Open access peer-reviewed chapter
Anticancer activity of quinones isolated from different organism.
Abstract
Cancer is a group of related diseases in which there is uncontrolled cell growth that spreads to the surrounding tissues and damages them. Cancer remains the disease with the leading cause of death worldwide, and incidence and mortality are increasing rapidly. The main cancer treatment is chemotherapy; however, the compounds used in this treatment have serious side effects for this reason, is necessary to develop new therapeutic strategies. Natural products are an excellent pharmacological alternative for the treatment of cancer and infections. In search of new compounds with cytotoxic and antimicrobial activity, we have found quinones that have a high pharmacological potency in the treatment of these health problems. Quinones are an aromatic system of one or diketone and are mainly isolated from plants, fungi, bacteria, and other organisms. These compounds are secondary metabolites derived from the oxidation of hydroquinones; they include benzoquinones, naphthoquinones, anthraquinones, and polyquinones. This review summarizes the activity of 152 anticancer and 30 antimicrobial quinones.
Keywords
- quinones
- cancer
- cytotoxic
- antimicrobial
- natural product
1. Introduction
Cancer is a group of a collection of related diseases where there is uncontrolled cell growth and spread into surrounding tissues, producing damage to them. In many cases, these cells form tumors and some cancer cells travel through the lymphatic system or blood to other places of the body and form new tumors.
Cancer remains the disease with major cause of death globally. In 2018, there were reported about 18 million new cases of cancer [1] and approximately 9.6 million deaths from this disease [2]; in addition, all over the world, the incidence and mortality of cancer are increasing. The risk of incidence of cancer is associated with age, infections, and human habits like poor diet, consumption of alcohol, tobacco, and others [3]; also, there are genetic predisposition and immune conditions [4].
Diseases due to the infections of bacteria and fungi are a very important health problem throughout the world. In 2019, the incidence of infection transmitted by food and water increased. The treatment of infection by bacteria is the administration of antibiotics; however, these drugs have been losing effectiveness because there is increased bacterial drug resistance [5]. The main causes of bacterial resistance are unnecessary prescriptions [6] and the unregulated antibiotics sale in many countries, leading to inadequate and unnecessary consumption [7]. Then, infections treatments become more expensive and have less effective.
From ancient times, natural products have been used in the treatment of different diseases, for example, in Egypt around 1550 BC, the “Ebers Papyrus” reported the use of 700 drugs [8]. Nowadays, natural products are an important source of compounds with great potential for the treatment of infections and different forms of cancer [9].
Quinones are an important family of natural products. They have a variety of biological effects, such as anticancer and antimicrobial activities [10, 11]. The 1,4-naphthoquinones, since ancient times, have been used as cosmetics for coloring skin, as well as the treatment of some diseases. These compounds have several activities like anti-inflammatory, antiviral, anticancer, and antibacterial, among others.
For example, juglone and plumbagin show an antimicrobial effect on bacteria and fungi, and they are defensive compounds in the plant. Cytosporaquine A-D and physcion exhibited cytotoxic activity against several human cell cancer lines.
The cytotoxic and antimicrobial activities of 1,4 naphthoquinones are due mainly to two carbonyl groups present in these compounds, which can accept one or two electrons to form a semiquinone radical or di-anion species and for their acid–base properties [10].
The present review focuses on the anticancer and antimicrobial activities of 182 quinones isolated from natural sources in the last 5 years (Tables 1 and 2).
Table 1.
