Transition metal complexes of phyllobilins – a new realm of bioinorganic chemistry

Li, Chengjie; Kräutler, Bernhard

doi:10.1039/c5dt00474h

Cited by 31 publications

(71 citation statements)

References 91 publications

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Section: Phyllobilins Display a Rich Structural Varietymentioning

confidence: 99%

“…Phyllobilanes (NCCs and DNCCs) display no capacity for coordination of (transition) metal ions . In contrast, their more unsaturated oxidation forms, the corresponding type‐I phyllochromobilins, such as YCCs and PiCCs, bind transition metals very effectively . Hence, the (hardly luminescent 15Z‐form of the) PxB 12 behaved as a bidentate ligand for zinc‐ions, furnishing an orange‐yellow 2 : 1 Zn(II)‐complex (Scheme ) that emitted green fluorescence .…”

Section: Phyllobilins Display a Rich Structural Varietymentioning

confidence: 99%

“…[41] In contrast, their more unsaturated oxidation forms, the corresponding type-I phyllochromobilins, such as YCCs and PiCCs, bind transition metals very effectively. [41] Hence, the (hardly luminescent 15Z-form of the) PxB 12 behaved as a bidentate ligand for zinc-ions, furnishing an orange-yellow 2 : 1 Zn(II)-complex (Scheme 6) that emitted green fluorescence. [42] The weakly luminescent PrB 13 behaved similarly, and behaved as a tridentate ligand for a variety of divalent transition metal ions.…”

Section: Bio-relevant Chemical Properties Of Phyllobilinsmentioning

confidence: 99%

“…[34] Bi-or tridentate binding of transition metal ions by phyllochromobilins modifies their reactivity. [41] Such binding of transition metal ions may be useful for the plant [41] by producing toxins against pathogens, [43] by providing a new source of photo-generated 1 O 2 , [44] or by playing a role in heavy metal transport and detoxification. [45] Beyond Chlorophyll Detoxification -Potential Bioactivities of Phyllobilins…”

Section: Bio-relevant Chemical Properties Of Phyllobilinsmentioning

confidence: 99%

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In Search of Bioactivity – Phyllobilins, an Unexplored Class of Abundant Heterocyclic Plant Metabolites from Breakdown of Chlorophyll

Moser

Kräutler

2019

Israel Journal of Chemistry

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The fate of the green plant pigment chlorophyll (Chl) in de‐greening leaves has long been a fascinating biological puzzle. In the course of the last three decades, various bilin‐type products of Chl breakdown have been identified, named phyllobilins (PBs). Considered ‘mere’ leftovers of a controlled biological Chl detoxification originally, the quest for finding relevant bioactivities of the PBs has become a new paradigm. Indeed, the PBs are abundant in senescent leaves, in ripe fruit and in some vegetables, and they display an exciting array of diverse heterocyclic structures. This review outlines briefly which types of Chl breakdown products occur in higher plants, describes basics of their bio‐relevant structural and chemical properties and gives suggestions as to ‘why’ the plants produce vast amounts of uniquely ‘decorated’ heterocyclic compounds. Clearly, it is worthwhile to consider crucial metabolic roles of PBs in plants, which may have practical consequences in agriculture and horticulture. However, PBs are also part of our plant‐based nutrition and their physiological and pharmacological effects in humans are of interest, as well.

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Section: Phyllobilins Display a Rich Structural Varietymentioning

confidence: 99%

Section: Phyllobilins Display a Rich Structural Varietymentioning

confidence: 99%

Section: Bio-relevant Chemical Properties Of Phyllobilinsmentioning

confidence: 99%

Section: Bio-relevant Chemical Properties Of Phyllobilinsmentioning

confidence: 99%

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In Search of Bioactivity – Phyllobilins, an Unexplored Class of Abundant Heterocyclic Plant Metabolites from Breakdown of Chlorophyll

