Abstract
C-Glycosylflavones represent a special group of flavonoid glycosides both with respect to their chemical structure and presumed different biogenetic origin. Their accumulation and distribution in various plant groups has frequently been interpreted systematically; however, the application of chemotaxonomic congruence sometimes has led to incoherent results. This indicates the necessity for studying C-glycosylflavones primarily as an accumulation tendency before using them as systematic markers. Taking this into account, the distribution of C-glycosylflavones within the Compositae has been compiled and, on the basis of available data, their integration into the complete flavonoid complement analyzed. These results have been compared to those from other selected angiosperm groups, with special regard to the occurrence of certain combinations of different flavonoid glycosides with C-glycosylflavones. Despite the lack of detailed systematic surveys, the biosynthetic capacity of C-glycosylflavone accumulation in the Compositae was found to be relatively high. Mono-and di-C-glycosylflavones, including some with complex structures, are accumulated in the tribes Anthemideae, Heliantheae, Cynareae and Lactuceae. The genera of the Anthemideae and Heliantheae exhibited a very similar C-glycosylflavone profile, thus suggesting possible affinities. The tribes Eupatorieae, Astereae, Inuleae, Vernonieae and Senecioneae apparently accumulated only a small number of less complex C-glycosylflavones. Strikingly, di-C-glycosylflavones were often combined with a series of flavonoid O-glycosides, whereas predominantly C-glycosylflavone profiles showed a low percentage of co-occurring flavonoid O-glycosides. These combination trends could possibly serve as additional chemical characters. Various combination trends have been found within the angiosperms surveyed here. Mostly C-glycosylflavones co-occurred with flavonol 3-O-glycosides and (or) flavone 7-O-glycosides. Mutual exclusivity appeared to be very rare. A predominantly C-glycosylflavone pattern frequently contained a few flavonoid O-glycosides only. By comparison, the Compositae seemed to accumulate di-C-glycosylflavones as a part of a flavonolor flavone-dominated pattern to a greater extent than the other taxa studied here. Taxa accumulating C-glycosylflavones as a main tendency exhibited different degrees of specialization with respect to the substitution patterns of individual compounds. These patterns are much more conclusive than the mere presence/absence criterion. The available data suggest a reconsideration of the present dogma on flavonoid evolution. There is little evidence that C-glycosylflavones truly represent an intermediate stage in the reduction trend from flavonols to flavones. More knowledge on the biosynthesis and function(s) of C-glycosylflavones would be helpful for their interpretation as systematic features.
Zusammenfassung
C-Glykosylflavone unterscheiden sich strukturchemisch, wahrscheinlich aber auch biogenetisch von den übrigen Flavonoidglykosiden. Daher wurde ihre Verbreitung und Akkumulation häufig systematisch interpretiert. Die Anwendung der “chemotaxonomischen Kongruenz” als Interpretationsmodell erscheint jedoch problematisch. Zum besseren Verständnis des Merkmals C-Glykosylflavon-Akkumulation wäre daher eine Analyse der Akkumulationstendenz per se notwendig. Dies berücksichtigend, wurde die Verbreitung von C-Glykosylflavonen bei den Compositae analysiert, wobei besonders auch ihre Integration im gesamten Flavonoidprofil diskutiert wird. Die Ergebnisse wurden mit ähnlichen Analysen bei verschiedenen Angiospermen-Gruppen verglichen und die Kombination mit verschiedenen Flavonoid-O-Glykosiden eingehender studiert. Trotz der geringen Zahl vergleichender Untersuchungen bei den Compositae erscheint ihre Biosynthesekapazität relativ hoch: in den Triben Anthemideae, Heliantheae, Cynareae und Lactuceae kommt es zur Akkumulation von auch komplexeren mono-und di-C-Glykosylflavonen. Dabei zeigen vor allem Gattungen der Anthemideae und Heliantheae weitgehend übereinstimmende C-Glykosylflavon-Profile. Dagegen werden in den Triben Eupatorieae, Astereae, Senecioneae, Vernonieae und Inuleae nur die biogenetisch einfacheren Derivate in geringerem Ausmass akkumuliert. Auffallenderweise kommen di-C-Glykosylflavone häufig in Kombination mit dominierenden Flavonoid-O-Glykosiden vor, während in Profilen mit dominierender C-Glykosylflavon-Ausstattung die entsprechenden Flavonoid-O-Glykoside mengenmässig stark zurücktreten. Diese Kombinationstendenzen könnten sich als zusätzliches chemisches Merkmal erweisen. Unterschiedliche Kombinationstendenzen wurden bei anderen Angiospermen-Gruppen beobachtet. Meistens wurden C-Glykosylflavone mit Flavonol-3-O-Glykosiden und (oder) Flavon-7-O-Glykosiden co-akkumuliert. Dabei kommt es selten zum wechselseitgen Ausschluss von C-Glykosylflavonen und Flavonoid-O-Glykosiden. Meist enthält ein dominierendes C-Glykosylflavon-Muster wenige Flavonoid-O-Glykoside. Im Vergleich dazu scheint die Kombination von di-C-Glykosylflavonen und dominierenden Flavonoid-O-Glykosiden bei den Compositae häufiger zu sein als bei den übrigen hier untersuchten Angiospermen. Taxa mit dominierenden C-Glykosylflavon-Profilen zeigen vielfach ein unterschiedliches Ausmass an Spezialisierung im Substitutionsmuster der einzelnen Derivate. Diese Muster erscheinen als chemische Merkmale bedeutsamer als das Merkmal “Vorkommen versus Fehlen.” Aufgrund der bisherigen Daten erscheint daher eine Revision des bestehenden Dogmas der Flavonoid-Evolution erforderlich, da es wenig Hinweise auf die postulierte Rolle der C-Glykosylflavone als Zwischenstufe im Flavonol-Flavon Reduktionstrend gibt. Mehr Informationen über Biosynthese und Funktion von C-Glykosylflavonen könnten zu einem besseren Verständnis dieses chemischen Merkmals beitragen.
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Valant-Vetschera, K.M. C-Glycosylflavones as an accumulation tendency: A critical review. Bot. Rev 51, 1–52 (1985). https://doi.org/10.1007/BF02861057
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DOI: https://doi.org/10.1007/BF02861057