Celular lines: 23132/87, BGC-823, GXF 251 L and SGC-7901 human gastric carcinoma cells; ASPC-1, BxPC-3, PAXF 1657 L and PAXF PANC1 adenocarcinoma of the pancreas; DLD-1, Caco-2, HCT-15, CXF HCT116, CXF HT29, HCT116, HRT-18 and HT29 colon adenocarcinoma cells; PRXF 22RV1, PRXF DU145, PRXF LNCAP, PRXF PC3M and DU-145 human prostate carcinoma; MCF-7, MDA-MB 231, MDA-MB-468, BT-20 and BT-474 Human breast carcinoma cell line; A2780, OVXF 1619 L, OVXF 899 L, OVXF OVCAR3,CAOV-3 and SKOV-3 Human ovarian cancer cells; A549, H-1299, LXF 1121 L, LXF 289 L, LXF 526 L, LXF 529 L, LXF 629 L, LXF H460, NCI-H187, NCI-H1437, NCIH1655, NCI-H358, NCI-H460 and NSCLC cancer lung cells; CNXF 498NL and CNXF SF268 cancer of Central nervous System cells; RXF 1781 L, RXF 393NL, RXF 486 L, RXF 944 L and ACHN human renal cancer; BXF 1218 L and BXF T24 cancer Bladder cells; XF498 and SF-268 human central nervous system cancer; MEXF 394NL, MEXF 462NL, MEXF 514 L, MEXF 520 L, SK-MEL-5, 518A2, B16F10, C33A, HSC3, SCC4, SCC9, SCC15, SCC25 melanoma cells; CRL2120 and SK-MEL-2 human skin cancer; BEL-7402 and HepG2; SiHa, KB3.1 and HeLa human cervical adenocarcinoma cells; Jurkat lymphoblastic, HL-60 and K562 leukemia cells; MIAPaCa-2 and PANC-1 human pancreatic adenocarcinoma cancer; UXF 1138 L cancer Uterus cells; OC3-IV2 Human oral cancer; PXF 1752 L pleuramesothelioma; SPC212 human mesotelioma cell; SYF mouse embryonic fibroblast deficient in C-Src; U251MG human glioblastoma; FaDu hypopharyngeal carcinoma; KKU-M156 human cholangiocarcinoma cells. WI38 human normal lung, HaCaT immortalized human keratinocytes, nontumorigenic cell line, Vero kidney of a normal monkey cell, L929 nonmalignant mouse fibroblasts and NIH 3 T3 nonmalignant mouse fibroblasts. Inhibitory concentration of 50% (IC50); Effective concentration of 50% (EC50); Growth inhibition of 50% (IG50); Assay of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MMT); Microscopy on a hemocytometer using trypan blue dye exclusion method (MHTBDE); Cytotoxicity Assay for fluorescence (CAF); Neutral red uptake assay (NR); Sulforhodamine B assay (SRB); Trypan Blue Exclusion assay (TBE); Alamar Blue reduction assay (ABR); Resazurin microplate assay (RM); Crystal violet assay (CV).
Table 2.
Quinones with antimicrobial activity.
Minimum inhibitory concentration (MIC).
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2. Anticancer and antimicrobial activity of quinones obtained from plants, animals, and microorganisms
The incidence of cancer has increased; in 2018, around 9.6 million deaths in the world were due to this disease. The drugs used in chemotherapy have side effects and the cancer cells can have resistance to these drugs. Therefore, the study of new molecules with anticancer activity has become important.
Infectious diseases are an international health public problem, especially in undeveloped countries. For the treatment of these diseases are used antibiotics; however, several microorganisms present resistance to these drugs.
The search for new compounds with these activities has become important. Plants, marine organisms, fungi, and bacteria are natural sources to obtain substances with pharmacological effects.
Quinones are natural products with different pharmacological activities, such as anticancer and antimicrobial effects. These compounds can be obtained by synthesis or the structure modified to increase their activity.
This chapter shows the revision of the literature generated in the last 5 years of quinones isolated from 65 plant species, bacteria, fungi, algae, or sponges. The plants were the most different species studied, followed by fungi with 10 species, Streptomyces with 4 strain investigated, and bacteria with only one studied. Nowadays, the study of marine organisms has become more important, with 3 species of sponges studied and from which these compounds have been isolated, and there was 1 scorpion studied.
The cytotoxic properties of isolated quinones in the period 2015 to 2020 were mainly determined by in vitro and in vivo studies. This was due to some factors such as the sensitivity of these tests and the consumption of small amounts of compound to obtain the results. There are different methods to carry out these tests. In this review, the activities were determined by the use of MTT, SRB, NR, IDO, iodide propidium, violet crystal, cell counting kits, resazurin reduction, sulforhodamine B, AGS, Trypan blue, immunophenotyping, Alamar blue, FITC Annexin V Apoptosis, the CCK-8 colorimetric method, and Annexin V/7-AAD.
The determination of antimicrobial activity was carried out by MIC, micro-dilution, and broth microdilution volatilization.
Quinones have good activity against numerous cell cancer lines; they also exhibit good antimicrobial activity. This situation, along with the wide variety of structures that these compounds exhibit, make them a very interesting topic to continue to explore for other mechanisms of action and the chemical modification of their structures, among other topics.
References
- 1.
Khalifa SAM, Elias N, Farag MA, Chen L, Saeed A, Hegazy MF, Moustafa MS, Abd El-Washed A, Al- Mousawi SM, Musharraf SG, Chang FR, Iwasaku A, Suenaga K, Alajlani M, Göransson U, El-Seedi HR. Marine Natural products: A source of novel anticancer drugs. Mar Drugs. 2019;17:491-522. DOI: 10.3390/md17090491 - 2.
