Open access peer-reviewed chapter - ONLINE FIRST

Cytotoxic and Antimicrobial Activities of Quinones Isolated from Different Organism

By Nimsi Campos-Xolalpa, Julia Pérez-Ramos, Ana Esquivel-Campos, Cuauhtemoc Pérez-González, Leonor Sánchez-Pérez and Salud Pérez-Gutiérrez

Submitted: September 23rd 2020Reviewed: December 22nd 2020Published: January 27th 2021

DOI: 10.5772/intechopen.95598

Downloaded: 41

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 1Tables 1 and 2).

Table 1.

Anticancer activity of quinones isolated from different organism.

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).

2. Anticancer and antimicrobial activity of quinones obtained from plants, animals, and microorganisms

3. Discussion

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.

Conflict of interest

The authors declare no conflict of interest.

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Nimsi Campos-Xolalpa, Julia Pérez-Ramos, Ana Esquivel-Campos, Cuauhtemoc Pérez-González, Leonor Sánchez-Pérez and Salud Pérez-Gutiérrez (January 27th 2021). Cytotoxic and Antimicrobial Activities of Quinones Isolated from Different Organism [Online First], IntechOpen, DOI: 10.5772/intechopen.95598. Available from:

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