Chemodiversity of exudate flavonoids in seven tribes of Cichorioideae and Asteroideae (Asteraceae)

Members of several genera of Asteraceae, belonging to the tribes Mutisieae, Cardueae, Lactuceae (all subfamily Cichorioideae), and of Astereae, Senecioneae, Helenieae and Heliantheae (all subfamily Asteroideae) have been analyzed for chemodiversity of their exudate flavonoid profiles. The majority of structures found were flavones and flavonols, sometimes with 6- and/or 8-substitution, and with a varying degree of oxidation and methylation. Flavanones were observed in exudates of some genera, and, in some cases, also flavonol- and flavone glycosides were detected. This was mostly the case when exudates were poor both in yield and chemical complexity. Structurally diverse profiles are found particularly within Astereae and Heliantheae. The tribes in the subfamily Cichorioideae exhibited less complex flavonoid profiles. Current results are compared to literature data, and botanical information is included on the studied taxa.     

FLAVONOIDS OF THE PRIMITIVE FERNS: STROMATOPTERIS,SCHIZAEA, GLEICHENIA,HYMENOPHYLLUM, AND CARDIOMANES

The flavonoids of the primitive leptosporangiate ferns Stromatopteris moniliformis, Schizaea bifida, Gleichenia cunninghamii, Cardiomanes reniforme, and Hymenophyllum demissum have been identified as 3-O-glycosides of the flavonols kaempferol and quercetin. None of the examined ferns produced flavonoids which are also common to the Psilotoceae. The Psilotaceae have previously been shown to produce O-glycosides of amentoflavone (biflavone) and apigenin (flavone) and traces of C-glycosylflavones (Wallace and Markham, 1978). These data imply that the primitive leptosporangiate ferns are not closely related to the Psilotaceae. The antiquity of rhamnose as a glycosyl moiety is suggested by its occurrence in both the primitive leptosporangiate ferns and in the Psilotaceae.     

Chemotaxonomy of the Hymenophyllaceae. II. C-GLYCOSYLFLAVONES AND FLAVONE-O-GLYCOSIDES OF TRICHOMANES S.L.

An analysis of 23 species of Trichomanes s. 1. indicates that the presence of C-glycosylflavones, especially mono-C-glycosylflavones, may be a basic characteristic for this genus. Except for the morphologically unique Cardiomanes reniforme, this feature appears to delimit the species of Trichomanes s. 1. from those of Hymenophyllum s. 1. Several species, primarily those classified within Didymoglossum (according to both Copeland and Morton), synthesize flavone-O-glycosides in addition to their C-glycosylflavone profiles. Two species, T. birmanicum and T. radicans, appear to be unique in synthesizing the di-C-glycosylflavones violanthin and isoviolanthin; five species (T. collariatum, T. scandins, T. birmanicum, T. bicorne, and T. alatum) appear to synthesize di-C-glycosylflavones but lack mono-C-glycosylflavones. Based on this and other studies, it may be appropriate to consider these C-glycosylflavone-producing plants as representing primitive leptosporangiate stock.     

TRIBAL INTERRELATIONSHIPS OF THE ASTERACEAE

Abstract— A cladistic analysis involving 27 tribes and subtribes of Asteraceae and 81 characters is presented. The terminal taxa are mainly those of present tribal classification, though some apparently poly- and paraphyletic tribes, notably the Mutisieae and the Inuleae, have been represented by sub-tribal taxa. Characters are assembled from all available sources. Corolla types, styles and stamens have provided many characters. The Lobeliaceae are used as an outgroup and are considered as the most probable sister group of the Asteraceae. There is a basal dichotomy in the family, the Mutisieae-Barnadesiinae being the monophyletic sister group of the remaining major, also monophyletic part of the family. The recent family division into two subfamilies about equal in size, the Cichorioideae and the Asteroideae, neither represents a basal dichotomy nor a sister group relationship within the Asteraceae. The Asteroideae are monophyletic and have their sister group within the paraphyletic Cichorioideae. Interrelationships among the cichorioid tribes are still unclear. The Lactuceae, Eremothamneae, Vernonieae and Liabeae may be one monophyletic group, and the Arctoteae, Carlineae, Echinopsideae and Cardueae another. The Mutisieae are a paraphyletic grade at the base of the family. Within the subfamily Asteroideae tribal interrelationships are also rather unclear. The Anthemideae and the Heliantheae sensu lato (including the Helenieae, Tageteae, Coreopsideae and all helenioid/helianthoid representatives sometimes placed in the Senecioneae) may be sister groups. The Heliantheae appear to be monophyletic and there is little support for the hypothesis that other tribes are derived from or have their sister group within the Heliantheae. The Astereae and the Eupatorieae may be sister groups, though a closer relationship between the Eupatorieae and the Heliantheae is possible. The Inuleae are a paraphyletic grade group at the base of the subfamily Asteroideae in the same way as the Mutiseae are a grade group at the base of the family.     

