New Aminophenoxazinones from a Marine Halomonas sp.: Fermentation, Structure Elucidation, and Biological Activity.

Bitzer, Jens; Grosse, Thomas; Wang, Linzhu; Lang, Siegmund; Beil, Winfried; Zeeck, Axel

doi:10.1002/chin.200633233

Cited by 9 publications

(12 citation statements)

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“…Furthermore, the 13 C-spectrum revealed ten quaternary C-atoms, three with a chemical shift lower than 165 ppm. With regard to the UV-spectrum of 1, with absorption maxima at 239, 259, 411 and 428 nm, strong similarities were found to the UV spectrum of 3 (237, 412 and 431 nm) [4]. Therefore, it was concluded that 1 was structurally related to 2-aminophenoxazin-3-one.…”

Section: Structure Elucidationmentioning

confidence: 89%

“…It was shown that in contrast to 4 this type of aminophenoxazinone does not intercalate in DNA, but causes an arrest of the cells in the G1 phase and forces cells directly to apoptosis [24]. The recently described new aminophenoxazinones isolated from a marine Halomonas strain, 2-amino-6-hydroxyphenoxazin-3-one and 2-amino-8-benzoyl-6-hydroxyphenoxazin-3-one [4], showed moderate cytotoxic activity against different human tumor cell lines. The new aminophenoxazinones described in this paper, 1 and 2 from Streptomyces griseus Acta 2871, having an unusual substitution pattern of the core structure, exhibited a strong inhibition of human hepatocellular carcinoma cells; 2 very strongly inhibited human breast carcinoma cells.…”

Section: Discussionmentioning

confidence: 99%

“…The compounds were named elloxazinone A (1) and elloxazinone B (2) respectively. These data did not correspond with those of other phenoxazinone-type pigments that are known to be widely distributed in nature, such as 2-aminophenoxazin-3-one (3) [3] from a streptomycete strain and three derivatives thereof isolated from a marine Halomonas strain [4], 2-ethanolamino-phenoxazin-3-one from a Streptomyces thioluteus strain [5], 2-amino-1-carboxy-phenoxazin-3-one from a Nocardiaceae strain [6], texazone from an unidentified actinomycete strain [7], chandrananimycins from a marine Actinomadura strain [8], as the fungal pigments cinnabarin [9] and tramesanguin [10]. The present work describes the fermentation, isolation and structure elucidation of elloxazinones and their biological activity.…”

Section: Introductionmentioning

confidence: 90%

“…Therefore, it was concluded that 1 was structurally related to 2-aminophenoxazin-3-one. The 2-aminophenoxazin-3-one core structure includes one C atom with a chemical shift lower than 165 ppm [4]. Therefore the two additional C atoms of 1 with a chemical shift of 170.1 and 165.3 ppm suggested a carboxylic acid, an amide or an ester group as substituents of the core structure.…”

Section: Structure Elucidationmentioning

confidence: 99%

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Elloxazinones A and B, New Aminophenoxazinones from Streptomyces griseus Acta 2871†

et al. 2007

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Two new aminophenoxazinone compounds with antitumor activity, elloxazinone A and B, were isolated from the culture filtrate of Streptomyces griseus Acta 2871. Their chemical structures were determined by mass spectrometry, NMR spectroscopy and X-ray analysis. Elloxazinones A and B showed a moderate inhibition of the proliferation of human cells from gastric adenocarcinoma in vitro but a strong inhibition of hepatocellular carcinoma cells whereas elloxazinone B strongly inhibited the proliferation of human breast carcinoma cells.

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Section: Structure Elucidationmentioning

confidence: 89%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 90%

Section: Structure Elucidationmentioning

confidence: 99%

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Elloxazinones A and B, New Aminophenoxazinones from Streptomyces griseus Acta 2871†

et al. 2007

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“…Some new aminophenoxazinones alkaloids isolated from a marine bacteria, Halomonas sp. have shown antibacterial and cytotoxic activities against some tumor cell lines, HM02 (gastric adecocarcinoma), HepG2 (hepatocellular carcinoma) and MCF-7 (breat adecocarcinoma) [26]. Moreover, some new terpenoids, namely aspergiterpenoid A, (-)-sydonol, and (-)-sydonic acid have been isolated [27].…”

Section: Effect Of Methanol Extract and Fractions In Inhibiting Spla2mentioning

confidence: 99%

Anti-Inflammatory Activity of Bacteria Associated With Marine Sponge (Haliclona Amboinensis) via Reducting No Production and Inhibiting Cyclooxygenase-1, Cyclooxygenase-2, and Secretory Phospholipase A2 Activities

