Topic review

Anti-Cancer Quinone

Subjects: Molecular Biology View times: 108
Submitted by: Yu-Jung Chang

Definition

Natural quinones are secondary metabolites of plant and are categorized as benzoquinone, naphthoquinone, phenanthrenequinone, and anthraquinone according to their aromatic carbon skeleton [3]. Quinones are highly electrophilic molecules that accept one- or two-electrons from flavoenzymes and iron-sulfur proteins to form semiquinone or hydroquinone. They exert cytotoxic effects through alkylating proteins or DNA and affect the redox cycle with their semiquinone radicals to generate reactive oxygen species.

1. Introduction

Medicinal plants and their metabolites are great sources for pharmaceutical applications. The metabolites in plants provide a rich variety of bioactive compounds with anticancer, antioxidant, anti-inflammatory, or antimicrobial activities. Some of these drugs such as paclitaxel, docetaxel, resveratrol, vincristine, and vinblastine are approved of and used extensively in treating several types of cancer, including breast, head and neck, testicular, and bladder cancers [1][2]. Natural quinones are secondary metabolites of plant and are categorized as benzoquinone, naphthoquinone, phenanthrenequinone, and anthraquinone according to their aromatic carbon skeleton [3]. Quinones are highly electrophilic molecules that accept one- or two-electrons from flavoenzymes and iron-sulfur proteins to form semiquinone or hydroquinone. They exert cytotoxic effects through alkylating proteins or DNA and affect the redox cycle with their semiquinone radicals to generate reactive oxygen species. Their cytotoxicity promotes inflammatory reactions, oxidizes DNA, and induces cell death. Quinone-based drugs such as doxorubicin and mitomycin C have been used clinically for cancer chemotherapy, but their adverse side effects and toxicity have been an issue [4]. Consequently, there is a continued search for the development of quinone-based agents displaying antitumor activity that are less toxic and have reduced side effects.

2. Datas

Isoplumbagin (5-hydroxy-3-methyl-1,4-naphthoquinone) can be isolated from the bark of Lawsonia inermis [5] and Plumbago europaea [6] and has been shown to exhibit anti-inflammatory activity against Carrageenan-induced rat paw oedema [7] and antimicrobial activity against invasive vaginitis strains [6]. Chronic inflammation facilitates the initiation and progression of cancer [8].

 

Figure 1. Schematic summary of the molecular mechanisms of isoplumbagin-mediated anti-cancer effect. 

The entry is from 10.3390/ijms21124378

References

  1. Fernanda Majolo; Luciana Knabben De Oliveira Becker Delwing; Diorge Jônatas Marmitt; Ivan Cunha Bustamante-Filho; Márcia Inês Goettert; Medicinal plants and bioactive natural compounds for cancer treatment: Important advances for drug discovery. Phytochemistry Letters 2019, 31, 196-207, 10.1016/j.phytol.2019.04.003.
  2. Jeong-Hyeon Ko; Gautam Sethi; Jae-Young Um; Muthu K Shanmugam; Frank Arfuso; Alan Prem Kumar; Anupam Bishayee; Kwang Seok Ahn; The Role of Resveratrol in Cancer Therapy. International Journal of Molecular Sciences 2017, 18, 2589, 10.3390/ijms18122589.
  3. Jin-Jian Lu; Jiao-Lin Bao; Guo-Sheng Wu; Wen-Shan Xu; Mingqing Huang; Xiuping Chen; Yi-Tao Wang; Quinones Derived from Plant Secondary Metabolites as Anti-cancer Agents. Anti-Cancer Agents in Medicinal Chemistry 2013, 13, 456-463, 10.2174/187152013804910389.
  4. Ivana Klopčič; Marija Sollner Dolenc; Chemicals and Drugs Forming Reactive Quinone and Quinone Imine Metabolites. Chemical Research in Toxicology 2018, 32, 1-34, 10.1021/acs.chemrestox.8b00213.
  5. Sarita Gupta; Mohd Ali; Mohd S. Alam; A naphthoquinone from Lawsonia inermis stem bark. Phytochemistry 1993, 33, 723-724, 10.1016/0031-9422(93)85484-9.
  6. Marzieh Sobhani; Mahdi Abbas-Mohammadi; Samad Nejad Ebrahimi; Atousa Aliahmadi; Tracking leading anti-Candida compounds in plant samples; Plumbago europaea. Iranian Journal of Microbiology 1970, 10, 187-193, .
  7. Gupta, S.A.M.; Pillai, K.K.; Alam, M.S.; Evaluation of anti-inflammatory activity of some constituents of Lawsonia inermis.. Fitoterapia 1993, 64, 365–366, .
  8. Lance L. Munn; Cancer and inflammation.. Wiley Interdisciplinary Reviews: Systems Biology and Medicine 2016, 9, e1370, 10.1002/wsbm.1370.

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