Chlorophyll Breakdown in Tobacco: On the Structure of Two Nonfluorescent Chlorophyll Catabolites

Berghold, Joachim; Eichmüller, Christian; Hörtensteiner, Stefan; Kräutler, Bernhard (2004). Chlorophyll Breakdown in Tobacco: On the Structure of Two Nonfluorescent Chlorophyll Catabolites. Chemistry & Biodiversity, 1(4), pp. 657-668. Wiley 10.1002/cbdv.200490057

[img] Text
ChemBiodiv_1_657.pdf - Published Version
Restricted to registered users only
Available under License Publisher holds Copyright.

Download (196kB)

In extracts of senescent leaves of the tobacco plant Nicotiana rustica, two colorless compounds with UV/VIS characteristics of nonfluorescent chlorophyll catabolites (NCCs) were detected and tentatively identified as Nr-NCCs. These two polar NCCs were found in similar amounts in the fresh extracts, and their constitutions could be determined by spectroscopic analysis. The data showed both of the two Nr-NCCs to have the same tetrapyrrolic core structure, as reported previously for all other NCCs from senescent higher plants. In the less polar catabolite, named Nr-NCC-2, this core structure was conjugated with a glucopyranose unit, as similarly discovered earlier in Bn-NCC-2, an NCC from oilseed rape (Brassica napus). The more polar NCC from tobacco leaves, Nr-NCC-1, carried an additional malonyl substituent at the 6′-OH group of the glucopyranosyl moiety. Partial (enzyme-catalyzed) hydrolysis of Nr-NCC-1 gave Nr-NCC-2, while enzyme-catalyzed malonylation of Nr-NCC-2 gave Nr-NCC-1, establishing the identity of their basic tetrapyrrole structure. In earlier work (on the polar NCCs from oilseed rape), only separate glucopyranosyl and malonyl functionalities were detected. Nr-NCC-1, thus, represents a further variant of the structures of NCCs from senescent higher plants and exhibits an unprecedented peripheral refunctionalization in chlorophyll catabolites.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Department of Biology > Institute of Plant Sciences (IPS) > Plant nutrition [discontinued]
08 Faculty of Science > Department of Biology > Institute of Plant Sciences (IPS)

UniBE Contributor:

Hörtensteiner, Stefan

Subjects:

500 Science > 580 Plants (Botany)

ISSN:

1612-1872

Publisher:

Wiley

Language:

English

Submitter:

Peter Alfred von Ballmoos-Haas

Date Deposited:

17 Dec 2015 15:34

Last Modified:

05 Dec 2022 14:50

Publisher DOI:

10.1002/cbdv.200490057

BORIS DOI:

10.7892/boris.74004

URI:

https://boris.unibe.ch/id/eprint/74004

Actions (login required)

Edit item Edit item
Provide Feedback