Monomethyl ethers of 4,5-dihydroxypipecolic acid from Petaladenium urceoliferum : Enigmatic chemistry of an enigmatic legume

Kite, Geoffrey C.; Cardoso, Domingos; Lewis, Gwilym P.; Zartman, Charles E.; Queiroz, Luciano Paganucci de; Veitch, Nigel C.

doi:10.1016/j.phytochem.2015.02.026

Cited by 2 publications

(2 citation statements)

References 22 publications

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“…In some species of the Fabaceae, Moraceae or Apocynaceae families several hydroxylated or otherwise substituted Pip derivatives exist as plant secondary metabolites (Figure g) (e.g. Schenk and Schütte, ; Kristensen et al ., ; Hatanaka and Kaneko, ; Romeo et al ., ; Kite et al ., ). For example, trans ‐4‐hydroxypipecolic acid was detected in Acacia species, and radiolabeling experiments suggest that the compound is derived from the direct hydroxylation of Pip (Fowden, ; Kunii et al ., ).…”

Section: Other Aspects Of Pip Metabolismmentioning

confidence: 97%

l‐lysine metabolism to N‐hydroxypipecolic acid: an integral immune‐activating pathway in plants

Hartmann

Zeier

2018

The Plant Journal

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l-lysine catabolic routes in plants include the saccharopine pathway to α-aminoadipate and decarboxylation of lysine to cadaverine. The current review will cover a third l-lysine metabolic pathway having a major role in plant systemic acquired resistance (SAR) to pathogen infection that was recently discovered in Arabidopsis thaliana. In this pathway, the aminotransferase AGD2-like defense response protein (ALD1) α-transaminates l-lysine and generates cyclic dehydropipecolic (DP) intermediates that are subsequently reduced to pipecolic acid (Pip) by the reductase SAR-deficient 4 (SARD4). l-pipecolic acid, which occurs ubiquitously in the plant kingdom, is further N-hydroxylated to the systemic acquired resistance (SAR)-activating metabolite N-hydroxypipecolic acid (NHP) by flavin-dependent monooxygenase1 (FMO1). N-hydroxypipecolic acid induces the expression of a set of major plant immune genes to enhance defense readiness, amplifies resistance responses, acts synergistically with the defense hormone salicylic acid, promotes the hypersensitive cell death response and primes plants for effective immune mobilization in cases of future pathogen challenge. This pathogen-inducible NHP biosynthetic pathway is activated at the transcriptional level and involves feedback amplification. Apart from FMO1, some cytochrome P450 monooxygenases involved in secondary metabolism catalyze N-hydroxylation reactions in plants. In specific taxa, pipecolic acid might also serve as a precursor in the biosynthesis of specialized natural products, leading to C-hydroxylated and otherwise modified piperidine derivatives, including indolizidine alkaloids. Finally, we show that NHP is glycosylated in Arabidopsis to form a hexose-conjugate, and then discuss open questions in Pip/NHP-related research.

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Section: Other Aspects Of Pip Metabolismmentioning

confidence: 97%

l‐lysine metabolism to N‐hydroxypipecolic acid: an integral immune‐activating pathway in plants

Hartmann

Zeier

2018

The Plant Journal

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“…1 ). Kite et al (2015) recently found chemical compounds in Petaladenium that are unique among Leguminosae confi rming the enigmatic status of this taxon.…”

Section: A M E R I C a N J O U R N A L O F B O T A N Y R E S E A R C mentioning

confidence: 99%

Flowers of the early‐branching papilionoid legume Petaladenium urceoliferum display unique morphological and ontogenetic features

Prenner

Cardoso

Zartman

et al. 2015

American J of Botany

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The floral ontogeny confirms the close affinity of P. urceoliferum with the florally heterogeneous, early-diverging papilionoid Amburaneae clade. The results strengthen the theory of a distinct experimental phase among early-branching papilionoid legumes during which a wider range of floral morphologies arose. Polysymmetry, monosymmetry, variable organ numbers, and a wide range of ontogenetic patterns laid the foundation for a successful canalization toward the more restricted but well-adapted dorsiventral papilionoid flag blossom.

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Monomethyl ethers of 4,5-dihydroxypipecolic acid from Petaladenium urceoliferum : Enigmatic chemistry of an enigmatic legume

Cited by 2 publications

References 22 publications

l‐lysine metabolism to N‐hydroxypipecolic acid: an integral immune‐activating pathway in plants

l‐lysine metabolism to N‐hydroxypipecolic acid: an integral immune‐activating pathway in plants

Flowers of the early‐branching papilionoid legume Petaladenium urceoliferum display unique morphological and ontogenetic features

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