Strychnos 1990 - 2004 - Crops for the Future

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Author Title Year Source title Reference Dasilva, B. A., A. P. Dearaujo, R. Mukherjee and A. D. Chiappeta Bisnordihydrotoxiferine and vellosimine from Strychnos divaricans root - spasmol 1993 Phytotherapy Research 7(6): 419-424 Abstract Bisnordihydrotoxiferine and vellosimine, two tertiary indole alkaloids have been isolated from the root of Strychnos divaricans. Bisnordihydrotoxiferine antagonized in a nonspecific manner, oxytocin and acetylcholine induced contractions in the rat uterus and acetylcholine and histamine responses in the guinea-pig ileum. Bisnordihydrotoxiferine, like verapamil, produced effects on voltage dependent Ca2+ channels. For example in guinea-pig ileum, bisnordihydrotoxiferine (pD2' 3.92+/- 0.09) and verapamil (pD2' 6.00+/-0.11) inhibited KCl induced contractions. Furthermore, bisnordihydrotoxiferine (pD2' 4.37+/-0.02) and verapamil (pD2 6.83+/-0.10) also antagonized CaCl2 induced contractions of K+-depolarized rat uterus. When compared with sodium nitroprusside, an antagonist of receptor operated Ca2+ channels, bisnordihydrotoxiferine had no effect. However, in the aorta, the alkaloid (IC50, 6.10 X 10(-6) M) antagonized the intracellular calcium dependent transient contractions of noradrenaline and it was about four times more potent than procaine (IC50, 2.30 x 10(-5) m), a known inhibitor of the release of Ca2+ from intracellular stores. Bisnordihydrotoxiferine may produce nonspecific spasmolytic actions mainly by inhibiting intracellular calcium mobilization and to a lesser extent by inhibiting voltage dependent calcium c h a n n e l s i n s m o o t h m u s c l e s . Author Title Year Source title Reference Diez A; Vila C; Sinibaldi ME; Troin Y; Rubiralta M Synthetic studies on indole alkaloids .6. Synthesis of tetrahydroakuammicine and 1993 Tetrahedron Letters 34(4): 733-736 Abstract The synthesis of dihydrocorynantheol (5) and of the pentacyclic Strychnos alkaloid tetrahydroakuammicine (4) is reported from 5-ethyl-N-hydroxyethyl-2-(1-phenylsulfonyl-3-indolyl)- 4-piperidineacetates (1) by means of a K(t)OBu/BF3.Et2O intramolecular cyclization.
Author Title Year Source title Reference Elmekkawy, S., M. R. Meselhy, Y. Kawata, S. Kadota, M. Hattori and T. Namba Metabolism of strychnine n-oxide and brucine n-oxide by human intestinal bacteri 1993 Planta Medica 59(4): 347-350 Abstract Anaerobic incubation of strychnine N-oxide with human intestinal bacteria resulted in its transformation to strychnine and 16-hydroxystrychnine. Similarly, brucine N-oxide was transformed t o b r u c i n e a n d 1 6 - h y d r o x y b r u c i n e . Author Title Year Source title Reference Fritz, H., M. Soleymanijamarani, J. W. Bats and H. J. Teuber Synthesis of the azocino[4.3-b]indole core structure of Strychnos alkaloids 1993 Liebigs Annalen Der Chemie (7): 705-710 Abstract Michael addition of ethylmalonic dimethyl or diethyl ester with cyclohexenone and subsequent Fischer indole ring closure afford the (tetrahydrocarbazolyl)malonic esters 4a-c. Decarboxylation of 4a leads to the corresponding butyric acid methyl ester 5 which is oxidized by DDQ to the 4-oxo derivative 6a (byproduct: carbazole 7). Oximation of 6a to 8a and acylation of the oxime group to Ob, c as well as hydrogenation of this group yield 9a, b. Subsequent hydrogenation of the tetrahydrocarbazole ring by means of borane/pyridine yields the hexahydrocarbazole derivatives 10a and b. By cyclisation in boiling o-xylene (sodium hydride catalysis) 10a is converted into the tetracyclic 1,5-methanoazocino[4.3-b]indole derivative 11a with an alkaloid analogous ethyl side chain. The X-ray structural analysis of the corresponding phenylsulfonyl derivative 11b confirms constitution and stereochemistry. As a diastereoisomer of 11a the byproduct 11c could be isolated. Author Title Year Source title Reference Abstract Magnus P; Giles M A new approach to the synthesis of the Strychnos alkaloids core structure 1993 Tetrahedron Letters 34(40): 6355 -
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