Amygdalin: Toxicity, Anticancer Activity and Analytical Procedures for Its Determination in Plant Seeds

Jaszczak-Wilke, Ewa; Polkowska, Żaneta; Koprowski, Marek; Owsianik, Krzysztof; Mitchell, Alyson E.; Bałczewski, Piotr

doi:10.3390/molecules26082253

Cited by 62 publications

(40 citation statements)

References 82 publications

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“…(2016) reported that sorghum grains also contain amygdalin. As other studies have not corroborated this observation (Pičmanová et al ., 2015; Thodberg et al ., 2018; Jaszczak-Wilke et al ., 2021), amygdalin production may be genotype-specific or stress induced. Further study is needed to identify other aldoxime derivatives in monocots.…”

Section: Discussionmentioning

confidence: 99%

SbCYP79A61 Produces Phenylacetaldoxime, a Precursor of Benzyl Cyanide and Phenylacetic Acid in Sorghum bicolor

Perez

Dai

Tomiczek

et al. 2022

Preprint

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Aldoximes are amino acid derivatives that serve as intermediates for numerous specialized metabolites including cyanogenic glycosides, glucosinolates, and auxins. Aldoxime formation is mainly catalyzed by cytochrome P450 monooxygenases of the 79 family (CYP79s) that can have broad or narrow substrate specificity. Aldoxime biosynthesis in the cereal sorghum (Sorghum bicolor) is not well characterized. This study identified nine CYP79-encoding genes in the genome of sorghum. A phylogenetic analysis of CYP79 showed that SbCYP79A61 formed a subclade with maize ZmCYP79A61, previously characterized to be involved in aldoxime biosynthesis. Functional characterization of this sorghum enzyme using transient expression in Nicotiana benthamiana and stable overexpression in Arabidopsis thaliana revealed that SbCYP79A61 catalyzes the production of phenylacetaldoxime (PAOx) from phenylalanine, but unlike the maize enzyme, displays no detectable activity against tryptophan. Additionally, targeted metabolite analysis after stable isotope feeding assays revealed that PAOx can serve as a precursor of phenylacetic acid (PAA) in sorghum and identified benzyl cyanide as an intermediate of PAOx-derived PAA biosynthesis in both sorghum and maize. Taken together, our results demonstrate that SbCYP79A61 produces PAOx in sorghum and may serve in the biosynthesis of other nitrogen-containing phenylalanine-derived metabolites involved in mediating biotic and abiotic stresses.HighlightIdentification of SbCYP79A61, an enzyme catalyzing the production of phenylacetaldoxime (PAOx) in sorghum, and identification of benzyl cyanide as an intermediate of PAOx-derived phenylacetic acid (PAA) biosynthesis in monocots.

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Section: Discussionmentioning

confidence: 99%

SbCYP79A61 Produces Phenylacetaldoxime, a Precursor of Benzyl Cyanide and Phenylacetic Acid in Sorghum bicolor

Perez

Dai

Tomiczek

et al. 2022

Preprint

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“…The final products of amygdalin enzymatic hydrolyzation—benzaldehyde together with hydrogen cyanide—are responsible for the bitter aroma and flavor of amygdalin in fruit and result in said amygdalin toxicity and also affect the activity of pepsin when taken orally [ 25 , 26 ]. However, the cytotoxicity results of Choi and his team [ 27 ] showed that amygdalin alone was not toxic after incubation for 24 h but showed cytotoxicity in terms of the inhibition of cell proliferation, reactive oxygen species (ROS) generation, and induction of apoptosis ( Figure 2 ) only after β-glucosidase treatment.…”

Section: Amygdalinmentioning

confidence: 99%

“…Sahin et al (2011) and Sauer at el. (2015) reported that, in children aged 2 and 4, 500 mg of amygdalin caused vomiting, apathy, diarrhea, accelerated breathing, and a blood cyanide concentration of 163 µg/L [ 26 , 36 ]. In an adult woman, 9 g of amygdalin caused vomiting, dizziness, and a blood cyanide concentration of 143 µg/L [ 37 ].…”

