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The use of diterpenoids as chemotaxonomic markers in the genus Cystoseira

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Abstract

The chemical analysis of secondary metabolites from brown algae belonging to the genus Cystoseira — collected from the French Mediterranean coast and the Atlantic coast of Morocco - has permitted us to identify the characteristic diterpenic constituents of studied species. The results were discussed and compared with those described in the literature on Sicilian species.

Initial evaluation of the results led us to propose, as a first hypothesis, the chemotaxonomic criteria which allow the species of the genus Cystoseira to be classified into three chemical groups: 1) without diterpenes, 2) with linear diterpenes and 3) with meroditerpenes (diterpenes with mixed biogenesis characterised by hydroquinonic methyl nucleus linked to a diterpenic chain). The first group corresponds to the most primitive species while the third, which can be subdivided into three other groups as a function of the structural complexity of the isolated diterpenoids (linear, cyclic or rearranged meroditerpenes), contains the most advanced ones.

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References

  • Amico, V., G. Oriente, M. Piattelli, G. Ruberto & C. Tringali, 1981. Novel acyclic diterpenes from the brown alga Cystoseira crinita. Phytochemistry 20: 1085–1088.

    Google Scholar 

  • Amico, V., G. Oriente, M. Piattelli, G. Ruberto & C. Tringali, 1982. Two novel phenolic compounds from the brown alga Cystoseira caespitosa. J. Chem. Research (S): 262–263

  • Amico, V., G. Oriente, M. Piattelli & G. Ruberto, 1983. New metabolites from the brown alga Cystoseira caespitosa. Gazz. Chim. Ital. 113: 217–218.

    Google Scholar 

  • Amico, V., F. Cunsolo, G. Oriente, M. Piattelli & G. Ruberto, 1984a. Cystoketal, a new metabolite from the brown alga Cystoseira balearica. J. Nat. Prod. 47: 947–952.

    Google Scholar 

  • Amico, V., F. Cunsolo, M. Piattelli & G. Ruberto, 1984b. Five novel tetraprenylhydroquinols from the brown alga Cystoseira algeriensis. Phytochemistry 23: 2017–2020.

    Google Scholar 

  • Amico, V., G. Oriente, M. Piattelli & G. Ruberto, 1984c. Cystalgerone, a novel metabolite from the brown alga Cystoseira algeriensis. Gazz. Chim. Ital. 114: 169–172.

    Google Scholar 

  • Amico, V., F. Cunsolo, M. Piattelli, G. Ruberto & F. Fronczek, 1984d. Balearone, a metabolite of the brown alga Cystoseira balearica. Tetrahedron 40: 1721–1725.

    Google Scholar 

  • Amico, V., F. Cunsolo, M. Piattelli & G. Ruberto, 1985a. Tetraprenyltoluquinols from the brown alga Cystoseira jabukae. Phytochemistry 24: 1047–1050.

    Google Scholar 

  • Amico, V., F. Cunsolo, M. Piattelli & G. Ruberto, 1985b. Acyclic tetraprenyltoluquinols from Cystoseira sauvageauana and their possible role as biogenetic precursors of the cyclic Cystoseira metabolites. Phytochemistry 24: 2663–2668.

    Google Scholar 

  • Amico, V., P. Neri, M. Piattelli & G. Ruberto, 1987a. Linear diterpenoids from Cystoseira balearica. Phytochemistry 26: 2637–2639.

    Google Scholar 

  • Amico, V., G. Oriente, P. Neri, M. Piattelli & G. Ruberto, 1987b. Tetraprenyltoluquinols from the brown alga Cystoseira stricta. Phytochemistry 26: 1715–1718.

    Google Scholar 

  • Amico, V., G. Giaccone, M. Piattelli & G. Ruberto, 1988a. Inheritance of chemical constituents in algae: tetraprenyltoluquinols of Cystoseira elegans × Cystoseira algeriensis. Phytochemistry 27: 1069–1071.

    Google Scholar 

  • Amico, V., M. Piattelli, P. Neri & G. Ruberto, 1988b. Meroterpenoids from Cystoseira spp. J. Nat. Prod. 51: 191–192.

    Google Scholar 

  • Amico, V., F. Cunsolo, P. Neri, M. Piattelli & G. Ruberto, 1988c. Antimicrobial tetraprenyltoluquinol derivatives from Cystoseira spinosa var. squarrosa. Phytochemistry 27: 1327–1331.

    Google Scholar 

  • Amico, V., M. Piattelli, F. Cunsolo, P. Neri & G. Ruberto, 1988d. Further novel diterpenoids of mixed biogenesis from a Cystoseira sp. Gazz. Chim. Ital. 118: 193–195.

    Google Scholar 

  • Amico, V., P. Neri, G. Oriente & M. Piattelli, 1989a. Tetraprenyltoluquinol derivatives from the brown alga Cystoseira zosteroides. Phytochemistry 28: 215–219.

    Google Scholar 

  • Amico, V., M. Piattelli, P. Neri & G. Ruberto, 1989b. Metabolites of mixed biogenesis from Cystoseira tamariscifolia (Huds.) Papenf. Gazz. Chim. Ital. 119: 467–470.

    Google Scholar 

  • Amico, V., M. Piattelli, F. Cunsolo, P. Neri & G. Ruberto, 1989c. Two epimeric irregular diterpenoid toluquinols from the brown alga Cystoseira stricta. J. Nat. Prod. 52: 962–969.

