TLC Luminescence of gramine and related indole alkaloids in phalaris arundinacea

Luminescence characteristics of gramine, dimethyltryptamine and related indoles on Si gel TLC are described, chromatographic conditions are devised which enhance the luminescence, and a fluorometric TLC scanning procedure is developed for the quantitative determination of gramine in Phalaris arundinacea. 5-Methoxy-and 5-hydroxyindoles are readily distinguished from the indoles lacking a polar substituent at position 5.     

The occurrence of 2-methyl-1,2,3,4-tetrahydro-β-carboline and variation in alkaloids in Phalaris arundinacea

2-Methyl-1,2,3,4-tetrahydro-β-carboline was isolated from reed canarygrass (Phalaris arundinacea L.) and the occurrence of 2-methyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline confirmed. Clones of reed canarygrass that contained N,N-dimethyltryptamine or 2-methyl-1,2,3,4-tetrahydro-β-carboline did not contain their respective methoxy or hydroxy derivatives. Five of the 12 clones tested contained either or both of 5-methoxy-N,N-dimethyltryptamine and 2-methyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline. The data suggest that clones that contain gramine are not likely to contain N,N-dimethyltryptamine and/or β-carbolines. Thus, an inverse biosynthetic relationship between gramine and the tryptamine and β-carboline alkaloids seems to exist. However, further work is needed to firmly establish any such relationship between these alkaloids.     

Alkaloids of Sri Lankan Strychnos nux-vomica

Twenty-two identified alkaloids have been isolated from the root bark and leaves of a Sri Lankan Strychnos species supplied as S. nux-vomica. T     

Indolethylamine N-methyltransferases of Phalaris tuberosa, purification and properties

Two S-adenosylmethionine-dependent indolethylamine N-methyltransferase activities were purified from soluble extracts of Phalaris tuberosa by fractionation with (NH₄)₂SO₄, and chromatography on DEAE-Sephadex. One enzyme methylated the primary indolethylamines and the other methylated the secondary indolethylamines in the plant. These two enzymes were similar in catalytic and bulk physical properties and could not be separated during purification or by A 1.5 Agarose or hydroxylapatite chromatography. The products of enzymic reactions were identified by TLC.     

Hemicelluloses of Arundo donax at different stages of maturity

The hemicellulosic composition of the internodes of Arundo donax depends on the maturity of the tissue. The percentage of xylose in the total hemicellulose increases with increasing plant maturity. The main hemicellulose is an arabino-4-O-methyl glucurono xylan which is already present in the youngest tissues and has the same structural features regardless of the age of the tissues. The average D.P. of this polysaccharide increases from about 60 to 150 with maturation of the plant tissue.     

Leaf alkaloids of Rauwolfia volkensii

Thirteen alkaloids were isolated and identified from the leaves of Rauwolfia volkensii. The alkaloids included E-seco heteroyohimbine, heteroyohimbine, sarpagan, dihydroindole, pleiocarpamine, picrinine and akuammicine types together with peraksine.     

Radioimmunoassay for quantitative determination of morphine in capsules of Papaver somniferum

A radioimmunoassay (RIA) procedure for the determination of pmol quantitites of morphine in capsule samples of Papaver somniferum was developed. An antiserum developed against a conjugate of morphine-3-hemisuccinate-BSA was relatively specific for morphine and possessed moderated cross-reactivity with codeine and mild cross-reactivity with thebaine, but none with narceine, papaverine, or noscapine. The standard curve was linear over a range of 0.01–0.20 ng. This assay allows for the rapid, sensitive and precise determination of morphine in unpurified aqueous extracts of capsule samples. The amounts of morphine in the aqueous extracts determined by radioimmunoassay were validated by high performance liquid chromatography (HPLC). The two methods show a high correlation coefficient (r = 0.98) with no significant difference in determinations of morphine content by RIA and HPLC.     

Alkaloids of Hunteria zeylanica

Twenty alkaloids were isolated from the leaves and stem bark of Hunteria zeylanica, collected in Kenya. They were: 3-epi-dihydrocorymine 3-acetate, norisocorymine, corymine, 3-epi-dihydrocorymine 17-acetate, picralinal, picrinine, 3-epi-dihydrocorymine, isositsirikine, lanceomigine, geissoschizol, gentianine, kopsinine, eburnamine, norpleiomutine, pleiocarpamine, tubotaiwine, pleiomutinine, 19′-epi-pleiomutinine, yohimbol and 10-hydroxy-16-epi-affinine.     

Alkaloids of Pterotaberna inconspicua

Sixteen alkaloids were isolated from the seeds and root-bark of Pterotaberna inconspicua, collected in Zaïre. They were voacangine 3-carbonitrile, voacangine, voacristine, 3,6-oxido-voacangine, vobasine, 10-hydroxycoronaridine, 10-hydroxyheyneanine, methuenine, apparicine, tubotaiwine, 16-epi-isositsirikine, 16-epimethuenine, 3,14-dihydroellipticine, an isomer of corynantheol, 16-epimethuenine N-oxide and tetra-hydroellipticine.     

Occurrence of N-cyano alkaloids in asian Strychnos species

The isolation of N-cyano-sec.-pseudostrychnine and N-cyano-sec.-pseudobrucine from the leaves of Strychnos wallichiana Steud. ex. DC. is reported. N-Cyano-sec.-pseudostrychnine and a N-cyano-sec.-pseudo-colubrine have been found among the alkaloids obtained from the stem bark of S. ignatii Berg.     

