Flavonol derivatives of Desmanthodium (compositae)

The flavonoids of three species of Desmanthodium are based upon kaempferol, quercetin and quercetagetin. Sugar substitutions comprise glucosides, galactosides, rhamnosides, rutinosides and diglucosides. Four different O-methylated compounds occur in field populations of the genus, but they are found in all species and are therefore not useful for sectional or subgeneric delimitations. The flavonoid profile of Desmanthodium is very similar to that of Clibadium, which parallels their close morphological affinity.     

Revision of the genus Clibadium (Asteraceae, Heliantheae)

Clibadium L. (Asteraceae, Heliantheae) is a genus of 29 species distributed throughout latin America, from Mexico to Peru, and in the West Indies, with high numbers of species in Costa Rica, Colombia, and Ecuador.Clibadium includes shrubs and small trees; usually with loosely aggregated capitula; herbaceous phyllaries arranged in 1–5 series; receptacles usually paleaceous throughout; corollas of pistillate florets 2–4-lobed; corollas of the staminate florets 4–5-lobed; purple to black anthers; and chromosome numbers alln=16. Two sections of species previously recognized are here considered as subgenera (subg.Paleata and subg.Clibadium) containing two and four sections, respectively.Clibadium subg.Paleata contains five species distributed in sects.Eggersia (3 spp.) andTrixidium (2 spp.), and subg.Clibadium has 24 species distributed among sects.Clibadium (6 spp.),Glomerata (9 spp.),Grandifolia (5 spp.), andOswalda (4 spp.).     

Further studies of flavonols of Clibadium (compositae)

The flavonoids of an additional eight species of Clibadium have been determined. The compounds are derivatives of kaempferol, quercetin and quercetagetin. O-Methylated quercetagetin derivatives were found in several taxa with the possibility that 6-methoxykaempferol may also exist in one collection. Kaempferol and quercetin exist as 3-O-glucosides, galactosides, rhamnosides, rutinosides and diglucosides although not all glycosides occur in each taxon. Quercetagetin derivatives occur as 7-O-glucosides. Observations on these newly investigated species confirm previous work in the genus that three types of flavonoid profiles exist: (1) kaempferol and quercetin 3-glycosides; (2) kaempferol and quercetin 3-glycosides plus quercetagetin 7-glucoside; and (3) kaempferol and quercetin 3-glycosides plus quercetagetin 7-glucoside and O-methylated derivatives of quercetagetin.     

Chromosome counts in Clibadium (Compositae,Heliantheae) from Latin America

New meiotic chromosome counts are reported from 86 populations from Mexico to Ecuador of 13 species ofClibadium (Compositae, Heliantheae). These, plus previous reports, yield a total of 120 counts from 20 of the approximately 39 species recognized in the genus (Arriagada, in prep.). All counts aren=16 with a few fragments or B-chromosomes observed sporadically in some populations. One population, containing what appear morphologically to be interspecific hybrids betweenC. mexiae andC. microcephalum, showed one tetravalent and fragments. Species in both historical sections (Clibadium andTrixidium, created by Candolle and maintained by Schulz) and from the five sections to be proposed in a new classification of the genus (Arriagada, in prep.) have now been counted. The uniformity of chromosome numbers withinClibadium is correlated with observed allopatric distribution of closely related taxa.     

Sesquiterpenoid and acetylenic constituents of seven Clibadium species

The investigation of seven Clibadium species resulted in the isolation of a new germacrolide from C. surinamense, trans-β-bergamotene, a new sesquiterpene from C. asperum and a new C-17 acetylenic alcohol from C. glomeratum. Five known acetylenic compounds were present in some members of the genus. In good agreement with morphological data, the presence of ichthyothereol and its acetate in several members of Clibadium suggest affiliation with the genus Ichthyothere within the subtribe Milleriinae (Heliantheae-Compositae).     

Flavonoid diversification in the polemoniaceae

Analysis of species representing most sections of all the genera in the family Polemoniaceae showed a range of variation in flavonoids comparable to variation already documented for gross morphological features, karyotypes and pollen grains. Three main groups of flavonoids predominate: (A) common flavonols (kaempferol, quercetin, myricetin); (B) 6-methoxyflavonols (patuletin, eupalitin, eupatolitin); and (C) C-glycosylflavones (apigenin and luteolin based). Cobaea, Loeselia], Polemonium, Allophyllum, Collomia and Gymnosteris have predominantly Group A flavonoids; Bonplandia, Ipomopsis and Eriastrum have predominantly Group B flavonoids; Phlox, Microsteris and Leptodactylon have predominantly Group C flavonoids; while the remaining genera (Cantua, Huthia, Gilia, Langloisia, Navarretia and Linanthus) either have flavonoids of all three groups, or some species within a genus have flavonoids of one group, while other species have flavonoids of another group. Linanthus, Gilia and Navarretia (3 of the larger genera in the family) show great flavonoid diversity, while Langloisia (4 species) has 2 species with Group A flavonoids and the other two species have Group B pigments. Two rare hydroxycoumarins, one being daphnetin, were detected in five genera but they proved to be only of limited systematic interest.     

