Y B, ZHENG Y S, FAN J H,et al. Synthesis and mosquito activity against the fourth-instar larvae of Aedes albopictus of emodin derivatives[J].China Sciencepap (中国科技论文), 2015, 10(12):1459-1463.
[30]
LUO Z Y, HUANG X, BAO G R. Study on the scavenging effects of the free anthraquinones from Rheum palmatumL.on superoxide anion radical[J]. Strait Pharm J (海峡药学), 2009, 21(12):43-45.
[31]
PAN X L, XIANG H, XIE Y F,et al. The compound、confirm and antioxidant activity of emodin-magnesium(Ⅱ) metal complex[J]. Chin Tradit Pat Med (中成药), 2013, 35(12):2757-2759,2768.
[32]
PAN X L, XIANG H, XIE Y F, et al. The compound、confirm and antioxidant activity of emodin-copper(Ⅱ) metal complex[J]. Lishizhen Med Mater Med Res (时珍国医国药), 2013, 24(12):2892-2894.
[33]
YANG L.Study on synthesis and anti-tumor activities of the transition metal complexes with emodin [D]. Chongqing: Chongqing University, 2014.
[34]
XING Z H, CHENG M C.Recent advances in pharmacological activity of rare earth salts and its complexes[J]. J Chin Soc Rare Earths (中国稀土学报), 2019, 37(3):273-283.
[35]
MAO Y, HONG H L, YANG F, et al.Study on bacteriostatic mechanism of emodin rare earth complexes[C].Abstracts of papers from the 9th national organic chemistry academic conference of the Chinese chemical society(6)(中国化学会第九届全国有机化学学术会议论文摘要集6). Changchun, 2015:10.
[36]
WU J,ZHU YY, ZHAO YH,et al.Synthesis and antiviral activities of novel 1,4-pentadien-3-one derivatives bearing an emodin moiety[J].Chin Chem Lett,2016,27(6):948-952.