Skip to main content
Log in

Flavonoid distribution of Mulinum (Apiaceae, Hydrocotyloideae, Mulineae)

  • Articles
  • Published:
Brittonia Aims and scope Submit manuscript

Abstract

Flavonoid chemistry of the genusMulinum and selected Mulineae taxa was studied. Both flavones and flavonols were identified as C- and O-glycosides. AllMulinum species contain 6,8-di-C-glycosyl chrysoeriol (flavone) and, with the exception of one, quercetin (flavonol). The presence of both flavones and flavonols in this genus weakens previous generalizations that the mulineae contain only flavonols and are primitive compared to other Apiaceae tribes. Based on the selected taxa studied,Azorella appears to differ from bothMulinum andGymnophyton in producing more kinds of flavonols, andGymnophyton appears similar toMulinum in the production of both chrysoeriol and quercetin as well as relatively few compounds. The flavonoid profile ofAsteriscium glaucum is reported as well. In general, a more homogeneous flavonoid compound composition for the Apiaceae is suggested.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature Cited

  • Bate-Smith, E. C. 1962. The phenolic constituents of plants and their taxonomic significance—I. Dicotyledons. J. Linn. Soc., Bot. 58: 95–173.

    Article  CAS  Google Scholar 

  • Crawford, D. C. &E. B. Smith. 1983a. The distribution of anthochlor floral pigments in North AmericanCoreopsis (Compositae): taxonomic and phyletic interpretations. Amer. J. Bot. 70: 355–362.

    Article  CAS  Google Scholar 

  • ——. 1983b. Leaf flavonoid chemistry of North AmericanCoreopsis (Compositae): intra-and intersectional variation. Bot. Gaz. 144: 577–583.

    Article  CAS  Google Scholar 

  • Crowden, R. K., J. B. Harborne &V. H. Heywood. 1969. Chemosystematics of the Umbelliferae—a general survey. Phytochemistry 8: 1963–1984.

    Article  CAS  Google Scholar 

  • Drude, C. G. O. 1897–1898. Umbelliferae. Pages 63–250.In: A. Engler & K. Prantl. Die natürlichen Pflanzenfamilien 3(8).

  • Giannasi, D. E. &T. I. Chuang. 1976. Flavonoid systematics of the genusPerideridia (Umbelliferae). Brittonia 28: 177–194.

    Article  CAS  Google Scholar 

  • — &D. J. Crawford. 1986. Biochemical systematics II. A reprise. Evol. Biol. 20: 25–248.

    CAS  Google Scholar 

  • Glassgen, W. E., V. Wray, D. Strack, J. W. Metzger &H. U. Seitz. 1992. Anthocyanins from cell suspension cultures ofDaucus carota. Phytochemistry 31: 1593–1601.

    Article  PubMed  CAS  Google Scholar 

  • Gonnet, J. F. 1986. Individual variation of flavonoid glycosides inChaerophyllum aureum. Biochem. Syst. & Ecol. 14: 409–415.

    Article  CAS  Google Scholar 

  • Gonzalez, J. A., A. Estevez-Braun, R. Estevez-Reyes, I. L. Bazzocchi, I. A. Moujir-Jimenez, A. G. Ravelo &A. G. Gonzalez. 1995. Biological activity of secondary metabolites fromBupleurum salicifloium (Umbelliferae). Experientia (Basel) 51: 35–39.

    CAS  Google Scholar 

  • Gornall, R. J. &B. A. Bohm. 1978. Angiosperm flavonoid evolution: a reappraisal. Syst. Bot. 3: 353–365.

    Article  Google Scholar 

  • Harborne, J. B. 1967. Comparative biochemistry of the flavonoids. Academic Press, London.

    Google Scholar 

  • — 1971. Flavonoid and phenylpropanoid patterns in the Umbelliferae. Pages 293–314.In: V. H. Heywood, editor. The biology and chemistry of the Umbelliferae. Academic Press, New York.

    Google Scholar 

  • — 1975. Biochemical systematics of flavonoids. Pages 1057–1095.In: J. B. Harborne, T. J. Mabry & H. Mabry. editors. The flavonoids. Academic Press, London.

    Google Scholar 

  • — 1977. Flavonoids and the evolution of the Angiosperms. Biochem. Syst. & Ecol. 5: 7–22.

    Article  CAS  Google Scholar 

  • —,V. H. Heywood &C. A. Williams. 1969. Distribution of myristian in the seeds of the Umbellifereae. Phytochemistry 8: 1729–1732.

    Article  CAS  Google Scholar 

  • —— &X. Y. Chen. 1986. Separation ofOstericum fromAngelica on the basis of leaf and mericarp flavonoids. Biochem. Syst. & Ecol. 14: 81–83.

    Article  CAS  Google Scholar 

  • Hiller, K. 1971. Chemosystematics of the Saniculoideae. Pp. 369–384.In: V. H. Heywood, editor. The biology and chemistry of the Umbelliferae. Academic Press, New York.

    Google Scholar 

  • Loyola, L. A., G. Morales, M. C. de la Torre, S. Pedreros &B. Rodriquez. 1990. 17-acetoxymulinic acid, a rearranged diterpenoid fromMulinum crassifolium. Phytochemistry 29: 3950–3951.

