Journal of New Developments in Chemistry

Journal of New Developments in Chemistry

Journal of New Developments in Chemistry

Current Issue Volume No: 2 Issue No: 2

In Brief Open Access Available online freely Peer Reviewed Citation

ANTHRAQUINONES-A Naturopathic Compound

1Department of Biotechnology, Faculty of Life Sciences and Informatics, Balochistan University of Information, Technology Engineering and Management Sciences, (BUITEMS), Quetta, Pakistan

Abstract

Anthraquinones is a potent aromatic compound that besides being used commercially it offers numerous therapeutic benefits such as inhibits cancer growth by inducing apoptosis, relive constipation, ease bowl movement etc. Anthraquinones are found naturally in some plants such as senna, buckthorn, yellow dock etc while it can also be produced using chemical routes such as anthracene oxidation, naphthalene oxidation, condensation of 1, 4-naphthoquinone with butadiene etc. However its intake should strictly be regulated since it may cause some serious side effects.

Author Contributions
Received 25 Dec 2018; Accepted 22 Jan 2019; Published 13 Feb 2019;

Academic Editor: Yanyan Jiang, Professor in School of Materials Science and Engineering, Shandong University, China.

Checked for plagiarism: Yes

Review by: Single-blind

Copyright ©  2019 Nida Tabassum Khan

License
Creative Commons License     This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

Competing interests

The authors have declared that no competing interests exist.

Citation:

Nida Tabassum Khan (2019) ANTHRAQUINONES-A Naturopathic Compound. Journal of New Developments in Chemistry - 2(2):25-28. https://doi.org/10.14302/issn.2377-2549.jndc-18-2569

Download as RIS, BibTeX, Text (Include abstract )

DOI 10.14302/issn.2377-2549.jndc-18-2569

Introduction

Anthraquinones are aromatic carbon-based complexes that are present in few herbs and edible plants either as anthrones or bianthrones 1. Anthraquinones and its derivatives are widely used in vat pigments/dyes, as additives in paper and pulp industry, in seed treatment method, as pesticides, in the production of hydrogen peroxide etc 2. In addition anthraquinones also contain healing and anticancerous properties 3 (Figure 1).

Figure 1.Chemical structure of Anthraquinone
 Chemical structure of             Anthraquinone

Enlisted Below are some Plants that are Enriched with Anthraquinones

Aloe (Aloe barbadensis)

Buckthorn

Senna (Cassia sp)

Yellow dock (Rumex crispus)

Rhubarb (Rheum palmatum)

Cascara sagrada (Rhamnus frangula) 4, 5.

Chemical Based Production of Anthraquinones

Several methods for the synthesis of anthraquinones is employed such as

Anthracene oxidation with concentrated nitric acid 6.

Chemical preparation of anthraquinones from benzene and phthalic anhydride 7.

Naphthalene oxidation with butadiene followed by dehydrogenation to obtain the desired anthraquinones 8.

Dimerization of styrene with phosphoric acid followed by vapor phase oxidation 9.

Anthracene oxidation either with chromic acid in sulfuric acid (48%) or oxidation with air 10.

Condensation of 1, 4-naphthoquinone with butadiene 11.

Anthraquinones is listed as one of the mostly consumed chemical in the United States which produces approximately 5000–25 000 tons of anthraquinones annually 12.

Medicinal Properties of Anthraquinones

Anthraquinones possess antiviral, antifungal, antibacterial, laxative, insecticidal and antioxidant properties which makes it suitable to be used in the treatment of various ailments 13, 14.

Health Benefits of Anthraquinones

Anthraquinones is used for the treatment of various medical conditions which is as follows:

Treatment of Constipation

Because of its laxative property, anthraquinones elevates the concentration of fluid in the large intestine and excites colon peristalsisthus allowing easy bowel movements. 15. Additionally increased osmotic secretion of chloride ions into the gut lumen results in succeeding excretion of water 16.

Treatment of Cancer

Anthraquinones inhibits the growth of cancerous cells by inducing apoptosis in HER2 breast cancer 17 and in mercury induced kidney cancers 18. It also impose cytotoxic activities on EOL-1 cell lines, leukemic 1301 and T cell lines 19.

Side Effects of Anthraquinones

Long term use of anthraquinones might have notable side effects some of which are as follows:

 Development of Melanesia coli, a condition in which the colon lining takes on a dark brownish black hue increasing the risk for cancer 20.

 Anthraquinone dependency is developed in individuals who has been using it as a laxative over prolonged periods 21.

 Over consumption of anthraquinones causes abdominal cramps, gastrointestinal discomforts, vomiting, dermatitis, nausea, bloody diarrhea and dizziness 22, 23.

 Hypokalemia, muscle damage, dehydration, kidney damage ,miscarriage due to reflex contractions in the uterus during pregnancy etc are some clinical condition that may occur due to prolonged use of anthraquinones 24, 25

Conclusion

Thus anthraquinone is for therapeutic purposes found to be naturally occurring in plants .However its prolonged use may have some side effects therefore its intake should be under doctor’s supervision.