Dutta S, Mahalanobish S, Saha S, Ghosh S, Sil PC. Natural products: An uncoming therapeutic approach to cancer. Food Chem Toxicol. 2019;128:240-255. DOI: 10.1016/j.fct.2019.04.012 - 3.
Gallagher EJ, Neel BA, Antoniou IM, Yakar S, LeRoith D. The increased risk of cancer in obesity and type 2 diabetes: potential mechanisms. In: Poretsky, L. Editor. Principle of Diabetes mellitus. Springer International Publishing, Cham; 2017. 731-753 pp. DOI: 10.1007/978-0-387-09841-8_36) - 4.
White MC, Holman DM, Boehm JE, Peipins LA, Grossman M, Henley SJ. Age and cancer risk. A potential modificable relationship. Am J Prev Med. 2014;46:S7-S15. DOI: 10.1016/j.amepre.2013.10.029 - 5.
Prestinaci F, Pezzotti P, Pantosti A. Antimicrobial resistance: A global multifaceted phenomenon. Pathog Glob Health. 2015;109:309–318. DOI: 10.1179/2047773215Y.0000000030 - 6.
Morehead MS, Scarbrough C. Emergence of global antibiotic resistance. Prim Care. 2018;45:467-484. DOI: 10.1016/j.pop.2018.05.006 - 7.
Morgan D, Okeke R, Laxminarayan R, Perencevich E, Weisenberg S. Non-prescription antimicrobial use worldwide: A systematic review. Lancet Infect Dis. 2011;11:692-701. DOI: 10.1016/S1473-3099(11)70054-8 - 8.
Borchardt JK. The beginnings of drugs therapy: ancient Mesopotamian medicine. Drug News Perspect. 2002;15:187-192. DOI: 10.1358/dnp.2002.15.3.840015 - 9.
Saha S, Sadhukhan P, Sil P. Genistein: a phytoestrogen with multifaceted therapeutic properties. Mini Rev Med Chem. 2014;14:920-940. DOI: 10.2174/1389557514666141029233442 - 10.
Asche C. Antitumour quinones. Mini Rev Med Chem. 2005;5:449-467. DOI: 10.2174/1389557053765556 - 11.
Saleem M, Nazir M, Ali MS, Hussain H, Lee YS, Riaz N, Jabbar A. Antimicrobial natural products: an update on future antibiotic drug candidates. Nat Prod Rep. 2010;27:238-254. DOI: 10.1039/b916096e - 12.
Hong-Ru W, Wei Z, Xiao-Yan P, Yuan G, Xian MU. Obulqasim, Hong-Fang L, Ying Z. Quinones and coumarins from Ajania salicifolia and their radical scavenging and cytotoxic activity. J Asian Nat Prod Res. 2015;17:1196-1203. DOI: 10.1080/10286020.2015.1117456 - 13.
Li Y, Dong C, Xu MJ, Lin WH. New alkylated benzoquinones from mangrove plant Aegiceras Corniculatum with anticancer activity. J Asian Nat Prod Res. 2020;22:121-130. DOI: 10.1080/10286020.2018.1540604 - 14.
Abdissa N, Gohlk, S, Frese M, Sewald N. Cytotoxic compounds from aloe megalacantha. Molecules. 2017;22:1136-1141. DOI:10.3390/molecules22071136 - 15.
Asaumi S, Kawakami S, Sugimoto S, Matsunami K, Otsuka H, Shinzato T. Alkylated benzoquinones: ardisiaquinones A–H from the leaves of Ardisia quinquegona and their anti-leishmania activity. Chem Pharm Bull. 2018;66:757-763. DOI: 10.1248/cpb.c18-00281 - 16.
Yuzbasioglu Baran M, Guvenalp Z, Saracoglu I, Kazaz C, Salih B, Demirezer LO, Kuruuzum-Uz A. Cytotoxic naphthoquinones from Arnebia densiflora (Nordm.) Ledeb and determining new apoptosis inducers. Nat Prod Res. 2020;34:1669-1677. DOI: 10.1080/14786419.2018.1525714 - 17.
Byeon SE, Yi YS, Lee J, Yang WS, Kim JH, Kim J, Hong S, Cho JY. Hydroquinone exhibits in vitro and in vivo anti-cancer activity in cancer cells and mice. Int J Mol Sci. 2018;19:903-916. DOI: 10.3390/ijms19030903 - 18.
Park SH, Phuc NM, Lee J, Wu Z, Kim J, Kim H, Kim ND, Lee T, Song KS, Liu KH. Identification of acetylshikonin as the novel CYP2J2 inhibitor with anti-cancer activity in HepG2 cells. Phytomedicine. 2017;15;24:134-140. DOI: 10.1016/j.phymed.2016.12.001 - 19.
