The distribution of hydroxycinnamic acid amides in flowering plants

Martin-Tanguy, J.; Cabanne, F; Perdrizet, E.; Martı́n, Carmen

doi:10.1016/s0031-9422(00)88735-x

Cited by 194 publications

(99 citation statements)

References 7 publications

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“…Deviating from all other NAAs in the Heliantheae tribe, the hydroxy cinnamamides (HCAAs) were found in Helianthus annuus (264) (Martintanguy et al, 1978).…”

Section: Q10mentioning

confidence: 99%

“…In addition to the common IBAs, 4-hydroxy PEAs (tyramides) (e.g. 83, 84, 85) occur, which are also found in several other families like Piperaceae and Rutaceae (Burden and Crombie, 1969;Greger et al, 1981;Kubo et al, 1984;Martintanguy et al, 1978;Matsuda et al, 2009;Stöhr et al, 1999). More recently, other tyramides, with an alkynic structure on the acid side, were identified in Anacyclus pyrethrum (Boonen et al, submitted for publication) (e.g.…”

Section: Q10mentioning

confidence: 99%

“…274) (Achenbach et al, 1986). The Solanaceae and at least seventeen other plant families produce the metabolic important hydroxy cinnamamides (HCAAs) (Amaranthaceae, Aristolochiaceae, Asteracae, Brassicaceae, Bromeliaceae, Caryophyllaceae, Convolvulaceae, Fabaceae, Hippocastanaceae, Lauraceae, Liliacea, Poaceae, Rhamnaceae, Rosaceae, Rutaceae, Salicaceae, Zygophyllaceae) (Cheng et al, 2004;Li et al, 1998;Martintanguy et al, 1978;Tanaka et al, 2003;Tofern et al, 1999;Wu et al, 1994). These NAAs are composed of hydroxycinnamate derivatives as fatty acid part (e.g.…”

Section: Q10mentioning

confidence: 99%

“…serotonin, tyramine) or polyamine (e.g. putrescine, spermidine) part (Facchini et al, 2002;Han et al, 2002;Kang et al, 2010;King and Calhoun, 2010;Martintanguy et al, 1978;Negrel et al, 1996;Park et al, 2009;Parr et al, 2005;Turnock et al, 2001;Yoshihara et al, 1981) (e.g. 263-269).…”

Section: Q10mentioning

confidence: 99%

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Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

130

109

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a b s t r a c tEthnopharmacological relevance: N-Alkylamides (NAAs) are a promising group of bioactive compounds, which are anticipated to act as important lead compounds for plant protection and biocidal products, functional food, cosmeceuticals and drugs in the next decennia. These molecules, currently found in more than 25 plant families and with a wide structural diversity, exert a variety of biologicalpharmacological effects and are of high ethnopharmacological importance. However, information is scattered in literature, with different, often unstandardized, pharmacological methodologies being used. Therefore, a comprehensive NAA database (acronym: Alkamid) was constructed to collect the available structural and functional NAA data, linked to their occurrence in plants (family, tribe, species, genus). Materials and methods: For loading information in the database, literature data was gathered over the period 1950-2010, by using several search engines. In order to represent the collected information about NAAs, the plants in which they occur and the functionalities for which they have been examined, a relational database is constructed and implemented on a MySQL back-end. Results: The database is supported by describing the NAA plant-, functional-and chemical-space. The chemical space includes a NAA classification, according to their fatty acid and amine structures. Conclusions: The Alkamid database (publicly available on the website http://alkamid.ugent.be/) is not only a central information point, but can also function as a useful tool to prioritize the NAA Q8 choice in the evaluation of their functionality, to perform data mining leading to quantitative structure-property relationships (QSPRs), functionality comparisons, clustering, plant biochemistry and taxonomic evaluations.

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“…Deviating from all other NAAs in the Heliantheae tribe, the hydroxy cinnamamides (HCAAs) were found in Helianthus annuus (264) (Martintanguy et al, 1978).…”

Section: Q10mentioning

confidence: 99%

Section: Q10mentioning

confidence: 99%

Section: Q10mentioning

confidence: 99%

Section: Q10mentioning

confidence: 99%

See 2 more Smart Citations

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

130

109

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“…The relationship among free polyamines, hydroxycinnamoylputrescines, cell division, and root formation is discussed. (10,14,25) suggest that polyamines are involved in auxin-induced root formation, although their specific role has yet to be elucidated in order to establish a causal relationship.Amides formed between hydroxycinnamic acids and amines are widely distributed in the plant kingdom (9,20,21,28). They are detected in high amounts in flowering parts ofvarious plants and have been linked to the process offlower formation (for reviews, see refs.…”

mentioning

confidence: 99%

Polyamines, Hydroxycinnamoylputrescines, and Root Formation in Leaf Explants of Tobacco Cultivated in Vitro

Burtin¹,

Martin-Tanguy²,

Paynot³

et al. 1990

Plant Physiol.

