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. 2016 Jul 13;64(27):5607-13.
doi: 10.1021/acs.jafc.6b02478. Epub 2016 Jul 1.

Quantification of Toxins in Soapberry (Sapindaceae) Arils: Hypoglycin A and Methylenecyclopropylglycine

Samantha L Isenberg  1 , Melissa D Carter  2 , Shelby R Hayes  3 , Leigh Ann Graham  1 , Darryl Johnson  3 , Thomas P Mathews  1 , Leslie A Harden  4 , Gary R Takeoka  4 , Jerry D Thomas  2 , James L Pirkle  2 , Rudolph C Johnson  2
Affiliations

Quantification of Toxins in Soapberry (Sapindaceae) Arils: Hypoglycin A and Methylenecyclopropylglycine

Samantha L Isenberg et al. J Agric Food Chem. .

Abstract

Methylenecyclopropylglycine (MCPG) and hypoglycin A (HGA) are naturally occurring amino acids found in some soapberry fruits. Fatalities have been reported worldwide as a result of HGA ingestion, and exposure to MCPG has been implicated recently in the Asian outbreaks of hypoglycemic encephalopathy. In response to an outbreak linked to soapberry ingestion, the authors developed the first method to simultaneously quantify MCPG and HGA in soapberry fruits from 1 to 10 000 ppm of both toxins in dried fruit aril. Further, this is the first report of HGA in litchi, longan, and mamoncillo arils. This method is presented to specifically address the laboratory needs of public-health investigators in the hypoglycemic encephalitis outbreaks linked to soapberry fruit ingestion.

Keywords: Acer; Aceraceae; Aesculus; Litchi; Sapindaceae; ackee; cyclopropylamino acids; hypoglycin A; lychee; methylenecyclopropylalanine; methylenecyclopropylglycine; rambutan; soapberry.

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Figures

Figure 1
Figure 1
Representative product ion mass spectra for (A) dns-MCPG and (B) dns-HGA. Both parent ions (m/z 361.1 and 375.1, respectively) dissociate to product ions at m/z 170.1 (quantitation ion) and m/z 157.1 (confirmation ion).
Figure 2
Figure 2
Extracted ion chromatograms of rambutan extract containing (A) no HGA added, (B) 1.00 ng/mL HGA, (C) 200 ng/mL HGA, (D) no MCPG added, (E) 1.00 ng/mL MCPG, (F) 200 ng/mL MCPG. Detection of HGA was based on the transition of dns-HGA m/z 375.1 → 170.1 (A-C). MCPG used the transition of dns-MCPG m/z 361.1 → 170.1 (D-F). The dashed lines indicate the chromatographic peak height.
Scheme 1
Scheme 1
Derivatization of MCPG and HGA with dansyl chloride (labeled sites of internal standards are represented by asterisks).
See this image and copyright information in PMC

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