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

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

SN - 0163-3864

VL - 65

SP - 542

EP - 547

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 4

ER -