Plant analysis by butterflies: occurrence of cyclopentenylglycines in Passifloraceae, Flacourtiaceae, and Turneraceae and discovery of the novel nonproteinogenic amino acid 2-(3'-cyclopentenyl)glycine in Rinorea
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Plant analysis by butterflies : occurrence of cyclopentenylglycines in Passifloraceae, Flacourtiaceae, and Turneraceae and discovery of the novel nonproteinogenic amino acid 2-(3'-cyclopentenyl)glycine in Rinorea. / Clausen, Vicki; Frydenvang, Karla Andrea; Koopmann, Ricarda; Jørgensen, Lise Bolt; Abbiw, Daniel K; Ekpe, Patrick; Jaroszewski, Jerzy W.
In: Journal of Natural Products, Vol. 65, No. 4, 2002, p. 542-7.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Plant analysis by butterflies
T2 - occurrence of cyclopentenylglycines in Passifloraceae, Flacourtiaceae, and Turneraceae and discovery of the novel nonproteinogenic amino acid 2-(3'-cyclopentenyl)glycine in Rinorea
AU - Clausen, Vicki
AU - Frydenvang, Karla Andrea
AU - Koopmann, Ricarda
AU - Jørgensen, Lise Bolt
AU - Abbiw, Daniel K
AU - Ekpe, Patrick
AU - Jaroszewski, Jerzy W
PY - 2002
Y1 - 2002
N2 - Following records about feeding habits of nymphalid butterflies, a novel nonproteinogenic L-amino acid, (S)-2-(3'-cyclopentenyl)glycine (11), was discovered in Rinorea ilicifolia, a species where the presence of a cyclopentanoid natural product of this kind was neither known nor anticipated from the taxonomic point of view. Another novel amino acid, (2S,1'S,2'S)-2-(2'-hydroxy-3'-cyclopentenyl)glycine (12), the stereochemistry of which was determined by single-crystal X-ray diffraction, was shown to occur in species belonging to Flacourtiaceae, Passifloraceae, and Turneraceae. These species, many of which serve as hosts for nymphalid butterflies (Acraeinae, Heliconiinae, Argynninae), also produce 2-(2'-cyclopentenyl)glycine. Cyclopentenylglycines are proposed to be novel chemical recognition templates for plant-insect interactions. Ratios between the epimers of (2S)-2-(2'-cyclopentenyl)glycine, which co-occur in plants, were determined by (1)H NMR spectroscopy. Contrary to a previous report, the (2S,1'R) epimer always appears to predominate over the (2S,1'S) epimer. Stereochemical aspects of biosynthesis of natural cyclopentanoid cyanogenic glycosides are discussed in relation to these findings.
AB - Following records about feeding habits of nymphalid butterflies, a novel nonproteinogenic L-amino acid, (S)-2-(3'-cyclopentenyl)glycine (11), was discovered in Rinorea ilicifolia, a species where the presence of a cyclopentanoid natural product of this kind was neither known nor anticipated from the taxonomic point of view. Another novel amino acid, (2S,1'S,2'S)-2-(2'-hydroxy-3'-cyclopentenyl)glycine (12), the stereochemistry of which was determined by single-crystal X-ray diffraction, was shown to occur in species belonging to Flacourtiaceae, Passifloraceae, and Turneraceae. These species, many of which serve as hosts for nymphalid butterflies (Acraeinae, Heliconiinae, Argynninae), also produce 2-(2'-cyclopentenyl)glycine. Cyclopentenylglycines are proposed to be novel chemical recognition templates for plant-insect interactions. Ratios between the epimers of (2S)-2-(2'-cyclopentenyl)glycine, which co-occur in plants, were determined by (1)H NMR spectroscopy. Contrary to a previous report, the (2S,1'R) epimer always appears to predominate over the (2S,1'S) epimer. Stereochemical aspects of biosynthesis of natural cyclopentanoid cyanogenic glycosides are discussed in relation to these findings.
KW - Animals
KW - Butterflies
KW - Crystallography, X-Ray
KW - Feeding Behavior
KW - Glycine
KW - Magnetic Resonance Spectroscopy
KW - Molecular Conformation
KW - Molecular Structure
KW - Passiflora
KW - Plants
M3 - Journal article
C2 - 11975497
VL - 65
SP - 542
EP - 547
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 4
ER -
ID: 40371737