Deoxyfusarubin

Deoxyfusarubin

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Category Others
Catalog number BBF-01346
CAS 132899-05-9
Molecular Weight 290.27
Molecular Formula C15H14O6

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Description

Deoxyfusarubin is produced by the strain of Nectria haematococca.

Specification

Synonyms 3,4-dihydro-3,9-dihydroxy-7-methoxy-3-methyl-1H-naphtho(2,3-c)pyran-5,10-dione
IUPAC Name 3,9-dihydroxy-7-methoxy-3-methyl-1,4-dihydrobenzo[g]isochromene-5,10-dione
Canonical SMILES CC1(CC2=C(CO1)C(=O)C3=C(C2=O)C=C(C=C3O)OC)O
InChI InChI=1S/C15H14O6/c1-15(19)5-9-10(6-21-15)14(18)12-8(13(9)17)3-7(20-2)4-11(12)16/h3-4,16,19H,5-6H2,1-2H3
InChI Key RYQOFJPFFVZQTC-UHFFFAOYSA-N

Properties

Boiling Point 584.6°C at 760 mmHg
Density 1.49 g/cm3

Reference Reading

1. 6-O-demethyl-5-deoxyfusarubin and its anhydro derivative produced by a mutant of the fungus Nectria haematococca blocked in fusarubin biosynthesis
D Parisot, M Devys, M Barbier J Antibiot (Tokyo). 1991 Jan;44(1):103-7. doi: 10.7164/antibiotics.44.103.
6-O-Demethyl-5-deoxyfursarubin and 6-O-demethyl-5-deoxyanhydrofusarubin have been isolated from the mutant redD169.yelY9 of the fungus Nectria haematococca blocked in fusarubin biosynthesis. These products were identified on the basis of physico-chemical data by comparison with known substances.
2. A highly diverse spectrum of naphthoquinone derivatives produced by the endophytic fungus Biatriospora sp. CCF 4378
Eva Stodůlková, Petr Man, Marek Kuzma, Jan Černý, Ivana Císařová, Alena Kubátová, Milada Chudíčková, Miroslav Kolařík, Miroslav Flieger Folia Microbiol (Praha). 2015 May;60(3):259-67. doi: 10.1007/s12223-014-0366-7. Epub 2014 Nov 22.
A strain of Biatriospora sp. CCF 4378 was tested for the production of secondary metabolites under submerged fermentation conditions. Eleven compounds were isolated from the culture broth, and the structures of these compounds were determined using HRMS, NMR and X-ray analysis. In addition to six known naphthoquinone derivatives, i.e. ascomycone A, ascomycone B, 6-deoxyfusarubine, 6-deoxyanhydrofusarubine, herbarine and balticol A, one derivative of 2-azaanthraquinone, 6-deoxybostrycoidine, was also identified. Four new natural pyranonaphthoquinones were found, and these natural products were pleorubrin A, pleorubrin B, pleorubrin C and pleorubrin D. The toxicity on human cell lines of the crude naphthoquinone fraction and pure 6-deoxybostrycoidin, ascomycone B, pleorubrin B and 6-deoxyfusarubin was tested. Ascomycone B and 6-deoxyfusarubin elicited rapid cytotoxicity at micromolar concentrations.

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