Antibody-targeted horseradish peroxidase associated with indole-3-acetic acid induces apoptosis in vitro in hematological malignancies

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Quantitative distribution of gibberellins and indole-acetic acid in pea (Pisum sativum L.) seedlings

The objective was to determine the distribution in pea seedling of GA (by thin layer chromatography) and IAA (by HPLC). Three samples of 30 7/day-old seedlings were sectioned into: apical meristem + plumular hook; stem elongation zone; stem non-elongation zone; cotyledons; root non-elongation zone; root tip. The material was frozen in liquid N and stored at -80 degrees C. The stem elongation zone, the apical meristem+plumular hook and the root tip had low IAA, whereas the stem non-elongation zone and root non-elongation zone had high IAA content. The stem elongation zone and apical meristem plumular hook had high GA, while root non-elongation zone had the lowest GA content.

Indole ring oxidation by activated leukocytes prevents the production of hypochlorous acid

Hypochlorous acid (HOCl) released by activated leukocytes has been implicated in the tissue damage that characterizes chronic inflammatory diseases. In this investigation, 14 indole derivatives, including metabolites such as melatonin, tryptophan and indole-3-acetic acid, were screened for their ability to inhibit the generation of this endogenous oxidant by stimulated leukocytes. The release of HOCl was measured by the production of taurine-chloramine when the leukocytes (2 x 10(6) cells/mL) were incubated at 37ºC in 10 mM phosphate-buffered saline, pH 7.4, for 30 min with 5 mM taurine and stimulated with 100 nM phorbol-12-myristate acetate. Irrespective of the group substituted in the indole ring, all the compounds tested including indole, 2-methylindole, 3-methylindole, 2,3-dimethylindole, 2,5-dimethylindole, 2-phenylindole, 5-methoxyindole, 6-methoxyindole, 5-methoxy-2-methylindole, melatonin, tryptophan, indole-3-acetic acid, 5-methoxy-2-methyl-3-indole-acetic acid, and indomethacin (10 µM) inhibited the chlorinating activity of myeloperoxidase (MPO) in the 23-72% range. The compounds 3-methylindole and indole-3-acetic acid were chosen as representative of indole derivatives in a dose-response study using purified MPO. The IC50 obtained were 0.10 ± 0.03 and 5.0 ± 1.0 µM (N = 13), respectively. These compounds did not affect the peroxidation activity of MPO or the production of superoxide anion by stimulated leukocytes. By following the spectral change of MPO during the enzyme turnover, the inhibition of HOCl production can be explained on the basis of the accumulation of the redox form compound-II (MPO-II), which is an inactive chlorinating species. These results show that indole derivatives are effective and selective inhibitors of MPO-chlorinating activity.

Droplet counter-current chromatography of indole alkaloids from Tabernaemontana hilariana

This paper reports the separation of the indole alkaloids from the benzene extract of the root barks of Tabernaemontana hilariana (Apocynaceae). The crude alkaloid fraction was fractionated by droplet counter-current chromatography using a low polarity mixture (hexane:ethyl acetate:ethanol:water). Nine indole alkaloids (3-hydroxycoronaridine, coronaridine, voacangine, 3-(2-oxopropyl) coronaridine, voacangine hydroxyindolenine, ibogamine, voacangine pseudoindoxyl, coronaridine pseudoindoxyl and tabernanthine) were identified using thin laver chromatography gas chromatography coupled with mass spectrometry and nuclear magnetic resonance spectroscopy. Copyright (C) 1999 John Wiley & Sons, Ltd.

Qualitative determination of indole alkaloids, triterpenoids and steroid of Tabernaemontana hilariana

This paper reports the separation and identification of indole alkaloids, steroids and triterpenoids from the ethanolic extracts of Tabernaemontana hilariana (Apocynaceae). The alkaloidal fractions from the ethanolic extracts obtained (root barks, green fruits, ripe fruits and seeds) were fractionated and analysed by thin-layer chromatography, capillary gas chromatography-flame ionization detection (cGC-FID) as well as by high-resolution gas chromatography-mass spectrometry (HRGC-MS). 3-Hydroxycoronaridine, ibogamine, coronaridine pseudoindoxyl, coronaridine, catharanthine, voacangine hydroxyindolenine, voacangine pseudoindoxyl, tabernanthine, tetraphyllicine, 3-hydroxyvoacangine, voacangine, isovoacangine and 3-oxocoronaridine were identified. The insoluble fraction of ethanolic extracts obtained from the root barks and green fruits were analysed and ten aliphatic constituents were also identified by cGC-FID and HRGC-MS. (C) 1998 Elsevier B.V. B.V. All rights reserved.

