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Chemistry in Paepalanthus and taxonomic implications
Biochemical Systematics and Ecology 32 (2004) 503–504 www.elsevier.com/locate/biochemsyseco
Chemistry in Paepalanthus and taxonomic implications A.L. Dokkedal a,, P.T. Sano b, W. Vilegas c a
Departamento de Cieˆncias Biolo´gicas, Faculdade de Cieˆncias, UNESP CP 473, Bauru, SP 17033-360, Brazil b Departamento de Botaˆnica, Instituto de Biocieˆncias, Universidade de Sa˜o Paulo, SP 05427-970, Brazil c Departamento de Quı´mica Orgaˆnica, Instituto de Quı´mica de Araraquara, UNESP CP 355, Araraquara, SP 14801-970, Brazil Received 28 April 2003; accepted 28 November 2003
Keywords: Eriocaulaceae; Paepalanthus Mart.; Flavonoids; Naphthopyranones; Chemotaxonomy; Cladistic analysis
1. Subject and source Paepalanthus chlorocephalus Silveira (WV 16), P. argenteus var. argenteus (Bongard) Hensold (SANO 920), and P. macrocephalus Koern. (WV 31) are herbaceous monocotyledons belonging to Eriocaulaceae. They were collected at Serra do Cipo´ (Minas Gerais, Brazil) in February 1998. Voucher specimens were deposited at Herbarium SPF, Brazil.
2. Previous work We have found flavonols and naphthopyranones derivatives for Paepalanthus species (Andrade et al., 1999; Vilegas et al., 1999a,b). For the related genera Leiothrix and Syngonanthus, the major constituents are flavones (luteolin O- and C-glycosides) (Dokkedal and Salatino, 1992; Coelho et al., 1999a,b).
Corresponding author. Tel.: +55-14-3103-6078; fax: +55-14-3103-6074. E-mail address: [email protected] (A.L. Dokkedal).
0305-1978/$ - see front matter # 2004 Published by Elsevier Ltd. doi:10.1016/j.bse.2003.11.004
504
A.L. Dokkedal / Biochemical Systematics and Ecology 32 (2004) 503–504
3. Present study The methanol extracts of dried leaves of the species were subjected to sephadex LH-20 eluted with MeOH. The compounds were identified using combined 200 MHz NMR techniques and mass spectroscopy (Electrospray-MS). For P. chlorocephalus, we identified the flavone nepetin as the major constituent. For P. argenteus var. argenteus, we have found the flavone derivatives jaceosidin and jaceosidin 7-glucoside as the major constituents. P. macrocephalus has yielded acylated flavonols, flavonol glycosides, paepalantine derivatives and dihydronaphthopyranones. 4. Chemotaxonomic significance The presence of 6-methoxyflavone derivatives as the major constituents of P. chlorocephalus and P. argenteus var. argenteus (P. subgen. Xeractis) reinforces the cladistic analysis of Giulietti et al. (2000), in which P. subg. Xeractis is closely related to Leiothrix and Syngonanthus, which also contain flavones rather than flavonols. The chemistry of P. macrocephalus (P. subsect. Aphorocaulon) is in agreement with Giulietti et al. (2000), where this taxon forms a sister group with P. subg. Actinoceplhalus, which has a similar chemical profile. Acknowledgements We are grateful to FAPESP and CNPq for funding and fellowship to W.V. and to FUNDUNESP for financial aid to A.L.D. References Andrade, F.D.P., Santos, L.C., Dokkedal, A.L., Vilegas, W., 1999. Phytochemistry 51, 411. Coelho, R.G., Vilegas, W., Parra, L.R., 1999a. Flavono´ides C-glicosilados de S. bisulcatus. In: 22th Annual meeting of Brazilian Chemical Society, Abstracts, pp. 17. Coelho, R.G., Vilegas, W., Parra, L.R., Sano, P.T., 1999b. Estudo quı´mico dos escapos de S. bisulcatus. In: III Meeting of the Phytochemistry Latin-American Society de Fitoquı´mica, Abstracts, pp. 71. Dokkedal, A.L., Salatino, A., 1992. Biochem. Syst. Ecol. 20, 31. Giulietti, A.M., Scatena, V.L., Sano, P.T., Parra, L.R., Queiroz, L.P., Harley, R.M., Menezes, N.L., Yseppon, A.M.B., Salatino, A., Salatino, M.L., Vilegas, W., Santos, L.C., Ricci, C.V., Bonfim, M.C.P., Miranda, E.B., 2000. Multidisciplinary Studies on Neotropical Eriocaulaceae. Monocots: Systematics and Evolutions. CSIRO Publishing, Australia, pp. 580–588. Vilegas, W., Dokkedal, A.L., Rastrelli, L., Piacente, S., Pizza, C., 1999a. J. Nat. Prod. 62, 746. Vilegas, W., Nehme, C.J., Dokkedal, A.L., Piacente, S., Rastrelli, L., 1999b. Phytochemistry 51, 403.