Moser

Kräutler

2019

Israel Journal of Chemistry

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“…[15a, 23] In analogy to NCCs, [28] YCCs [5] and bilirubin [22] DYCCsa re also ag roup of new potentialn atural anti-oxidants that may help to prolong the viability of senescent leaf tissue. [29] Formyloxobilin-type PxBs, such as the YCC 2, [5,27] are unique photoswitches that feature an amazing structurals imilarity with some of the established heme-derived bilins. [30] Dioxobilin-typeP xBs, such as the DYCC 4,a re even more closely related structurally to heme-derived bilins,s uch as bilirubin (BR) [22] and the growing range of blueabsorbing tetrapyrrolicp igments in cyanobacteriochromes.…”

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confidence: 99%

Yellow Dioxobilin‐Type Tetrapyrroles from Chlorophyll Breakdown in Higher Plants—A New Class of Colored Phyllobilins

Erhart

Liu

et al. 2019

Chemistry A European J

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In senescent leaves chlorophyll (Chl) catabolites typically accumulate as colorless tetrapyrroles, classified as formyloxobilin‐type (or type‐I) or dioxobilin‐type (type‐II) phyllobilins (PBs). Yellow type‐I Chl catabolites (YCCs) also occur in some senescent leaves, in which they are generated by oxidation of colorless type‐I PBs. A yellow type‐II PB was recently proposed to occur in extracts of fall leaves of grapevine ( Vitis vinifera ), tentatively identified by its mass and UV/Vis absorption characteristics. Here, the first synthesis of a yellow type‐II Chl catabolite (DYCC) from its presumed natural colorless type‐II precursor is reported. A homogenate of a Spatiphyllum wallisii leaf was used as “green” means of effective and selective oxidation. The synthetic DYCC was fully characterized and identified with the yellow grapevine leaf pigment. As related yellow type‐I PBs do, the DYCC functions as a reversible photoswitch by undergoing selective photo‐induced Z / E isomerization of its C15=C16 bond.

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Der Chlorophyllabbau in höheren Pflanzen – Phyllobiline als weitverbreitete, aber kaum sichtbare Zeichen von Reifung, Seneszenz und Zelltod

Kräutler

2016

Angewandte Chemie

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Die herbstlichen Farben sind von je her faszinierend und immer noch ein höchst rätselhaftes Phänomen. Vor einigen Jahren wurde entdeckt, dass beim Abbau von Chlorophyll (Chl) in Blättern und Früchten Bilin‐ähnliche Chl‐Kataboliten gebildet werden, die als Phyllobiline bezeichnet werden. Dank intensiver chemisch‐biologischer Zusammenarbeiten ist es inzwischen gelungen, die Schlüsselprozesse des Chl‐Abbaus in seneszenten Blättern und reifenden Früchten aufzuklären. Das Chl wird rasch zu farblosen und größtenteils photoinaktiven Phyllobilinen abgebaut, was offenbar primär ein Teil eines Entgiftungsprozesses ist. In manchen seneszenten Blättern und in den Schalen reifer Bananen reichern sich hingegen fluoreszierende Chl‐Kataboliten an und bewirken dort ein eindrucksvolles, blaues Leuchten. Die strukturellen Besonderheiten, die chemischen Eigenschaften und die Häufigkeit der Phyllobiline in der Biosphäre lassen damit biologische Funktionen vermuten, die immer noch darauf warten, entdeckt zu werden.

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Transition metal complexes of phyllobilins – a new realm of bioinorganic chemistry

Abstract: Phyllobilins may function as natural ligand molecules for biologically important transition metal ions, giving complexes with remarkable chemical and photophysical properties.

Cited by 31 publications

References 91 publications

In Search of Bioactivity – Phyllobilins, an Unexplored Class of Abundant Heterocyclic Plant Metabolites from Breakdown of Chlorophyll

In Search of Bioactivity – Phyllobilins, an Unexplored Class of Abundant Heterocyclic Plant Metabolites from Breakdown of Chlorophyll

Yellow Dioxobilin‐Type Tetrapyrroles from Chlorophyll Breakdown in Higher Plants—A New Class of Colored Phyllobilins

Der Chlorophyllabbau in höheren Pflanzen – Phyllobiline als weitverbreitete, aber kaum sichtbare Zeichen von Reifung, Seneszenz und Zelltod

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