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In vitro formation of roots is obtained directly, without intermediate growth of callus, from foliar explants of a tobacco (Nicotiana tabacum) plant cultured on Murashige and Skoog medium containing IAA. Auxin-induced root formation was accompanied by significant changes in hydroxycinnamoylputrescine levels. Increasing levels were found in leaf explants during the first 14 days in culture; this was followed by a sharp decline after 20 days. Early changes in putrescine conjugates were detected in leaf explants before the visible appearance of roots. An early and transitory accumulation of hydroxycinnamoylputrescines was observed in the roots. Free polyamines (putrescine, spermidine, and spermine) in leaf explants and roots were always at a low level and only small changes in their concentrations were observed, a-DL-difluoromethylarginine and a-DL-difluoromethylomithine, specific, irreversible inhibitors of arginine decarboxylase and ornithine decarboxylase, respectively, inhibited putrescine accumulation and root initiation and reduced the fresh and dry weights of leaf explants. These effects were reversed by free putrescine or hydroxycinnamoylputrescines. The results reported here suggest that hydroxycinnamoylputrescines are associated with root formation. The relationship among free polyamines, hydroxycinnamoylputrescines, cell division, and root formation is discussed. (10,14,25) suggest that polyamines are involved in auxin-induced root formation, although their specific role has yet to be elucidated in order to establish a causal relationship.Amides formed between hydroxycinnamic acids and amines are widely distributed in the plant kingdom (9,20,21,28). They are detected in high amounts in flowering parts ofvarious plants and have been linked to the process offlower formation (for reviews, see refs. 20 and 31). Other factors leading to an increase in conjugated polyamines are fungal and viral infections, (for reviews see refs. 20 and 31). Recent results (8,22) report that a change in morphology or growth of tobacco leaf explants in vitro is accompanied by changes in putrescine levels, and the largest changes occur in conjugated putrescine content specifically.Are polyamines and conjugated polyamines esssential for root formation, or are they simply secondary by-products of a growth response? One way to approach this question is by utilizing specific inhibitors of polyamine synthesis and then examining the physiological properties of tissues.Previous reports have shown that in tobacco plants putrescine is synthesized from arginine (by ADC' via agmatine) and ornithine (by ODC).This study reports results of DFMA, a specific enzymeactivated ADC inhibitor, and DFMO, a specific enzymeactivated ODC inhibitor, on organogenesis, growth, free polyamine, and conjugated polyamine (hydroxycinnamoylputrescine) levels of tobacco leaf explants cultivated in vitro in a medium that induces root formation. MATERIALS AND METHODS Biological Material and Growth ConditionsNicotiana tabacum var Xanthi n.c. was utilized in ...

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Ion-pair HPLC determination of hydroxycinnamic acid monoconjugates of putrescine, spermidine and spermine

et al. 2000

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The terminal hydroxycinnamic acid monoconjugates of putrescine, spermidine and spermine were resolved and quantified in extracts of plant tissues using sodium hexanesulphonate as an ion‐pair reagent and a double methanol gradient. Extracts were prepared from acidic methanol:water (80:20) that had been back‐extracted with hexane, and fractionated on C‐18 solid phase extraction and carboxymethyl cation exchange cartridges. The chromatographic conditions were capable of separating N1‐ and N8‐coumaroyl and feruloyl spermidine, which differ only by the disposition of the secondary amine in the polyamine side chain. Reliable detection limits for most compounds were less than 5 µg/mL (approximately 10−5 M in the plant extract) and extraction efficiencies were 91% as determined using the novel internal standard, N1‐coumaroyl hexanediamine. Copyright © 2000 John Wiley & Sons, Ltd.

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The distribution of hydroxycinnamic acid amides in flowering plants

Cited by 194 publications

References 7 publications

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Polyamines, Hydroxycinnamoylputrescines, and Root Formation in Leaf Explants of Tobacco Cultivated in Vitro

Ion-pair HPLC determination of hydroxycinnamic acid monoconjugates of putrescine, spermidine and spermine

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