Bromotyrosine-derived metabolites from an Indonesian marine sponge in the family Aplysinellidae (Order Verongiida)

Dai, Jingqiu; Parrish, Stephen M.; Yoshida, Wesley Y.; Yip, M.L. Richard; Turkson, James; Kelly, Michelle; Williams, Philip G.

doi:10.1016/j.bmcl.2015.11.086

Cited by 19 publications

(17 citation statements)

References 19 publications

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“…All of this information allowed us to establish the structure of 1 , named anomoian B, as having a framework (tyrosine)–(“3-aminopropanol”)–(tyramine), similar to that found in the purpuramines. 6 , 8 …”

Section: Resultsmentioning

confidence: 99%

“… 1 However, the bromotyrosine derivatives that are distinctive of this type of sponges 2 have been used as chemotaxonomic markers and have been proved to be a useful tool to facilitate taxonomic identification. 3 Since the first report of (+)-aeroplysinin-1, 3 marine sponges of the order Verongida have been found to produce many bromotyrosine derivatives such as aerothionin, 4 purealidins, 5 , 6 purpurealidins, 7 purpuramines, 6 , 8 aplysamines, 3 pseudoceralidinone A, 9 and purealines. 10 Despite this, Verongida is not the only order of sponges where bromotyrosine derivatives have been found.…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxic Anomoian B and Aplyzanzine B, New Bromotyrosine Alkaloids from Indonesian Sponges

et al. 2017

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Two new bromotyrosine derivatives, anomoian B (1) and aplyzanzine B (2), were isolated, respectively, from the organic extracts of a Verongida sponge belonging to the Hexadella genus and from a two-sponge association (Jaspis sp. and Bubaris sp.), both collected off the coast of Indonesia. The planar structure of 1 and 2 was determined by 1D and 2D NMR experiments and by high-resolution mass spectrometry, while their absolute stereochemistry was assigned by comparison with optical rotation values of known bromotyrosines and by chemical degradation. Both compounds showed moderate antiproliferative activity against a panel of different cancer cell lines. Their cytotoxic activity is facilitated through the induction of apoptosis, which is mediated neither by the generation of reactive oxygen species nor by the inhibition of histone deacetylases in these cell lines.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cytotoxic Anomoian B and Aplyzanzine B, New Bromotyrosine Alkaloids from Indonesian Sponges

et al. 2017

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“…Bromotyrosines are a large and structurally diverse group of bromine-containing marine alkaloids which have shown a variety of biological functions including antimicrobial, antiviral, antifungal and in particular, anticancer activity [5,6,7,8] Bromotyrosines are mainly isolated from the marine sponges of the order Verongida. For representative articles about secondary metabolites of Verongida order, see, for example, Fattorusso group’s work [9,10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antiproliferative Activity of Marine Bromotyrosine Purpurealidin I and Its Derivatives

et al. 2018

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The first total synthesis of the marine bromotyrosine purpurealidin I (1) using trifluoroacetoxy protection group and its dimethylated analog (29) is reported along with 16 simplified bromotyrosine derivatives lacking the tyramine moiety. Their cytotoxicity was evaluated against the human malignant melanoma cell line (A-375) and normal skin fibroblast cells (Hs27) together with 33 purpurealidin-inspired simplified amides, and the structure–activity relationships were investigated. The synthesized simplified analogs without the tyramine part retained the cytotoxic activity. Purpurealidin I (1) showed no selectivity but its simplified pyridin-2-yl derivative (36) had the best improvement in selectivity (Selectivity index 4.1). This shows that the marine bromotyrosines are promising scaffolds for developing cytotoxic agents and the full understanding of the elements of their SAR and improving the selectivity requires further optimization of simplified bromotyrosine derivatives.

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“…Bromotyrosine alkaloids are a large group of marine sponge metabolites mainly from the order Verongida, found at the coasts of Southeast Asia, Oceania, Japan and China [ 4 – 7 ]. Sponges have already shown to be a very fertile source of new toxins as they contain many secondary metabolites [ 8 , 9 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel purpurealidin analogs and evaluation of their effect on the cancer-relevant potassium channel KV10.1

et al. 2017

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In the search for novel anticancer drugs, the potassium channel KV10.1 has emerged as an interesting cancer target. Here, we report a new group of KV10.1 inhibitors, namely the purpurealidin analogs. These alkaloids are produced by the Verongida sponges and are known for their wide variety of bioactivities. In this study, we describe the synthesis and characterization of 27 purpurealidin analogs. Structurally, bromine substituents at the central phenyl ring and a methoxy group at the distal phenyl ring seem to enhance the activity on KV10.1. The mechanism of action of the most potent analog 5 was investigated. A shift of the activation curve to more negative potentials and an apparent inactivation was observed. Since KV10.1 inhibitors can be interesting anticancer drug lead compounds, the effect of 5 was evaluated on cancerous and non-cancerous cell lines. Compound 5 showed to be cytotoxic and appeared to induce apoptosis in all the evaluated cell lines.

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Bromotyrosine-derived metabolites from an Indonesian marine sponge in the family Aplysinellidae (Order Verongiida)

Cited by 19 publications

References 19 publications

Cytotoxic Anomoian B and Aplyzanzine B, New Bromotyrosine Alkaloids from Indonesian Sponges

Cytotoxic Anomoian B and Aplyzanzine B, New Bromotyrosine Alkaloids from Indonesian Sponges

Synthesis and Antiproliferative Activity of Marine Bromotyrosine Purpurealidin I and Its Derivatives

Synthesis of novel purpurealidin analogs and evaluation of their effect on the cancer-relevant potassium channel KV10.1

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