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

Vicki Clausen; Karla Andrea Frydenvang; Ricarda Koopmann; Lise Bolt Jørgensen; Daniel K Abbiw; Patrick Ekpe; Jerzy W Jaroszewski

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

Vicki Clausen, Karla Andrea Frydenvang, Ricarda Koopmann, Lise Bolt Jørgensen, Daniel K Abbiw, Patrick Ekpe, Jerzy W Jaroszewski

20 Citationer (Scopus)

Abstract

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.

Originalsprog	Engelsk
Tidsskrift	Journal of Natural Products
Vol/bind	65
Udgave nummer	4
Sider (fra-til)	542-7
Antal sider	6
ISSN	0163-3864
Status	Udgivet - 2002
Udgivet eksternt	Ja

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Citationsformater

Clausen, V., Frydenvang, K. A., Koopmann, R., Jørgensen, L. B., Abbiw, D. K., Ekpe, P., & Jaroszewski, J. W. (2002). 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. Journal of Natural Products, 65(4), 542-7.

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 et al.

I: Journal of Natural Products, Bind 65, Nr. 4, 2002, s. 542-7.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

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title = "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",

abstract = "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.",

keywords = "Animals, Butterflies, Crystallography, X-Ray, Feeding Behavior, Glycine, Magnetic Resonance Spectroscopy, Molecular Conformation, Molecular Structure, Passiflora, Plants",

author = "Vicki Clausen and Frydenvang, {Karla Andrea} and Ricarda Koopmann and J{\o}rgensen, {Lise Bolt} and Abbiw, {Daniel K} and Patrick Ekpe and Jaroszewski, {Jerzy W}",

year = "2002",

language = "English",

volume = "65",

pages = "542--7",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

number = "4",

}

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 -