Foliar flavonoids of North American Solanum section Solanum

A total of ten flavonoids, all flavonols, were isolated from leaves of eleven species of Solanum sect. Solanum. Most species had relatively few compounds, primarily quercetin 3-O-glycosides. Little intraspecific variation in flavonoids was observed, except in S. americanum were it correlated with previously recognized races. Flavonoid data are of little help in determining ancestries of polyploid species, but do rule out S. sarrachoides as a progenitor of S. villosum and S. nigrum. Solanum sarrachoides is unique among species examined in having free flavonoid aglycones as well as extensive 3-O-methoxylation.     

Flavonoids of the Chenopodium L. genus of world flora

Data on the composition of flavonoids in the Chenopodium L. species of world flora and the available information on their biological activity are given. The main flavonoids of fat-hens are 3-O-glycosides of caempferol, quercetin, and isoramnetin. Flavones are characteristic of some species. The Chenopodoum species are also characteristic of some species. The Chenopodium spp. are interesting as a source of raw material containing flavonoids.     

Flavonoids and the chemotaxonomy of three Sophora species

Sophora microphylla, S. prostrata and S. tetraptera are distinguishable from one another by their leaf flavonoids. S. microphylla is distinguished by the present of rhamnosylvitexin and rhamnosylisovitexin and S. tetraptera by the presence of apigenin-7-O-rhamnosylglucoside-4′-O-glucoside and the 7-O-glucosides of apigenin, 7,4′-dihydroxyflavone, luteolin and 7,3′,4′-trihydroxyflavone. Sophora prostrata lacks all these flavonoids, but has several pigments which are common to all three species.     

Ecological considerations of amino acids and flavonoids in Sarracenia species

Leaf extracts of 43 plants representing all 10 species of the genus Sarracenia were analyzed by 2D-PC, high voltage electrophoresis and G. C., for their amino acids and flavonoids. All species contained only low concentrations of common amino acids and common flavonoids. The taxonomic and ecological significance of these results are discussed.     

Leaf flavonoid chemistry of Coreopsis (Compositae) section Palmatae

Examination of leaf flavonoids of all taxa ofCoreopsis sectionPalmatae revealed that most members synthesize an array of common flavone (mostly luteolin and apigenin) glycosides. Each diploid species or diploid member of a species is characterized by a particular ensemble of compounds. These taxa includeC. major, C. verticillata, C. pulchra, C. palmata, andC. tripteris. The latter species differs from all other taxa in producing flavonol (kaempferol and quercetin) glycosides and what appear to be 6-oxygenated compounds. Tetraploids ofC. verticillata exhibit the same flavonoids as diploid members of the species, thus flavonoid chemistry supports the hypothesis that they originated from diploids within the species. Certain populations of hexaploid and octoploidC. major are similar chemically to diploids, suggesting they also originated as intraspeciflc polyploids. Other populations of these polyploids exhibit a flavonoid profile which differs from the profile of the diploids, and this profile is nearly identical to the octoploidCoreopsis × delphinifolia. The latter taxon has been viewed by Smith (1976) and Mueller (1974) as an interspecific hybrid betweenC. verticillata andC. major and/orC. tripteris. Species-specific compounds from the former species occur inC. × delphinifolia but no compounds unique to either of the latter two species are discernable. Flavonoid chemistry is not useful in ascertaining whether either or both species have been involved withC. verticillata in producing plants referable toC. × delphinifolia. There is morphological intergradation between octoploidC. major andC. × delphinifolia, and all plants not appearing to be “pure”C. major exhibit a flavonoid chemistry likeC. × delphinifolia. All plants of sectionPalmatae considered to be alloploids (includingC. × delphinifolia) produce the same array of leaf flavonoids, including several “novel” compounds not expressed in the putative parental taxa. Two of the “novel” flavonoids are present in the geographically restricted diploidC. pulchra. The systematic and phylogentic significance of this is not readily apparent.     