Section: Amygdalinmentioning

confidence: 99%

Inflammation, It’s Regulation and Antiphlogistic Effect of the Cyanogenic Glycoside Amygdalin

et al. 2021

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The inflammatory reaction accompanies in part or in full any disease process in the vascularized metazoan. This complicated reaction is controlled by regulatory mechanisms, some of which produce unpleasant symptomatic manifestations of inflammation. Therefore, there has been an effort to develop selective drugs aimed at removing pain, fever, or swelling. Gradually, however, serious adverse side effects of such inhibitors became apparent. Scientific research has therefore continued to explore new possibilities, including naturally available substances. Amygdalin is a cyanogenic glycoside present, e.g., in bitter almonds. This glycoside has already sparked many discussions among scientists, especially about its anticancer potential and related toxic cyanides. However, toxicity at different doses made it generally unacceptable. Although amygdalin given at the correct oral dose may not lead to poisoning, it has not yet been accurately quantified, as its action is often affected by different intestinal microbial consortia. Its pharmacological activities have been studied, but its effects on the body’s inflammatory response are lacking. This review discusses the chemical structure, toxicity, and current knowledge of the molecular mechanism of amygdalin activity on immune functions, including the anti-inflammatory effect, but also discusses inflammation as such, its mediators with diverse functions, which are usually targeted by drugs.

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“…Mostly these are ethanol, methanol, ethyl acetate, and water, but also 0.1% citric acid solution under reflux is used to increase the efficiency of extraction. To obtain a high-quality oil free of amygdalin, the extraction procedure should be optimized or cold-pressing can be carried out [22].…”

Section: Introductionmentioning

confidence: 99%

Assessing the Fatty Acid, Carotenoid, and Tocopherol Compositions of Seeds from Apple Cultivars (Malus domestica Borkh.) Grown in Norway

Akšić

Lazarević²,

Šegan

et al. 2021

Foods

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Apple production generates large amounts of apple pomace including seeds, leading to high transportation costs, public health hazards and undesirable odor. A new reuse strategy of this kind of waste could solve environmental issues and/or create unconventional sources of health beneficial products. In total, seeds from 75 apple cultivars grown in Norway (both domestic and international) have been analyzed for the first time for oil content and fatty acid profile together with tocopherols and carotenoids quantification in defatted seeds. Seeds from cultivar Håkonseple had the highest oil content (22.10%), with linoleic, oleic acid, and palmitic acid as the most abundant fatty acids. The levels of β-carotene and lycopene carotenoids and α-tocopherol were the highest in defatted seeds of the cultivar Sureple Grøn. Principal component analysis separated cultivars according to the total oil content. The Norwegian apple cultivars Håkonseple, Kviteple, Tolleivseple, Vinterrosenstrips, and Tokheimseple are recommended for obtaining vegetable oil due to their high oil contents, while cultivar Sureple Grøn can be separated due to its high levels of β-carotene, lycopene and total tocopherols.

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Amygdalin: Toxicity, Anticancer Activity and Analytical Procedures for Its Determination in Plant Seeds

Cited by 62 publications

References 82 publications

SbCYP79A61 Produces Phenylacetaldoxime, a Precursor of Benzyl Cyanide and Phenylacetic Acid in Sorghum bicolor

SbCYP79A61 Produces Phenylacetaldoxime, a Precursor of Benzyl Cyanide and Phenylacetic Acid in Sorghum bicolor

Inflammation, It’s Regulation and Antiphlogistic Effect of the Cyanogenic Glycoside Amygdalin

Assessing the Fatty Acid, Carotenoid, and Tocopherol Compositions of Seeds from Apple Cultivars (Malus domestica Borkh.) Grown in Norway

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