Lithothamnin A, the First Bastadin-like Metabolite from the Red Alga <i>Lithothamnion fragilissimum</i>

Wyk, Albert W. W. Van; Zuck, Karina M.; McKee, Tawnya C.

doi:10.1021/np1006795

Cited by 15 publications

(21 citation statements)

References 21 publications

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“…In in vivo experiments DBHB, however, failed to increase the survival of B16F10 melanoma-bearing mice, which we suspected to be due to strong binding of the compound to serum albumin. The aforementioned bastadin like lithothamnins, which show meta-meta linkages between the aromatic rings, that have so far not been reported from sponges, also showed moderate cytotoxic properties, as demonstrated for lithothamnin A [92]. This compound exhibited antiproliferative activities against five human tumor cell lines, LOX (IC 50 = 9.5 µM), SNB-19 (IC 50 = 7.6 µM), OVCAR-3 (IC 50 = 7.6 µM), COLO-205 (IC 50 = 19.0 µM), and MOLT-4 (IC 50 = 19.0).…”

Section: Bastadins -Antifouling Agents Regulators Of Cellular Ca 2+homeostasis and Potential Anticancer Drug Candidatesmentioning

confidence: 82%

“…The facts that genes of flavin-dependent halogenases, enzymes which are presumably responsible for the incorporation of bromine into the aromatic moieties of bastadins, are known from sponge symbionts [15], and the occurrence of bastadin-like metabolites, called lithothamnins, in the red alga Lithothamnion fragilissimum [92], suggest that bastadin type compounds may perhaps either be of symbiotic origin or that symbionts are involved in the biosynthesis of bastadin type compounds.…”

Section: Bastadins -Antifouling Agents Regulators Of Cellular Ca 2+hmentioning

confidence: 99%

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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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Section: Bastadins -Antifouling Agents Regulators Of Cellular Ca 2+homeostasis and Potential Anticancer Drug Candidatesmentioning

confidence: 82%

Section: Bastadins -Antifouling Agents Regulators Of Cellular Ca 2+hmentioning

confidence: 99%

Sponge Derived Bromotyrosines: Structural Diversity through Natural Combinatorial Chemistry

Niemann

Marmann

Lin

et al. 2015

Natural Product Communications

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“…This metabolite is an unusual bastadin-like molecule with a unique meta-meta linkage between the aromatic rings. 426…”

Section: Red Algaementioning

confidence: 99%

Marine natural products

et al. 2013

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This review covers the literature published in 2011 for marine natural products, with 870 citations (558 for the period January to December 2011) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1152 for 2011), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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“…Only one halophenol is known from this family. Lithothamnin A ( 18 ), the first bastadin-like analogue isolated from a red alga, was described in 2011 from Lithothamnion fragilissimum collected east of Lighthouse Reef, Palau Island ( Figure 3 , Supplementary Table S1 ) [ 17 ]. Compound 18 , with five bromines, exhibited modest antiproliferative activity against several human tumor cell lines, including melanoma (LOX), astrocytoma (SNB-19), ovarian serous adenocarcinoma (OVCAR-3), colon adernocarcinoma (COLO-205), and acute lymphyoblastic leukemia (MOLT-4) cell lines, showing IC 50 values between 7.6 and 19.0 µM [ 17 ].…”

Section: Haloaryl Secondary Metabolites Isolated From Macroalgaementioning

confidence: 99%

Isolation and Potential Biological Applications of Haloaryl Secondary Metabolites from Macroalgae

et al. 2019

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Macroalgae have been reported as an important source of halogenated aromatic secondary metabolites, being the majority of these derivatives isolated from red algae. Halophenols and haloindoles are the most common haloaryl secondary metabolites isolated from these marine organisms. Nevertheless, some halogenated aromatic sesquiterpenes and naphthalene derivatives have also been isolated. Most of these secondary metabolites showed interesting biological activities, such as antitumor, antimicrobial, antidiabetic, and antioxidant. This review describes in a systematic way the distribution and natural occurrence of halogenated aromatic secondary metabolites from extracts of red, brown, and green algae, as well as biological activities reported for these compounds.

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Lithothamnin A, the First Bastadin-like Metabolite from the Red Alga Lithothamnion fragilissimum

Cited by 15 publications

References 21 publications

Sponge Derived Bromotyrosines: Structural Diversity through Natural Combinatorial Chemistry

Sponge Derived Bromotyrosines: Structural Diversity through Natural Combinatorial Chemistry

Marine natural products

Isolation and Potential Biological Applications of Haloaryl Secondary Metabolites from Macroalgae

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