Chen Y, Chen ZY, Chen L, Zhang JY, Fu LY, Tao L, Zhang Y, Hu XX, Shen XC. Shikonin inhibits triple-negative breast cancer-cell metastasis by reversing the epithelial-to-mesenchymal transition via glycogen synthase kinase 3β-regulated suppression of β-catenin signaling. Biochem Pharmacol. 2019;166:33-45. DOI: 10.1016/j.bcp.2019.05.001 - 20.
Vukic MD, Vukovic NL, Djelic GT, Popovic SL, Zaric MM, Baskic DD, Krstic GB, Tesevic VV, Kacaniova MM. Antibacterial and cytotoxic activities of naphthoquinone pigments from Onosma visianii Clem. Excli J. 2017;16:73-88. DOI: 10.17179/excli2016-762 - 21.
Trivedi R, Müller GA, Rathore MS, Mishra DP, Dihazi H. Anti-leukemic activity of Shikonin: role of ERP57 in Shikonin induced apoptosis in acute myeloid leukemia. Cell Physiol Biochem. 2016;39:604-16. DOI: 10.1159/000445652 - 22.
Spyrelli ED, Kyriazou AV, Virgiliou C, Nakas A, Deda O, Papageorgiou VP, Assimopoulou AN, Gika HG. Metabolic profiling study of shikonin's cytotoxic activity in the Huh7 human hepatoma cell line. Mol Biosyst. 2017;13:841-851. DOI: 10.1039/C6MB00830E - 23.
Pavan V, Ribaudo G, Zorzan M, Redaelli M, Pezzani R, Mucignat-Caretta C, Zagotto G. Antiproliferative activity of Juglone derivatives on rat glioma. Nat Prod Res. 2017;31:632-638. DOI: 10.1080/14786419.2016.1214830 - 24.
Zhou YY, Guo S, Wang Y, Song HJ, Gao HR, Zhang XJ, Sun YP, Liu Y, Yang BY, Kuang HX. α-Tetralone glycosides from the green walnut husks of Juglans mandshurica Maxim. and their cytotoxic activities. Nat Prod Res. 2020;34:1805-1813. DOI: 10.1080/14786419.2018.1561681 - 25.
Zhou Y, Yang B, Jiang Y, Liu Z, Liu Y, Wang X, Kuang H. Studies on cytotoxic activity against HepG-2 cells of naphthoquinones from green walnut husks of Juglans mandshurica Maxim. Molecules. 2015;20:15572-15588. DOI: 10.3390/molecules200915572 - 26.
Wu J, Zhang H, Xu Y, Zhang J, Zhu W, Zhang Y, Chen L, Hua W, Mao Y. Juglone induces apoptosis of tumor stem-like cells through ROS-p38 pathway in glioblastoma. BMC Neurology. 2017;17:70-76. DOI: 10.1186/s12883-017-0843-0 - 27.
De U, Son JY, Jeon Y, Ha SY, Park YJ, Yoon S, Ha KT, Choi WS, Lee BM, Kim IS, Kwak JH, Kim HS. Plumbagin from a tropical pitcher plant (Nepenthes alata Blanco) induces apoptotic cell death via a p53-dependent pathway in MCF-7 human breast cancer cells. Food Chem Toxicol. 2019;123:492-500. DOI: 10.1016/j.fct.2018.11.040 - 28.
Sameni S, Hande MP. Plumbagin triggers DNA damage response, telomere dysfunction and genome instability of human breast cancer cells. Biomed. Pharmacother. 2016;82:256-268. DOI: 10.1016/j.biopha.2016.05.007 - 29.
Kuete V, Omosa LK, Tala VR, Midiwo JO, Mbaveng AT, Swaleh S, Karaosmanoğlu O, Sivas H. Cytotoxicity of Plumbagin, Rapanone and 12 other naturally occurring Quinones from Kenyan Flora towards human carcinoma cells. BMC Pharmacol Toxico. 2016;17:1-10. DOI: 10.1186/s40360-016-0104-7 - 30.
Mancilla IA, Coatti GC, Biazi BI, Zanetti TA, Baranoski A, Marques LA, Corveloni AC, Lepri SR, Mantovani MS. Molecular pathways related to the control of proliferation and cell death in 786-O cells treated with plumbagin. Mol Biol Rep. 2019;46:6071-6078. DOI: 10.1007/s11033-019-05042-9 - 31.
Ku HJ, Kwon OS, Kang BS, Lee DS, Lee HS, Park JW. IDH2 knockdown sensitizes tumor cells to Emodin cytotoxicity in vitro and in vivo. Free Radic Res. 2016;50:1089-1097. DOI: 10.1080/10715762.2016.1178739 - 32.
