Two New Bromotyrosine-Derived Metabolites From an Australian Marine Sponge, Aplysina sp

Xynas, R; Capon, Robert J.

doi:10.1071/ch9891427

Cited by 65 publications

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“…[21] and detected in all Aplysinidea species. The optical rotation confirmed that the absolute configurations of metabolites 6 -8 were the same as those reported in the literature [13] [20] [21].…”

supporting

confidence: 88%

“…Although formation of 3 during extraction with EtOH cannot be ruled out, its bioactivity was considered worth to be investigated. In comparison to 4 and its 4-epimer, 5, the presence of the EtO group at C(1) in 3 causes upfield shifts of the 13 C-NMR signals of the CH 2 (7) C-atom by Dd À 1.3 and the amide C-atom by Dd À 0.8 C(8), and a downfield shift of Dd þ 1.1 for C(1).…”

mentioning

confidence: 97%

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Bioactive Metabolites from the Sponge Suberea sp.

Shaker¹,

Zinecker²,

Ghani³

et al. 2010

Chemistry & Biodiversity

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Two new brominated compounds, subereaphenol K (2) and 2-(3,5-dibromo-1-ethoxy-4-oxocyclohexa-2,5-dien-1-yl)acetamide (3), together with subereaphenol B (methyl 2-(2,4-dibromo-3,6-dihydroxyphenyl)acetate; 1) with a revised structure, and five dibromotyrosine-derived metabolites, 4-8, were isolated from the sponge Suberea sp. and characterized by 1D- and 2D-NMR spectroscopic and HR-MS spectrometric data. Compounds 1, 2, 6, and 8 exhibited various weak or moderate bioactivities, including antimicrobial and cytotoxic activities. Furthermore, compounds 1 and 2 inhibited human recombinant phosphodiesterase 4 (PDE4) with IC₅₀ values of 2 μM, whereas compounds 6 and 8 were less active.

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confidence: 88%

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confidence: 97%

Bioactive Metabolites from the Sponge Suberea sp.

Shaker¹,

Zinecker²,

Ghani³

et al. 2010

Chemistry & Biodiversity

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“…23) Synthetic aplysamine-1 (3) and the hydrochloride salt of Nacetylpurpurealidin E (12-HCl) 24) were spectroscopically identical with reported data [13][14][15] (Chart 3). In conclusion, we succeeded in the first total synthesis of dispyrin (1) and purpurealidin E (2), and the chemical conversion of 2 to aplysamine-1 (3), from commercially available tyramine as a common starting material.…”

Section: Resultssupporting

confidence: 54%

“…4) Because of these interesting activities, a number of synthetic studies on these alkaloids have been reported. [5][6][7][8][9][10][11] Dispyrin (1) 12) isolated from Agelas dispar (Agelasidae) and purpurealidin E (2) 13) isolated from Psammaplysilla purpurea (Verongiidae) contain a structural motif similar to aplysamine-1 (3) 14,15) isolated from Pseudoceratina verroucosa (Aplysinellidae), a brominated phenol having a 3-dimethylamino-1-propane ( Fig. 1), known as the histamine H 3 receptor antagonist.…”

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confidence: 99%

Total Synthesis of Dispyrin, Purpurealidin E, and Aplysamine-1

Yoshida

Yamaguchi

2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…130) Related benzimidazole structures are WAY-361754 and analogs that exhibit improvement of cognitive functions in animal studies. 131) Enlargement of the alkylamine scaffold results in an amine-alkoxyphenyl one, which is related to that of the natural ligand aplysamine-1 132) (Fig. 5).…”

Section: )mentioning

confidence: 99%

Histamine H3 Receptor Antagonists Go to Clinics

Sander

Kottke

Stark

2008

Biological & Pharmaceutical Bulletin

184

118

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INTRODUCTIONThe biogenic amine histamine, 2-(1H-imidazol-4-yl)-ethanamine, is produced by decarboxylation of L-histidine and is implicated in a wide range of physiological and pathophysiological functions. It is metabolised by histamine N tmethyltransferase (HMT) and mono-or diaminoxidase. Histamine is mainly acting via four distinct metabotropic histamine receptor subtypes (H 1 R-H 4 R), which have meanwhile all been cloned. Whereas antagonists for H 1 R and H 2 R subtypes have been blockbusters in therapy of allergy and ulcer, respectively, antagonists for H 3 R and H 4 R subtypes are not on the market. The recently described H 4 R seems to be involved in inflammatory and immunomodulatory processes. H 3 Rs play a central role in neurotransmission of histamine and in control of many other neurotransmitters. Several antagonists are in preclinical and some in clinical stage of development. PHARMACOLOGICAL BACKGROUND Auto-and HeteroreceptorThe H 3 R was first described in 1983 as a presynaptic autoreceptor, which mediates synthesis of histamine and inhibition of its release from histaminergic neurons in slices of rat cerebral cortex. 1) Localisation studies in rodents show a predominance in distinct regions of the central nervous system (CNS) as the H 3 R is mainly located in cerebral cortex, hippocampus, amygdala, nucleus accumbens, globus pallidus, striatum, and hypothalamus 2-5) ( Fig. 1). In addition, it is expressed in the peripheral nervous system, e.g. in gastrointestinal tract, airways and cardiovascular system. 6) Molecular aspects of the receptor, [7][8][9][10] structure-activity relationships (SAR) of ligands, [11][12][13][14][15][16][17][18][19] and pharmacology [20][21][22][23][24][25][26] have recently been resumed in many excellent reviews. This contribution focuses on the development of clinical candidates and the multifaceted potential indications targeted.In mammalian brain histaminergic neurons originate in the tuberomammillary nucleus (TMN) spreading into above mentioned brain regions, where they control histamine levels by regulation of synthesis and liberation rates 27) and modulate different neuronal systems. 28) H 3 R expression is not solely restricted to histaminergic neurons: due to its function as a heteroreceptor it can be found on colocalised neurons, and H 3 R activation modulates the release of various important neurotransmitters, i.e. dopamine, [29][30][31][32][33] acetylcholine, [34][35][36][37] norepinephrine, 38,39) serotonin, 40,41) GABA, [42][43][44] glutamate, 45) and substance P. [46][47][48] Therefore, histaminergic neurons and the cross-linkage between major neurotransmitter systems are involved in many (patho)physiological brain functions, including vigilance, memory processes, feeding behaviour and locomotor activity (Fig. 2). Interneuron cross-talk and adaptive processes seem to be important factors in H 3 Rmediated signalling. Molecular AspectsThe human histamine H 3 receptor (hH 3 R) cDNA firstly described 1999 encodes a 445 amino acid protein and belongs to the his...

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Two New Bromotyrosine-Derived Metabolites From an Australian Marine Sponge, Aplysina sp

Cited by 65 publications

References 0 publications

Bioactive Metabolites from the Sponge Suberea sp.

Bioactive Metabolites from the Sponge Suberea sp.

Total Synthesis of Dispyrin, Purpurealidin E, and Aplysamine-1

Histamine H3 Receptor Antagonists Go to Clinics

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