A biogeographical analysis of Muhlenbergia (Poaceae: Chloridoideae: Cynodonteae: Muhlenbergiinae)

A phylogeny based on the analysis of six DNA sequence markers (ITS, ndhA intron, rpl32-trnL, rps3, rps16 intron, and rps16-trnK) is used to infer ancestral areas and divergence times, and reconstruct the biogeographical history and evolution of 150 of the 183 (82%) species of Muhlenbergia. Our results suggest that the genus originated 9.3 mya in the Sierra Madre (Occidental and Oriental) in Mexico, splitting into six lineages: M. ramulosa diverging 8.2 mya, M. subg. Muhlenbergia at 5.9 mya, M. subg. Pseudosporobolus at 5.9 mya, M. subg. Clomena at 5.4 mya, M. subg. Bealia at 4.3 mya, and M. subg. Trichochloa at 1 mya, each of these with a high probability of Sierra Madrean origin. Our results further suggest that founder-event speciation from Sierra Madre to South America occurred independently multiple times in all five subgenera during the Pleistocene and late Pliocene. One long-distance dispersal event most likely originating from Central or Eastern North America to East and Central Asia occurred 1.6–1 mya in M. subg. Muhlenbergia. In our cladogram, members of M. subg. Trichochloa show little genetic resolution, suggesting very low levels of divergence among the species, and this may be a consequence of rapid radiation.     

Flavonoid variation in Melampodium

Five species of Melampodium have been studied for their flavonoid components. Melampodium aureum, M. divaricatum and M. longipilum exhibited simple arrays of kaempferol and quercetin 3-O-mono-and diglycosides. Melampodium bibracteatum afforded the same simple glycosides plus quercetagetin 3-methyl ether. Melampodium americanum had the most complex pattern with simple flavonol glycosides being accompanied by five O-methylated derivatives of quercetagetin plus 6-hydroxykaempferol 3-methyl ether. Three populations of M. bibracteatum gave identical flavonoid profiles as did 15 collections of M. bibracteatum.     

External flavonoid aglycones of Viguiera series Viguiera (asteraceae: heliantheae)

Distribution of external flavonoid aglycones supports other data to suggest that Viguiera series Viguiera (series Dentatae Blake) is a mixed taxonomic grouping. Two species, V. dentata and V. potosina, lack external flavonoid aglycones, whereas the remaining species of the series all produce external flavonoid aglycones and appear to form a natural taxonomic group. The latter group, which consists of species from Baja California and nearby xeric areas, exhibits a diversity of flavonoid types, with different diploid species variously producing flavonols, simple flavones, 6-methoxyflavones, 6-hydroxy,7-methoxyflavones and a chalkone as major compounds. Polyploid species exhibit combinations of flavonoid types from possible diploid ancestors. Compounds of the 6-hydroxy,7-methoxyflavone type appear to characterize the group of species from Baja California and nearby areas within Viguiera.     

Flavonoids of five Hieracium species of British Columbia

Five Hieracium species were examined for flavonoid constituents: H. albertinum, H. albiflorum, H. cynoglossoides, H. gracile and H. umbellatum. The major compounds present in all species were mono- and diglycosides, of apigenin and luteolin. Chrysoeriol occurred per se in several species. Quercetin-3-O-glucoside was seen only in H. umbellatum. Species specific patterns of flavonoid glycosides were evident in all five taxa; H. albertinum and H. cynoglossoides showed the greatest similarity which reflects their morphological similarity. Limited examination of artificial hybrids showed additivity of flavonoid glycoside patterns.     