Moreira TF, Sorbo JM, Souza FDO, Fernandes BC, Ocampos FMM, de Oliveira DMS, Arcaro CA, Assis RP, Barison A, Miguel OG, Baviera AM, Soares CP, Brunetti IL. Emodin, Physcion, and crude extract of Rhamnus sphaerosperma var. pubescens induce mixed cell death, increase in oxidative stress, DNA damage, and inhibition of AKT in cervical and Oral squamous carcinoma cell lines. Oxid Med Cell Longev. 2018;2018:1-18. DOI: 10.1155/2018/2390234 - 33.
Li R, Li W, You Y, Guo X, Peng Y, Zheng J. Metabolic activation and cytotoxicity of Aloe-Emodin mediated by sulfotransferases. Chem Res Toxicol. 2019;32:1281-1288. DOI: 10.1021/acs.chemrestox.9b00081 - 34.
Du Y, Zhang J, Tao Z, Wang C, Yan S, Zhang X, Huang M. Aloe emodin exerts potent anticancer effects in MIAPaCa-2 and PANC-1 human pancreatic adenocarcinoma cell lines through activation of both apoptotic and autophagic pathways, sub-G1 cell cycle arrest and disruption of mitochondrial membrane potential (ΛΨm). J BUON. 2019;24:746-753. PMID: 31128032 - 35.
Zhou M, Xing HH, Yang Y, Wang YD, Zhou K, Dong W, W, Li GP, Hu WY, Liu Q, Li XM, Hu QF. Three new anthraquinones from the twigs of Cassia fistula and their bioactivities. J Asian Nat Prod Res. 2017;19:1073-1078. DOI: 10.1080/10286020.2017.1285911 - 36.
Ribeiro V, Andrade PB, Valentão P, Pereira DM. Benzoquinones from Cyperus spp. trigger IRE1α-independent and PERK-dependent ER stress in human stomach cancer cells and are novel proteasome inhibitors. Phytomedicine. 2019;63:153017. DOI: 10.1016/j.phymed.2019.153017 - 37.
Nordin N, Majid NA, Mohan S, Dehghan F, Karimian H, Rahman MA, Ali HM, Hashim NM. Cleistopholine isolated from Enicosanthellum pulchrum exhibits apoptogenic properties in human ovarian cancer cells. Phytomedicine. 2016;23:406-416. DOI: 10.1016/j.phymed.2016.02.016 - 38.
Bigolin A, Maioral MF, Stefanes NM, Zatelli GA, Philippus AC, Falkenberg MB, Santos-Silva MC. Cytotoxic mechanisms of primin, a natural quinone isolated from Eugenia hiemalis, on hematological cancer cell lines. Anticancer Drugs. 2020;31:709-717. DOI: 10.1097/CAD.0000000000000937 - 39.
Thanuphol P, Asami Y, Shiomi K. Wongnoppavich A, Tuchinda P, Soonthornchareonnon N. Marcanine G, a new cytotoxic 1-azaanthraquinone from the stem bark of Goniothalamus marcanii Craib. Nat Prod Res. 2018;32:1682-1689. DOI: 10.1080/14786419.2017.1396588 - 40.
Zhu H, Zheng Z, Zhang J, Liu X, Liu Y, Yang W, Liu Y, Zhang T, Zhao Y, Liu Y, Su X, Gu X. Anticancer effect of 2,7-dihydroxy-3-methylanthraquinone on human gastric cancer SGC-7901 cells in vitro and in vivo. Pharm Biol. 2016;54:285-92. DOI: 10.3109/13880209.2015.1033563 - 41.
Cimmino A, Mathieu V, Evidente M, Ferderin M, Moreno Y, Banuls L, Masi M, De Carvalho A, Kiss R, Evidente A. Glanduliferins A and B, two new glucosylated steroids from Impatiens glandulifera, with in vitro growth inhibitory activity in human cancer cells. Fitoterapia. 2016;109:138-45. DOI: 0.1016/j.fitote.2015.12.016 - 42.
Feilcke R, Arnouk G, Raphane B, Richard K, Tietjen I, Andrae-Marobela K, Erdmann F, Schipper S, Becker K, Arnold N, Frolov A, Reiling N, Imming P, Fobofou SAT. Biological activity and stability analyses of knipholone anthrone, a phenyl anthraquinone derivative isolated from Kniphofia foliosa Hochst. J Pharm Biomed Anal. 2019;174:277-285. DOI: 10.1016/j.jpba.2019.05.065 - 43.
