α-(Methylenecyclopropyl)glycine from <i>Litchi</i> seeds

Gray, David O.; Fowden, L.

doi:10.1042/bj0820385

Cited by 94 publications

(54 citation statements)

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“…ANALOGS OF THREONINE, VALINE, LEUCINE, AND ISOLEUCINE a-(Methylenecyclopropy1)glycine (17), a hypoglycemic amino acid isolated from the seed of Litchi chinensis (lychee, family Sapindaceae) (191) , possesses a carbon skeleton having geometrical features intermediate between those of leucine and isoleucine. The amino acid inhibits the growth of seedlings of Phaseolus aureus (19), and this inhibition can be reversed completely by leucine (but not isoleucine).…”

Section: Miscellaneous Analogs and Toxic Amino Acidsmentioning

confidence: 99%

Toxic Amino Acids: Their Action as Antimetabolites

Fowden¹,

Lewis²,

Tristram³

1967

Advances in Enzymology - And Related Areas of Molecular Biology

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Section: Miscellaneous Analogs and Toxic Amino Acidsmentioning

confidence: 99%

Toxic Amino Acids: Their Action as Antimetabolites

Fowden¹,

Lewis²,

Tristram³

1967

Advances in Enzymology - And Related Areas of Molecular Biology

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“…Fruits of species related to ackee and some others contain several varieties of nonprotein amino acids with cyclopropane rings, e.g. OL-(methylenecyclopropyl)glycine from Litchi chinensis and Acer genus as well as B. sapida [3,6,7], (3-(methylenecyclopropyl)~(3-methylalanine from Aesculus californica [8] and cis-and trans-cu-(carboxycyclopropyl)glycine from the seeds of A. parvifzora and A. pavia and B. sapida [9]. Methylene groups in non-* Present address: Department of Biochemistry, University College London, London W.C.l, England.…”

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confidence: 99%

Biochemistry of hypoglycin

Manchester

1974

FEBS Letters

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Hypoglycin A, P_(methylenecyclopropyl)alanine, is a non-protein amino acid first isolated [l] from the unripe fruit of the ackee, Blighia sapida, a tree much cultivated in Jamaica where the fleshy aril constitutes an important item of diet, particularly of the lower income groups. The unripe ackee aril may contain around 1 mg of hypoglycin per g wet weight and the seeds two to three times as much, but as the fruit ripens the content of the aril decreases to less than 0.01% of the amino acid [2] . Hypoglycin is found in the seeds both as the free amino acid and the y-glutamyl dipeptide conjugate, hypoglycin B

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“…In 1962 the c6 homolog a-(methylenecyclopropy1)glycine (XIIIa) was isolated from seed of another member of the Sapindaceae, Litchi chinensis. It too was shown to possess hypoglycemic properties (29). All three compounds have been demonstrated to coexist together with y-glutamyl-a-(methylenecyclopropy1)glycine (XIIIb) in seeds of Billia hippocastanurn (Hippocastanaceae) and Acer pseudoplatanus (Aceraceae) (30).…”

Section: Structures and Occurrencesmentioning

confidence: 99%