Identification of phenylacetic acid as a natural auxin in the shoots of higher plants

Wightman, F.; Lighty, Douglas L.

doi:10.1111/j.1399-3054.1982.tb00278.x

Cited by 155 publications

(85 citation statements)

References 24 publications

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“…FAO is indispensable for the conversion of lipids (dietary or from lipid storage) to ketone bodies (42). Moreover, PAGN is endogenously formed in humans by phenylacetate, which could be related to oxidation of phenyl containing fatty acids (43) or through the exogenous intake contained in plant food sources (44). Differences in excretion of PAGN are described that reflect changes in GNG and the tricarboxylic acid (TCA) cycle (45).…”

Section: Metabolites From Protein Lipid and Carbohydrate Metabolic Pmentioning

confidence: 99%

Metabolomic Pattern Analysis after Mediterranean Diet Intervention in a Nondiabetic Population: A 1- and 3-Year Follow-up in the PREDIMED Study

et al. 2014

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The Mediterranean diet (MD) is considered a dietary pattern with beneficial effects on human health. The aim of this study was to assess the effect of an MD on urinary metabolome by comparing subjects at 1 and 3 years of follow-up, after an MD supplemented with either extra-virgin olive oil (MD+EVOO) or nuts (MD+Nuts), to those on advice to follow a control low-fat diet (LFD). Ninety-eight non-diabetic volunteers were evaluated, using metabolomic approaches, corresponding to MD+EVOO (n=41), MD+Nuts (n=27) or LFD (n=30) groups. The 1 H-NMR urinary profiles were examined at baseline, after 1 and 3 years of follow-up. Multivariate data analysis (OSC-PLS-DA and HCA) methods were used to identify the potential biomarker discriminating groups, exhibiting a urinary metabolome separation between MD groups against baseline and LFD. Results revealed that the most prominent hallmarks concerning MD groups were related to the metabolism of carbohydrates (3-hydroxybutyrate, citrate, cis-aconitate), creatine, creatinine, amino acids (proline, Nacetylglutamine, glycine, branched-chain amino acids and derived metabolites), lipids(oleic and suberic acids), and microbial co-metabolites (phenylacetylglutamine, pcresol). Otherwise, hippurate, trimethylamine-N-oxide, histidine and derivates (methylhistidines, carnosine, anserine) and xanthosine were predominant after LFD. The application of NMR-based metabolomics enabled the classification of individuals regarding their dietary pattern and highlights the potential of this approach for evaluating changes in the urinary metabolome at different time points of follow-up in response to specific dietary interventions.2

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Section: Metabolites From Protein Lipid and Carbohydrate Metabolic Pmentioning

confidence: 99%

Metabolomic Pattern Analysis after Mediterranean Diet Intervention in a Nondiabetic Population: A 1- and 3-Year Follow-up in the PREDIMED Study

et al. 2014

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“…PA is a natural metabolite of phenylalanine that was originally described as a plant growth hormone. 5 Normally found in micromolar concentrations in human plasma, PA has a long clinical history as treatment for conditions associated with hyperammonemia such as in children with urea cycle disorders. 6,7 This clinical experience has indicated that millimolar blood serum levels can be achieved without significant adverse effects; prolonged treatment with sodium phenylacetate (up to 6 years) of children with inborn errors of urea synthesis have shown only very rare evidence of clinical toxicity.…”