    Article  CAS  Google Scholar 

  • —,B. Rodriquez, J. Jimenez-Barbero, S. Pedreros, M. C. de la Torre &A. Perales. 1991. Mulinenic acid, a rearranged diterpenoid fromMulinum crassifolium. Amer. Soc. Pharmacogn. 54: 1404–1408.

    CAS  Google Scholar 

  • —,J. Borquez, G. Morales &A. San Martin. 1996. Mulinolic acid, a diterpenoid fromMulinum crassifolium. Phytochemistry 43: 165–168.

    Article  CAS  Google Scholar 

  • ————. 1997a. Mulinol, a diterpenoid fromAzorella compacta. Phytochemistry 45: 1465–1467.

    Article  CAS  Google Scholar 

  • ————. 1997b. Diterpenoids fromAzorella compacta. Phytochemistry 44: 649–651.

    Article  CAS  Google Scholar 

  • Mabry, T. J. 1974. Chemistry of disjunct taxa. Pages 63–66.In: G. Bendz, J. Santesson & V. Runnstrom-Reio, editors. Chemistry in botanical classification. Nobel Symposium 25. Academic Press, New York.

    Google Scholar 

  • —,K. R. Markham &M. B. Thomas. 1970. The systematic identification of flavonoids. Springer-Verlag, New York.

    Google Scholar 

  • Markham, K. R. 1982. Techniques of flavonoid identification. Academic Press, New York.

    Google Scholar 

  • Matsushita, A. &S. Iseda. 1965. Flavonoids of the flowers ofOenanthe stolonifers. J. Agric. Chem. Soc. Japan 39: 317–318.

    CAS  Google Scholar 

  • Neuman, P. R., B. N. Timmermann &T. J. Mabry. 1979. Laboratory manual for the systematic identification of flavonoids. Privately published, University of Texas, Austin.

    Google Scholar 

  • Nicoletti, M., A. Di Fabio, A. D'Andrea, G. Salvatore, C. Van Baren &J. D. Coussio. 1996. Diterpenoid acids fromMulinum spinosum. Phytochemistry 43: 1065–1067.

    Article  CAS  Google Scholar 

  • Pacheco, P., D. J. Crawford, T. F. Stuessy &M. Silva O. 1985. Flavonoid evolution inRobinsonia (Compositae) of the Juan Fernandez Islands. Amer. J. Bot. 72: 989–998.

    Article  CAS  Google Scholar 

  • Poli, F., B. Tirillini, B. Tosi, G. Sacchetti &A. Bruni. 1995. Histological localization of coumarins in different organs ofSmyrnium perfoliatum (Apiaceae). Phyton (Horn) 35: 209–217.

    CAS  Google Scholar 

  • Saleh, N. A. M., S. I. El-Negoumy, M. N. El-Hadidi &H. A. Hosni. 1983. Comparative study of the flavonoids of some local members of the Umbelliferae. Phytochemistry 22: 1417–1420.

    Article  CAS  Google Scholar 

  • Schopke, T., M. Janka, M. Nimtz, V. Wray, &K. Hiller. 1998. Saniculoside R-1: a new triterpenoid saponin fromSanicula europaea. Pl. Med. 64: 83–85.

    Article  CAS  Google Scholar 

  • Smitt, U. W. 1995. A chemotaxonomic investigation ofThapsia villosa L., Apiaceae (Umbelliferae). J. Linn. Soc., Bot. 119: 367–377.

    Article  Google Scholar 

  • Stuessy, T. F. &D. J. Crawford. 1983. Flavonoids and phylogenetic reconstruction. Pl. Syst. Evol. 143: 83–107.

    Article  CAS  Google Scholar 

  • Valant-Vetschera, K. M. 1985. C-glycosylflavones as an accumulation tendency: a critical review. Bot. Rev. (Lancaster) 51: 1–52.

    Google Scholar 

  • Wells, E. F. &B. A. Bohm. 1980. Chemotaxonomic studies in the Saxifragaceae s.l. 15. The flavonoids of subsectionVillosae sectionHeuchera in the genusHeuchera. Canad. J. Bot. 58: 1459–1463.

    CAS  Google Scholar 

  • Wollenweber, E., M. Dorr &A. Rustiyan. 1995.Dorema aucheri, the first umbelliferous plant found to produce exudate flavonoids. Phytochemistry 38: 1417.

    Article  CAS  Google Scholar 

  • Whalen, M. D. 1978. Foliar flavonoids ofSolanum sectionAndroceras: a systematic survey. Syst. Bot. 3: 257–276.

    Article  CAS  Google Scholar 

  • Zech, J. C. 1992. Systematics of the genusMulinum Pers. (Apiaceae, Hydrocotyloideae, Mulineae). Ph.D. dissertation. The Ohio State University, Columbus.

    Google Scholar 

  • — 1995. Nomenclatural novelties onMulinum (Apiaceae). Kurtizana 24: 192.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zech, J.C. Flavonoid distribution of Mulinum (Apiaceae, Hydrocotyloideae, Mulineae). Brittonia 51, 415–421 (1999). https://doi.org/10.2307/2666525

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.2307/2666525

Key words

Navigation