Strychnos 1990 - 2004 - Crops for the Future

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Author Title Year Source title Reference Wins, P., I. Margineanu, J. Penelle, L. Angenot, T. Grisar and L. Bettendorff Bisindole alkaloids from Strychnos guianensis are effective antagonists of nicotini 2003 Naunyn-Schmiedebergs Archives of Pharmacology 367(3): 253-259 Abstract Several mono- and bisindole quaternary alkaloids isolated from the stem bark of Strychnos guianensis have recently been shown to be effective blockers of neuromuscular transmission in mice. In this study, we used a human clonal cell line (TE671) expressing muscle-type nicotinic acetylcholine receptors. The agonist carbamylcholine activated a receptor-mediated Rb-86(+) efflux and this activation was antagonized by the indole alkaloids, the most active being bisindole bisquaternary compounds. The most effective antagonist, guiachrysine, had an IC50 around 0.43 muM in the presence of 0.5 mM carbamylcholine, compared to 0.16 muM for d-tubocurarine, the most potent curarizing alkaloid. Guiaflavine and 5',6'-dehydroguiaflavine were slightly less effective. Monoindole compounds were 10 to 100 times less potent than bisindole alkaloids. Kinetic analysis showed that the inhibition of the carbamylcholine-dependent Rb-86(+) efflux by guiaflavine was of mixed competitive and uncompetitive type. The competitive component (K-I = 0.21 muM) is presumably due to binding at the acetylcholine site, while the uncompetitive component (K'(I) = 0.92 m u M ) m a y b e d u e t o o p e n c h a n n e l b l o c k . Author Title Year Source title Reference Zlotos, D. P. Iso-caracurine v, a novel unexpected decomposition product of caracurine v 2003 Journal of Natural Products 66(1): 119-120 Abstract The structure of iso-caracurine V (3), an unexpected decomposition product of the Strychnos alkaloid caracurine V (1), was determined by NMR spectroscopy. Compound 3, which was probably previously regarded as bisnortoxiferine I (2), is a one-sided ring closed product of 2.
Author Title Year Source title Reference Belem-Pinheiro, M. L., R. P. C. Couceiro, A. F. I. Da Rocha, F. J. Q. Monte and J. A new strychnobrasiline base of Strychnos mattogrossensis 2002 Natural Product Letters 16(4): 229-233 Abstract A new strychnobrasiline derivative, 12-hydroxy-10, 11-dimethoxystrychnobrasiline 1, has been isolated from the stem barks of Strychnos mattogrossensis. Its structure was established by spectroscopy analysis (1D and 2D NMR, MS, IR, UV) and literature data comparison. Two other known indoline alkaloids were also obtained from the heartwood, 12-hydroxy-11- methoxystrychnobrasiline 2 and strychnobrasiline 3. Author Title Year Source title Reference Bennasar ML; Zulaica E; Alonso Y; Vidal B; Vazquez JT; Bosch J Addition of chiral enolates to n-alkyl-3-acylpyridinium salts. Total synthesis of (+ 2002 Tetrahedron-Asymmetry 13(1): 95-106 Abstract Chiral enolates of indolylacetyl derivatives 6a-f undergo addition to pyridinium salt 7 with complete trans-selectivity and varied diastereofacial selectivities to give, after acid-induced cyclization of the intermediate 1,4-dihydropyridines, the vinoxine-related tetracycles 8a-f. Starting from (S)-prolinol indolylacetamide 6e, subsequent elaboration of the ethylidene substituent from tetracycle 8e and removal of the chiral auxiliary has resulted in a straightforward synthesis of (+)-16-epivinoxine and (-)-vinoxine. (C) 2002 Elsevier Science Ltd. All rights reserved. Author Title Year Source title Reference Abstract Biswas, S., T. Murugesan, S. Sinha, K. Maiti, J. R. Gayen, M. Pal and B. P. Saha Antidiarrhoeal activity of Strychnos potatorum seed extract in rats 2002 Fitoterapia 73(1): 43-47 -
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