SYMPOSIUM ON THE BIOCHEMISTRY AND PHYSIOLOGY OF AUXIN ACTION: METABOLISM AND BIOSYNTHESIS OF 3-INDOLEACETIC ACID AND RELATED INDOLE COMPOUNDS IN PLANTS

1962 ◽  
Vol 40 (5) ◽  
pp. 689-718 ◽  
Author(s):  
F. Wightman
1961 ◽  
Vol 200 (4) ◽  
pp. 794-796 ◽  
Author(s):  
Robert M. Donaldson ◽  
Horacio A. Dolcini ◽  
Seymour J. Gray

The urinary excretion of indican and of free and total indoleacetic acid is significantly increased in the rat in the presence of a localized area of intestinal stasis produced surgically by the creation of a pouch in the small intestine. Tryptamine, serotonin and 5-hydroxyindoleacetic acid excretion in the urine is not altered. Evidence that intestinal stasis and bacterial activity within the pouch are responsible for the increased amounts of indican and indoleacetic acid in the urine is supported by the facts that a) indole compounds are not increased in the urine when the intestinal pouch is formed so that peristalsis keeps it empty, b) removal of the intestinal pouch results in a reduction of indican and indoleacetic acid to normal levels within 24 hours and c) oral administration of neomycin promptly reduces the excretion of these compounds to normal levels.


1974 ◽  
Vol 52 (8) ◽  
pp. 698-705 ◽  
Author(s):  
Elnora A. Schneider ◽  
F. Wightman

In barley seedlings, tryptophan is the precursor of the simple indole alkaloid gramine, and also of tryptamine, which is important as a potential precursor of the plant growth hormone 3-indoleacetic acid. The present investigation was designed to study the distribution of free tryptophan and its derivatives within the seedlings, and to follow the changes in these compounds with time. Development of the enzyme tryptophan decarboxylase, which catalyzes the conversion of tryptophan to tryptamine, was also studied. An increase in free tryptophan was detected within 2 h of soaking the seed; this compound reached high values in very young tissues, and then declined. Gramine and its precursors, 3-aminomethylindole and N-methyl-3-aminomethylindole, were confined to the shoots; all three compounds appeared together at the inception of shoot growth. Quantitatively, gramine was the most important compound present and reached a concentration of 623 μg/g fresh weight (25 times that of free tryptophan) on the 9th day, and then declined. Isolated embryos were capable of synthesizing gramine at about one quarter the normal rate, indicating that these embryos have a considerable inherent capacity for tryptophan synthesis and are not wholly dependent on tryptophan released by the endosperm. Tryptophan decarboxylase and tryptamine were found only in the shoot, and both enzyme and product appeared after the 1st week of growth, when the rate of gramine synthesis was beginning to decline. 5-Hydroxytryptamine began to accumulate in both shoot and root after about 2 weeks of growth, and N-methyl-5-hydroxytryptamine was also present in the roots. The close parallel between the gramine pathway of the barley shoot and the analagous hordenine pathway of the root, in which tyrosine is the precursor amino acid, is discussed.


Blood ◽  
1958 ◽  
Vol 13 (3) ◽  
pp. 239-244 ◽  
Author(s):  
JERRY DREXLER

Abstract Indole and indoleacetic acid are shown to inhibit the growth of a vitamin B12 dependent microorganism, a mutant strain of Escherichia coli. It is suggested that the mechanism of that inhibition may be a competitive inhibition of some enzymatic system necessary for the utilization of vitamin B12.


1966 ◽  
Vol 44 (5) ◽  
pp. 675-684 ◽  
Author(s):  
R. F. Norris

A relatively simple and rapid spectrophotometric technique for quantitatively assaying indoleacetic acid (IAA) has now been used for determining the levels of free tryptophan in wheat seedlings (Trilicum vulgare L. var. Thatcher). This technique showed relatively large quantities of tryptophan, and a bioassay, lesser amounts of an auxin (probably IAA), to be present in 11-day-old dark-grown wheat seedlings. The quantities recovered were 200 to 400 μg of tryptophan and 0.30 to 0.60 μg of auxin (IAA equivalents) from 1.0 g of dried plant material.Inclusion of (2-chloroethyl)trimethylammonium chloride (CCC) in the growing medium of the wheat seedlings caused a reduction in the levels of both free tryptophan and the auxin, the magnitude of the effect increasing with increasing dose of CCC. At the highest rate used, 2500 mg per liter of CCC, tryptophan was reduced by approximately 35% and the auxin by approximately 50 to 60%. The evidence presented here indicates that the decreased level of auxin in CCC-treated plants reported by previous workers may have been due to a decreased level of tryptophan. It is therefore suggested that the effects of CCC on plants could be due to direct or indirect changes induced in the metabolism of their indole compounds.


