Halogenated phenol and indole constituents of acorn worms

https://doi.org/10.1016/0305-0491(80)90306-5Get rights and content

Abstract

  • 1.

    1. Distribution of halophenols and haloindoles in four species of Enteropneusta is reported.

  • 2.

    2. The “iodoform-like” odor of the animals is due to bromophenols in the genus Balanoglossus and to 3-haloindoles in the genera Ptychodera and Glossobalanus.

  • 3.

    3. Distribution of metabolites among different species may result from variation in competing halogenation and oxidation processes which operate from common precursors.

References (23)

  • D.B. Harper et al.

    Plant growth-regulating substances. XXXI. Metabolism of certain 2,6-disubstituted phenols within plant tissues

    Ann. Appl. Biol.

    (1971)
    D.B. Harper et al.

    Plant growth-regulating substances. XXXI. Metabolism of certain 2,6-disubstituted phenols within plant tissues

    Chem. Abstr.

    (1971)
  • Cited by (69)

    • Occurrence of halogenated natural products in highly consumed fish from polluted and unpolluted tropical bays in SE Brazil

      2018, Environmental Pollution
      Citation Excerpt :

      High concentrations of bromophenols and bromoanisoles were surprising because of their low log Kow values, suggesting possible high concentrations of these compounds in the water phase (Vetter, 2006). Many studies have detected bromophenols and bromoanisoles in a broad spectrum of marine organisms (Higa et al., 1980; Whitfield et al., 1999; Whitfield et al., 1999a,b; Flodin and Whitfield, 2000; Vetter and Janussen, 2005). Alonso et al. (2017) detected bromoindoles and bromoanisoles in dolphins (Tursiops truncatus) from coastal Rio de Janeiro and pointed out that the coral Sun (Tubastrea spp.) is a known producer of these substances in the Brazilian coast (Alonso et al., 2017).

    • Environmental concentrations and toxicology of 2,4,6-tribromophenol (TBP)

      2018, Environmental Pollution
      Citation Excerpt :

      Since its detection in the marine environment in the 1970s (Sheikh and Djerassi, 1975), TBP was found in a huge variety of marine organisms similar to at least 50 other brominated phenols (Gribble, 2000). It was for instance detected in marine algae (e.g. Ulva lacuta; Flodin et al., 1999; Flodin and Whitfield, 1999a), sponges (Whitfield et al., 1997) (e.g. Phorbas glaberrimus; Vetter and Janussen, 2005), phoronids (e.g. Phoronopsis viridis; Sheikh and Djerassi, 1975), mollusks (e.g. Tapes philippinarum and Ostrea rivularis; Chung et al., 2003), crustaceans (e.g. Metapenaeus ensis and Charybdis feriatus; Chung et al., 2003; Whitfield et al., 1988), hemichordates (e.g. Ptychodera flava and Balanaglossus carnosus; Higa and Scheuer, 1980; Sheikh and Djerassi, 1975), and fish (e.g. Siganus canaliculatus and Epinepheus areolatus; (Chung et al., 2003; Whitfield et al., 1998). Interestingly, only some of these groups actually synthesize TBP.

    • Polyhalogenated Alkaloids in Environmental and Food Samples

      2012, Alkaloids: Chemistry and Biology
      Citation Excerpt :

      Beside more complex larger halogenated natural products with an indole-building block (among them the well-known tyrian purple (39), which is produced by marine mollusks), there are also simple naturally produced bromoindoles (BIs) (40–42,44–49), 3-chloroindole, 6-bromo-3-chloroindole (43), and brominated 1-methylindoles (50–53) (Figure 14). Since the 1970s, different simple brominated indoles and 1-methylindoles were discovered in acorn worms, the red seaweed Laurentia sp. and the brittle star.101–105 The simple bromoindoles add a iodoform odor to these species.101,102

    • Occurrence of Halogenated Alkaloids

      2012, Alkaloids: Chemistry and Biology
    • Oral exposure of adult zebrafish (Danio rerio) to 2,4,6-tribromophenol affects reproduction

      2010, Aquatic Toxicology
      Citation Excerpt :

      In addition to production, TBP is formed by photolytic degradation of tetrabromobisphenol-A (TBBPA) (Eriksson and Jakobsson, 1998), which is one of the most used BFRs. Natural production of TBP has been proposed in marine organisms, such as marine worms and algae (Weber and Ernst, 1978; Higa et al., 1980; Chen et al., 1991; Whitfield et al., 1999; Gribble, 2000). TBP is detected in various environmental compartments; for example, in marine and fresh waters (IUCLID, 2003; Reineke et al., 2006; Sim et al., 2009), sediments (Watanabe et al., 1985; Tolosa et al., 1991; Sim et al., 2009), algae (Whitfield et al., 1999; Flodin and Whitfield, 2000), crustaceans (Whitfield et al., 1997), fish (Whitfield et al., 1998), marine mammals (Vetter and Janussen, 2005), human blood and milk (Hovander et al., 2002; Thomsen et al., 2002), indoor air and dust (Takigami et al., 2009), sewage sludge (Öberg et al., 2002), and in flue gas from combustion of bromine containing waste (Öberg et al., 1987).

    View all citing articles on Scopus
    View full text