Chloroplast DNA restriction site variation and phylogenetic interrelationships of some genera of the Heliantheae sensu lato (Asteraceae)

Phylogenetic interrelationships of 12 genera of the Heliantheae s. lat., as well as two genera of the Anthemideae and Eupatorieae, were assessed by chloroplast DNA restriction site analysis. The 14 investigated species represented Guizotia, Helianthus, Melampodium, Rudbeckia, Sigesbeckia, Tridax , and Verbesina (Heliantheae s. str.), Helenium, Hymenoxys , and Palafoxia (Helenieae), Porophyllum (Tageteae), Coreopsis (Coreopsideae), Pleurocoronis (Eupatorieae), and Anthemis , (Anthemideae). Using 9 enzymes, 39 phylogenetically informative sites were found. Wagner parsimony analysis of the data yielded 10 equally parsimonious cladograms. Well supported relationships displayed by all cladograms included (1) a clade comprising all the genera (Heliantheae s. lat. and Eupatorieae) except Anthemis (Anthemideae), (2) a clade consisting of the genera of the Heliantheae s. str. with Pleurocoronis (Eupatorieae) nested among them, (3) a subclade of the former comprising Pleurocoronis, Guizotia , and Sigesbeckia , and (4) the generic pair of Helenium and Hymenoxys.     

THE TAXONOMIC SIGNIFICANCE OF ANTHOCHLORS IN THE SUBTRIBE COREOPSIDINAE (COMPOSITAE,HELIANTHEAE)

Anthochlors (chalcones and aurones) are found in a number of plant families including the Compositae. Within this family they were once thought to occur only in the subtribe Coreopsidinae of the tribe Heliantheae. More recent studies show them to occur also in the tribes Cardueae, Eupatorieae, Helineae, Inuleae, and Lactuceae. This has suggested that anthochlors are no longer good taxonomic markers for the Coreopsidinae. A survey of 69 of approximately 210 genera of the Heliantheae shows anthochlors present only in the Coreopsidinae except for Helianthus, Simsia, Tithonia, and Viguiera, closely related genera of the subtribe Helianthinae. Of the 32 genera of the Coreopsidinae recently recognized, 30 were surveyed from available material and all contain anthochlors except Guardiola and Venegasia. The results indicate that, despite some variation, anthochlors are still good taxonomic markers for the Coreopsidinae. This represents the only case within the family in which a particular type of flavonoid is taxonomically diagnostic at the subtribal level.     

THE MORPHOLOGY OF THE INFLORESCENCE OF RAGWEEDS (AMBROSIA-FRANSERIA : COMPOSITAE)

Payne, Willard W. (U. Michigan, Ann Arbor.) The morphology of the inflorescence of ragweeds (Ambrosia-Franseria: Compositae). Amer. Jour. Bot. 50(9): 872–880. Illus. 1963.—The ragweeds possess an inflorescence which is highly modified in relation to anemophily. Several trends from primitive to specialized character expressions may be seen in the morphology of the unisexual capitula and florets. An evolutionary scheme is presented whereby the catkinlike, acropetally maturing, staminate spike and the sessile, centrifugally developing, fruiting involucre cluster are derived from basic inflorescence types within the Compositae. Morphological evidence suggests that: (1) the taxa Ambrosia and Franseria should be combined under the older generic name Ambrosia; (2) the ragweeds and their relatives as a group appear to occupy a position intermediate between the Heliantheae and Anthemideae, as currently delimited within the Compositae.     

The relationships of 8 tribes of the compositae as suggested by plastocyanin amino acid sequence data

Partial amino acid sequences of the plastocyanins from 22 members of 8 tribes of the Compositae are separated by ancestral amino acid sequence methods into 3 groups. These groups agree generally with those of previous classifications of the species from which the plastocyanins were obtained, based mainly on morphological characters, although closer relationships between the Cichorieae and Cynareae, between the Heliantheae, Senecioneae and Calenduleae and between the Astereae and Inuleae are suggested by the sequence data.     