Turbinatine, a potential key intermediate in the biosynthesis of corynanthean-type indole alkaloids

Extraction of the leaves of Chimarrhis turbinata has led to the isolation of turbinatine (1), a new corynanthean-type indole alkaloid, besides four known indole alkaloids, strictosidine, 5alpha-carboxystrictosidine, vallesiachotamine, and isovallesiachotamine. The structural determination of 1 was based on 1D and 2D spectroscopic data. An evaluation of the DNA-damaging activities of the isolates was performed by means of a bioassay using mutant strains of Saccharomyces cerevisiae, which indicated these compounds were weakly active.

Indole glucoalkaloids from Chimarrhis turbinata and their evaluation as antioxidant agents and acetylcholinesterase inhibitors

As part of our study on bioactive agents from Brazilian rainforest plants, two new glucoalkaloids, 3,4-dehydro-strictosidine (1) and 3,4-dehydro-strictosidinic acid (2), were isolated from Chimarrhis turbinata, along with seven known glucoalkaloids, cordifoline (3), strictosidinic acid (4), strictosidine (5), 5alpha-carboxystrictosidine (6), turbinatine (7), desoxycordifoline (8), and harman-3-carboxylic acid (9). The structures of the new alkaloids were established on the basis of comprehensive spectral analysis, mainly 1D and 2D NMR experiments, as well as high-resolution HRESIMS. Alkaloid 3 showed strong free-radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) as well as pronounced antioxidant activity evidenced by redox properties measured by ElCD-HPLC. Additionally, alkaloids 1-9 were submitted to TLC screening for acetylcholinesterase inhibitors. Both 7 and 8 were shown to be moderate acetylcholinesterase inhibitors at a concentration of 0.1 and 1.0 muM, respectively. In an in vitro rat brain assay, 7 showed moderate activity (IC50 1.86 muM), compared to the standard compound, galanthamine (IC50 0.92 muM).

Interactions of indole acetic acid with EGF and FSH in the culture of ovine preantral follicles

The mechanisms that regulate the gradual exit of ovarian follicles from the non-growing, primordial pool are very poorly understood. The objective of this study was to evaluate the effects of adding indole acetic acid (IAA), epidermal growth factor (EGF) and follicle stimulating hormone (FSH) to the media for in vitro culture of ovine ovarian fragments and determine their effects on growth activation and viability of preantral follicles. The ovarian cortex was divided into small fragments; one fragment was immediately fixed in Bouin (control). The other fragments were cultured for 2 or 6 days in culture plates with: minimum essential medium (MEM) supplemented with insulin-transferrin-selenium (ITS), pyruvate, glutamine, hypoxantine, bovine serum albumine and antibiotics (MEM+); MEM+ plus IAA (40 ng/mL); MEM+ plus EGF (100 ng/mL); MEM+ plus FSH (100 ng/mL); MEM+ plus IAA + EGF; MEM+ plus IAA + FSH; MEM+ plus EGF + FSH; or MEM+ plus IAA + EGF + FSH. After 2 or 6 days of culture in each treatment, the pieces of ovarian cortex were fixed in Bonin for histological examination. Follicles were classified as primordial or developing (primary and secondary) follicles. Compared to the control, in all media tested, the percentages of primordial follicles were reduced (P < 0.05) and the percentages of developing follicles were increased (P < 0.05) after 2 or 6 days of culture. Furthermore, culture of ovarian cortex for 6 days reduced the percentages of healthy, viable follicles when compared with the control (P < 0.05), except for cultures supplemented with IAA + EGF and EGF + FSH. In conclusion, the addition of IAA and EGF or EGF and FSH to the culture media were the most effective treatments to sustain the health and viability of activated ovine primordial follicles during in vitro culture. (c) 2005 Elsevier B.V. All rights reserved.

Gas chromatographic analysis of indole alkaloids from Tabernaemontana hilariana

A fast and efficient procedure was elaborated to identify the alkaloid constituents from Tabernaemontana hilariana (Apocynaceae). The strategy based on fractioning of the crude alkaloid fraction in small silica cartridges followed by thin-layer chromatography (TLC), capillary gas chromatography-flame ionization detection as well as high-resolution gas chromatography-mass spectrometry afforded voacangine, coronaridine, ibogamine, voacangine pseudoindoxyl, voacangine hydroxyindolenine, 3-hydroxycoronaridine and 3-(2-oxopropyl)coronaridine. (C) 1997 Elsevier B.V. B.V.

Indole-3-carbinol attenuates the deleterious gestational effects of bisphenol A exposure on the prostate gland of male F1 rats

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Indole monoterpene alkaloids from Chimarrhis turbinata DC Prodr.: a contribution to the chemotaxonomic studies of the Rubiaceae family

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

The triad indole-3-acetic acid ethyl ester/esterase/horseradish peroxidase as a new cytotoxic prodrug/enzyme combination

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)