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).

New antioxidant C-glucosylxanthones from the stems of Arrabidaea samydoides

Three new C-glucosylxanthones, 2-(2'-O-trans-caffeoyl)-C-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (1), 2-(2'-O-trans-cinnamoyl)-C-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (2), and 2-(2'-O-trans-coumaroyl)-C-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (3), were isolated from the stems of Arrabidaea samydoides, in addition to three known C-glucosylxanthones, mangiferin (4), 2-(2'-O-benzoyl)-C-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (5), and muraxanthone (6). Their chemical structures were assigned on the basis of MS and 1D and 2D NMR experiments. Xanthones 1-6 showed moderate free radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) as well as antioxidant activity evidenced by redox properties measured on ElCD-HPLC.

seco-Irldoids from Calycophyllum spruceanum (Rubiaceae)

Three seco-iridoids 7-methoxydidcrrosidc, 6'-O-acetyldiderroside and 8-O-tigloyldiderroside, were isolated from the wood bark of Calycophyllum spruceanum together with the known iridoids loganetin, loganin and the seco-iridoids secoxyloganin, kingiside and diderroside. Their structures were elucidated by means of NMR and MS spectral data analysis. Using NOE correlations and coupling constants, the relative stereochernistry of the new derivatives was established. 7-Methoxydiderroside, 6'-O-acetyldiderroside and the known secoxyloganin and diderroside showed in vitro activity against trypomastigote forms of Trypanosonla Cruzi, with IC50 values of 59.0, 90.2, 74,2 and 84.9 mug/mL, respectively and were compared to the standard gentian violet (IC50 7.5 mug/ml). (C) 2003 Elsevier Ltd. All rights reserved.

Iridoids from the aerial parts of Verbena littoralis (Verbenaceae)

The iridoids, 6S-hydroxy-8S-methyl-4-methylene-hexahydro-cyclopenta[c]pyran-3-one and 6S,9S-dihydroxy-8S-methyl-4methylene-hexahydro-cyclopenta[c]pyran-3-one, were isolated from the aerial parts of Verbena littoralis. Their structures and stereochemistry were elucidated by means of NMR spectral data analysis. Both compounds showed moderate in vitro activity against gram positive and negative bacteria as well as moderate in vivo intestinal peristaltic action in mouse. The iridoids also showed moderate free radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) as well as antioxidant activity, the latter being evidenced by redox properties measured using EICD-HPLC. (C) 2004 Elsevier Ltd. All rights reserved.