Chemosystematic aspects of flavonoid distribution in twenty-two taxa of Helenium

Distributional data for 12 flavonoids in twenty-two taxa of Helenium are presented. Flavonoids identified to date are all flavones based on luteolin and apigenin. Chemosystematic interpretations are made concerning several species and species groups.     

Flavonoid variation in the genus briza

During a survey of 6 Eurasian and 10 South American Briza species for leaf flavonoids, 27 components were found. Twelve of these were identified: tricin 5-glucoside, tricin 7-glucoside, quercetin 3-glucoside, kaempferol 3-glucoside, vitexin, isovitexin, orientin, iso-orientin, and the 4′-O-glucoside of all 4 glycoflavones, 3 of which are reported for the first time. The Eurasian species, with the exception of Briza maxima, are remarkably uniform in their flavonoid pattern, accumulating mainly vitexin and isovitexin; whereas the South American species are characterized by the presence of orientin, iso-orientin and 9 unidentified flavonoids. In Briza media and the South American species, ploidy level is shown to play a large part in flavonoid variation. Examination of 12 diploid and 8 autotetraploid plants of B. media revealed that diploids accumulate vitexin and isovitexin, whereas tetraploids accumulate orientin and iso-orientin, autotetraploidy having apparently upset regulatory genes in the formation of the flavone C-glycosides. Mild alkaline treatment of both isovitexin and iso-orientin was found to give 100% conversion to the corresponding 8-C-glucoside.     

Phenolics from the culms of five bamboo species in the Tangjiahe and Wolong Giant Panda Reserves,Sichuan, China

Phenolic compounds were studied in the culms of five bamboo species collected in China: Yushania chungii, Fargesia robusta, Fargesia denudata, Fargesia rufa and Fargesia scabrida. All the species are eaten by giant panda (Ailuropoda melanoleuca). The culms contained phenolic acids and flavonoids in small concentrations, except for F. robusta, which did not contain flavonoids in detectable amounts. The species differed from each other in their phenolic composition. For example, F. rufa with the highest number of compounds clearly differed from other species. There were also differences among sampling sites, which reflect the differences among genotypes. Furthermore, there were clear ontogenetic differences in the culms: some compounds were present in mature culms but not in young (1–2 year old) culms, while the concentrations of other compounds decreased with increasing age. Over all, the composition and concentrations of soluble phenolic compounds in the bamboo culms were affected by species, age and site.     

The application of multiplex fluorimetric sensor for the analysis of flavonoids content in the medicinal herbs family Asteraceae,Lamiaceae, Rosaceae

Background

The aim of our research work was to quantify total flavonoid contents in the leaves of 13 plant species family Asteraceae, 8 representatives of family Lamiaceae and 9 plant species belonging to family Rosaceae, using the multiplex fluorimetric sensor. Fluorescence was measured using optical fluorescence apparatus Multiplex(R) 3 (Force-A, France) for non-destructive flavonoids estimation. The content of total flavonoids was estimated by FLAV index (expressed in relative units), that is deduced from flavonoids UV absorbing properties.

Results

Among observed plant species, the highest amount of total flavonoids has been found in leaves of Helianthus multiflorus (1.65 RU) and Echinops ritro (1.27 RU), Rudbeckia fulgida (1.13 RU) belonging to the family Asteraceae. Lowest flavonoid content has been observed in the leaves of marigold (Calendula officinalis) (0.14 RU) also belonging to family Asteraceae. The highest content of flavonoids among experimental plants of family Rosaceae has been estimated in the leaves of Rosa canina (1.18 RU) and among plant species of family Lamiaceae in the leaves of Coleus blumei (0.90 RU).

Conclusions

This research work was done as pre-screening of flavonoids content in the leaves of plant species belonging to family Asteraceae, Lamiaceae and Rosaceae. Results indicated that statistically significant differences (P > 0.05) in flavonoids content were observed not only between families, but also among individual plant species within one family.     