Chemistry in Paepalanthus and taxonomic implications A.L. Dokkedal a,, P.T. Sano b, W. Vilegas c a
Departamento de Cieˆncias Biolo´gicas, Faculdade de Cieˆncias, UNESP CP 473, Bauru, SP 17033-360, Brazil b Departamento de Botaˆnica, Instituto de Biocieˆncias, Universidade de Sa˜o Paulo, SP 05427-970, Brazil c Departamento de Quı´mica Orgaˆnica, Instituto de Quı´mica de Araraquara, UNESP CP 355, Araraquara, SP 14801-970, Brazil Received 28 April 2003; accepted 28 November 2003
Keywords: Eriocaulaceae; Paepalanthus Mart.; Flavonoids; Naphthopyranones; Chemotaxonomy; Cladistic analysis
1. Subject and source Paepalanthus chlorocephalus Silveira (WV 16), P. argenteus var. argenteus (Bongard) Hensold (SANO 920), and P. macrocephalus Koern. (WV 31) are herbaceous monocotyledons belonging to Eriocaulaceae. They were collected at Serra do Cipo´ (Minas Gerais, Brazil) in February 1998. Voucher specimens were deposited at Herbarium SPF, Brazil.
2. Previous work We have found flavonols and naphthopyranones derivatives for Paepalanthus species (Andrade et al., 1999; Vilegas et al., 1999a,b). For the related genera Leiothrix and Syngonanthus, the major constituents are flavones (luteolin O- and C-glycosides) (Dokkedal and Salatino, 1992; Coelho et al., 1999a,b).
Corresponding author. Tel.: +55-14-3103-6078; fax: +55-14-3103-6074. E-mail address: [email protected] (A.L. Dokkedal).
0305-1978/$ - see front matter # 2004 Published by Elsevier Ltd. doi:10.1016/j.bse.2003.11.004
504
A.L. Dokkedal / Biochemical Systematics and Ecology 32 (2004) 503–504
3. Present study The methanol extracts of dried leaves of the species were subjected to sephadex LH-20 eluted with MeOH. The compounds were identified using combined 200 MHz NMR techniques and mass spectroscopy (Electrospray-MS). For P. chlorocephalus, we identified the flavone nepetin as the major constituent. For P. argenteus var. argenteus, we have found the flavone derivatives jaceosidin and jaceosidin 7-glucoside as the major constituents. P. macrocephalus has yielded acylated flavonols, flavonol glycosides, paepalantine derivatives and dihydronaphthopyranones. 4. Chemotaxonomic significance The presence of 6-methoxyflavone derivatives as the major constituents of P. chlorocephalus and P. argenteus var. argenteus (P. subgen. Xeractis) reinforces the cladistic analysis of Giulietti et al. (2000), in which P. subg. Xeractis is closely related to Leiothrix and Syngonanthus, which also contain flavones rather than flavonols. The chemistry of P. macrocephalus (P. subsect. Aphorocaulon) is in agreement with Giulietti et al. (2000), where this taxon forms a sister group with P. subg. Actinoceplhalus, which has a similar chemical profile. Acknowledgements We are grateful to FAPESP and CNPq for funding and fellowship to W.V. and to FUNDUNESP for financial aid to A.L.D. References Andrade, F.D.P., Santos, L.C., Dokkedal, A.L., Vilegas, W., 1999. Phytochemistry 51, 411. Coelho, R.G., Vilegas, W., Parra, L.R., 1999a. Flavono´ides C-glicosilados de S. bisulcatus. In: 22th Annual meeting of Brazilian Chemical Society, Abstracts, pp. 17. Coelho, R.G., Vilegas, W., Parra, L.R., Sano, P.T., 1999b. Estudo quı´mico dos escapos de S. bisulcatus. In: III Meeting of the Phytochemistry Latin-American Society de Fitoquı´mica, Abstracts, pp. 71. Dokkedal, A.L., Salatino, A., 1992. Biochem. Syst. Ecol. 20, 31. Giulietti, A.M., Scatena, V.L., Sano, P.T., Parra, L.R., Queiroz, L.P., Harley, R.M., Menezes, N.L., Yseppon, A.M.B., Salatino, A., Salatino, M.L., Vilegas, W., Santos, L.C., Ricci, C.V., Bonfim, M.C.P., Miranda, E.B., 2000. Multidisciplinary Studies on Neotropical Eriocaulaceae. Monocots: Systematics and Evolutions. CSIRO Publishing, Australia, pp. 580–588. Vilegas, W., Dokkedal, A.L., Rastrelli, L., Piacente, S., Pizza, C., 1999a. J. Nat. Prod. 62, 746. Vilegas, W., Nehme, C.J., Dokkedal, A.L., Piacente, S., Rastrelli, L., 1999b. Phytochemistry 51, 403.