Alcaloides des feuilles du Crioceras dipladeniiflorus

Three alkaloids have been isolated from leaves of Crioceras dipladeniiflorus. Two of them, 12-methoxy-voaphylline and criophylline are new and their structures have been determined. The third has been identified as andrangine an alkaloid isolated recently from another Apocynaceae Craspidospermum verticillatum.     

Antirhine and antirhine metho-salt from the leaves of Strychnos camptoneura

The isolation of antirhine and antirhine metho-salt from the leaves of Strychnos camptoneura is described. The conformation of antirhine is discuss     

Characterization of a 5-methyltryptophan resistant strain of Catharanthus roseus cultured cells

Strains of Catharanthus roseus suspension cells resistant to growth inhibition by various tryptophan analogs were selected. Tryptophan synthetase and anthranilate synthetase from the resistant cells differed from the normal cell enzymes by being more resistant to feedback inhibition by tryptophan. Though these altered enzymes allowed the free tryptophan level of the resistant cells to be 3–40 times higher than that of normal cells, the accumulation of tryptamine or ajmalicine could not be detected in the resistant cells.     

Alcaloïdes minoritaires de Capuronetta elegans (Apocynaceae)

Two monomeric and three dimeric new indole alkaloids derived from cleavamine have been isolated from the leaves and stem barks of Capuronetta elegans. Structural determination was made by physical and chemical correlations with the known major alkaloids of the plants.     

Lipids,amino acids,sugars, hardiness and growth of Festuca arundinacea

Tall fescue (Festuca arundinacea Schreb. cv S.170) plants were grown in environments differing only in temperature: 6/4, 16/14 or 21/19°. The content of total and individual sugars and amino acids in leaf laminae and roots did not relate closely to the hardiness of the organ. The unsaturation of lipid fatty acids alone was clearly unrelated to hardiness because the difference in unsaturation was greater in the neutral lipids, glycolipids and phospholipids from roots than from leaves but only the latter differed in hardiness. Total amounts of lipids could have been related to hardiness but phospholipids and glycolipids in the roots were not. At least some of these changes may be related to adaptation of growth to temperature.     

Two carboxy- and two hydroxymethyl-substituted aristololactams from Aristolochia argentina

Four new aristololactams have been isolated from Aristolochia argentina. The evidence indicates them to be 10-amino-3-hydroxymethyl-2,4-dimethoxyphenanthrene-1-carboxylic acid lactam, 10-amino-3-hydroxymethyl-2,4,6-trimethoxyphenanthrene-1-carboxylic acid lactam, 10-amino-2-hydroxy-4-methoxyphenanthrene-1,3-dicarboxylic acid lactam and 10-amino-2-hydroxy-4,6-dimethoxyphenanthrene-1,3-dicarboxylic acid lactam.     

Alkaloids of stem and rootbark of Tabernaemontana dichotoma

During chemical investigation for compounds possessing biological activity in the stem and rootbark of Tabernaemontana dichotoma, 22 alkaloids were isolated. Ten monomeric alkaloids were identified, viz. (?)-apparicine, coronaridine, 3-oxocoronaridine, 3-ketopropylcoronaridine, 19R-heyneanine, 3-ketopropyl-19R-heyneanine, ibogamine, isomethuenine, perivine and vobasine. Two of the monomeric alkaloids isolated were new, one was identified as 3,19R-oxidocoronaridine and the other one is not yet identified. The other ten alkaloids isolated were dimeric compounds, three were identified as tabernamine, voacamine and 3′R/S-hydroxyvoacamine. Five of the dimers were new alkaloids related to tabernamine and ervahanine type structures and identified as 3′R/S-hydroxytabernamine, 3′R/S-hydroxy-N₄-demethyltabernamine, N₄-demethyltabernamine and 3′R/S-hydroxy-N₄-demethytervahanine A and B. The remaining two alkaloids are partially characterized.     

Alkaloids of Rauwolfia cumminsii stem

24 indole alkaloids were isolated from the stem bark of Rauwolfia cumminsii and 21 identified. The alkaloids comprised E-seco, sarpagan, dihydroindole, yohimbine, heteroyohimbine, 18-hydroxyyohimbine ester and anhydronium types together with peraksine and deacetylpicraline. The probable biosynthesis of the alkaloids is discussed.     

Alkaloids and iridoids from Strychnos nux-vomica fruits

The alkaloid mixtures present in the fruit pericarp and fruit pulp of Strychnos nux-vomica L. are qualitatively very similar to that found in the seeds. In addition to alkaloids previously known to occur in this plant, small amounts of 4-hydroxystrychnine and the new base N-methyl- sec.-pseudo-β-colubrine have been isolated. Cantleyine, which is a non-indolic base and an artefact, has also been obtained. The iridoid mixture in the fruit pulp is predominantly loganin with small amounts of related compounds, including the biogenetically important secologanin.     

Medium- and light-induced formation of serpentine and anthocyanins in cell suspension cultures of Catharanthus roseus

By irradiation with fluorescent light, medium-induced cell cultures of Catharanthus roseus accumulated anthocyanins and the indole alkaloid serpentine. The formation of both compounds was inhibited by phosphate and nitrogen-containing mineral salts and stimulated by high sucrose concentrations. The accumulation of serpentine was preceded by an increase and subsequent decrease of its biogenetic precursor ajmalicine, which was the predominant alkaloid of medium-induced cultures in the dark. High concentrations of serpentine or anthocyanins were observed only in a small proportion of all cells present in a medium-induced culture. The aglycones of the anthocyanins were identified as petunidin, malvidin and hirsutidin.