Contribution à la phytochimie du genre Gentiana. X. Etude des composés flavoniques et xanthoniques dans les feuilles de Gentiana vernaL.

One new ( 1 ) and one previously identified ( 2 ) flavone-C-glycosides were isolated from leaves of Gentiana verna L . by means of column chromatography. The columns used were polyamid and cellulose. The structure of the new compound was established as iso-orientin-2″-O-glucoside by means of UV. and NMR. spectrosocpy. The known compound was shown to be isoorientin-4′-O-glucoside.     

Contribution à la phytochimie du genre Gentiana III. Etude des composés flavoniques et xanthoniques dans les feuilles de Gentiana lutea L. (2me communication)

The xanthone isogentisin and two flavonic heterosides (isocrientin-4′-O-glucoside and isovitexin-4′-O-glucoside) have been isolated from leaves of Gentiana lutea L. by means of column chromatography on polyamide. The determination of the structures and the NMR. spectra of the acetylated derivatives are reported.     

Contribution à la phytochimie du genre Gentiana,XIII. Etude des composés flavoniques et xanthoniques dans les feuilles de Gentiana campestris L. 2ème communication

Phytochemistry of genus Gentiana XIII. Study of flavocic and xantonic compounds in the leaves of Gentiana campestris L. 2nd communication. By means of column chromatography on polyamide, we have isolated from the leaves of Gentiana campestris L. a new xanthone-O-glucoside, the 3,4-dimethoxy-5, 8-dihydroxy-xanthone-1-O-β-D-glucopyranoside ( 2 ) and its aglucone, the 3,4-dimethoxy-1,5,8-trihydroxy-xanthone ( 1 ). The C-glucosides mangiferin ( 3 ) and swertisin ( 4 ) have also been isolated and identified.     

Contribution à la phytochimie du genre Gentiana I. Etude des composés flavoniques et xanthoniques dans les feuilles de Gentiana lutea L. (1re communication)

Six polyphenolheterosides have been isolated from the leaves of G. lutea L. by means of thin layer and column chromatography on polyamide. The xanthones mangiferin (III) and gentioside (IV), the flavones isoorientin (V) isovitexin (VI) and two new heterosides (E and F) have been isolated. E gave isoorientin and glucose on hydrolysis and F isovitexin, glucose and gentiobiose. Structure identification has been achieved by UV., IR. and NMR. spectroscopy as well as by synthesis of the corresponding aglycones.     

Contribution à la phytochimie du genre Gentiana IX. Etude de composés flavoniques et xanthoniques dans les feuilles de gentiana CampestrisL. 1ère communication

Two new xanthone-O-glycoside, the 1,3,5-trihydroxy-xanthone-8-O-β-D -glucopyranoside ( 3 ), the 1,5-dihydroxy-3-methoxyxanthone-8-O-β-D -glucopyranoside ( 4 ), have been isolated from the leaves of Gentiana campestris L . by means of column chromatography on polyamid. Two known xanthones ( 1 , 2 ) which are respectively the aglycones of 3 and 4 and a flavone: iso-orientine ( 5 ) have also been isolated and identified.     

Etude des composés flavoniques et xanthoniques dans les feuilles de Gentiana ciliataL

Study of the flavonic and xanthonic compounds in the leaves of Gentiana ciliata L . Fifteen 1,3,7,8-oxygenated xanthones ( 1 – 15 ) were isolated from the leaves of Gentiana ciliata L. (genus Gentianopsis). Among these were six new glycosides: glucosyl-1-decussatin 6 , glucosyl-1-gentiacaulein ( 8 ), primeverosyl-8-isogentiacaulein ( 9 ), glucosyl-3-isogentiacaulein ( 10 ), glucosyl-1-swertianin ( 12 ) and primeverosyl-7-swertianin ( 13 ). Three known flavone C-glucosides were also found ( 16 – 18 ).     

Contribution à la phytochimie du genre Gentiana. VII. Etude des composés flavoniques et xanthoniques dans les feuilles de Gentiana vernaL. (1ère communication)

A new xanthone-O-glycoside, the 1,7-dihydroxy-3-methoxyxanthone-8-O-β-D-glucopyranoside ( 7 ), has been isolated from the leaves of Gentiana verna L. by means of column chromatography on polyamid. Six known xanthones: 1-hydroxy-3,7,8-trimethoxyxanthone-1-O-primerveroside ( 2 ); 1,7,8-trihydroxy-3-methoxyxanthone ( 3 ); 7-hydroxy-3,8-dimethoxyxanthone-1-O-primeveroside ( 4 ); 7,8-dihydroxy-3-methoxyxanthone-1-O-primeveroside ( 5 ); mangiferin 6 and the flavone C-glycoside isoorientin 8 have also been isolated and identified.     