Baghdadi MA, Al-Abbasi FA, El-Halawany AM, Aseeri AH, Al-Abd AM. Anticancer profiling for coumarins and related O-naphthoquinones from Mansonia gagei against solid tumor cells in vitro. Molecules. 2018;23:1020-1033. DOI: 10.3390/molecules23051020 - 44.
Kuete V, Mbaveng AT, Sandjo LP, Zeino M, Efferth T. Cytotoxicity and mode of action of a naturally occurring naphthoquinone, 2-acetyl-7-methoxynaphtho [2, 3-b] furan-4, 9-quinone towards multi-factorial drug-resistant cancer cells. Phytomedicine. 2017;33:62-68. DOI: 10.1016/j.phymed.2017.07.010 - 45.
Abu N, Zamberi NR, Yeap SK, Nordin N, Mohamad NE, Romli MF, Rasol NE, Subramani T, Ismail NH, Alitheen NB. Subchronic toxicity, immunoregulation and anti-breast tumor effect of Nordamnacantal, an anthraquinone extracted from the stems of Morinda citrifolia L. BMC Complem Altern M. 2018;18:18-31. DOI: 10.1186/s12906-018-2102-3 - 46.
Alobaedi OH, Talib WH, Basheti IA. Antitumor effect of thymoquinone combined with resveratrol on mice transplanted with breast cancer. Asian Pac J Trop Med. 2017;10:400-408. DOI: 10.1016/j.apjtm.2017.03.026 - 47.
Houdkova M, Rondevaldova J, Doskocil I, Kokoska L. Evaluation of antibacterial potential and toxicity of plant volatile compounds using new broth microdilution volatilization method and modified MTT assay. Fitoterapia. 2017;118:56-62. DOI: 10.1016/j.fitote.2017.02.008 - 48.
Arumugam P, Subramanian R, Priyadharsini JV, Gopalswamy J. Thymoquinone inhibits the migration of mouse neuroblastoma (Neuro-2a) cells by down-regulating MMP-2 and MMP-9. Chin J Nat Med. 2016;14:904-912. DOI: 10.1016/S1875-5364(17)30015-8 - 49.
Bowen L, Li C, Bin L, Ying T, Shijun L, Junxing D. Chemical constituents, cytotoxic and antioxidant activities of extract from the rhizomes of Osmunda japonica Thunb. Nat Prod Res. 2020;34:847-850. DOI: 10.1080/14786419.2018.1501692 - 50.
Bajpai VK, Alam MB, Quan KT, Choi HJ, An H, Ju MK, Lee SH, Huh YS, Han YK, Na M. Cytotoxic properties of the anthraquinone derivatives isolated from the roots of Rubia philippinensis. BMC Complem Altern Med. 2018;18:200-206. DOI: 10.1186/s12906-018-2253-2 - 51.
Boueroy P, Saensa-Ard S, Siripong P, Kanthawong S, Hahnvajanawong C. Rhinacanthin-C extracted from Rhinacanthus nasutus (L.) inhibits cholangiocarcinoma cell migration and invasion by decreasing MMP-2, uPA, FAK and MAPK pathways. Asian Pac J Cancer Prev. 2018;19:3605-3613. DOI: 10.31557/APJCP.2018.19.12.3605 - 52.
Boonyaketgoson S, Rukachaisirikul V, Phongpaichit S, Trisuwan K. Naphthoquinones from the leaves of Rhinacanthus nasutus having acetylcholinesterase inhibitory and cytotoxic activities. Fitoterapia. 2018;124: 206-210 DOI: 10.1016/j.fitote.2017.11.011 - 53.
Dias RB, de Araújo TBS, de Freitas RD, Rodrigues ACBDC, Sousa LP, Sales CBS, Valverde LF, Soares MBP, Dos Reis MG, Coletta RD, Ramos EAG, Camara CA, Silva TMS, Filho JMB, Bezerra DP, Rocha CAG. β-Lapachone and its iodine derivatives cause cell cycle arrest at G2/M phase and reactive oxygen species-mediated apoptosis in human oral squamous cell carcinoma cells. Free Radic Biol Med. 2018;126:87-100. DOI: 10.1016/j.freeradbiomed.2018.07.022 - 54.
Zada S, Hwang JS, Ahmed M, Lai TH, Pham TM, Kim DH, Kim DR. Protein kinase A activation by β Lapachone is associated with apoptotic cell death in NQO1 overexpressing breast cancer cells. Oncol Rep. 2019;42:1621-1630. DOI: 10.3892/or.2019.7243 - 55.
Zhang Q, Chen L, Hu LJ, Liu WY, Feng F, Qu W. Two new ortho benzoquinones from Uncaria rhynchophylla. Chin J Nat Med. 2016;14:232-235. DOI: 10.1016/S1875-5364(16)30021-8 - 56.
