scholarly journals Identification of a Hydrolyzable Tannin, Oenothein B, as an Aluminum-Detoxifying Ligand in a Highly Aluminum-Resistant Tree, Eucalyptus camaldulensis

2013 ◽  
Vol 164 (2) ◽  
pp. 683-693 ◽  
Author(s):  
Ko Tahara ◽  
Koh Hashida ◽  
Yuichiro Otsuka ◽  
Seiji Ohara ◽  
Katsumi Kojima ◽  
...  
Keyword(s):  
Eucalyptus Camaldulensis ◽  
Hydrolyzable Tannin ◽  
Resistant Tree ◽  
Oenothein B

scholarly journals Dehydroquinate dehydratase/shikimate dehydrogenases involved in gallate biosynthesis of the aluminum-tolerant tree species Eucalyptus camaldulensis

Planta ◽  
2020 ◽  
Vol 253 (1) ◽  
Author(s):  
Ko Tahara ◽  
Mitsuru Nishiguchi ◽  
Evelyn Funke ◽  
Shin-Ichi Miyazawa ◽  
Takafumi Miyama ◽  
...  
Keyword(s):  
Tree Species ◽  
Toxic Metal ◽  
Shikimate Pathway ◽  
Eucalyptus Camaldulensis ◽  
In Vitro Assays ◽  
Shikimate Dehydrogenase ◽  
Hydrolyzable Tannin ◽  
Oenothein B ◽  
Phenolic Constituent

Abstract Main conclusion Eucalyptus camaldulensis EcDQD/SDH2 and 3 combine gallate formation, dehydroquinate dehydratase, and shikimate dehydrogenase activities. They are candidates for providing the essential gallate for the biosynthesis of the aluminum-detoxifying metabolite oenothein B. Abstract The tree species Eucalyptus camaldulensis shows exceptionally high tolerance against aluminum, a widespread toxic metal in acidic soils. In the roots of E. camaldulensis, aluminum is detoxified via the complexation with oenothein B, a hydrolyzable tannin. In our approach to elucidate the biosynthesis of oenothein B, we here report on the identification of E. camaldulensis enzymes that catalyze the formation of gallate, which is the phenolic constituent of hydrolyzable tannins. By systematical screening of E. camaldulensis dehydroquinate dehydratase/shikimate dehydrogenases (EcDQD/SDHs), we found two enzymes, EcDQD/SDH2 and 3, catalyzing the NADP+-dependent oxidation of 3-dehydroshikimate to produce gallate. Based on extensive in vitro assays using recombinant EcDQD/SDH2 and 3 enzymes, we present for the first time a detailed characterization of the enzymatic gallate formation activity, including the cofactor preferences, pH optima, and kinetic constants. Sequence analyses and structure modeling suggest the gallate formation activity of EcDQD/SDHs is based on the reorientation of 3-dehydroshikimate in the catalytic center, which facilitates the proton abstraction from the C5 position. Additionally, EcDQD/SDH2 and 3 maintain DQD and SDH activities, resulting in a 3-dehydroshikimate supply for gallate formation. In E. camaldulensis, EcDQD/SDH2 and 3 are co-expressed with UGT84A25a/b and UGT84A26a/b involved in hydrolyzable tannin biosynthesis. We further identified EcDQD/SDH1 as a “classical” bifunctional plant shikimate pathway enzyme and EcDQD/SDH4a/b as functional quinate dehydrogenases of the NAD+/NADH-dependent clade. Our data indicate that in E. camaldulensis the enzymes EcDQD/SDH2 and 3 provide the essential gallate for the biosynthesis of the aluminum-detoxifying metabolite oenothein B.

scholarly journals Oenothein B, a dimeric hydrolyzable tannin of cyclic structure.

1989 ◽  
Vol 37 (8) ◽  
pp. 2269-2271 ◽  
Author(s):  
Tsutomu HATANO ◽  
Taeko YASUHARA ◽  
Muneto MATSUDA ◽  
Kazufumi YAZAKI ◽  
Takashi YOSHIDA ◽  
...  
Keyword(s):  
Cyclic Structure ◽  
Hydrolyzable Tannin ◽  
Oenothein B

Identification of UDP glucosyltransferases from the aluminum-resistant tree Eucalyptus camaldulensis forming β-glucogallin, the precursor of hydrolyzable tannins

2018 ◽  
Vol 152 ◽  
pp. 154-161 ◽  
Author(s):  
Ko Tahara ◽  
Mitsuru Nishiguchi ◽  
Andrej Frolov ◽  
Juliane Mittasch ◽  
Carsten Milkowski
Keyword(s):  
Eucalyptus Camaldulensis ◽  
Hydrolyzable Tannins ◽  
Resistant Tree

ALTURA E SOBREVIVÊNCIA DE Eucalyptus camaldulensis Dehnh EM DIFERENTES ESPAÇAMENTOS AOS 14 MESES APÓS PLANTIO EM CAMPO EM ALVORADA DO GURGUÉIA –PIAUÍ

2018 ◽  
Author(s):  
Silva Raynara Ferreira da ◽  
Sousa Moema Barbosa de ◽  
Silva Aluísio Costa ◽  
Marinho Eduardo Silva ◽  
Dias Bruna Anair Souto
Keyword(s):  
Eucalyptus Camaldulensis ◽  
Eucalyptus Camaldulensis Dehnh
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