Structural characterization of hypoglycin B, a diastereomeric dipeptide from the ackee fruit (<i>Blighia sapida</i> Koenig) by NMR experiments

Bowen‐Forbes, Camille S.; Minott, Donna A.

doi:10.1002/mrc.2497

Cited by 9 publications

(16 citation statements)

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“…The method used for isolation, along with the NMR characterization of hypoglycins A and B, are detailed in previous papers. 32,33 Sample Preparation. For the seasonality studies, ackee fruits were harvested during two bearing seasons: March 2003 (season 1, S1) and JulyÀSeptember (season 2, S2) of the same year.…”

Section: Isolation Of Hypoglycin a And Hypoglycin B Standardsmentioning

confidence: 99%

Tracking Hypoglycins A and B over Different Maturity Stages: Implications for Detoxification of Ackee (Blighia sapida K.D. Koenig) Fruits

Bowen‐Forbes

Minott

2011

J. Agric. Food Chem.

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Consumption of improperly ripened ackee ( Blighia sapida K.D. Koenig) often results in fatalities. The causal toxin, hypoglycin A, decreases in the edible arilli upon maturity; regulation of hypoglycin A in the arilli is thus critical. Hypoglycin B, also toxic, is confined to the seeds. Hypoglycins A and B were tracked in ackees grown in Jamaica over different maturity stages using RP-HPLC. Studies on the 'Butter' and 'Cheese' ackee varieties and across two different harvest seasons were conducted. In 'Cheese' ackees, hypoglycin A decreased from about 8000 mg/kg in the green arilli and seeds to 271 and 1451 mg/kg, respectively, in the ripe fruit whereas hypoglycin B levels in the seeds increased from 1629 to 11774 mg/kg. The strong inverse relationship demonstrated that hypoglycin B in the seeds serves as a sink for hypoglycin A from the ripening arilli and is thereby involved in the detoxification mechanism of the fruit.

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Section: Isolation Of Hypoglycin a And Hypoglycin B Standardsmentioning

confidence: 99%

Tracking Hypoglycins A and B over Different Maturity Stages: Implications for Detoxification of Ackee (Blighia sapida K.D. Koenig) Fruits

Bowen‐Forbes

Minott

2011

J. Agric. Food Chem.

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“…The fruit should be allowed to open and ripen naturally on the tree as fresh arils of the ripened fruits are edible but the unripe fruit is not. B. sapida (Ackee) a known fish poison and the hypoglycin A and B have been identified as the toxicant in the seed (Bowen-Forbes and Minott, 2009;Moya, 2001;Natalini et al, 2000). The fruit is rich in essential fatty acids, vitamin A, zinc, and protein (Oladiji et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

Isolation, partial purification and characterization of antifungal trypsin inhibitor protease from the seed of Blighia sapida K.D. Koenig (Ackee)

Nwozo¹,

Iwuoha²,

Waryo³

et al. 2014

Afr. J. Biotechnol.

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Seed proteins have been evaluated for their nutritive value and biological activity. Proteases and proteinase inhibitors have been of immense benefit to both agriculture and therapeutic purposes. The seed proteins of Blighia sapida was evaluated for both structure and biological activity in this study. The matured dried seeds were pulverized and sequentially extracted using 10 mM Tris/HCl pH 7.4, 10 mM ammonium acetate and 10 mM sulphuric acid. Crude protein extracts were concentrated and the protein concentrations were estimated. Proteins were purified by 70% ammonium sulphate precipitation, Sephadex G50 reversed phase chromatography and finally by HPLC on a C18 column. Two bands were obtained from SDS-PAGE electrophoresis and they were identified by ESI/MS using in gel tryptic digestion. The seed protein from B. Sapida consists of two single polypeptide chains each with mass of about 24 to 27 KDa as established by a combination of SDS-PAGE and ESI/MS. Proteins exhibited protease activity, which was confirmed by zymography. Protease activity was characterized for effect of temperature, pH, divalent metal ions and chelating agents. The crude protein from the seed of B. sapida showed antimicrobial activity and the antifungal activity was comparable with the reference drug, Ticonazole.

