Flavonoid chemistry of Calyceraceae Bruce A. Bohm, Alan Reid, Melanie DeVore, and Tod F. Stuessy Abstract: Flavonoid profiles were determined for I I species representing five genera of Calyceraceae: Acicatpha, Boopis, Calycera, Garnocarpha, and Nastanthus. Kaempferol, quercetin, 6-methoxykaempferol, and 6-methoxyquercetin (patuletin) were unequivocally identified. Kaempferol and quercetin occurred as 3-0-mono- and 3-0-diglycosides, whereas the latter two flavonols were observed only as aglycones. Several unidentified phenolic compounds were also noted. The simplest profile in the family consisted solely of the kaempferol and quercetin glycosides in Acicatpha, Gamocatpha, and one specimen of Calycera leucanthema. Morphological evidence suggests that Acicatpha represents prototypical Calyceraceae and that a close relationship exists between primitive Calyceraceae and some basal members of Asteraceae (subfamily Barnadesioideae). This last possibility is reinforced by the similarity of flavonoid profiles of Acicatpha and members of Barnadesioideae. Key words: Calyceraceae, Asteraceae, Compositae, Barnadesioideae, flavonoids. RCsumC : Les auteurs ont ditermint les patrons des flavono'ides chez 11 espbces reprksentant 5 genres de Calyceraceae : Acicatpha, Boopis, Calycera, Gamocatpha et Nastanthus. Le kaempferol, la quercCline, le 6-mCthoxykaempf6rol et la 6-mCthoxyquercttine (patulktine) ont CtC clairement identifits. Le kaempfkrol et la quercCtine se retrouvent sous forme de 3-0-mono- et de 3-0-diglycosides alors que les deux autres flavonols se presentent sous forme d'aglycones. Plusieurs autres composts phCnoliques non-identifies ont t t t Cgalement observCs. Le profile le plus simple observe dans la famille ne comporte que les glycosides de kaempferol et de quercttine chez l'Acicatpha, le Gamocatpha et un specimen du Calycera leucanthema. Les donnCs morphologiques suggbrent que le genre Acicarpha reprCsente les Calyceraceae prototypiques, et qu'il existe une Ctroite relation entre les Calyceraceae primitives et certains membres de base des Asteraceae (sous-famille Barnadesioideae). Cette dernibre possibilitC est supportee par la similarit6 des patrons des flavono'ides de I'Acicatpha et des membres des Barnadesioideae. Mots elks : Calyceraceae, asteraceae, compositae, Barnadesioideae, flavono'ides. [Traduit par la rCdaction] Introduction Calyceraceae L. C. Richard comprises six genera with 50 (Hansen 1992) to 60 species (Cronquist 1981). Members of the family occur widely in South America with one species known on the Falkland Islands. The constituent genera are Acicarpha Juss., Boopis Juss., Calycera Cavanilles, Gamo- carpha DC., Moschopsis Phil., and Nastanthus Miers. Boopis and Calycera are the largest genera with over a dozen species each. The family has attracted a good deal of atten- tion in recent years owing to its candidacy as a sister group to the Asteraceae (Hansen 1992; Gustafsson and Bremer 1995; DeVore and Stuessy 1995). Received April 12, 1995. B.A. Bohml and A. Reid. Department of Botany, The University of British Columbia, Vancouver, BC V6T 124, Canada. M. DeVore. Department of Biology, Sam Houston State University, Huntsville, TX 77341, U.S.A. T.F. Stuessy2. Department of Plant Biology, Ohio State University, Columbus, OH 43210, U.S.A. ' Author to whom all corresondence should be addressed. Natural History Museum of Los Angeles Co., 900 Exposition Blvd., Los Angeles, CA 90007, U.S.A. A review of the taxonomic history of Calyceraceae shows that in most cases, the family has been accorded a position near Asteraceae, if not in the same order, then in a closely related one. For instance, Wagenitz (1964) placed Caly- ceraceae and Asteraceae in his Campanulales. Cronquist (1981), after having placed Calyceraceae in Dipsacales in an earlier publication, reconsidered the situation and accorded it its own order, Calycerales, which agrees with Takhtajan's (1986, 1987) views. Dahlgren (1983) spread these various families around with the Asteraceae in Asterales, Calycera- ceae in Dipsacales, and Goodeniaceae in Goodeniales. These three orders were assigned to Asteriflorae (along with Cam- panulales), Corniflorae, and Gentianiflorae, respectively (Dahlgren 1983). Thorne (1992) sees Asterales as com- prising Asteraceae and Calyceraceae. A concise summary of the features characterizing the family and its taxonomic history appeared in Larnrners' (1992) circumscription of Campanulales. We undertook an examination of the flavonoids of Caly- ceraceae with the hope that these additional data might provide a better understanding of the relationships with Asteraceae. This seemed timely in view of recent efforts to arrive at phylogenetic relationships among Asteraceae and related families (Gustafsson and Bremer 1995 and citations therein). Also, a recent examination of the flavonoids of Bar- Can. I. Bot. 73: 1962-1965 (1995). Printed in Canada / IrnprirnC au Canada Can. J. Bot. Downloaded from www.nrcresearchpress.com by Renmin University of China on 06/03/13 For personal use only.