Acylierte Anthocyane III.

Birkofer, Leonhard; Kaiser, Christelmargot; Donike, M.; Koch, W.

doi:10.1515/znb-1965-0504

Cited by 27 publications

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“…Petunia-based research started over a century ago (and at the University of Amsterdam some 70 years ago) ( Saunders, 1910 ; Bianchi, 1959 ) with studies on flower shape and pigmentation, including chemical analyses of anthocyanin pigments and other flavonoids ( Birkhofer et al., 1963a ; Birkhofer et al., 1963b ; Birkhofer et al., 1965 ; Ando et al., 1999 ) and the inbreeding of commercial varieties for genetic analyses. Since then, the petunia has proven to be a very suitable system for studying flower pigmentation and several other processes related to the development of petals, in particular cells in the petal epidermis.…”

Section: Introductionmentioning

confidence: 99%

The Amsterdam petunia germplasm collection: A tool in plant science

et al. 2023

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Petunia hybrida is a plant model system used by many researchers to investigate a broad range of biological questions. One of the reasons for the success of this organism as a lab model is the existence of numerous mutants, involved in a wide range of processes, and the ever-increasing size of this collection owing to a highly active and efficient transposon system. We report here on the origin of petunia-based research and describe the collection of petunia lines housed in the University of Amsterdam, where many of the existing genotypes are maintained.

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Section: Introductionmentioning

confidence: 99%

The Amsterdam petunia germplasm collection: A tool in plant science

et al. 2023

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Struktur und molekulare Stapelung von Anthocyanen — Variation der Blütenfarben

Goto

Kondo

1991

Angewandte Chemie

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1914 machte Willstätter die überraschende Beobachtung, daß ein Pigment verschiedene Farben hervorbringen kann. So findet sich in der blauen Kornblume und in der roten Rose das gleiche Pigment: Cyanin. Die Vielfalt an Blütenfarben führte Willstätter auf unterschiedliche pH‐Werte in Lösung zurück. Anthocyan ändert in der Tat die Farbe mit dem pH‐Wert: Es erscheint rot in saurer, violett in neutraler und blau in alkalischer wäßriger Lösung. Willstätters pH‐Wert‐Theorie zur Erklärung der Blütenfarbenvariation ist immer noch in wichtigen Lehrbüchern der Organischen Chemie zu finden. Vor kurzem jedoch zeigten erneute Untersuchungen, daß die Farbvariation und die Stabilisierung von Anthocyanen in wäßriger Lösung andere Ursachen haben könnten, nämlich Selbstassoziation, Copigmentierung und intermolekulare sandwichartige Stapelung. Die Stapelung käme hauptsächlich durch intermolekulare oder intramolekulare hydrophobe Wechselwirkungen zwischen aromatischen Ringen etwa von Anthocyanidinen, Flavonen und aromatischen Säuren zustande. Zusätzlich könnten Wasserstoffbrücken und Charge‐Transfer‐Wechselwirkungen eine Rolle spielen. Die interessantesten Molekülkomplexe von Anthocyanen sind Metalloanthocyane wie Commelinin und Protocyanin (Pigment der blauen Kornblume). Diese rein blau erscheinenden Komplexe bestehen aus jeweils sechs Anthocyan‐ und sechs Flavonmolekülen sowie zwei Metall‐Ionen. Ihr Molekulargewicht beträgt beinahe 10000. Ein annähernder Strukturvorschlag liegt für Commelinin vor.

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Structure and Molecular Stacking of Anthocyanins—Flower Color Variation

Goto

Kondo

1991

Angew. Chem. Int. Ed. Engl.

460

305

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In 1913 Willstatter made the striking observation that the same pigment can give rise to different colors. Thus, the same pigment, cyanin, is found in the blue cornflower and in the red rose. Willstatter attributed the variety of flower colors to different pH values in solution. Indeed, anthocyanin changes its color with pH; it appears red in acidic, violet in neutral, and blue in basic aqueous solution. Willsfutter's pH-theory for explaining flower color variation is still to be found in major text books of organic chemistry. Very recently, however, reinvestigation has disclosed that the color variation and stabilization of anthocyanins in aqueous solution could have other causes, namely self-association, copigmentation and intramolecular sandwich-type stacking. The stacking would be mainly brought about by intermolecular or intramolecular hydrophobic interaction between aromatic nuclei such as anthocyanidins, flavones and aromatic acids. In addition, hydrogen bonds and charge transfer interactions may also be involved. The most interesting molecular complexes of anthocyanins are the metalloanthocyanins such as commelinin and protocyanin (blue cornflower pigment). These seemingly pure blue complexes each consist of six anthocyanin and six flavone molecules and two metal ions; their molecular weight is nearly 10000. A structure is proposed for commelinin.

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Acylierte Anthocyane III.

Cited by 27 publications

References 0 publications

The Amsterdam petunia germplasm collection: A tool in plant science

The Amsterdam petunia germplasm collection: A tool in plant science

Struktur und molekulare Stapelung von Anthocyanen — Variation der Blütenfarben

Structure and Molecular Stacking of Anthocyanins—Flower Color Variation

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