Flavonoid patterns and systematics in Eleusine

A survey of leaf flavonoids was conducted on Eleusine coracana ssp. coracana and ssp. africana, E. indica, E. multiflora, E. tristachya, E. floccifolia, and E. compressa. Twenty phenolic compounds were detected. Those identified were: orientin, isoorientin, vitexin, isovitexin, saponarin, violanthin, lucenin-1, and tricin. The study revealed a general generic flavonoid pattern except for E. compressa, which occupies an isolated position in Eleusine. Flavonoids of the perennial E. floccifolia and the annuals E. multiflora and E. tristachya are markedly different from those of cultivated E. coracana, suggesting that these species are only distantly related to the crop. The morphologically well defined E. coracana—africana—indica group also forms a unit in respect of flavonoids. Subspecies africana exhibits a higher flavonoid similarity to ssp. coracana (finger millet) than does E. indica. The weedy race of ssp. africana usually combines flavonoids of both the wild and domesticated subspecies. The flavonoid pattern of the dedza race of ssp.africana is identical to that of finger millet, suggesting either a direct origin of the crop from this race, or extensive introgression from the crop into ssp. africana. A lack of qualitative differences in flavonoids between cultivated races of finger millet is indicative of the genetic stability of these compounds. The flavonoid data confirms the domestication of finger millet from ssp. africana.     

Flavonoid constituents of Eupatorium odoratum

Isosakuranetin and a new chalcone, odoratin, have been isolated from the leaves of Eupatorium odoratum. The structure of odoratin has been shown to be 2′-hydroxy-4,4′,5′,6′-tetramethoxy chalcone.     

Flavonoid glycosides and sulphates from the dilleniaceae

In a leaf survey of sixty species from eight genera of the Dilleniaceae, the following flavonoids were characterized: myricetin 3,7,3′,4′-tetramethyl ether, mearnsetin 3-rhamnoside, ombuin 3,3′-disulphate, isorhamnetin 3,7,4′-trisulphate, kaempferol 3,7,4′-trisulphate and apigenin 7-galactosidesulphate.     

Flavonoid aglycones from leaf resins of two species of Heterotheca (compositae)

Twenty-nine flavonoid aglycones have been identified from two populations each of Heterotheca grandiflora and H. psammophila. Considerable qualitative variation was found between populations of the same species. Overall, H. grandiflora is more complex in its flavonoid profile, accumulating a total of 24 compounds based on eight skeletal types, compared with 13 compounds based on four skeletal types in H. psammophila.     

Comparative phytochemistry and systematics of Anacyclus

Leaf flavonoids of 13 Anacyclus taxa have been identified and compared. The most common compounds are 3-, 7- or 5-glycosylated flavonols which, together with the accumulation of 2 diosmetin 7-glycosides, help to delimitate species groups according to recent morphological and cytological findings. In addition to quercetagetin, quercetagetin 3'-methyl ether, patuletin and spinacetin have been isolated as 7-glucosides from the yellow disc and ray flowers of Anacyclus radiatus. The distribution patterns of polyacetylenes and particularly related amides, characterize different Anacyclus species and apparently contribute to a more natural interpretation of relationships with other genera, which may also be underlined by the distribution of cyanogenic glycosides.     

High pressure liquid chromatographic analysis of flavonoid chemical markers in petals from Gerbera flowers as an adjunct for cultivar and germplasm identification

Flavonoids present in petals from Gerbera flowers were resolved and quantitated by high pressure liquid chromatography (HPLC). The anthocyanins isolated from 18 cultivars, ranging in color from orange through lavender, were pelargonidin and cyanidin 3-malonylglucosides accompanied by smaller amounts of pelargonidin and cyanidin 3-glucosides. Related flavonoid copigments were apigenin and luteolin 4′-glucosides and 7-glucosides, apigenin 7-malonylglucoside, kaempferol and quercetin 3-glucosides, 4′-glucosides and 3-malonylglucosides. Both qualitative and quantitative differences in these flavonoid chemical markers distinguished cultivars with very similar colors. Malonyl esters of anthocyanins are easily degraded by HCl and conventional extraction and purification procedures were adjusted to preserve their natural state.     

Flavonol derivatives of the genus Clibadium (compositae)

The flavonoids of eleven species of Clibadium are all based on the flavonols kaempferol, quercetin and quercetagetin. Glucose and galactose sugar substitutions occur in all taxa, while rhamnosides, arabinosides, xylosides, rutinosides and diglucosides are less widely distributed. O-Methylated compounds provide the most meaningful taxonomic information and serve to divide the species into two groups. Infraspecific variation of flavonoids is commonplace. This is the first report of flavonoids in Clibadium.     

Flavonoid pigments of butterflies in the genus Melanargia

Flavonoid pigments (18) were identified in the wings and body of Melanargia galathea: tricin, tricin 7-glucoside, tricin 7-diglucoside, tricin 4′-glucoside, luteolin, luteolin 7-glucoside, luteolin 7-diglucoside, luteolin 7-triglucoside, apigenin, apigenin 7-glucoside, orientin, orientin 7-glucoside, iso-orientin, iso-orientin 7-glucoside, vitexin 7-glucoside, vitexin 7-glucoside, isovitexin, isovitexin 7-glucoside and a novel but incompletely identified tricin 4′-conjugate. Examination of the wings and bodies of individual M. galathea, M. galathea var. procida, M. lachesis, M. russiae, M. larissa, M. occitanica and M. ines butterflies from a number of different populations in Europe by 2D PC revealed that variation in their flavonoid patterns was so minor that the flavonoid pattern of these Melanargia spp. may be considered constant. The concentration of flavonoids in the wings of each butterfly was greater than that in the body, as is the covering of scales. Not all flavonoids are located in the scales; some are also located in the reproductive tissues of the female. With the exception of the tricin 4′-conjugate which was absent from the egg and first instar larvae before feeding commences, these flavonoids were present in all the life stages of M. galathea. The presence of tricin 4′-conjugate in Melanargia but its absence from the larval food plants suggests that this compound is synthesized by the insect and that flavonoids are not merely sequestered from the diet but are also partly metabolized.     