Les relations entre les prairies du Triseto-Polygonion et les mégaphorbiaies de l''Adenostylion: l''analyse flavonique d''espèces communes aux deux groupements

Relationships between two plant communities in the south-western Alps, high-altitude manured meadows (Triseto-Polygonion) and lower tall grass prairies (Adenostylion) have been examined by means of the flavonoid analysis of specimens belonging to six species common to those two associations. The species, collected at eight stations of the Ligurian Alps and the Ubaye valley, are: Trollius europaeus (Ranunculaceae), Chaerophyllum aureum (Umbellifereae), Silene cucubalus (Caryophyllaceae), Polygonum bistorta) (Polygonaceae), Alchemilla vulgaris (Rosaceae) and Centaurea montana (Compositae). In every species, factorial analysis of correspondence was applied to the distribution of flavonoid glycosides. This led to the partition of the populations into two groups according to the two sectors (Ligurian Alphs Ubaye valley) of the collection area. Secondly, populations of two species, Alchemilla vulgaris and Centaurea montana, exhibited further correlation of their flavonoid pattern with their phytosociological origin.     

Flavonoids of Helianthus series Microcephali

Ray flower and leaf flavonoids were investigated for the three species of Helianthus series Microcephali. Ray flowers of all species contain coreopsin, sulphurein, and quercetin 7-O-glucoside; those of H. microcephalus also contain quercetin 3-O-glucoside. A mixture of flavonoid aglycones, mostly methoxylated flavones, occurs in leaves of H. microcephalus, but not in H. glaucophyllus or H. laevigatus which also lack the glandular trichomes that in Helianthus are typically associated with flavonoid aglycones. The presence of compounds with the 6,8,4′ pattern of methoxylation in H. microcephalus suggests that the series is more similar in flavonoids to series Angustifolii than to series Corona-solis.     

Biosystematics of the monocotyledoneae—flavonoid patterns in leaves of the liliaceae

In a leaf survey of 168 species of the Liliaceae, most of the major flavonoid classes were found to be represented in the family. Flavonols occurred most frequently: quercetin and kaempferol were detected in 40% and 42% of the sample respectively, while the flavones luteolin and apigenin were present in only 24% and 20% of the sample. Methylated derivatives, i.e. isorhamnetin, diosmetin and tricin were rare. Procyanidins were present in 17 species, flavonoid sulphates in only one species and flavone C-glycosides in only three species. Anthraquinone pigments were identified in species of Aloe Asphodeline and Asphodelus. Three new flavonoid glycosides were characterised during the course of the survey: diosmetin 7-diglucoside in Colchicum byzanthinum and tricin 7-fructosylglucoside and tricin 7-rutinoside-4′-glucoside in Hyacinthus orientalis cv. ‘Quean of the Pinks’. On the basis of the flavonoid survey, the subfamilies of the Liliaceae may be grouped into those containing flavonols only, those with flavones only or those having both flavonols and flavones. Members of the related families: Amaryllidaceae (17 species), Agavaceae (1 species) and Xanthorrhoeaceae (1 species) contained only flavonols. The subfamilies Scilloideae, Asphodeloideae and Melanthioideae show the most chemical variation whilst the Wurmbaeoideae and Lilioideae are the most homogeneous groups. The tribe Scilleae is unusual in that both flavone- and flavonol-containing genera occur and a wide variety of flavonoid types are represented. A comparison of the leaf flavonoids of the Liliaceae with those found in families related to the grasses showed that all except two classes of flavonoid compound (5-methylated flavones and 5-deoxyflavonoids) found in the Juncaceae. Cyperaceae, Palmae and Gramineae are present in the Liliaceae thus supporting the view that all four families could have arisen from Liliaceae-like ancestors.     

Flavonoids of the Muhlenbergia montana complex

Specimens from natural populations of Muhlenbergia montana (Nutt.) Hitch. and related species were analysed for their flavonoid content. Twenty-four flavonoids from 14 species were separated and 22 of the compounds identified. Most were glycosylated derivatives of luteolin, apigenin and tricin. Two flavonols, quercetin 3-O-rutinoside and quercetin 3-O-glycoside, and two flavanones were also identified. Flavonoid patterns were distinct for all perennial species and identical for the two annual species examined. Phenetic analysis of the flavonoid characters does not support the inclusion of the annual species M. crispiseta and M. peruviana as part of the M. montana complex.     

