Venoterpine--a new monoterpenoid alkaloid from the fruits of Alstonia venenata R.Br.
About: This article is published in Tetrahedron Letters.The article was published on 1968-01-01. It has received 13 citations till now.
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TL;DR: Secostrychnosin (1), a new secoiridoid, as well as seven compounds never before isolated from nature: 4-tert-butyl-2-oxazolidinone (2), 3-acetoxyindole (3), indole-2carboxylic acid (4), benzocaine (5), 3acetylindole(6), butylparaben (7) and 2-hydroxy-3-methoxybenzaldehyde (8), together with fifty other known compounds, have been isolated from the
Abstract: Secostrychnosin (1), a new secoiridoid, as well as seven compounds never before isolated from nature: 4-tert-butyl-2-oxazolidinone (2), 3-acetoxyindole (3), indole-2-carboxylic acid (4), benzocaine (5), 3-acetylindole (6), butylparaben (7) and 2-hydroxy-3-methoxybenzaldehyde (8), together with fifty other known compounds, have been isolated from the stem of Strychnos cathayensis. These compounds include twenty-three alkaloids, twelve benzenoids, four steroids, three flavonoids, three iridoids, two triterpenoids, two secoiridoids, two fatty acids, one lignan, one acetophenone, one coumarin, one chromane, one tetraterpenoid, one tannin, and one organic acid. The structures of these compounds were determined by means of spectralanalyses.
27 citations
TL;DR: New pyridine monoterpene alkaloids have been synthesized from the iridoid glycosides 8-epi-loganin, cornin, and antirrinoside by treatment with beta-glucosidase and aqueous NH4-OAc.
Abstract: New pyridine monoterpene alkaloids (PMTAs) have been synthesized from the iridoid glycosides 8-epi-loganin, cornin, and antirrinoside by treatment with beta-glucosidase and aqueous NH4-OAc. The PMTA from antirrinoside contained an 8-alpha-OAc group from the opened 7,8-epoxide moiety. Treatment of genipin, the aglycone of geniposide, with HCl(g) and NH3(g) yielded the PMTA racemigerine, a known plant isolate, in which the C=C-CH2OH side chain was converted to C=C-CH3. Reaction of geniposide with beta-glucosidase and aqueous NH4OAc led to oligomeric alkaloids, but at high dilution a dimer was obtained whose structure was formally that of a Diels-Alder adduct between racemigerine and a dihydropyridine. These biomimetic semisyntheses were analyzed in terms of reaction mechanisms and the relative paucity of known plant PMTAs in comparison with the multitudinous occurrence of their presumed iridoid glycoside precursors.
23 citations
TL;DR: In this article, die absolute Konfiguration ist durch ORD-CD, Vergleiche mitl-(−)-actinidin ableitbar, and RW-47 und Venoterpin sind identisch.
Abstract: RW-47 und Venoterpin sind identisch. Die absolute Konfiguration ist durch ORD-CD, Vergleiche mitl-(−)-actinidin ableitbar.
11 citations
01 Jan 1970
TL;DR: In this paper, ausgezeichnete naturlich vorkommenden Pyridinverbindungen durch spezifische biochemische Funktionen oder durch besondere physiologische Wirkungen is presented, and einige dieser Pyridinstrukturen treten im Grundstoffwechsel aller Organismen auf.
Abstract: Bei den zahlreichen Pyridinverbindungen aus dem Tier- und Pflanzenreich handelt es sich entweder um einfache Abkommlinge dieser Base, die sich durch verschiedenartige Substitution unterscheiden, oder um komplizierter gebaute Naturstoffe, die den Pyridinkern als ein charakteristisches Strukturelement enthalten. Vielfach sind die naturlich vorkommenden Pyridinverbindungen durch spezifische biochemische Funktionen oder durch besondere physiologische Wirkungen ausgezeichnet. Einige dieser Pyridinstrukturen treten im Grundstoffwechsel aller Organismen auf, andere sind nur Inhaltsstoffe einiger hoherer Pflanzen oder Ausscheidungsprodukte bestimmter Mikroorganismen. Wegen dieser Vielgestaltigkeit kommt den Naturstoffen der Pyridinreihe besonderes biogenetisches Interesse zu.
6 citations
01 Jan 1968
TL;DR: In addition to pachycarpine, thermopsine, N-methylcytisine, rhombifoline, and cytisine, there was isolated the new alkaloid thermopsamine that on dehydration with phosphorus pentoxide gives dehydrosparteine.
Abstract: Publisher Summary As the technique of isolation becomes more sophisticated, well-known alkaloids are revealed in sources not hitherto suspected; the isolation of Cinchona alkaloids from the leaves of the olive tree can serve as an example. The chapter discusses plants and their contained alkaloids. The first known natural occurrence of a 2,6-naphthyridine has been reported. Thin-layer chromatography of an alcoholic extract of the plant Antirrhynum majus L. gave a base (C 9 H 8 N 2 ) whose spectral examination indicated that it is 4-methyl-2,6-naphthyridine. Other possible isomers were excluded on the basis of the NMR spectral data. Bellendena montana R.Br. is the first plant of the Proteacea that has been shown to elaborate alkaloids. Bellendine (C 12 H 15 O 2 N) was isolated in 0.001370 yields. Traces of two other bases were also indicated. Bellendine is of some interest in that its structure was determined by X-ray methods without the incorporation of a heavy atom into a crystalline derivative. In addition to pachycarpine, thermopsine, N-methylcytisine, rhombifoline, and cytisine, there was isolated the new alkaloid thermopsamine that on dehydration with phosphorus pentoxide gives dehydrosparteine. Oxidation with the Oppenauer reagent gives an oxo compound, and treatment with hydrogen iodide and phosphorus in acetic acid generates pachycarpine; hence the given structure as 13-hydroxysparteine. The major constituent of the alkaloids from the leaves of the plant Spathiostemon javensis Blume was N b -methyltetrahydroharman; the first example of a carboline found in Euphorbiaceae.
6 citations
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70 citations
TL;DR: In this article, the proton resonance spectra of pyridine, 2,6-pyridine-d2, 3,pyridine-d1, and 4, pyridines have been obtained for the pure liquids under conditions of high resolution.
Abstract: The proton resonance spectra of pyridine, 2,6-pyridine-d2, 3-pyridine-d1, and 4-pyridine-d1 have been obtained for the pure liquids under conditions of high resolution. The spectra have been analyz...
67 citations
TL;DR: A monoterpenoid alkaloid, isolated from Rauwolfia verticillata (Lour.) Bail, has been shown to be related to the alkaloids of the actinidine group and is considered to be (I).
Abstract: A new monoterpenoid alkaloid, isolated from Rauwolfia verticillata (Lour.) Bail. of Hong Kong, has been shown to be related to the alkaloids of the actinidine group and is considered to be (I).
15 citations