Panthong K, Hongthong S, Kuhakarn C, Piyachaturawat P, Suksen K, Panthong A, Chiranthanut N, Kongsaeree P, Prabpai S, Nuntasaen N, Reutrakul V. Pyranonaphthoquinone and anthraquinone derivatives from Ventilago harmandiana and their potent anti-inflammatory activity. Phytochemistry. 2020;169:112182. DOI: 10.1016/j.phytochem.2019.112182 - 57.
Yu HB, Yin ZF, Gu BB, Zhang JP, Wang SP, Yang F, Lin HW. Cytotoxic meroterpenoids from the marine sponge Dactylospongia elegans. Nat Prod Res. 2019:1-7. DOI: 10.1080/14786419.2019.1633644 - 58.
Neupane RP, Parrish SM, Neupane J, Yoshida WY, Yip ML, Turkson J, Harper MK, Head JD, Williams PG. Cytotoxic sesquiterpenoid quinones and quinols, and an 11-membered heterocycle, Kauamide, from the Hawaiian marine sponge Dactylospongia elegans. Mar Drugs. 2019;17:423-428. DOI: 10.3390/md17070423 - 59.
Luo X, Li P, Wang K, de Voogd NJ, Tang X, Li G. Cytotoxic sesquiterpenoid quinones from South China Sea sponge Dysidea sp. Nat Prod Res. 2019;1-6. DOI: 10.1080/14786419.2019.1679132 - 60.
Ito T, Nguyen HM, Win NN, Vo HQ, Nguyen HT, Morita H. Three new sesquiterpene aminoquinones from a Vietnamese Spongia sp. and their biological activities. J Nat Med. 2018;72:298–303. DOI: 10.1007/s11418-017-1130-5 - 61.
Yen I, Lee SY, Lin KT, Lai FY, Kuo MT, Chang WL. In vitro anticancer activity and structural characterization of ubiquinones from Antrodia cinnamomea mycelium. Molecules. 2017;22:747-752. DOI: 10.3390/molecules22050747 - 62.
Li JL, Jiang X, Liu X, He C, Di Y, Lu S, Huang H, Lin B, Wang D, Fan B. Antibacterial anthraquinone dimers from marine derived fungus Aspergillus sp. Fitoterapia. 2019;133:1-4. DOI: 10.1016/j.fitote.2018.11.015 - 63.
Wang M, Sun ZH, Chen YC, Liu HX, Li HH, Tan GH, Li SN, Guo XL, Zhang W. Cytotoxic cochlioquinone derivatives from the endophytic fungus Bipolaris sorokiniana derived from Pogostemon cablin. Fitoterapia. 2016;110:77-82. DOI: 10.1016/j.fitote.2016.02.005 - 64.
He W, Zhou XJ, Qin XC, Mai YX, Lin XP, Liao SR, Yang B, Zhang T, Tu ZC, Wang JF, Liu Y. Quinone/hydroquinone meroterpenoids with antitubercular and cytotoxic activities produced by the sponge-derived fungus Gliomastix sp. ZSDS1-F7. Nat Prod Res. 2017;31:604-609. DOI: 10.1080/14786419.2016.1207076 - 65.
Le Pogam P, Le Lamer AC, Siva B, Legouin B, Bondon A, Graton J, Jacquemin D, Rouaud I, Ferron S, Obermayer W, Babu KS, Boustie J. Minor Pyranonaphthoquinones from the Apothecia of the Lichen Ophioparma ventosa. J Nat Prod. 2016;79:1005-1011. DOI: 10.1021/acs.jnatprod.5b01073 - 66.
Zhang HM, Ju CX, Li G, Sun Y, Peng Y, Li YX, Peng XP, Lou HX. Dimeric 1,4-benzoquinone derivatives with cytotoxic activities from the marine-derived Fungus Penicillium sp. L129. Mar Drugs. 2019;17:383-389. DOI: 10.3390/md17070383 - 67.
Mishra PD, Verekar SA, Deshmukh SK, Joshi KS, Fiebig HH, Kelter G. Altersolanol A: a selective cytotoxic anthraquinone from a Phomopsis sp. Lett Appl Microbiol. 2015;60:387-391. DOI: 10.1111/lam.12384 - 68.
Otto C, Hahlbrock T, Eich K, Karaaslan F, Jürgens C, Germer CT, Wiegering A, Kämmerer U. Antiproliferative and antimetabolic effects behind the anticancer property of fermented wheat germ extract. BMC Complement Altern Med. 2016;1;16:160. DOI: 10.1186/s12906-016-1138-5 - 69.
