Plant cyanogenic glycosides: an overview

Authors

  • Dwi Hartanti Department of Pharmaceutical Biology, Faculty of Pharmacy, Universitas Muhammadiyah Purwokerto, Purwokerto, Central Java, Indonesia http://orcid.org/0000-0002-6600-7251
  • Arinda Nur Cahyani Department of Pharmaceutical Biology, Faculty of Pharmacy, Universitas Muhammadiyah Purwokerto, Purwokerto, Central Java, Indonesia

DOI:

https://doi.org/10.22219/farmasains.v5i1.10047

Keywords:

Cyanogenic glycosides, phytochemistry, toxicity

Abstract

The cyanogenic glycosides have consisted of α-hydroxy nitrile aglycone and a sugar moiety that producing hydrogen cyanide (HCN) during the hydrolysis process. This HCN-producing property underlines the toxicity of the plants commonly associated with these compounds in humans and animals. However, new evidence shows that the toxicity of these compounds is lower than those theoretically caused by the equivalent released HCN. In order to provide a deeper understanding of cyanogenic glycosides, an overview of these compounds is given in this article. It covers the chemistry, distribution, biosynthesis, toxicity, determination, as well as extraction and isolation of the compounds.

 

References

Abraham, K., Buhrke, T., & Lampen, A. (2016). Bioavailability of cyanide after consumption of a single meal of foods containing high levels of cyanogenic glycosides: A crossover study in humans. Archives of Toxicology, 90(3), 559-574. doi:10.1007/s00204-015-1479-8

Ahn, Y. O., Saino, H., Mizutani, M., Shimizu, B., & Sakata, K. (2007). Vicianin hydrolase is a novel cyanogenic beta-glycosidase specific to beta-vicianoside (6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside) in seeds of Vicia angustifolia. Plant and Cell Physiology, 48(7), 938-947. doi:10.1093/pcp/pcm065

Aikman, K., Bergman, D., Ebinger, J., & Seigler, D. (1996). Variation of cyanogenesis in some plant species of the midwestern United States. Biochemical and Systematic Ecology, 24(7-8), 637-645. doi:10.1016/S0305-1978(96)00069-5

Bolarinwa, I. F., Orfila, C., & Morgan, M. R. A. (2015). Determination of amygdalin in apple seeds, fresh apples, and processed apple juices. Food Chemistry, 170, 437-442. doi:10.1016/j.foodchem.2014.08.083

Bone, K., & Mills, S. (2013). Principles of Herbal Pharmacology. In Principles and Practice of Phytotherapy: Modern Herbal Medicine (2nd ed.). London, UK: Churchill Livingstone.

Campa, C., Schmitt-Kopplin, P., Cataldi, T. R. I., Bufo, S. A., Freitag, D., & Kettrup, A. (2000). Analysis of cyanogenic glycosides by micellar capillary electrophoresis. Journal of Chromatography B: Biomedical Sciences and Applications, 739(1), 95-100. doi:10.1016/S0378-4347(99)00375-8

Choudhury, D., Sahu, J. K., & Sharma, G. D. (2012). Value addition to bamboo shoots: A review. Journal of Food Sciences and Technology, 49(4), 407-414.

Cressey, P., & Reeve, J. (2019). Metabolism of cyanogenic glycosides: A review. Food and Chemical Toxicology, 125, 225–232. doi:10.1016/j.fct.2019.01.002

Dellagreca, M., Fiorentino, A., Monaco, P., Previtera, L., & Simonet, A. M. (2000). Cyanogenic glycosides from Sambucus Nigra. Natural Product Letter, 14(3), 175-182.

Dewick, P. M. (2009). The Acetate Pathway: Fatty Acids and Polyketides. In Medicinal Natural Products: A Biosynthetic Approach (3rd ed.). Hoboken, NJ:John Wiley & Sons Ltd.

Eyjólfsson, R. (1970). Isolation and structure determination of triglochinin, a new cyanogenic glucoside from Triglochin maritimum. Phytochemistry, 9(4), 845-851.

Gleadow, R. M., Haburjak, J., Dunn, J. E., Conn, M. E., & Conn, E. E. (2008). Frequency and distribution of cyanogenic glycosides in Eucalyptus. Phytochemistry, 69(9), 1870-1874.