Contribution à la phytochimie du genre Gentiana. II. Etude des cyclitols dans les feuilles de Gentiana lutea L.

L -(+)-bornesitol has been isolated from the leaves of G. lutea L . in the proportion of 1,6% by weight of dried material. Meso-inositol has also been detected by chromatography. Distribution of L -(+)-bornesitol and its taxonomic interest are discussed.     

Contribution à la phytochimie de genre Gentiana. XXIV.. Nouveaux C-glycosides flavoniques dans les feuilles de Gentiana asclepiadeaL.

Phytochemistry of genus Gentiana, XXIV. New C-glycosylflavones from the leaves of Gentiana asclepiadea L. p-Hydroxybenzoyl-2″-isoorientin-4′-O-β-D-glucoside ( 1 ) was isolated from the leaves of Gentiana asclepiadea L. by means of column chromatography. This is the first occurrence in nature of a p-hydroxybenzoate of isoorientin. p-Hydroxybenzoyl-2″-isoorientin ( 2 ) was also shown to be present in the same plant.     

Contribution à la phytochimie du genre Gentiana,VI. Etude des xanthones dans les feuilles de Gentiana bavarica L.

Ten tetraoxygenated xanthones (1-hydroxy-3, 7, 8-trimethoxyxanthone I; 1, 7-dihydroxy-3, 8-dimethoxyxanthone II; 1, 7, 8-trihydroxy-3-methoxyxanthone III; 1, 3, 7, 8-tetrahydroxyxanthone IV; 3, 7, 8-trimethoxyxanthone-1-O-primeveroside V; 7-hydroxy-3, 8-dimethoxyxanthone-1-O-primeveroside VI; 1, 8-dihydroxy-3-methoxyxanthone-7-O-acetylrutinoside VII; 7, 8-dihydroxy-3-methoxyxanthone-1-O-primeveroside VIII; 3, 7, 8-trihydroxyxanthone-1-O-primeveroside IX; 3, 7, 8-trihydroxyxanthone-1-O-glucoside X) have been isolated from leaves of Gentiana bavarica L . by means of column chromatography on polyamid. Among these xanthones, VI, VII, VIII and IX were not encountered before in nature.     

Contribution à la phytochimie du genre Gentiana. XXVI.. Identification d'une nouvelle di-O-glucosyl cinnamoyl-C-glucosylflavone extraite des feuilles de Gentiana X marcailhouana RY.

Phytochemistry of Genus Gentiana. XXVI. Identification of a New Di-O-glucosyl Cinnamoyl-C-glucosylflavone in the Leaves of Gentiana X marcailhouana RY . A new di-O-glucosyl cinnamoyl-C-glucosylflavone has been identified as 4′-O-β-D -glucosyl-2″-O-[2-O-β-D -glucosyl-2,4,5-trihydroxy-(E)-cinnamoyl]isoorientin ( 1 ).     

Contribution à la phytochimie du genre Gentiana,XIX. Identification de nouveaux C-glucosides flavoniques dans Gentiana pyrenaicaL

Phytochemistry of genus Gentiana, XIX: Identification of new C-glycosylflavones in Gentiana pyrenaica L . Five flavone C-glucosides [6-C-β-D -glucopyranosyl-tricine ( 1 ) or isopyrenine; 7-O-β-D -glucopyranosyl-6-C-β-D -glucopyranosyltricine ( 2 ) or isopyrenine-7-O-glucoside; isoscoparine-7-O-glucoside ( 3 ); 7-O-β-D -glucopyranosyl-6-C-β-D -glucopyranosylacacetine ( 4 ) and isovitexine-7-O-glucoside ( 5 ) or saponarine] as well as the flavonol glucoside isoquercitrine ( 9 ) have been isolated chromatographically, using polyamide and cellulose columns, from the aerial parts of Gentiana pyrenaica L . 1 and 2 are new compounds and the first glycoflavones trisubstituted on cycle B. Compound 4 is also encountered for the first time in nature.     

Contribution à la phytochimie du genre Gentiana. V. Identification d'un nouveau O-glucoside de C-glucoside flavonique dans les feuilles de Gentiana nivalis L

A new flavonic heteroside, isoorientin-3′-O-glucoside, has been isolated from leaves of Gentiana nivalis L . by means of column chromatography on polyamide. The determination of the structure is described.     