Flavonoid systematics of Potamogeton subsections Perfoliati and Praelongi (Potamogetonaceae)

The flavonoid pigments of Potamogeton praelongus Wulfen, P. perfoliatus L., and P. richardsonii (A. Benn.) Rydberg were isolated and identified. Five flavone glycosides based on three aglycone types and one C-glycosylflavone were identified. Potamogeton perfoliatus and P. richardsonii are most similar in flavonoid composition. The greatest number of compounds are found in P. praelongus with the other two species having a subset of its profile. The flavonoid data suggest that P. richardsonii arose by means other than hybridization between P. perfoliatus and P. praelongus.     

A review of the phylogeny and classification of the Asteraceae

The Asteraceae are commonly divided into two large subfamilies, the Cichorioideae (syn. Lactucoideae; Mutisieae, Cardueae, Lactuceae, Vernonieae, Liabeae, Arctoteae) and the Asteroideae (Inuleae, Astereae, Anthemideae, Senecioneae, Calenduleae, Heliantheae, Eupatorieae). Recent phylogenetic analyses based on morphological and chloroplast DNA data conclusively show that the Mutisieae-Barnadesiinae are the sister group to the rest of the family and that the Asteroideae tribes form a monophyletic group. The Vernonieae and Liabeae are sister tribes and the Eupatorieae are nested within a paraphyletic Heliantheae; otherwise tribal interrelationships are still largely uncertain. The Mutisieae-Barnadesiinae are excluded from the Mutisieae and elevated to the new subfamily Barnadesioideae. The two subfamilies Barnadesioideae and Asteroideae are monophyletic, whereas the status of the Cichorioideae remains uncertain. Analyses of chloroplast DNA data support the monophyly of the Cichorioideae; however, morphological data indicate that the subfamily is paraphyletic. Further studies are needed to test the monophyly of the Cichorioideae, as well as to further resolve tribal interrelationships in the two larger subfamilies.     

Vorkommen und biologische Bedeutung von Benzopyranen (Chromenen) und Benzofuranen in denAsteraceae

Benzopyrans (chromenes) and benzofurans are characteristic natural products of theAsteraceae and are found together with their biogenetic precursors primarily in the tribesAnthemideae, Astereae, Eupatorieae, Heliantheae, Inuleae, andSenecioneae. The accumulation of benzopyrans and benzofurans supports an arrangement of the tribes of theAsteraceae into two groups as suggested recently based on morphological characters. The methods for analysing this class of natural products are demonstrated with the American genusEncelia. Experiments on the localization of benzopyrans and benzofurans inEncelia species indicate that these compounds are stored in resin ducts. Several benzopyrans and benzofurans are biologically active and are repellent as well as toxic towards herbivorous insects. Experiments on structure — activity relationships indicate the biological activities as being influenced by the heterocycle (pyranvs. furan) as well as by the substituents of the aromatic ring. In addition, several tested compounds showed phototoxic activities.

Vorgetragen auf der Tagung der Deutschen Botanischen Gesellschaft, Wien, September 1984.     

Comprehensive profiling and natural variation of flavonoids in rice

Flavonoids constitute a major group of plant phenolic compounds. While extensively studied in Arabidopsis, profiling and natural y occurring variation of these compounds in rice (Oryza sativa), the mon...     

中国菊科植物的系统分类与区系的初步研究

为1993年"菊科植物的系统分类与区系地理的初步探讨"(世界)一文的姊妹篇,重点论述我国菊科的系统分类及其区系地理成分。文中介绍了分布我国的菊科240属隶于2亚科、5超族、11族中的系统位置。论述了我国菊科植物区系地理成分的特点是:1.大洲间共同分布或洲际间断分布的属多,且具明显的热带亲缘;2.与亚洲国家,包括中亚国家或亚洲热带国家共同分布的属多,尤其是成"中亚-青藏高原-喜马拉雅山"地区分布的属多;3.中国特有属多,其中我国西南省区特有属最多。文中还讨论了分布我国菊科各族祖先种的起源、迁移以及我国区系地理热带亲缘和"横断山脉-喜马拉雅山脉(东)森林植物亚区"菊科植物分布的特点。     