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confidence: 99%

Inhibition of estrogen-dependent breast cell responses with phenylacetate

et al. 2001

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The aromatic fatty acid phenylacetate (PA) and its analogs have come under intense investigation due to their ability to cause the growth arrest of a variety of neoplasia, including human breast cancer. We have determined that PA and its halide derivative 4-chlorophenylacetate (4-CPA) showed marked antiproliferative activity on 3 of 6 human breast cancer cell lines tested. Interestingly, the 3 cell lines that were growth inhibited by PA and 4-CPA were estrogen receptor (ER) positive (T47-D, MCF-7 and ZR-75-1) whereas those that were little affected by these compounds were ER-negative (MDA-MB-157, MDA-MB-231 and SK-Br-3). Dose response studies indicated that 4-CPA inhibited the growth of the sensitive (ER؉) cell lines with a potency 3-4 times that of PA. These findings suggest that there is "crosstalk" between the PA and estrogen signaling pathways such that PA can directly inhibit estrogen-dependent events. This hypothesis was directly tested in vitro using ER؉ MCF-7 cells that were stably transfected with a luciferase reporter construct driven by the full length ( Key words: phenylacetate; breast cancer; estrogen; receptorBreast cancer is 1 of the most prevalent types of cancer observed in women, developing in approximately 1 of 9 women sometime during their lifetime. The etiology of this malignancy is known to involve a complex interplay of genetic, environmental, and hormonal factors that influence the physiological status of the host. 1,2 With regards to the latter factor, there is considerable data that implicate the involvement of steroid hormones, especially estrogen, in the development and progression of breast cancer. This fact has lead to the use of antiestrogens in the therapeutic intervention of this disease. To date, the clinical use of antiestrogens has been limited to compounds that inhibit estrogen signaling at the level of the estrogen receptor (ER) by competing with the ligand (i.e., estrogen) for receptor binding. 3 Although shown to be extremely useful, the clinical results are often unpredictable due to the complex functional activity of ERs liganded with different antiestrogen compounds or the ability of the receptors to undergo changes (mutations or otherwise) that can alter their functional characteristics or response to estrogen antagonists. 4 Thus, there is a need to develop therapeutic compounds that can inhibit the estrogen signaling pathway by mechanisms that may not depend upon competitive ligand binding to the ER.Aromatic fatty acids, of which phenylacetate (PA) is a prototype, constitute a new class of low toxicity drugs with demonstrated antitumor activity in experimental models and in humans. PA is a natural metabolite of phenylalanine that was originally described as a plant growth hormone. 5 Normally found in micromolar concentrations in human plasma, PA has a long clinical history as treatment for conditions associated with hyperammonemia such as in children with urea cycle disorders. 6,7 This clinical experience has indicated that millimolar blood serum levels can be achiev...

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“…Benzene acetic acid has been reported from the endophytic fungus Chaetomium fusiforme (Guo et al 2008). It is a type of auxin (Wightman and Lighty 1982) and is an antimicrobial produced by metapleural glands of most ant species for controlling fungal pathogens (Fernandez-Marin et al 2015). Dehydromevalonic lactone has been reported to be produced during the solid-state fermentation of Monascus ruber, and is reported to impart fragrance (Vidyalakshmi et al 2009).…”

Section: Discussionmentioning

confidence: 99%

Metabolite analysis of endophytic fungi from cultivars of Zingiber officinale Rosc. identifies myriad of bioactive compounds including tyrosol

Anisha

Radhakrishnan

2017

3 Biotech

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Endophytic fungi associated with rhizomes of four cultivars of Zingiber officinale were identified by molecular and morphological methods and evaluated for their activity against soft rot pathogen Pythium myriotylum and clinical pathogens. The volatile bioactive metabolites produced by these isolates were identified by GC-MS analysis of the fungal crude extracts. Understanding of the metabolites produced by endophytes is also important in the context of raw consumption of ginger as medicine and spice. A total of fifteen isolates were identified from the four varieties studied. The various genera identified were Acremonium sp., Gliocladiopsis sp., Fusarium sp., Colletotrichum sp., Aspergillus sp., Phlebia sp., Earliella sp., and Pseudolagarobasidium sp. The endophytic community was unique to each variety, which could be due to the varying host genotype. Fungi from phylum Basidiomycota were identified for the first time from ginger. Seven isolates showed activity against Pythium, while only two showed antibacterial activity. The bioactive metabolites identified in the fungal crude extracts include tyrosol, benzene acetic acid, ergone, dehydromevalonic lactone, N-aminopyrrolidine, and many bioactive fatty acids and their derivatives which included linoleic acid, oleic acid, myristic acid, nhexadecanoic acid, palmitic acid methyl ester, and methyl linoleate. The presence of these varying bioactive endophytic fungi may be one of the reasons for the differences in the performance of the different ginger varieties.

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Identification of phenylacetic acid as a natural auxin in the shoots of higher plants

Cited by 155 publications

References 24 publications

Metabolomic Pattern Analysis after Mediterranean Diet Intervention in a Nondiabetic Population: A 1- and 3-Year Follow-up in the PREDIMED Study

Metabolomic Pattern Analysis after Mediterranean Diet Intervention in a Nondiabetic Population: A 1- and 3-Year Follow-up in the PREDIMED Study

Inhibition of estrogen-dependent breast cell responses with phenylacetate

Metabolite analysis of endophytic fungi from cultivars of Zingiber officinale Rosc. identifies myriad of bioactive compounds including tyrosol

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