A phytochemical investigation of the tertiary phenolic alkaloidal fraction of the stems of CHASMANTHERA DEPENDENS H OCHST. (Menispermaceae) has yielded the tetrahydroprotoberberine type alkaloids govanine ( identical with(-)-tetrahydropseudocolumbamine) [1] and coreximine [2]; the pavine type alkaloid bisnorargemonine [3] and the morphinandienone type alkaloid pallidine [4].

a e r h e i m S v e n d s e n , B. C h i n g o v a and G. Z o l o t o v i t c h The fennel plant has been known for a long time in Bulgaria. At present it is cultivated extensively in the south-eastern and north-eastern parts of the country. Indigenous populations of the two varieties of the subspecies Foe~zictrltrm capillaceurn (G a 1 i b.) H o 1 m b o e are grown: var. d u l~e -annual (sweet) fennel and var. vzilgareperennial (bitter) fennel.There are considerable differences between these varieties with respect to habitus, morphological characteristics and plant development as well as to content and chemical composition of the volatile oil. Earlier information on fennel is summarized by G u e n t h e r (1950), G i l d e m e i s t e r and H o f f m a n n (1961) and H e e g e r (1956) whereas more recent evidence is to be found in the works of T o t h (1967) a n d c h i n g o v a (in press).Research on fennel has been carried out for 9 years at the Institute for Roses, Aromatic and Medicinal Plants in Kazanlik. By the method of individual-family selection several prospective families of the two varieties were produced. In 1967 the first hybrids were developed by the method of sexual generative hybridization ( C h i n g o v a -In press).T h e object of the present study was to examine three not so far investigated problems in fennel by using the adventages of gas chromatography:1. The composition of the essential oils from the individual Foeniculum species and .the influence of oil recovery technique (water-steam or steam distillation) thereon.2. Comparison of the original essential oil in the fruits with that recovered by distillation.3. The inheritance pattern of some of the fruit characteristics and especially of the essential oil components from the sexual hybrids compared with the parent plants. Experimental MaterialsThe fruit samples were collected from plants grown in Kazanlik. The three hybrid plants were produced by the crossing of selected families of annual and perennial fennel. Data for thc individual samples are presented in Table 1.

The (1)HNMR (CDCl (3)) data on 28 tetrahydroprotoberberine alkaloids have shown that it is possible, from the chemical shift values observed for the aromatic protons, not only to determine the substitution pattern but also the type of substituents carried on the two sites in rings A and D within this class of alkaloids.

A modified, simple method for screening of fresh plant material for glycosidic bound volatile compounds is described. The plant material is "stabilized" in boiling water, possible occurring volatile compounds removed by hydrodistillation, the remaining aqueous extract treated with beta-glucosidase, and the volatile compounds, liberated by the enzymatic hydrolysis, isolated and analysed by gas chromatography. In MELISSA OFFICINALIS and MENTHA SPICATA relatively large amounts of glycosidic bound eugenol and some aliphatic alcohols were found, but only small amounts of such monoterpene alcohols occurring in the volatile oils.

The essential oil of OCIMUM GRATISSIMUM, growing wild in Rwanda, was investigated by LSC, GLC, and GC-MS. The oil contained 35% thymol and 11% eugenol, which may indicate the occurrence of a new chemotype of the species. A large amount of hydrocarbons (42%) including 18% P-cymene was also found. The oil showed a relatively strong antimicrobial effect. The oil of O. GRATISSIMUM, cultivated in Rwanda from seeds collected in Cameroon, consisted of 47% thymol and only 0.3% eugenol. This sample contained 49% hydrocarbons, including 23% gamma-terpinene. Most of the constituents detected in the oil samples were not previously known to be present in the essential oil of O. GRATISSIMUM.

From the stem bark of STRYCHNOS SPINOSA two tertiary alkaloids were isolated. By means of their spectral data they were identified as 11-methoxy-diaboline and 12-hy-droxy-11-methoxy-diaboline.

By means of a prefractionation of the monoterpene hydrocarbon mixture-o f the essential oil of the fruits of Carum carvi L. on a silicagel column by elution with pentane, collection of a number of small fractions and subsequent analysis of each fraction by means of gus chromatography on 8 m long packed columns the following compounds were found:

a e r h e i m S v e n d s e n Auf die Möglichkeit, die Zusammensetzung des ätherischen Oles in kleinen Mengen Pflanzenmaterial durch Gaschromatographie zu studieren, haben wir schon in einigen Veröffentlichungen hingewiesen (K a r 1 s e n U. B a e r h e i m Sv e n ds e n , 1966a, 1966b). Die Voraussetzung solcher Untersuchungen war, über eine 'Technilc zu verfügen, mit der das frische PflanzenmateriaI direkt gaschromatographisch untersucht werden kann. Die von uns früher verwendete, sehr einfache Apparatur, wobei das Pflanzenmaterial (etwa 10 mg) in einem mit dem indifferenten Trägergas durchströmten System mit Hilfe von einem Magneten in den Einspritzblock des Gaschromatographen eingetragen und wieder herausgenommen werde11 konnte, haben wir durch eine von der Firma Becker Delft N. V. für Pyrolyseuntersuchungen entwickelte Apparatur ersetzt'. Die Apparatur besteht aus einer an dem Gaschromatographen befestigten, gasdichten Schleuse, welche die Einführung einer Stange aus rostfreiem Stahl in den Einspritzblock des Gaschromatographen zuläßt. An dem einen Ende der Stange haben wir den Heizdraht des Pyrolyseapparates durch ein ,,Körbchena für das Pflanzenmaterialvon dem gleichen Typ wie früher verwendetersetzt. Dieses Körbchen mit dem Pflanzenmaterial kann durch das gasdichte Schleusensystem glatt in den Trägergasstrom einund ausgeführt werden. Das Pflanzenmaterial (etwa 5-10 rng) wird 10-15 Sekunden lang im Einspritzblock bei einer Temperatur von etwa 200" gehalten. Während des kurzen Erwärmens des Pflanzenmaterials im indifferenten Trägergasstrom findet ein fast augenblickliches Verdampfen der flüchtigen Stoffe statt. Diese Stoffe werden mit dem Trägergas sofort in die Chromatographiesäule geführt, in der die Trennung der Bestandteile stattfindet. Abbildung 1 stellt eineSkizze der benutzten Apparatur dar. Mit Hilfe der beschriebenen Apparatur und Technik haben wir die Schwankungen in der Zusammensetzung der Monoterpenkohlenwasserstoffe in den Blättern von Rosmarinus officinalis L. einer Untersuchung unterworfen. Die Blätter wurden im Monat März direkt nach der Einsammlung gaschromatographisch untersucht. Für eine Analyse benötigte man etwa 5 mg frisches Pflanzenrnaterial. Die Der Firma Becker Delfl N. V., Delfl, Holland, danken wir auch an dieser Stelle für die uns ziir Verfügung gestellte Apparatur. Heruntergeladen von: Universite Laval. Urheberrechtlich geschützt.