Contribution à la phytochimie du genre Gentiana XXI; Les cinnamoyl-C-glucosylflavones et leurs O-glucosides dans Gentiana punctataL.

Phytochemistry of genus Gentiana XXI: The cinnamoyl-C-glucosylflavones and their O-glucosides in Gentiana punctata L . Three new ( 1 – 3 ) and three previously identified ( 4 – 6 ) cinnamoyl-C-glucosyl-flavones have been isolated from the leaves of Gentiana punctata L . The structures of the new compounds were established as: trans-cafeoyl-2″-iso-orientin-4′-O-β-D -glucoside ( 1 ), trans-feruloyl-2″-isovitexin-4′-O-β-D -glucoside ( 2 ) and trans-feruloyl-2″-isovitexin ( 3 ). Isoscoparine ( 8 ) and O-β-D -glucosyl-2″-iso-orientin ( 7 ) were also isolated and identified.     

Contribution à la phytochimie du genre Gentiana. XXII. Identification de nouveaux O-glucosides de la mangiférine dans Gentiana asclepiadeaL.

Phytochemistry of genus Gentiana. XXII. Identification of new O-glucosides of mangiferin in Gentiana asclepiadea L. Two new O-glucosides of mangiferin (mangiferin-7-O-β-D -glucoside ( 1 ) and mangiferin-6-O-β-D -glucoside ( 2 )) have been isolated from the leaves of Gentiana asclepiadea L . This is the first full structure elucidation of naturally occurring O-glucosides of C-glucosylxanthones. The known C-glucosylflavone, saponarin ( 5 ) was also identified.     

Contribution à la phytochimie du genre Gentian,XI Identification de nouveaux dérivés de l'iso-orientine extraits des feuilles de Gentiana burseri Lapeyr

Two new derivates of iso-orientin have been isolated and identified from the leaves of Gentiana burseri, LAPEYR. The structure of the new compounds were established as: trans-cafeoyl-2″-iso-orientin (1) and p-β-D-glucosyl-trans-cafeoyl-2″-iso-orientin-4′-O-β-D-glucoside (2).     

Contribution à la phytochimie du genre Gentiana. XIV: Identification de nouveaux dérivés de l'isoorientine extraits des feuilles de Gentiana burseri LAPEYR (2e communication)

Phytochemistry of genus Gentiana XIV: Identification of new derivatives of iso-orientin in the leaves of Gentiana burseri LAPEYR . 2nd Communication. Two new derivatives of iso-orientin have been isolated and identified. The structures of the new compounds were established as: trans-feruloyl-2″-iso-orientin ( 1 ) and trans-feruloyl-2″-iso-orientin-4′-O-β-D -glucoside ( 2 ).     

Contribution à la phytochimie du genre Gentiana,XVIII. Structure du gentiabavarutinoside,un nouveau glycoside xanthonique acylé isolé de Gentiana bavaricaL

Phytochemistry of genus Gentiana, XVIII: Structure of gentiabavarutinoside, a new acylated xanthone glycoside from Gentiana bavarica L. In a previous work [1], we isolated from Gentiana bavarica L . an acylated xanthone glycoside (1,8-dihydroxy-3-methoxy-xanthone-7-O-acetylrutinoside 1 or gentiabavarutinoside) without locating the acetyl group. By ¹³C-NMR. spectroscopy, the attach position of the acetyl is now shown to be at 4 of the rhamnose moiety. In addition, a new compound ( 2 ), the desacetyl derivative of 1 , has also been isolated and identified.     

Etudes sur les composés organométalliques. Partie XXI. Contribution à l'étude de la décomposition du tétracyclohexyltitane

Studies on Organometallic Compounds. Contribution to the Study of Thermal Decomposition of Tetracyclohexyltitanium Thermal decomposition of tetracyclohexyltitanium proceeds in a different manner for the solid compound and for etheral solution. We propose an explanation of the decomposition mechanisms based on radical reactivities and compare our results with previous literature data.     

Identification des composés phénoliques dans les feuilles de Homogyne alpina,Petasites albus,Petasites hybridus et Adenostyles alliariae

Four polyphenolheterosides have been isolated from the leaves of Homogyne alpina, Petasites albus, Petasites hybridus and Adenostyles alliariae by means of thin layer and column chromatography on polyamide. Isoquercitrine (II) has been isolated from Petasites albus, Petasites hybridus and Adenostyles alliariae; Astragaline (III) from Petasites albus and Petasites hybridus; Glucoluteoline (IV) from Adenostyles alliariae and Rutine (I) from Homogyne alpina. Piceine (V) has also been isolated from Homogyne alpina.