Comparative study of the halogenated tyrosine derivatives from Demospongiae (Porifera)

Makarieva, Tatyana N.; Stonik, Valentin A.; Alcolado, Pedro M.; Elyakov, Y.B.

doi:10.1016/0305-0491(81)90159-0

Cited by 19 publications

(25 citation statements)

References 7 publications

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“…In agreement with the analysis performed by Makarieva et al 10 our investigation confirmed the presence of aeroplysinin 1, 1, 12 and 2 13 as secondary metabolites of V. gigantea. In addition, our specimen yielded bromotyrosinederived compounds 6-17, a sesquiterpene hydroquinone ether (18), 14 and a bromotryptamine derivative (19).…”

supporting

confidence: 95%

Chemistry of Verongida Sponges. 10. Secondary Metabolite Composition of the Caribbean Sponge Verongula gigantea

et al. 2000

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A detailed analysis of the secondary metabolites of the Caribbean sponge Verongula gigantea has been performed. A number of bromotyrosine derivatives, 1, 2, and 6-17, were identified, one of which (17) is a novel compound. Its structure was determined on the basis of spectroscopic evidence. Additionally, aureol (18) and 5, 6-dibromo-N,N-dimethyltryptamine (19) were isolated from one of the five analyzed specimens.

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supporting

confidence: 95%

Chemistry of Verongida Sponges. 10. Secondary Metabolite Composition of the Caribbean Sponge Verongula gigantea

et al. 2000

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“…As shown in a study by Makarieva et al involving 25 Cuban sponges, only those belonging to the order Aplysinidae were able to produce brominated tyrosine derivatives. Out of this group, only four, namely Aplysina archeri, Verongula rigida, V. gigantea and Aiolochroia crassa were able to synthesize aeroplysinin-1, but in strikingly different amounts in relation to sponge dry weight [72]. Both reports give further evidence for a bioconversion of sponge alkaloids, as shown for A. aerophoba and A. cavernicola [66] [72].…”

Section: Aeroplysinin-1mentioning

confidence: 70%

Sponge Derived Bromotyrosines: Structural Diversity through Natural Combinatorial Chemistry

Niemann

Marmann

Lin

et al. 2015

Natural Product Communications

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Sponge derived bromotyrosines are a multifaceted class of marine bioactive compounds that are important for the chemical defense of sponges but also for drug discovery programs as well as for technical applications in the field of antifouling constituents. These compounds, which are mainly accumulated by Verongid sponges, exhibit a diverse range of bioactivities including antibiotic, cytotoxic and antifouling effects. In spite of the simple biogenetic building blocks, which consist only of brominated tyrosine and tyramine units, an impressive diversity of different compounds is obtained through different linkages between these precursors and through structural modifications of the side chains and/or aromatic rings resembling strategies that are known from combinatorial chemistry. As examples for bioactive, structurally divergent bromotyrosines psammaplin A, Aplysina alkaloids featuring aerothionin, aeroplysinin-1 and the dienone, and the bastadins, including the synthetically derived hemibastadin congeners, have been selected for this review. Whereas all of these natural products are believed to be involved in the chemical defense of sponges, some of them may also be of particular relevance to drug discovery due to their interaction with specific molecular targets in eukaryotic cells. These targets involve important enzymes and receptors, such as histone deacetylases (HDAC) and DNA methyltransferases (DNMT), which are inhibited by psammaplin A, as well as ryanodine receptors that are targeted by bastadine type compounds. The hemibastadins such as the synthetically derived dibromohemibastadin are of particular interest due to their antifouling activity. For the latter, a phenoloxidase which catalyzes the bioglue formation needed for firm attachment of fouling organisms to a given substrate was identified as a molecular target. The Aplysina alkaloids finally provide a vivid example for dynamic wound induced bioconversions of natural products that generate highly efficient chemical weapons precisely when and where needed.

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“…Makarieva et al later reported the isolation of the (-)-enantiomer of LL-PPA216 (66, [α] D = −6.5°) from Aplisina sp. collected in Cuba (55). Another isomer 67 was identified from the marine sponge Aplysina aerophoba by Norte et al in 1988 and its absolute configuration was determined as R, R by X-ray analysis (21).…”

Section: Introductionmentioning

confidence: 99%

The Marine Bromotyrosine Derivatives

Peng¹,

Jing²,

Hamann³

2005

The Alkaloids: Chemistry and Biology

101

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Comparative study of the halogenated tyrosine derivatives from Demospongiae (Porifera)

Cited by 19 publications

References 7 publications

Chemistry of Verongida Sponges. 10. Secondary Metabolite Composition of the Caribbean Sponge Verongula gigantea

Chemistry of Verongida Sponges. 10. Secondary Metabolite Composition of the Caribbean Sponge Verongula gigantea

Sponge Derived Bromotyrosines: Structural Diversity through Natural Combinatorial Chemistry

The Marine Bromotyrosine Derivatives

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