Metabolites-BOC Sciences


(+)-Aeroplysinin-1 - CAS 28656-91-9

Catalog number: BBF-04190

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Catalog Number BBF-04190
CAS 28656-91-9
Description (+)-Aeroplysinin-1 is a metabolite originally isolated from the marine sponge V. aerophoba with diverse biological activity. It is a tertiary alcohol.
Related CAS55057-73-3
Molecular Formula C9H9Br2NO3
Molecular Weight 338.98
Synonyms NSC 170364; Aeroplysinin 1; (+)-shy-Aeroplysinin-1; (1S,6R)-3,5-Dibromo-1,6-dihydroxy-4-methoxy-2,4-cyclohexadiene-1-acetonitrile; Aeroplysinin; Aeroplysinin I; (1S-trans)-3,5-dibromo-1,6-dihydroxy-4-methoxy-2,4-cyclohexadiene-1-acetonitrile
IUPAC Name 2-[(1S,6R)-3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl]acetonitrile
Canonical SMILES COC1=C(C(C(C=C1Br)(CC#N)O)O)Br
InChI InChI=1S/C9H9Br2NO3/c1-15-7-5(10)4-9(14,2-3-12)8(13)6(7)11/h4,8,13-14H,2H2,1H3/t8-,9-/m0/s1
Boiling Point 479.6°C at 760 mmHg
Melting Point 120-121°C
Purity ≥95%
Density 2.01 g/cm3
Solubility Soluble in Acetone, Methanol
Appearance Solid Powder
1.Aeroplysinin-1, a Sponge-Derived Multi-Targeted Bioactive Marine Drug.
García-Vilas JA1,2, Martínez-Poveda B3, Quesada AR4,5, Medina MÁ6,7. Mar Drugs. 2015 Dec 22;14(1):1. doi: 10.3390/md14010001.
Organisms lacking external defense mechanisms have developed chemical defense strategies, particularly through the production of secondary metabolites with antibiotic or repellent effects. Secondary metabolites from marine organisms have proven to be an exceptionally rich source of small molecules with pharmacological activities potentially beneficial to human health. (+)-Aeroplysinin-1 is a secondary metabolite isolated from marine sponges with a wide spectrum of bio-activities. (+)-Aeroplysinin-1 has potent antibiotic effects on Gram-positive bacteria and several dinoflagellate microalgae causing toxic blooms. In preclinical studies, (+)-aeroplysinin-1 has been shown to have promising anti-inflammatory, anti-angiogenic and anti-tumor effects. Due to its versatility, (+)-aeroplysinin-1 might have a pharmaceutical interest for the treatment of different pathologies.
2.The brominated compound aeroplysinin-1 inhibits proliferation and the expression of key pro- inflammatory molecules in human endothelial and monocyte cells.
Martínez-Poveda B1, García-Vilas JA, Cárdenas C, Melgarejo E, Quesada AR, Medina MA. PLoS One. 2013;8(1):e55203. doi: 10.1371/journal.pone.0055203. Epub 2013 Jan 28.
Aeroplysinin-1 is a brominated antibiotic used by some sponges for defense against bacterial pathogen invasion. Aeroplysinin-1 has a wide spectrum of anti-tumoral action and behaves as a potent anti-angiogenic compound for bovine aortic endothelial cells. In this study, we demonstrate anti-angiogenic effects of aeroplysinin-1 on human endothelial cells. Furthermore, the response of angiogenesis related genes to aeroplysinin-1 treatment was studied in human endothelial cells by using gene arrays. The major changes were observed in thrombospondin 1 (TSP-1) and monocyte chemoattractant protein-1 (MCP-1), both of which were down-regulated. These inhibitory effects of aeroplysinin-1 were confirmed by using independent experimental approaches. To have a deeper insight on the anti-inflammatory effects of aeroplysinin-1 in endothelial cells, cytokine arrays were also used. This experimental approach confirmed effects on MCP-1 and TSP-1 and showed down-regulation of several other cytokines.
3.An aeroplysinin-1 specific nitrile hydratase isolated from the marine sponge Aplysina cavernicola.
Lipowicz B1, Hanekop N, Schmitt L, Proksch P. Mar Drugs. 2013 Aug 21;11(8):3046-67. doi: 10.3390/md11083046.
A nitrile hydratase (NHase) that specifically accepts the nitrile aeroplysinin-1 (1) as a substrate and converts it into the dienone amide verongiaquinol (7) was isolated, partially purified and characterized from the Mediterranean sponge Aplysina cavernicola; although it is currently not known whether the enzyme is of sponge origin or produced by its symbiotic microorganisms. The formation of aeroplysinin-1 and of the corresponding dienone amide is part of the chemical defence system of A. cavernicola. The latter two compounds that show strong antibiotic activity originate from brominated isoxazoline alkaloids that are thought to protect the sponges from invasion of bacterial pathogens. The sponge was shown to contain at least two NHases as two excised protein bands from a non denaturating Blue Native gel showed nitrile hydratase activity, which was not observed for control samples. The enzymes were shown to be manganese dependent, although cobalt and nickel ions were also able to recover the activity of the nitrile hydratases.
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