Flavonoid distribution patterns in Leucanthemum and related species from North Africa

Flavonoid data is reported for 16 species including eight species of Leucanthemum from North Africa, four from Europe and related species in the Chrysanthemum-Leucanthemum complex. Flavonols, especially quercetin, isorhaamnetin, kaempferol, patuletin and spinacetin, are predominant in the North African species. Flavones, which are common in Leucanthemum species in Europe, are of very rare occurrence in the North African species. The relationship of the species based on the distribution of flavonoid glycosides and aglycones from the ray florets is discussed.     

Flavonoids of Astilbe and Rodgersia compared to Aruncus

The flavonoid profiles of Astilbe (four taxa studied) and Rodgersia (two taxa studied) are based on simple flavonol glycosides. Astilbe has 3-O-mono-, 3-O-di-, and 3-O-triglycosides of kaempferol, quercetin, and myricetin, while Rodgersia has only mono- and diglycosides of kaempferol and quercetin. Astilbe×arendsii was also shown to accumulate dihydrochalcone glycosides. The flavonoid profile of Rodgersia is the simplest recorded so far in the herbaceous Saxifragaceae. The flavonoids of two species of Aruncus were shown to be based upon kaempferol and quercetin 3-O-mono- and 3-O-diglycosides. One of the species also exhibited an eriodictyol glycoside. The triglycoside differences were not considered important, but the differences in myricetin occurrences were taken as evidence against derivation of Saxifragaceae from an Aruncus-like ancestor. Should such an event be proposed, however, serious consideration would have to be given to the current pattern of myricetin occurrence in the two families.     

Flavonoid diversity and geographic endemism in Parthenium

The distribution of 34 flavonoids detected in the North American species of Parthenium indicates that flavonoid diversity and structural types are correlated with biological aspects of different species types. Widespread species occurring in a variety of habitat types are characterized by greater numbers of flavonoids, primarily as the result of flavonoid glycoside diversity; while species which are geographically isolated in limestone or gypsum habitats are characterized by a tendency to depauperate flavonoid patterns with major methylated aglycone components. The possibility that glycosylation is related to self-detoxification and preservation of toxic phenolic potential is discussed. It is shown that parallel chemical adaptations, similar to the well-known parallel morphological adaptations of unrelated species which coexist in certain habitats, may occur     

Flavonoid similarities among five species of Isocoma

The flavonoid profiles of the leaf resins from Isocoma veneta, I. tenuisecta, I. acradenia, I. drummondii, and I. eremophila were identified by TLC co-chromatography with authentic samples. Thirty flavonoid aglycones were identified, most of which are methylated, based on apigenin, luteolin, kaempferol, quercetin, scutellarein (I. veneta)only, and 6-OH-kaempferol (I. tenuisectaonly). Cluster analyses were performed using Jaccard similarities of both presence/absence data and of biosynthetic step indices. The latter method yielded consistently higher similarity coefficients and is believed to be a truer indication of the chemical similarities among Isocoma species.     

Flavonoids and the systematics of Luffa

Flavonoids were characterized from leaves and flowers of six species of Luffa. Each species had a distinct flavonoid pattern. Based on leaf flavonoids, Luffa is separable into two groups of species: L. graveolens and L. operculata contain only flavonols. L. acutangula, L. aergyptiaca, L. echinata and L. forskalii contain only flavones. Flavonoid data indicate that the New World disjunct species. L. operculata, is most closely related to L. graveolens.     

Flavonoids of Agastache section Agastache

Flavonoids were characterized from the leaves, stems and inflorescences of eight species of labiates of section Agastache. Within the North American species of the section, there is a trend of reduction in number of compounds from the western to the eastern United States species. Asian Agastache rugosa has a flavonoid profile identical to that found in the western North American species.     