References

  1. 1.J P Brown. (1980) A review of the genetic effects of naturally occurring flavonoids, anthraquinones and related compounds. Mutation Research/Reviews in Genetic Toxicology. 75(3), 243-277.
  1. 2.Duval J, Pecher V, Poujol M, Lesellier E. (2016) Research advances for the extraction, analysis and uses of anthraquinones: A review. Industrial crops and products. 94, 812-833.
  1. 3.J W Lown. (1993) Anthracycline and anthraquinone anticancer agents: current status and recent developments. , Pharmacology & therapeutics 60(2), 185-214.
  1. 4.H S Yun-Choi, J H Kim, Takido M. (1990) Potential inhibitors of platelet aggregation from plant sources, V. Anthraquinones from seeds of Cassia obtusifolia and related compounds. , Journal of natural products 53(3), 630-633.
  1. 5.Delmulle L, Demeyer K. (2010) Anthraquinones in plants: source, safety and applications in gastrointestinal health.NottinghamUniversityPress.
  1. 6.J L Riebsomer. (1945) The Reactions of Nitrogen Tetroxide with Organic Compounds. Chemical reviews. 36(2), 157-233.
  1. 7.Wang Y, W R Miao, Liu Q, L B Cheng, G R Wang. (2002) Synthesis of anthraquinone from phthalic anhydride with benzene over zeolite catalyst. In Studies in Surface Science and Catalysis.Elsevier 142, 1007-1014.
  1. 8.Halcourt K, Losacker P, Martin M, Schenk N, Schwerdtel W. (1980) . U.S. Patent No. 4,220,597. Washington, DC: U.S. Patent and Trademark Office .
  1. 9.Corson B B, DORSKY J, J E Nickels, W M Kutz, H I Thayer. (1954) . Dimerization of Styrene in the Presence and Absence of Solvent. The Journal of Organic Chemistry 19(1), 17-26.
  1. 10.F L Warren. (1943) Aerobic oxidation of aromatic hydrocarbons in the presence of ascorbic acid: The reaction with anthracene and 3: 4-benzpyrene. , Biochemical Journal 37(3), 338.
  1. 11.L F Fieser. (1948) Naphthoquinone Antimalarials.III.Diene Synthesis of1,4Naphthoquinones1. , Journal of the American Chemical Society 70(10), 3165-3174.
  1. 12. (2013) on the Evaluation. , I.W.G.ANTHRAQUINONE
  1. 13.Huang Q, Lu G, H M Shen, M C Chung, C N Ong. (2007) Anti-cancer properties of anthraquinones from rhubarb. Medicinal research reviews. 27(5), 609-630.
  1. 14.Singh R, Chauhan S M S. (2004) 9, 10-Anthraquinones and other biologically active compounds from the genus Rubia. , Chemistry & biodiversity 1(9), 1241-1264.
  1. 15.Breimer D D, A J Baars. (1976) Pharmacokinetics and metabolism of anthraquinone laxatives. , Pharmacology 14(1), 30-47.
  1. 16.Cirillo C, Capasso R. (2015) Constipation and botanical medicines: an overview. , Phytotherapy Research 29(10), 1488-1493.
  1. 17.Chang C Y, H L Chan, H Y Lin, T D Way, M C Kao et al. (2012) Rhein induces apoptosis in human breast cancer cells. Evidence-Based Complementary and Alternative Medicine.
  1. 18.S A CHOWDHURY, KISHINO K, SATOH R, HASHIMOTO K, KIKUCHI H et al. (2005) Tumor-specificity and apoptosis-inducing activity of stilbenes and flavonoids. , Anticancer Research 25(3), 2055-2063.
  1. 19.Chang P, K H Lee. (1984) Cytotoxic antileukemic anthraquinones from Morinda parvifolia. , Phytochemistry 23(8), 1733-1736.
  1. 20.S B Widjanarko, Wijayanti N, Sutrisno A. (2013) Laxative potential of the konjac flour (Amorphophallus muelleri Blume) in treatment of loperamide induced constipation on Sprague Dawley rats. , Int J Med Health Biomed Bioeng Pharm Eng 7(11), 729-733.
  1. 21.Hallmann F. (2000) Toxicity of commonly used laxatives. , Medical Science Monitor 6(3), 618-628.
  1. 22.S A Müller-Lissner. (1993) Adverse effects of laxatives: fact and fiction. , Pharmacology 47(1), 138-145.
  1. 23.R F Chen, Y C Shen, H S, J F Liao, L K Ho et al. (2004) Evaluation of the anti‐ inflammatory and cytotoxic effects of anthraquinones and anthracenes derivatives in human leucocytes. , Journal of pharmacy and pharmacology 56(7), 915-919.
  1. 24.Cheung K K, W Y So, A P Kong, R C Ma, F C Chow. (2014) Life-threatening hypokalemic paralysis in a young bodybuilder. Case reports in endocrinology.
  1. 25.Müller-Lissner S. (2009) The pathophysiology, diagnosis, and treatment of constipation. , Deutsches Ärzteblatt International 106(25), 424.

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