Simocyclinone D4

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Category Antibiotics
Catalog number BBF-02913
CAS
Molecular Weight 897.83
Molecular Formula C46H43NO18

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Description

It is produced by the strain of Streptomyces antibioticus Tu 6040. It has moderate anti-gram-positive bacteria activity and has inhibitory effect on a variety of tumor cells. It inhibits HMO2, MCF7 and HEP G2 cells with GI50 (μmol/L) of 0.30, 5.6 and 8.5, respectively.

Specification

IUPAC Name [(2R,3R,4R,6R)-3-acetyloxy-2-methyl-6-(2,7,9,11,13-pentahydroxy-5-methyl-3,18-dioxo-19-oxapentacyclo[8.8.1.01,10.02,7.012,17]nonadeca-4,12(17),13,15-tetraen-14-yl)oxan-4-yl] (2E,4E,6E,8E)-10-[(4,7-dihydroxy-2-oxochromen-3-yl)amino]-10-oxodeca-2,4,6,8-tetraenoate
Canonical SMILES CC1C(C(CC(O1)C2=C(C3=C(C=C2)C(=O)C45C(C3O)(O4)C(CC6(C5(C(=O)C=C(C6)C)O)O)O)O)OC(=O)C=CC=CC=CC=CC(=O)NC7=C(C8=C(C=C(C=C8)O)OC7=O)O)OC(=O)C
InChI InChI=1S/C46H43NO18/c1-21-16-31(50)45(60)43(59,19-21)20-32(51)44-41(57)35-27(40(56)46(44,45)65-44)15-14-25(37(35)54)29-18-30(39(22(2)61-29)62-23(3)48)63-34(53)11-9-7-5-4-6-8-10-33(52)47-36-38(55)26-13-12-24(49)17-28(26)64-42(36)58/h4-17,22,29-30,32,39,41,49,51,54-55,57,59-60H,18-20H2,1-3H3,(H,47,52)/b6-4+,7-5+,10-8+,11-9+/t22-,29-,30-,32?,39-,41?,43?,44?,45?,46?/m1/s1
InChI Key BYRCKZGAZLSMGB-BAPBEFBESA-N

Properties

Appearance Yellow Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Neoplastics (Tumor)
Melting Point >200°C
Solubility Soluble in Methanol

Reference Reading

1. Simocyclinones: diversity of metabolites is dependent on fermentation conditions
J Schimana, M Walker, A Zeeck, P Fiedler J Ind Microbiol Biotechnol. 2001 Sep;27(3):144-8. doi: 10.1038/sj.jim.7000024.
Simocyclinones, a novel group of angucyclinone antibiotics, are produced by Streptomyces antibioticus Tü 6040. The compounds show antibacterial and antitumor properties. In submerged cultivation, the production of simocyclinones is strongly dependent on the carbon and nitrogen sources used in a chemically defined medium. Productivity of distinct components and diversity of simocyclinone compounds are influenced by the medium composition. Four series of simocyclinone compounds were detected by high-performance liquid chromatography (HPLC) diode array detector (DAD) and HPLC electrospray ionization (ESI) mass spectrometry (MS) analysis, isolated and the structures determined by nuclear magnetic resonance (NMR) techniques. Under optimized conditions, simocyclinone D8 was produced in an amount of 300 mg l(-1) and simocyclinone C4 in a concentration up to 50 mg l(-1).
2. Simocyclinones, novel cytostatic angucyclinone antibiotics produced by Streptomyces antibioticus Tü 6040. I. Taxonomy, fermentation, isolation and biological activities
J Schimana, H P Fiedler, I Groth, R Süssmuth, W Beil, M Walker, A Zeeck J Antibiot (Tokyo). 2000 Aug;53(8):779-87. doi: 10.7164/antibiotics.53.779.
Two novel angucyclinone-type antibiotics, simocyclinones D4 and D8, were detected in the mycelium extract of Streptomyces antibioticus Tü 6040 by HPLC-diode-array and HPLC-electrospray-mass-spectrometry screening. The compounds show antibiotic activities against Gram-positive bacteria and cytostatic effects on various tumor cell lines.
3. Simocyclinones, novel cytostatic angucyclinone antibiotics produced by Streptomyces antibioticus Tü 6040 II. Structure elucidation and biosynthesis
Meike Holzenkämpfer, Martina Walker, Axel Zeeck, Judith Schimana, Hans-Peter Fiedler J Antibiot (Tokyo). 2002 Mar;55(3):301-7. doi: 10.7164/antibiotics.55.301.
The simocyclinones D4 (1) and D8 (2), members of a novel class of antibiotics, were isolated from the mycelial extract of Streptomyces antibioticus Tü 6040 and consist of angucyclinone, deoxysugar, octatetraene dicarboxylate and aminocoumarin structural elements. The structure elucidation was done by one and two dimensional NMR experiments, and other spectroscopic methods in combination with incorporation experiments using 13C labelled precursors.

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