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“…It is worth noting that, besides the 2 species mentioned above, both of which displayed a medium to medium-strong response, seeds from a number of other maples also showed a medium response or stronger to Fowden and Pratt's hypoglycin A assay, including Acer palmatum (Japanese maple), Acer saccharum (sugar maple) and Acer spicatum (mountain maple) and various cultivars and subspecies of these trees. Currently, we do not know whether seeds of these species are ingested by horses to any degree, nor have we had the opportunity to confirm Fowden and Pratt's observations of hypoglycin A levels with more quantitative testing.We have isolated several hundred milligrams of purified hypoglycin A from A. negundo seed tissues and have confirmed by 1 H nuclear magnetic resonance spectroscopy and mass spectrometry that the structure is identical to that of hypoglycin A obtained from ackee [8]. Based on preliminary data from longitudinal and geographical quantitative studies of hypoglycin A levels in A. negundo seeds (currently under way in the laboratory of A.D.H.…”

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confidence: 85%

“…We have isolated several hundred milligrams of purified hypoglycin A from A. negundo seed tissues and have confirmed by 1 H nuclear magnetic resonance spectroscopy and mass spectrometry that the structure is identical to that of hypoglycin A obtained from ackee . Based on preliminary data from longitudinal and geographical quantitative studies of hypoglycin A levels in A. negundo seeds (currently under way in the laboratory of A.D.H.…”

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confidence: 87%

Clarifying the role of maples in atypical myopathy

Gillman

Hegeman

Sharp

2014

Equine Veterinary Journal

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Recently, Stephanie Valberg and colleagues identified ingestion of Acer negundo (box elder) seeds as a probable cause of seasonal pasture myopathy in the USA [1]. Other recent work by Votion, Valberg and colleagues [2] and included in this issue of Equine Veterinary Journal has demonstrated that atypical myopathy in Europe is likely to have the same causal factor.The chemical in maple seeds suspected to cause these myopathies, known as hypoglycin A (2S-2-amino-3-(2-methylidenecyclopropyl)-propanoic acid), is a nonproteinogenic amino acid, which, following ingestion and metabolic activation, becomes a potent inhibitor of acyl-CoA dehydrogenase, a key enzyme active in fatty acid metabolism.At present it is not entirely clear what the risk factors for the occurrence of either form of myopathy are, as they pertain to the presence of different maple species in areas where horses reside. There are many more questions than there are answers. This editorial aims to summarise the current state of knowledge regarding plants that may play a role in this disease and suggest areas that need further study.Maples are classified within the family Sapindaceae, known as the soapberry family, along with a number of other plants, such as horse chestnut (Aesculus species) and lychee (Litchi chinensis). Ackee (Blighia sapida), the national fruit of Jamaica, is a member of this family that contains hypoglycin A in its fruit. Hypoglycin A varies in concentration in ackee fruits based on maturity, with unripe fruits containing a larger quantity of this toxin and ripe fruits a much smaller concentration [3]. When unripe fruit is ingested by humans, it may result in a disease known as Jamaican vomiting sickness, which in severe cases leads to death.Jordan and Burrows [4] were the first to report a water-soluble toxin in the seeds and pods of ackee fruit. In 1954, this toxin was isolated and 2 amino acids identified by Hassall et al. [5], who named them hypoglycin A and hypoglycin B because of their hypoglycaemic activity. In 1958, Feng and Patrick [6] described the effect of hypoglycin A on animals, noting that it caused 'drowsiness progressing to coma, and when large doses were given the animals died'. Besides ackee fruit, and now maple seed, we are not aware of any literature implicating any other plants contributing to hypoglycin A poisoning in mammals, though related compounds have been observed in other genera of Sapindaceae (including 2-amino-4-methylhex-4-enoic acid in Aesculus californica [California buckeye], and hypoglycin B, the γ-glutamyl dipeptide of hypoglycin A, in Billia hippocastanum).Currently, there is very little information on the concentration of hypoglycin A in the seeds of various maples. One of the authors of this article (A.D.H.) has quantified hypoglycin A in 2 maple species, namely Acer negundo (box elder) and Acer pseudoplatanus (sycamore maple; A. D. Hegeman, unpublished results). This is consistent with work by Fowden and Pratt [7], who provided a qualitative description of a strong hypoglycin A response in ...

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Structural characterization of hypoglycin B, a diastereomeric dipeptide from the ackee fruit (Blighia sapida Koenig) by NMR experiments

Cited by 9 publications

References 10 publications

Tracking Hypoglycins A and B over Different Maturity Stages: Implications for Detoxification of Ackee (Blighia sapida K.D. Koenig) Fruits

Tracking Hypoglycins A and B over Different Maturity Stages: Implications for Detoxification of Ackee (Blighia sapida K.D. Koenig) Fruits

Isolation, partial purification and characterization of antifungal trypsin inhibitor protease from the seed of Blighia sapida K.D. Koenig (Ackee)

Clarifying the role of maples in atypical myopathy

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