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.     

11,13-Dehydrodesacetylmatricarin and other sesquiterpene lactones from Artemisia ludoviciana var. Ludoviciana and the identity of artecanin and chyrsartemin B

11,13-Dehydrodesacetylmatricarin, achillin, parishin-C, vulgarin and artecanin were isolated from A. ludoviciana var. ludoviciana. The identity of artecanin and chrysartemin-B was confirmed and ¹³ C NMR and ¹H NMR data are described.     

Anthocyanins of the Sterculiaceae: Flavonoid scores and Hennigian phylogenetic systematics

Published results of the distribution of anthocyanins in the Sterculiaceae have been re-interpreted on the basis of the phylogenetic status of the compounds present. A flavonoid score system was less useful than a cladistic interpretation based on Hennigian arguments.     

Distribution of ent-kaurene synthetase in Helianthus annuus and Marah macrocarpus

Kaurene synthetases catalyse the biosynthesis of ent-kaurene, a precursor of the gibberellins. In 4-day-old dark- or light-grown Helianthus annuus seedlings, the cotyledons contained over 90% of the synthetase activity. The low enzyme activity in the seedling hypocotyls and roots is not a consequence of inhibitory factors in these tissues. The cotyledons not only have the highest kaurene synthetase activity, but also have the highest inhibitory activity. The differences in kaurene synthetase activities in the different tissues cannot be explained on the basis of the levels of inhibitor(s) in the extracts. The mature perennial root of Marah macrocarpus has very low kaurene synthetase activity, in contrast to the liquid endosperm of immature seeds of the same plant which is a rich source of the enzyme.     

Polyacetylenes of Artemisia vulgaris

During a re-examination of Artemisia vulgaris, a series of new acetylenic products, in addition to those previously known, was found. Trideca-1,3,5-triene-7,9,11-triyne and tetradeca-4,6-diene-8,10,12-triyne-1-ol, new compounds to the species, were fully characterized from the root extract, and heptadeca-1,7,9-triene-11,13,15- triyne, cis-dehydromatricaria ester and tetradeca-6-ene-8,10,12-triyne-3-one were found in the flowers, previously stated to contain no polyacetylenes. Three further polyacetylenes, known from related plants of the Anthemideae, were not fully characterized, but their presence was indicated.     

Flavonoid variation in Xanthisma texanum: Infrapopulation and interpopulation variation

Fourteen flavonoids were isolated from Xanthisma texanum. Chemosystematic interpretations are made concerning the origin and distribution of the infraspecific taxa of the species.     

Systematics of the genus Floridichthys

Samples representing the three nominal subspecies of Floridichthys carpio were examined electrophoretically. Although the populations in Florida could not be distinguished completely from the populations in Yucatan by morphology, 5 of the 30 electrophoretic characters demonstrated fixed differences between Florida and Yucatan populations. Based on the observed genetic differentiation between Florida and Yucatan populations and the absence of genetic differentiation within those populations, we conclude that the Yucatan population has diverged to the species level. We, therefore, propose to elevate the nominal Yucatan subspecies Floridichthys carpio polyommus to a species status.     

The intracellular distribution of tocopherols in Calendula officinalis leaves

From Calendula officinalis leaves, five cellular subtractions (chloroplasts, mitochondria, Golgi membranes, microsomes and cytosol) were obtained and their purity was checked. The contents of α-,γ- and δ-tocopherols were determined in these fractions. There were no tocopherols in Golgi membranes and cytosol. γ-Tocopherol and δ-tocopherol were found in the chloroplasts, mitochondria and microsomes, whereas α-tocopherol was present only in the chloroplasts.     

Notes on African species of the genus Anisopappus Hook. & Arn. (Asteraceae)

Two new species of the genus Anisopappus Hook. & Arn. (Asteraceae) are described A. athanasioides Paiva & Ortiz, from Angola, and A. pseudopinnatifidus Ortiz & Paiva, from Namibia. The morphological variability of the A. chinensia-A. africanus complex is studied and two new combinations are proposed: A. chinensis subsp. africanus (Hook. fil.) Ortiz & Paiva and A. chinensis subsp. lobatus (Wild) Ortiz & Paiva.     

Five mikanolide derivatives from mikania cynanchifolia and their biogenetic relationships

The investigation of the aerial parts of Mikania cynanchifolia afforded, in addition to miscandenin, five new sesquiterpene lactones, miscandenin-1,2-epoxide, an isomiscandenin and three further dilactones related to mikanolide. The structures of these new compounds were elucidated by high field ¹H NMR spectroscopy. The biogenetic relationships of the sesquiterpene lactones are briefly discussed.     

Notes on African species of the genus Anisopappus Hook. & Arn. (Asteraceae)

Two new species of the genus Anisopappus Hook. & Arn. (Asteraceae) are described: A. athanasioides Paiva & Ortiz, from Angola, and A. pseudopinnaididus Ortiz & Paiva, from Namibia. The morphological variability of the A. chinensis-A. africanus complex is studied and two new combinations are proposed: A. chinensis subsp. africanus (Hook, fil.) Ortiz & Paiva and A. chinensis subsp. lobatus (Wild) Ortiz & Paiva.