4-Deoxyaurone formation in Bidens ferulifolia (Jacq.) DC.

The formation of 4-deoxyaurones, which serve as UV nectar guides in Bidens ferulifolia (Jacq.) DC., was established by combination of UV photography, mass spectrometry, and biochemical assays and the key step in aurone formation was studied. The yellow flowering ornamental plant accumulates deoxy ty...

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Autores principales:	Silvija Miosic, Katrin Knop, Dirk Hölscher, Jürgen Greiner, Christian Gosch, Jana Thill, Marco Kai, Binita Kumari Shrestha, Bernd Schneider, Anna C Crecelius, Ulrich S Schubert, Aleš Svatoš, Karl Stich, Heidi Halbwirth
Formato:	article
Lenguaje:	EN
Publicado:	Public Library of Science (PLoS) 2013
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/cfbfeb740c1844a4af5719538d848616
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spelling	oai:doaj.org-article:cfbfeb740c1844a4af5719538d8486162021-11-18T07:46:23Z4-Deoxyaurone formation in Bidens ferulifolia (Jacq.) DC.1932-620310.1371/journal.pone.0061766https://doaj.org/article/cfbfeb740c1844a4af5719538d8486162013-01-01T00:00:00Zhttps://www.ncbi.nlm.nih.gov/pmc/articles/pmid/23667445/?tool=EBIhttps://doaj.org/toc/1932-6203The formation of 4-deoxyaurones, which serve as UV nectar guides in Bidens ferulifolia (Jacq.) DC., was established by combination of UV photography, mass spectrometry, and biochemical assays and the key step in aurone formation was studied. The yellow flowering ornamental plant accumulates deoxy type anthochlor pigments (6'-deoxychalcones and the corresponding 4-deoxyaurones) in the basal part of the flower surface whilst the apex contains only yellow carotenoids. For UV sensitive pollinating insects, this appears as a bicoloured floral pattern which can be visualized in situ by specific ammonia staining of the anthochlor pigments. The petal back side, in contrast, shows a faintly UV absorbing centre and UV absorbing rays along the otherwise UV reflecting petal apex. Matrix-free UV laser desorption/ionisation mass spectrometric imaging (LDI-MSI) indicated the presence of 9 anthochlors in the UV absorbing areas. The prevalent pigments were derivatives of okanin and maritimetin. Enzyme preparations from flowers, leaves, stems and roots of B. ferulifolia and from plants, which do not accumulate aurones e.g. Arabidopsis thaliana, were able to convert chalcones to aurones. Thus, aurone formation could be catalyzed by a widespread enzyme and seems to depend mainly on a specific biochemical background, which favours the formation of aurones at the expense of flavonoids. In contrast to 4-hydroxyaurone formation, hydroxylation and oxidative cyclization to the 4-deoxyaurones does not occur in one single step but is catalyzed by two separate enzymes, chalcone 3-hydroxylase and aurone synthase (catechol oxidase reaction). Aurone formation shows an optimum at pH 7.5 or above, which is another striking contrast to 4-hydroxyaurone formation in Antirrhinum majus L. This is the first example of a plant catechol oxidase type enzyme being involved in the flavonoid pathway and in an anabolic reaction in general.Silvija MiosicKatrin KnopDirk HölscherJürgen GreinerChristian GoschJana ThillMarco KaiBinita Kumari ShresthaBernd SchneiderAnna C CreceliusUlrich S SchubertAleš SvatošKarl StichHeidi HalbwirthPublic Library of Science (PLoS)articleMedicineRScienceQENPLoS ONE, Vol 8, Iss 5, p e61766 (2013)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Silvija Miosic Katrin Knop Dirk Hölscher Jürgen Greiner Christian Gosch Jana Thill Marco Kai Binita Kumari Shrestha Bernd Schneider Anna C Crecelius Ulrich S Schubert Aleš Svatoš Karl Stich Heidi Halbwirth 4-Deoxyaurone formation in Bidens ferulifolia (Jacq.) DC.
description	The formation of 4-deoxyaurones, which serve as UV nectar guides in Bidens ferulifolia (Jacq.) DC., was established by combination of UV photography, mass spectrometry, and biochemical assays and the key step in aurone formation was studied. The yellow flowering ornamental plant accumulates deoxy type anthochlor pigments (6'-deoxychalcones and the corresponding 4-deoxyaurones) in the basal part of the flower surface whilst the apex contains only yellow carotenoids. For UV sensitive pollinating insects, this appears as a bicoloured floral pattern which can be visualized in situ by specific ammonia staining of the anthochlor pigments. The petal back side, in contrast, shows a faintly UV absorbing centre and UV absorbing rays along the otherwise UV reflecting petal apex. Matrix-free UV laser desorption/ionisation mass spectrometric imaging (LDI-MSI) indicated the presence of 9 anthochlors in the UV absorbing areas. The prevalent pigments were derivatives of okanin and maritimetin. Enzyme preparations from flowers, leaves, stems and roots of B. ferulifolia and from plants, which do not accumulate aurones e.g. Arabidopsis thaliana, were able to convert chalcones to aurones. Thus, aurone formation could be catalyzed by a widespread enzyme and seems to depend mainly on a specific biochemical background, which favours the formation of aurones at the expense of flavonoids. In contrast to 4-hydroxyaurone formation, hydroxylation and oxidative cyclization to the 4-deoxyaurones does not occur in one single step but is catalyzed by two separate enzymes, chalcone 3-hydroxylase and aurone synthase (catechol oxidase reaction). Aurone formation shows an optimum at pH 7.5 or above, which is another striking contrast to 4-hydroxyaurone formation in Antirrhinum majus L. This is the first example of a plant catechol oxidase type enzyme being involved in the flavonoid pathway and in an anabolic reaction in general.
format	article
author	Silvija Miosic Katrin Knop Dirk Hölscher Jürgen Greiner Christian Gosch Jana Thill Marco Kai Binita Kumari Shrestha Bernd Schneider Anna C Crecelius Ulrich S Schubert Aleš Svatoš Karl Stich Heidi Halbwirth
author_facet	Silvija Miosic Katrin Knop Dirk Hölscher Jürgen Greiner Christian Gosch Jana Thill Marco Kai Binita Kumari Shrestha Bernd Schneider Anna C Crecelius Ulrich S Schubert Aleš Svatoš Karl Stich Heidi Halbwirth
author_sort	Silvija Miosic
title	4-Deoxyaurone formation in Bidens ferulifolia (Jacq.) DC.
title_short	4-Deoxyaurone formation in Bidens ferulifolia (Jacq.) DC.
title_full	4-Deoxyaurone formation in Bidens ferulifolia (Jacq.) DC.
title_fullStr	4-Deoxyaurone formation in Bidens ferulifolia (Jacq.) DC.
title_full_unstemmed	4-Deoxyaurone formation in Bidens ferulifolia (Jacq.) DC.
title_sort	4-deoxyaurone formation in bidens ferulifolia (jacq.) dc.
publisher	Public Library of Science (PLoS)
publishDate	2013
url	https://doaj.org/article/cfbfeb740c1844a4af5719538d848616
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4-Deoxyaurone formation in Bidens ferulifolia (Jacq.) DC.

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