Ge X, Sun C, Feng Y, Wang L, Peng J, Che Q, Gu Q, Zhu T, Li D, Zhang G. Anthraquinone Derivatives from a Marine-Derived Fungus Sporendonema casei HDN16-802. Mar Drugs. 2019;17:334. DOI: 10.3390/md17060334 - 70.
Li JS, Zhang H, Qi H, Wang JD, Xiang WS. Bioactive naphthoquinone and anthrone derivatives from endophytic Micromonospora sp. NEAU-gq13. J Asian Nat Prod Res. 2019;21:1151-1160. DOI: 10.1080/10286020.2018.1520222 - 71.
Xu C, Sun X, Jin M, Zhang X. A novel benzoquinone compound isolated from deep-sea hydrothermal vent triggers apoptosis of tumor cells. Mar Drugs. 2017;15:200-206. DOI: 10.3390/md15070200 - 72.
Carretero-Molina D, Ortiz-López FJ, Martín J, Oves-Costales D, Díaz C, de la Cruz M, Cautain B, Vicente F, Genilloud O, Reyes F. New Napyradiomycin Analogues from Streptomyces sp. Strain CA-271078. Mar Drugs. 2019;18:22. DOI: 10.3390/md18010022 - 73.
Nain-Perez, A, Barbosa LC, Rodríguez-Hernández D, Kramell AE, Heller L, Csuk R. Natural abenquines and synthetic analogues: preliminary exploration of their cytotoxic activity. Bioorg Med Chem Lett. 2017;27:1141-1144. DOI: 10.1016/j.bmcl.2017.01.079 - 74.
Zhou B, Jiang YJ, Ji YY, Zhang HJ, Shen L. Lactoquinomycin C and D, two new medermycin derivatives from the marine-derived Streptomyces sp. SS17A. Nat Prod Res. 2020;34:1213-1218. DOI: 10.1080/14786419.2018.1556265 - 75.
Abdelfattah MS, Elmallah MI, Mohamed AA, Ishibashi M. Sharkquinone, a new ana-quinonoid tetracene derivative from marine-derived Streptomyces sp. EGY1 with TRAIL resistance-overcoming activity. J Nat Med. 2017;71:564-569. DOI: 10.1007/s11418-017-1086-5 - 76.
Farooq U, Khan S, Naz S, Khan A, Khan A, Ahmed A, Riaz N. Three new anthraquinone derivatives isolated from Symplocos racemosa and their antibiofilm activity. Chin J Nat Medicines. 2017;15:944-949. DOI: 10.1016/s1875-5364(18)30011-6 - 77.
Viegas FPD, Espuri PF, Oliver JC, Silva NC, Dias ALT, Marques MJ, Soares MG. Leishmanicidal and antimicrobial activity of primin and primin-containing extracts from Miconia willdenowii. Fitoterapia. 2019;138:104297. DOI: 10.1016/j.fitote.2019.104297 - 78.
Xavier MR, Santos MMS, Queiroz MG, de Lima Silva MS, Goes AJS, De Morais Jr MA. Lawsone, a 2-hydroxy-1, 4-naphthoquinone from Lawsonia inermis (henna), produces mitochondrial dysfunctions and triggers mitophagy in Saccharomyces cerevisiae. Mol Biol Rep. 2020;47:1173-1185. DOI: 10.1007/s11033-019-05218-3 - 79.
Balansa W, Mettal U, Wuisan ZG, Plubrukarn A, Ijong FG, Liu Y, Schäberle TF. A new sesquiterpenoid aminoquinone from an Indonesian marine sponge. Mar drugs. 2019;17:158-163. DOI: 10.3390/md17030158 - 80.
Narmani A, Teponno RB, Arzanlou M, Surup F, Helaly SE, Wittstein K, Praditya DF, Babai-Ahari A, Steinmann E, Stadler M. Cytotoxic, antimicrobial and antiviral secondary metabolites produced by the plant pathogenic fungus Cytospora sp. CCTU A309. Fitoterapia. 2019;134:314-322. DOI: 10.1016/j.fitote.2019.02.015 - 81.
Carcamo-Noriega EN, Sathyamoorthi S, Banerjee S, Gnanamani E, Mendoza-Trujillo M, Mata-Espinosa D, Hernández-Pando R, Veytia-Bucheli JI, Possani LD,Z are RN. 1, 4-Benzoquinoneantimicrobial agents against Staphylococcus aureus and Mycobacterium tuberculosis derived from scorpion venom. Proc Natl Acad Sci U S A. 2019;116:12642-12647. DOI: 10.1073/pnas.1812334116