Isomerization and Stabilization of Amygdalin from Peach Kernels

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2023 Jun 10

PMID 37299025

Authors

Decai Zhang

Jianfen Ye

Yu Song

Yingying Wei

Shu Jiang

Yi Chen

Xingfeng Shao

Affiliations

Soon will be listed here.

Abstract

In this study, isomerization conditions, cytotoxic activity, and stabilization of amygdalin from peach kernels were analyzed. Temperatures greater than 40 °C and pHs above 9.0 resulted in a quickly increasing isomer ratio (L-amygdalin/D-amygdalin). At acidic pHs, isomerization was significantly inhibited, even at high temperature. Ethanol inhibited isomerization; the isomer rate decreased with the ethanol concentration increasing. The growth-inhibitory effect on HepG2 cells of D-amygdalin was diminished as the isomer ratio increased, indicating that isomerization reduces the pharmacological activity of D-amygdalin. Extracting amygdalin from peach kernels by ultrasonic power at 432 W and 40 °C in 80% ethanol resulted in a 1.76% yield of amygdalin with a 0.04 isomer ratio. Hydrogel beads prepared by 2% sodium alginate successfully encapsulated the amygdalin, and its encapsulation efficiency and drug loading rate reached 85.93% and 19.21%, respectively. The thermal stability of amygdalin encapsulated in hydrogel beads was significantly improved and reached a slow-release effect in in vitro digestion. This study provides guidance for the processing and storage of amygdalin.

Citing Articles

Transcriptome analysis reveals genes associated with the bitter-sweet trait of apricot kernels.

Zhang Y, Bao W, Wuyun T, Huang M, Chen C, Ao D For Res (Fayettev). 2024; 4:e007.

PMID: 39524411 PMC: 11524293. DOI: 10.48130/forres-0024-0004.

References

Gouda M, Bekhit A, Tang Y, Huang Y, Huang L, He Y . Recent innovations of ultrasound green technology in herbal phytochemistry: A review. Ultrason Sonochem. 2021; 73:105538. PMC: 8048006. DOI: 10.1016/j.ultsonch.2021.105538. View

Supramaniam J, Adnan R, Mohd Kaus N, Bushra R . Magnetic nanocellulose alginate hydrogel beads as potential drug delivery system. Int J Biol Macromol. 2018; 118(Pt A):640-648. DOI: 10.1016/j.ijbiomac.2018.06.043. View

Lee H, Moon A . Amygdalin Regulates Apoptosis and Adhesion in Hs578T Triple-Negative Breast Cancer Cells. Biomol Ther (Seoul). 2016; 24(1):62-6. PMC: 4703354. DOI: 10.4062/biomolther.2015.172. View

Del Cueto J, Moller B, Dicenta F, Sanchez-Perez R . β-Glucosidase activity in almond seeds. Plant Physiol Biochem. 2018; 126:163-172. DOI: 10.1016/j.plaphy.2017.12.028. View

He X, Wu L, Wang W, Xie P, Chen Y, Wang F . Amygdalin - A pharmacological and toxicological review. J Ethnopharmacol. 2020; 254:112717. DOI: 10.1016/j.jep.2020.112717. View

Uchiyama N, Kim I, Kikura-Hanajiri R, Kawahara N, Konishi T, Goda Y . HPLC separation of naringin, neohesperidin and their C-2 epimers in commercial samples and herbal medicines. J Pharm Biomed Anal. 2007; 46(5):864-9. DOI: 10.1016/j.jpba.2007.04.004. View

Makarevic J, Rutz J, Juengel E, Kaulfuss S, Tsaur I, Nelson K . Amygdalin influences bladder cancer cell adhesion and invasion in vitro. PLoS One. 2014; 9(10):e110244. PMC: 4198254. DOI: 10.1371/journal.pone.0110244. View

Mosmann T . Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983; 65(1-2):55-63. DOI: 10.1016/0022-1759(83)90303-4. View

Camacho D, Uy S, Cabrera M, Lobregas M, Fajardo T . Encapsulation of folic acid in copper-alginate hydrogels and it's slow in vitro release in physiological pH condition. Food Res Int. 2019; 119:15-22. DOI: 10.1016/j.foodres.2019.01.053. View

10.

Zhu C, Han M, Liang X, Guan B, Li P, Wang L . Hydrogen-Bond-Assisted Sequential Reaction of Silyl Glyoxylates: Stereoselective Synthesis of Silyl Enol Ethers. Org Lett. 2020; 23(1):54-59. DOI: 10.1021/acs.orglett.0c03683. View

11.

Attia A, Salama A, Eldiasty J, Mosallam S, El-Naggar S, El-Magd M . Amygdalin potentiates the anti-cancer effect of Sorafenib on Ehrlich ascites carcinoma and ameliorates the associated liver damage. Sci Rep. 2022; 12(1):6494. PMC: 9021277. DOI: 10.1038/s41598-022-10517-0. View

12.

Zhou C, Qian L, Ma H, Yu X, Zhang Y, Qu W . Enhancement of amygdalin activated with β-D-glucosidase on HepG2 cells proliferation and apoptosis. Carbohydr Polym. 2014; 90(1):516-23. DOI: 10.1016/j.carbpol.2012.05.073. View

13.

Go M, Kim H, Yu J, Choi S . Toxicity and Toxicokinetics of Amygdalin in Maesil ( Prunus mume) Syrup: Protective Effect of Maesil against Amygdalin Toxicity. J Agric Food Chem. 2018; 66(43):11432-11440. DOI: 10.1021/acs.jafc.8b03686. View

14.

Lee S, Oh A, Shin S, Kim H, Kang W, Chung S . Amygdalin Contents in Peaches at Different Fruit Development Stages. Prev Nutr Food Sci. 2017; 22(3):237-240. PMC: 5642807. DOI: 10.3746/pnf.2017.22.3.237. View

15.

Zhang N, Zhang Q, Yao J, Zhang X . Changes of amygdalin and volatile components of apricot kernels during the ultrasonically-accelerated debitterizing. Ultrason Sonochem. 2019; 58:104614. DOI: 10.1016/j.ultsonch.2019.104614. View

16.

Sohail R, Abbas S . Evaluation of amygdalin-loaded alginate-chitosan nanoparticles as biocompatible drug delivery carriers for anticancerous efficacy. Int J Biol Macromol. 2020; 153:36-45. DOI: 10.1016/j.ijbiomac.2020.02.191. View

17.

Bolarinwa I, Orfila C, Morgan M . Amygdalin content of seeds, kernels and food products commercially-available in the UK. Food Chem. 2014; 152:133-9. DOI: 10.1016/j.foodchem.2013.11.002. View

18.

Wahab M, Breitbach Z, Armstrong D, Strattan R, Berthod A . Problems and Pitfalls in the Analysis of Amygdalin and Its Epimer. J Agric Food Chem. 2015; 63(40):8966-73. DOI: 10.1021/acs.jafc.5b03120. View

19.

Yu L, Ye H, Zheng L, Chen L, Chu K, Liu X . Determination of the epimerization rate constant of amygdalin by microemulsion electrokinetic chromatography. Electrophoresis. 2011; 32(2):218-22. DOI: 10.1002/elps.201000287. View

20.

Azhar A, Amran N, Yusup S, Yusoff M . Ultrasonic Extraction of 2-Acetyl-1-Pyrroline (2AP) from Using Ethanol as Solvent. Molecules. 2022; 27(15). PMC: 9370269. DOI: 10.3390/molecules27154906. View