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. 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 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 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. 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,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. 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. XXV. Etude des composés flavoniques et xanthoniques dans les feuilles de Gentiana X marcailhouana RY. Nouveaux cinnamoyl-C-glucosides flavoniques

Phytochemistry of genus Gentiana XXV: Study of the flavonic and xanthonic compounds in leaves of Gentiana X marcailhouana RY . New cinnamoyl-C-glucosyl-flavones Nine flavonic compounds: isoorientin ( 1 ), isovitexin ( 2 ), isoorientin-4′-O-β-D -glucoside ( 3 ), isovitexin-4′-O-β-D -glucoside ( 4 ), luteolin-7-O-β-D -glucoside ( 5 ), trans-cafeoyl-2′′-isoorientin ( 6 ), trans-feruloyl-2′′-isoorientin ( 7 ), trans-p-coumaroyl-2′′-isoorientin ( 8 ), p-O-β-D -glucosyl-trans-cafeoyl-2′′-isoorientin ( 9 ) and three xanthones: gentioside ( 10 ), isogentisine ( 11 ), mangiferin ( 12 ), have been identified from leaves of Gentiana X marcailhouana RY . Compounds 8 and 9 were described for the first time. The cyclitol L -(+)-bornesitol ( 13 ) has been also isolated.     

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,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.     

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.     

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 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 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. 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 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.     

Phytochemistry of genus Gentiana, XX. Identification of new di-O-glucosides of C-glucosylflavones in Gentiana asclepiadea l (author's transl)

Phytochemistry of genus Gentiana, XX. Identification of new di-O-glucosides of C-glucosylflavones in Gentiana asclepiadea L. Two new O-glucosides of C-glucoside flavonic compounds [isoorientin-2″,4′-di-O-β-D -glucoside ( 1 ) and isovitexin-2″-4′-O-β-D -glucoside ( 2 )] have been isolated from leaves of Gentiana asclepiadea L . This is the first case of di-O-glucosides of C-glucoside flavones occurring in nature.     

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.     

Triterpenoids and Iridoid Glycosides from Gentiana dahurica

One new and six known pentacyclic triterpenoids, 1 and 4 – 9 , resp., along with two new and three known iridoid glycosides, 2 and 3 , and 10 – 12 , resp., were isolated from the roots of Gentiana dahurica (‘Qin‐Jiao’). The new structures were elucidated by means of spectroscopic and chemical methods as 1β,2α,3α,24‐tetrahydroxyursa‐12,20(30)‐dien‐28‐oic acid ( 1 ), 6′‐O‐acetylgentiopicroside ( 2 ), and 3′‐acetylgentiopicroside ( 3 ). Isolated compounds were tested for their cytotoxicity against the MCF‐7 human breast cancer cell line using the MTT assay. Among them, triterpenoids 2α,3β,24‐trihydroxyurs‐12‐en‐28‐oic acid ( 6 ) and 3β,24‐dihydroxyurs‐12‐en‐28‐oic acid ( 9 ) were found to have moderate cytotoxic effects with IC₅₀ values of 20.9 and 21.7 μg/ml, respectively. Additionally, the chemotaxonomic significance of the identified secondary metabolites is briefly discussed.     

New Iridoid and Secoiridoid Glucosides from the Roots of Gentiana manshurica

One new iridoid glucoside, 4″‐O‐β‐D ‐glucosyl‐6′‐O‐(4‐O‐β‐D ‐glucosylcaffeoyl)linearoside ( 1 ), and two new secoiridoid glucosides, 6′‐O‐acetylsweroside ( 2 ) and 6′‐O‐acetyl‐3′‐O‐[3‐(β‐D ‐glucopyranosyloxy)‐2‐hydroxybenzoyl]sweroside ( 3 ), were isolated from the dried roots of Gentiana manshurica (Gentianaceae), together with 11 known ones, including one iridoid glucoside, five secoiridoid glucosides, and five triterpenes. The structures of the new compounds were determined on the basis of detailed spectroscopic analyses and acidic hydrolysis.