Flavonoids of Helianthus series Angustifolii

Leaf and ray flower flavonoids were investigated for the seven species of Helianthus series Angustifolii. Flavone aglycones occur in small glandular trichomes located on leaf undersurfaces of H. angustifolius, H. floridanus and H. simulans. Other species lacked both glandular trichomes and flavone aglycones. Flavonol glycosides occur in low concentrations in leaves of all species but were not characterized. Anthochlors (chalkones) occur in leaves of H. heterophyllus and H. longifolius. Ray flower flavonoids include anthochlor and flavonol glycosides and occur in the basal region of the ligule producing a band of UV A around the head. Anthochlors are the predominant ray flower flavonoids in H. angustifolius, H. heterophyllus and H. longifolius, whereas they are absent and quercetin 7-glucoside is present in H. carnosus and H. floridanus. Cladistic analysis of flavonoid and morphological characters indicates that evolution in the series has been a radiation from ancestral types rather than a linear sequence of progressively more derived species.     

Flavonoid data and populational observations in support of hybrid status for Populus acuminata

Flavonoid distribution and populational composition at the collection sites of several samples of Populus acuminata strongly suggest that this taxon is an inter-sectional hybrid between P. angustifolia, sect. Tacamahaca and any one of two or three different species of the section Aigeiros, when the entire range is considered. In the vicinity of the type locality, the Aigeiros parent is P. sargentii. Within any population, foliage of trees of P. acuminata is characterized by morphological intermediacy and an essentially additive flavonoid profile, as compared to the two parental taxa present. In habit the trees resemble those of P. sargentii, and habitats at the collection sites were found to be somewhat intermediate. Fifteen flavonoid compounds were consistently present in samples of the putative hybrid. Twelve of these had diagnostic value because they were absent in one of the parental species. One compound, apigenin 7-O-diglucoside, was found only in P. acuminata. In part, our identifications correspond to compounds reported by Crawford in a morphological and chemical study of P. acuminiata.     

Foliar flavonoid aglycones of Phoebanthus

The diploid Phoebanthus tenuifolius and the tetraploid P. grandiflorus yielded identical complements of foliar flavonoid aglycones, including the compounds nepetin, jaceosidin, and hymenoxin. Flavonoid data do not resolve the origin of the tetraploid species. The similarity between the flavonoids of Phoebanthus and those earlier reported for Helianthus would support a merger of the two genera.     

Myricetin in Tagetes: Chemosystematic significance

Myricetin 3- and 7-glucosides, as well as other flavonoid glycosides were identified in four species of Tagetes. The presence of myricetin glucosides in Asteraceae is reported for the first time. Some chemosystematic and evolutionary implications are discussed.     

Anthochlors and other flavonoids as honey guides in the compositae

Anthochlor pigments have been recorded for the first time in three species of Helianthus and in Viguiera laciniata. Yellow flavonols based on quercetagetin or gossypetin have been found in yellow flowered species of Eriophyllum and Geraea. In Eriophyllum, all seven species studied contain quercetagetin and/or patuletin 7-glucosides. In those species containing UV honey guides, either yellow flavonoid or colourless quercetin glycosides can be responsible for producing strongly UV absorbent zones on the flowers. Thus in Helianthus, honey guides in some species result from UV absorbance by the chalcone coreopsin and the aurone sulphurein, whilst in H. annuus they result from absorbance by quercetin 3- and 7-glucosides. Furthermore, the occurrence of yellow flavonoids in flowers is not directly correlated with the presence of UV nectar guides. A detailed study of the distribution of chalcone in Coreopsis bigelovii flowers revealed that the anthochlor was present in epidermal cells on both upper and lower surfaces.     

Flavonoids in the leaves of Thymus: a chemotaxonomic survey

The flavonoid aglycone analysis of 20 Thymus taxa (most Iberic or Balearic endemics) shows the presence of luteolin, apigenin, acacetin, genkwanin, 6-hydroxyluteolin, xanthomicrol, cirsimaritin; four partially identified flavones, of which three are 6-OR-substituted and one flavonol. The differences observed between T. capitatus (L.) Hoffmanns. et Link (subgenus Coridothymus (Reichenb. fil.) Borbás) and the other species belonging to the subgenus Thymus (L.) Jalas, seem enough to maintain the separation of the two groups, but within the same genus, as proposed in Flora Europaea.