Andriani

Marlina

Mohamad

et al. 2017

Asian J Pharm Clin Res

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Objective: This study aimed to investigate the anti-inflammatory activity of methanol extract and fractions of bacteria associated with sponge (Haliclona amboinensis) and to evaluate their effect in reducing NO production and inhibiting cyclooxygenase-1 (COX-1), cyclooxgenase-2 (COX-2) and secretory phospholipase A2 (sPLA2) activity.Methods: All bacterial isolates were cultured and supernatants were collected for the extraction of secondary metabolites using diaion HP-20 to obtain methanol extracts. Evaluation of cytotoxicity property was carried out on macrophage cell lines (RAW264.7) by 3-(4,5-dimethylthiazol-2-yl) 2,5-diphenyl tetrazoliumbromide assay. Anti-inflammatory screening was done by inducible nitric oxide assay on RAW264.7 cell lines with lipopolysaccharide (LPS) stimulation. Dianion HP-20 was used to remove salt content. A selected methanol extract was subjected to further fractionations by C-18 reverse phase and their anti-inflammatory potential was evaluated by COX-1 and COX-2, and sPLA2 enzymatic assay.Results: Seven methanol extracts showed no cytotoxic property against RAW 264.7 cell line (inhibitory concentration 50% > 30 µg/ml) and selected for anti-inflammatory screening assay. Result showed methanol extract HM 1.2 reduced NO production >80% and it has been selected for phytochemical screening, further fractionations and assay. Phytochemical screening showed alkaloids and terpenoids present in the HM 1.2. The HM 1.2 and its fractions (F1, F2, F1C1, F1C2, F1C3, and F1C4) were proven to inhibit COX-1, COX-2, and sPLA2 activity in the range of 60.516-116.886%, 20.554-116.457%, and 70.2667-114.8148%, respectively. Conclusions:This study revealed that bacteria associated with H. amboinensis have produced anti-inflammatory activity via reducing NO production and inhibiting COX-1, COX-2, and sPLA2 activity.

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Synthesis of cinnabarinic acid by metabolically engineered Pseudomonas chlororaphis GP72

Yue

Song

et al. 2019

Biotech & Bioengineering

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Cinnabarinic acid is a valuable phenoxazinone that has broad applications in the pharmaceutical, chemical, and dyeing industries. However, few studies have investigated the production of cinnabarinic acid or its derivatives using genetically engineered microorganisms. Herein, an efficient synthetic pathway of cinnabarinic acid was designed and constructed in Pseudomonas chlororaphis GP72 for the first tim, which was more straightforward and robust than the known eukaryotic biosynthetic pathways. First, we screened and identified trans‐2,3‐dihydro‐3‐hydroxyanthranilic acid (DHHA) dehydrogenases from Escherichia coli MG1655 (encoded by entA), Streptomyces sp. NRRL12068 (encoded by bomO) and Streptomyces chartreusis NRRL3882 (encoded by calB3) based on the structural similarity of the substrate and product, and the DHHA dehydrogenase encoded by calB3 was selected for the synthesis of cinnabarinic acid due to its high DHHA conversion rate. Subsequently, cinnabarinic acid was synthesized by the expression of the DHHA dehydrogenase CalB3 and the phenoxazinone synthase CotA in the DHHA‐producing strain P. chlororaphis GP72, resulting in a cinnabarinic acid titer of 20.3 mg/L at 48 hr. Further fermentation optimization by the addition of Cu2+, H2O2, and with adding glycerol increased cinnabarinic acid titer to 136.2 mg/L in shake flasks. The results indicate that P. chlororaphis GP72 may be engineered as a microbial cell factory to produce cinnabarinic acid or its derivatives from renewable bioresources.

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New Aminophenoxazinones from a Marine Halomonas sp.: Fermentation, Structure Elucidation, and Biological Activity.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 9 publications

References 1 publication

Elloxazinones A and B, New Aminophenoxazinones from Streptomyces griseus Acta 2871†

Elloxazinones A and B, New Aminophenoxazinones from Streptomyces griseus Acta 2871†

Anti-Inflammatory Activity of Bacteria Associated With Marine Sponge (Haliclona Amboinensis) via Reducting No Production and Inhibiting Cyclooxygenase-1, Cyclooxygenase-2, and Secretory Phospholipase A2 Activities

Synthesis of cinnabarinic acid by metabolically engineered Pseudomonas chlororaphis GP72

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