Nutrients ◽  
2021 ◽  
Vol 13 (4) ◽  
pp. 1131 ◽  
Author(s):  
Federico Di Marco ◽  
Francesco Trevisani ◽  
Pamela Vignolini ◽  
Silvia Urciuoli ◽  
Andrea Salonia ◽  
...  

Pasta is one of the basic foods of the Mediterranean diet and for this reason it was chosen for this study to evaluate its antioxidant properties. Three types of pasta were selected: buckwheat, rye and egg pasta. Qualitative–quantitative characterization analyses were carried out by HPLC-DAD to identify antioxidant compounds. The data showed the presence of carotenoids such as lutein and polyphenols such as indoleacetic acid, (carotenoids from 0.08 to 0.16 mg/100 g, polyphenols from 3.7 to 7.4 mg/100 g). To assess the effect of the detected metabolites, in vitro experimentation was carried out on kidney cells models: HEK-293 and MDCK. Standards of β-carotene, indoleacetic acid and caffeic acid, hydroalcoholic and carotenoid-enriched extracts from samples of pasta were tested in presence of antioxidant agent to determine viability variations. β-carotene and indoleacetic acid standards exerted a protective effect on HEK-293 cells while no effect was detected on MDCK. The concentrations tested are likely in the range of those reached in body after the consumption of a standard pasta meal. Carotenoid-enriched extracts and hydroalcoholic extracts showed different effects, observing rescues for rye pasta hydroalcoholic extract and buckwheat pasta carotenoid-enriched extract, while egg pasta showed milder dose depending effects assuming pro-oxidant behavior at high concentrations. The preliminary results suggest behaviors to be traced back to the whole phytocomplexes respect to single molecules and need further investigations.


Author(s):  
Takayoshi Awakawa

AbstractThe teleocidin B family members are terpene indole compounds isolated from Streptomyces bacteria, and they strongly activate protein kinase C (PKC). Their unique structures have attracted many researchers in the natural product chemistry and pharmacology fields, and numerous isolation and bioactivity studies have been conducted. The accumulated information has facilitated the identification of the enzymatic reactions in teleocidin biosynthesis, and new developments in structural biology have strongly aided efforts to clarify the finer points of these reactions. This review describes the recent biochemical and structural biological studies to reveal their reaction mechanisms, with a primary focus on the terpene cyclization triggered by the C-N bond formation by P450 oxygenase (TleB), the prenyltransferase (TleC), and the methyltransferase (TleD). This new knowledge will benefit future engineering studies to create unnatural PKC activators.


ChemBioChem ◽  
2021 ◽  
Author(s):  
Barindra Sana ◽  
Timothy Ho ◽  
Srinivasaraghavan Kannan ◽  
Ding Ke ◽  
Eunice Li ◽  
...  
Keyword(s):  

2017 ◽  
Vol 12 (3) ◽  
pp. 1934578X1701200 ◽  
Author(s):  
Katarzyna Sułkowska-Ziaja ◽  
Anna Maślanka ◽  
Agnieszka Szewczyk ◽  
Bożena Muszyńska

The content of two groups of compounds with biological activity (non-hallucinogenic indole compounds and free phenolic acids) were analyzed in extracts of fruiting bodies of four species of Phellinus: P. igniarius, P. pini, P. pomaceus and P. robustus. The presence of indole compounds in methanolic extracts was analyzed by high-performance liquid chromatography and thin-layer chromatography coupled with densitometric detection. Three metabolites (serotonin, tryptamine, and L-tryptophan) were identified. The contents of individual indole compounds ranged from 1.70 (tryptamine in P. robustus) to 8.32 mg x 100 g1 dry weight (L-tryptophan in P. robustus). Four free phenolic acids were detected in methanolic extracts by the HPLC method. The total content ranged from 9.9 mg x 100 g1 DW (P. igniarius) to 32.5 mg x 100 g1 DW (P. robustus).


1945 ◽  
Vol 106 (4) ◽  
pp. 420-431 ◽  
Author(s):  
J. M. Beal ◽  
A. Geraldine Whiting

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