Halogenated phenol and indole constituents of acorn worms
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Cited by (69)
Occurrence of halogenated natural products in highly consumed fish from polluted and unpolluted tropical bays in SE Brazil
2018, Environmental PollutionCitation 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 PollutionCitation 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 BiologyCitation 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 BiologyOral exposure of adult zebrafish (Danio rerio) to 2,4,6-tribromophenol affects reproduction
2010, Aquatic ToxicologyCitation 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).
Bromophenol accumulation and sediment contamination by the marine annelids Notomastus lobatus and Thelepus crispus
2005, Biochemical Systematics and Ecology