Majak, W., & Cheng, K. J. (1987). Hydrolysis of the cyanogenic glycosides amygdalin, prunasin and linamarin by ruminal microorganisms. Canadian Journal of Animal Science, 67(4), 1133-1137.

Müller-Schwarze, D. (2009). Test for Cyanogenic Compounds in Plants. In D. Müller-Schwarze (Ed.), Hands-On Chemical Ecology (pp. 69-73). New York, NY: Springer. doi:10.1007/978-1-4419-0378-5

Olsen, K. M., Sutherland, B. L., & Small, L. L. (2007). Molecular evolution of the Li/li chemical defence polymorphism in white clover (Trifolium repens L.). Molecular Ecology, 16(19), 4180-4193. doi:10.1111/j.1365-294X.2007.03506.x

Panter, K. E. (2018). Cyanogenic Glycoside - Containing Plants. In R. C. Gupta (Ed.), Veterinary Toxicology: Basic and Clinical Principles (Third Ed., pp. 935-940). Houston, TX: Elsevier Inc. doi:10.1016/B978-0-12-811410-0.00064-7

PubChem. (2019). Explore Chemistry. U.S. National Library of Medicine. Retrieved from https://pubchem.ncbi.nlm.nih.gov/

Roulard, R., Fontaine, J., Jamali, A., Cailleu, D., Tavernier, R., Guillot, X., ... & Mesnard, F. (2017). Use of qNMR for speciation of flaxseeds (Linum usitatissimum) and quantification of cyanogenic glycosides. Analytical and Bioanalytical Chemistry, 409(30), 7011-7026. doi:10.1007/s00216-017-0637-7

Schulz, V., Hansel, R., Blumenthal, M., & Tyler, V. E. (2004). Rational Phytotherapy: A Reference Guide for Physicians and Pharmacists (5th ed.). Berlin, Germany: Springer-Verlag Berlin Heidelberg.

Seigler, D. S. (1975). Isolation and characterization of naturally occuring cyanogenic compounds. Phytochemistry, 14(1), 9-29.

Shlichta, J. G., Glauser, G., & Benrey, B. (2014). Variation in cyanogenic glycosides across populations of wild lima beans (Phaseolus lunatus) has no apparent effect on bruchid beetle performance. Journal of Chemical Ecology, 40(5), 468-475. doi:10.1007/s10886-014-0434-0

Sun, Z., Zhang, K., Chen, C., Wu, Y., Tang, Y., Georgiev, M. I., ... & Zhou, M. (2018). Biosynthesis and regulation of cyanogenic glycoside production in forage plants. Applied Microbiology and Biotechnology, 102(1), 9-16. doi:10.1007/s00253-017-8559-z

Tivana, L. D., Da Cruz Francisco, J., Zelder, F., Bergenståhl, B., & Dejmek, P. (2014). Straightforward rapid spectrophotometric quantification of total cyanogenic glycosides in fresh and processed cassava products. Food Chemistry, 158, 20-27. doi:10.1016/j.foodchem.2014.02.066

Vetter, J. (2017). Plant Cyanogenic Glycosides. In P. Gopalakrishnakone, C. R. Carlini, & R. Ligabue-Braun (Eds.), Plant Toxins (pp. 288-315). Berlin, Germany: Springer Science+ Business Media. doi:10.1007/978-94-007-6464-4

Waszkowiak, K., Gliszczynska-Swiglo, A., Barthet, V., & Skrety, J. (2015). Effect of extraction method on the phenolic and cyanogenic glucoside profile of Flaxseed extracts and their antioxidant capacity. Journal of American Oil Chemists’ Society, 92, 1609-1619. doi:10.1007/s11746-015-2729-x

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Published

2020-07-25

How to Cite

Hartanti, D., & Cahyani, A. N. (2020). Plant cyanogenic glycosides: an overview. Farmasains : Jurnal Farmasi Dan Ilmu Kesehatan, 5(1), 1-6. https://doi.org/10.22219/farmasains.v5i1.10047

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Section

Biology Pharmacy and Natural Product