Fujianmycin A

Fujianmycin A

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Category Antibiotics
Catalog number BBF-01448
CAS 96695-57-7
Molecular Weight 322.31
Molecular Formula C19H14O5

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Description

It is produced by the strain of Streptomyces sp. Fujianmycin A has anti-subtilis activity.

Specification

Synonyms (3s,4r)-4,8-dihydroxy-3-methyl-3,4-dihydrotetraphene-1,7,12(2h)-trione; O-Demethylrubiginone A2; 4,8-Dihydroxy-3-methyl-3,4-dihydrotetraphene-1,7,12(2H)-trione
IUPAC Name (3S,4R)-4,8-dihydroxy-3-methyl-3,4-dihydro-2H-benzo[a]anthracene-1,7,12-trione
Canonical SMILES CC1CC(=O)C2=C(C1O)C=CC3=C2C(=O)C4=C(C3=O)C(=CC=C4)O
InChI InChI=1S/C19H14O5/c1-8-7-13(21)14-10(17(8)22)5-6-11-16(14)19(24)9-3-2-4-12(20)15(9)18(11)23/h2-6,8,17,20,22H,7H2,1H3/t8-,17+/m0/s1
InChI Key WWVNIBVFNYKUQY-WNWIJWBNSA-N

Properties

Appearance Yellow Acicular Crystalline
Antibiotic Activity Spectrum fungi
Melting Point 182-185°C

Reference Reading

1. Saccharosporones A, B and C, cytotoxic antimalarial angucyclinones from Saccharopolyspora sp. BCC 21906
Chollaratt Boonlarppradab, Chanwit Suriyachadkun, Pranee Rachtawee, Wilunda Choowong J Antibiot (Tokyo). 2013 Jun;66(6):305-9. doi: 10.1038/ja.2013.16. Epub 2013 Apr 3.
Three new angucyclinones, saccharosporones A, B and C, together with (+)-ochromycinone, (+)-rubiginone B2, tetrangulol methyl ether and fujianmycin A, were obtained from fermentation of the terrestrial actinomycete of the genus Saccharopolyspora BCC 21906 isolated from a soil collected in Chanthaburi Province, Thailand. Structures of the new compounds and their relative configurations were assigned by NMR spectral data interpretation. Saccharosporones A and B exhibited antimalarial activity against Plasmodium falciparum K1 with IC50 values of 4.1 and 3.9 μM. Both metabolites also possessed cytotoxic activities against cancer cell lines (KB, MCF-7 and NCI-H187) and nonmalignant Vero cell, while saccharosporone C only showed cytotoxic activity against NCI-H187.
2. Angucyclinones from an Indonesian Streptomyces sp
Serge Fotso, Taifo Mahmud, T Mark Zabriskie, Dwi Andreas Santosa, Sulastri, Philip J Proteau J Nat Prod. 2008 Jan;71(1):61-5. doi: 10.1021/np0704102. Epub 2007 Dec 15.
Six new angucyclinone polyketides named panglimycins A-F were isolated together with the three known metabolites (+)-fujianmycin A, (+)-ochromycinone, and emycin C from the bioassay-guided fractionation of the extract of the Indonesian Streptomyces strain ICBB8230. The new compounds are highly oxygenated angucyclinones that appear to be biosynthetically derived from ochromycinone or fujianmycin. Their structures were determined by X-ray crystal analysis, interpretation of 1D- and 2D-NMR spectra, and comparison of the data with those of structurally related known natural products. Despite structural similarities to angucyclinones with antibiotic activities, the panglimycins did not exhibit any growth inhibition when tested against several bacteria and fungi.

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