Flavonoid and anthocyanin patterns and the systematic relationships in Collomia

Analyses of extracts among populations of the 14 species of Collomia revealed the occurrence of 13 mono-, di- and triglycosides based on the flavonoids, acacetin, kaempferol, patuletin and quercetin. The glycosides included those having arabinose, galactose, glucose and rhamnose as mono-, bio- or triosides at the 3-, 5-, 3,7- or 7-position. Analyses of floral extracts from ten species revealed the occurrence of two anthocyanins, cyanidin and delphinidin 3-(p-coumarylglucosyl)-5-glucoside. Nearly all the species express distinctive flavonoid patterns, although the differences are based on relatively minor changes in position or type of glycosidic substitution. Use of the minimum biosynthetic step distance (MBSD), an index of similarity, revealed that a mean of 5.6 steps separated the 14 species. The four perennial species of section Collomiastrum showed a high degree of similarity and differed consistently from species of the two annual sections Courtoisia and Collomia by lacking quercetin-5-glucoside and kaempferol-3-arabinosylgalactoside. In contrast, flavonoid patterns among species within sections Courtoisia and Collomia showed a relatively low degree of similarity. The dissimilarity between C. diversifolia and C. heterophylla (section Courtoisia) is consistent with their divergent patterns of pollen morphology and ecological distribution. Three groups of species within section Collomia were defined generally by shared patterns of flavonoids, which are correlated to some degree with floral, pollen and vegetative morphology.     

Flower pigment composition of Crocus species and cultivars used for a chemotaxonomic investigation

A survey of floral anthocyanins and other flavonoids by analytical high-performance liquid chromatography (HPLC) was performed among 70 species and subspecies, 43 cultivars and six artificial hybrids of Crocus and the results were compared with taxonomical delimitations established by Mathew (The Crocus. B.T. Batsford Ltd, London, 1982).Nine anthocyanins were detected. The Crocus species and cultivars were placed into seven chemotypes according to their contents of 3,7-di-O-, 3,5-di-O-glucosides or 3-O-rutinosides of delphinidin and petunidin and to the presence of 3,7-di-O-malonyl-glucosides of petunidin and malvidin and delphinidin 3-O-glucoside-5-O-malonylglucoside. These malonated anthocyanins have only been found in Crocus and may be characteristic for this genus.The same 18 flavonoids were detected in every taxon. However, quantitative differences were noted and four chemotypes of Crocus were defined by their major contents of flavonoids. Six of the flavonoids appear to be unique for Crocus.The anthocyanin/flavonoid patterns of some of the taxa provide a valuable supplement to the taxonomy based on morphological and cytological patterns. Most chemotypes were represented in several series but the chemical data were useful in distinguishing different species. For all series except Series h the chemical data were very similar for all subspecies or accessions within a species, and chemotypes within a series were more similar than between series. However for six species, the analyses suggest that they should be further investigated using other methods, to evaluate their relations to other series.     

The distribution of flavonoids in chloroplasts of twenty five species of vascular plants

A survey was made of the major flavonoids in whole leaf extracts and in chloroplast preparations from twenty five species of vascular plants including Anthophyta (20), Coniferophyta (1), Ginkophyta (1), Pterophyta (2), and Arthrophyta (1). The chloroplasts variously contained derivatives of flavones, C-glycosylflavones, flavonols, flavanones, isoflavones, 3-deoxyanthocyanidins, and anthocyanins. Twenty three species contain one or more flavonoids in isolated chloroplast, usually in a pattern quite similar to that found in whole-leaf extracts but occasionally showing enrichment of one or more flavonoids in the chloroplasts. Flavonoids are apparently absent from chloroplasts of Phaseolus aureus and Morus alba although whole-leaf extracts of these species are rich in quercetin derivatives.     

Ueber den abbau von polyphenolen durch pilze der gattung Fusarium

The ability of 16 Fusarium species to degrade polyphenols was investigated. Phenols, benzoic acids, cinnamic acids, flavonoids and isoflavones are efficiently catabolized by all strains investigated. o-coumaric acid is transformed into 4-hydroxycoumarin by 7 species. A pronounced capability for methyl ether cleavage is demonstrated by stepwise o-demethylation of veratric acid and 5,7,4′-trimethoxyisoflavone. The latter compound is degraded via the sequence: 5,7,4′-trimethoxyisoflavone → 5,4′-dimethoxy-7-hydroxyisoflavone → biochanin A → genistein → orobol → ring fission products.     

Chemical constituents from the stems of Tripterygium regelii

Phytochemical investigation on the stems of Tripterygium regelii resulted in the isolation of fourteen compounds, including six flavonoids (1–6), seven lignans (7–13), and one cyanogenic glycoside (14). This is the first report of the four dimeric flavonoids bis-8, 8′-catechinylmethane (2), bis (8-epicatechinyl) methane (3), bis-6, 8′-catechinylmethane (4) and montahomobisflavan B (5) from a species of Tripterygium. Previously, these dimeric flavonoids have been mainly identified from species of gymnosperms. This research has shown that the main secondary metabolisms identified in T. regelii were flavonoids and lignans. These data enable this species to be differentiated from T. wilfordii and T. hypoglaucum that contain the triptolide-resembling diterpenoids.