    Google Scholar 

  • Amico, V., M. Piattelli, F. Cunsolo, M. Recupero & G. Ruberto, 1990. Tetraprenyltoluquinols as chemotaxonomic markers in the genus Cystoseira: C. barbatula and C. barbata. Gazz. Chim. Ital. 120: 9–12.

    Google Scholar 

  • Banaigs, B., C. Francisco, E. Gonzalez, L. Codomier & W. Fenical, 1982. Hydroxylated diterpenoid hydroquinones from Cystoseira elegans: significant products or artefacts? Tetrahedron letters 23: 3271–3272.

    Google Scholar 

  • Banaigs, B., C. Francisco, E. Gonzalez & W. Fenical, 1983a. Diterpenoid metabolites from the marine alga Cystoseira elegans. Tetrahedron 39: 629–638.

    Google Scholar 

  • Banaigs, B., B. Marcos, C. Francisco, E. Gonzalez & W. Fenical, 1983b. A hydroxylated diterpenoid substituted quinol from the brown alga Cystoseira elegans. Phytochemistry 22: 2865–2867.

    Google Scholar 

  • Banaigs, B., C. Francisco, E. Gonzalez & L. Codomier, 1984. Lipids from the brown alga Cystoseira barbata. Phytochemistry 23: 2951–2952.

    Google Scholar 

  • Fleury, B. G., A. Kelekom & V. L. Teixeira, 1992. Taxonomic and phylogenetic study of brown algae (orders Dictyotales and Fucales). Proceedings of the seventh international symposium on Marine Natural Products, Tipolitografia De Rosa & Memoli, Cava de Tirreni: 190.

    Google Scholar 

  • Francisco, C., G. Combaut, J. Teste & M. Prost, 1978. Eleganolone, nouveau cétol diterpénique linéaire de la Pheophycée Cystoseira elegans. Phytochemistry 17: 1003–1005.

    Google Scholar 

  • Francisco, C., B. Banaigs, R. Valls & L. Codomier, 1985. Mediterraneol A, a novel rearranged diterpenoid-hydroquinone from the marine alga Cystoseira mediterranea. Tetrahedron Letters 26: 2629–2632.

    Google Scholar 

  • Francisco, C., B. Banaigs, M. Rakba, J. Teste & A. Cave, 1986a. Mediterraneols: a novel biologically active class of rearranged diterpenoid metabolites from Cystoseira mediterranea (Pheophyta). J. Org. Chem. 51: 1115–1120.

    Google Scholar 

  • Francisco, C., B. Banaigs, J. Teste & A. Cave, 1986b. Cystoseirols: novel rearranged diterpenoids of mixed biogenesis from Cystoseiraceae (brown marine algae). J. Org. Chem. 51: 2707–2711.

    Google Scholar 

  • Giaccone, G. & A. Bruni, 1971. Le cistoseire delle coste Italiane. Ann. Univ. Ferrara (N. S.) Ser. IV. Bot. 4: 45–70.

    Google Scholar 

  • Giaccone, C. & A. Bruni, 1973. Le cistoseire e la vegetazione sommersa del Mediterraneo. Atti Ist. Ven. Sci. Lett. Arti 131: 59–103.

    Google Scholar 

  • Piattelli, M., 1990. Chemistry and taxonomy of Sicilian Cystoseiraspecies. New J. Chem. 14: 777–782.

    Google Scholar 

  • Piattelli, M., 1991. Chemistry of marine algae: overview and current status. OEbalia 17: 357–380.

    Google Scholar 

  • Piovetti, L., P. Deffo, R. Valls & G. Peiffer, 1991. Determination of sterols and diterpenoids from brown algae (Cystoseiraceae). J. Chromatogr. 588: 99–105.

    Google Scholar 

  • Piovetti, L., R. Valls, P. Deffo & A. Praud, 1992. Secondary metabolites from Cystoseira stricta and Cystoseira crinita of the French Mediterranean coast. Proceedings of the seventh international symposium on Marine Natural Products, Tipolitografia De Rosa & Memoli, Cava de Tirreni: 162–163.

    Google Scholar 

  • Roberts, M., 1978. Active speciation in the taxonomy of the genus Cystoseira C. Ag.. In D. E. G. Irvine & J. H. Price(eds), Modern approches to the taxonomy of red and brown algae. Academic Press, Lond.: 399–422.

    Google Scholar 

  • Valls, R., L. Piovetti, B. Banaigs & A. Praud, 1993. Secondary metabolites from Morocco brown algae of the genus Cystoseira. Phytochemistry 32: 961–966.

    Google Scholar 

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Authors and Affiliations

  1. Laboratoire d'Analyse et Valorisation des Biomolécules, Université d'Aix-Marseille III, BP 157, F-13388, Marseille cedex 13, France

    Robert Valls

  2. Laboratoire de Recherches de Chimie Marine des Organometalliques, Université de Toulon et du Var, BP 132, F-83957, La Garde cedex, France

    Louis Piovetti & Annie Praud

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  1. Robert Valls
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  2. Louis Piovetti
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  3. Annie Praud
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Valls, R., Piovetti, L. & Praud, A. The use of diterpenoids as chemotaxonomic markers in the genus Cystoseira . Hydrobiologia 260, 549–556 (1993). https://doi.org/10.1007/BF00049069

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