Phylogenetic relationships of New Zealand Asteraceae inferred from ITS sequences

Forty-five sequences from members of all genera of Asteraceae indigenous to New Zealand and 50 published sequences representing the tribal diversity in the family were analyzed to assess the utility of ITS sequences to resolve phylogenetic relationships. Previous studies using chloroplast DNA sequences and morphology provided support for several clades in the Asteraceae, yet the relationships among some of these were uncertain. The results from ITS analysis were largely consistent with these earlier studies. The New Zealand species are included in at least six clades, most of these corresponding to recognized tribes. Our results have also clarified the tribal affinities of a few anomalous genera. Haastia, previously aligned with the Gnaphalieae or the Astereae, is nested in the Senecioneae. Centipeda, previously included in the Astereae or Anthemideae, emerges near the Heliantheae. The relationships of Abrotanella remain unresolved. Received August 8, 2001 Accepted November 6, 2001     

FLAVONOID DIVERSIFICATION IN THE ACHILLEA AGERATIFOLIA AND A. CLAVENNAE GROUPS (ASTERACEAE)

The Achillea ageratifolia and A. clavennae groups (Asteraceae, tribe Anthemideae) were investigated for intra- and interspecific leaf flavonoid variation. Numerous flavonoid glycosides, mostly unidentified, and variously methylated free aglycones based on scutellarein, 6-hydroxyluteolin, quercetagetin, and 6-hydroxy-kaempferol were detected. The distribution of methylated aglycones among individuals of A. ageratifolia was used to model the putative biosynthetic pathways. Several steps in the biosynthesis probably involve enzymes (methyltransferases) with strict positional specificities and broader substrate specificities. Geographical patterns in the flavonoid content of A. ageratifolia were only partly consistent with the current concept of A. ageratifolia. Different flavonoid profiles in A. ageratifolia do not appear to be of crucial importance in its adaptation to different habitats. The species of the A. clavennae group were clearly separable on flavonoid profiles and the presence of a hybrid population was supported by the flavonoid data. Interspecific differences in number of glycosides in relation to the number of free aglycones are discussed.     

Foliar flavonoids of eastern North AmericanVitis (Vitaceae) north of Mexico

Twenty-one flavonoid glycosides were isolated from the leaves of 22 North AmericanVitis L. taxa, representing two subgenera and five series. Three chemical groups were evident: one producing flavonols, flavones, and C-glycosylflavones, a second producing flavonols and flavones, and a third producing only flavonols. These three chemical groups did not correspond to any of the subgeneric groupings based on morphology. However, flavonoid distributions within series in each subgenus correlate well with morphological data. Parallel flavonoid evolution within each series is thought to account for this lack of subgeneric and interserial flavonoid distinction. The flavonoid data indicate that seriesCordifoliae of subgenusVitis, particularlyV. vulpina L., is the most closely related group to subgenusMuscadinia (Planch.)Rehder, and represents an evolutionary link between the two subgenera.     

Evolution of host-parasite relationships of Golovinomyces (Ascomycete: Erysiphaceae) inferred from nuclear rDNA sequences

To understand the evolution of host-parasite relationships in the genus Golovinomyces (Ascomycete: Erysiphaceae), which are obligate parasitic fungi of plants, we investigated the phylogenetic relationships of the genus based on 60 internal transcribed spacer (ITS) and 41 28S rDNA sequences. Five major groups, each represented by isolates from a single tribe of the Asteraceae, were identified in the taxa analyzed in this study. Host plants of four groups were strictly restricted to the Asteraceae. The fifth group, the Lactuceae group, is a large group composed of isolates collected from the tribe Lactuceae of the Asteraceae and all other plant families, which suggests a close affinity between Golovinomyces and the Asteraceae in the early stages of their evolution. Tree topology comparisons between the asteraceous hosts and their parasites suggest that Golovinomyces diverged along with the phylogeny of host tribes Carsueae, Astereae, Heliantheae, and Lactuceae of the Asteraceae. However, a conflict of branching order between the tribe Anthemideae and their parasites suggests that host-jumping has occurred in the tribe Anthemideae. Consequently, we suggest that there are two different phases in the evolutionary history of the host-parasite relationships of Golovinomyces. One phase is divergence in accord with the phylogeny of their hosts, which occurred within the Asteraceae. The another phase is host-jumping, which occurred from the Asteraceae to other families and within the Asteraceae.     

The chemosystematics of local members of the subtribe gnaphaliinae (Compositae)

Eight species belonging to the genera Filago, Ifloga, Achyrocline, Helichrysum and Pseudognaphalium, subtribe Gnaphaliinae, tribe Inuleae (Compositae), were investigated for their flavonoid glycosides. All glycosides were found to belong to the aglycones kaempferol, quercetin, apigenin and luteolin. Calycopterin and its 3'-methyl ether were present in the free form.