Sakyomicin C

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Category Antibiotics
Catalog number BBF-02852
CAS 86413-76-5
Molecular Weight 470.47
Molecular Formula C25H26O9

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Description

It is a Benzoquinone antibiotic produced by the strain of Nocardia sp. M-53. It has activity against gram-positive bacteria and mycobacteria. In vivo, 6 mg/kg of Sakyomicin C had no effect against sarcoma 180A and leukemia P338 cells.

Specification

Synonyms Benz[a]anthracene-1,7,12(2H)-trione,3,4,4a,12b-tetrahydro-3,4a,8-trihydroxy-3-methyl-12b-[[(2R,5R,6R)-tetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl]oxy]-, (3R,4aS,12bR)-; Benz[a]anthracene-1,7,12(2H)-trione,3,4,4a,12b-tetrahydro-3,4a,8-trihydroxy-3-methyl-12b-[(tetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)oxy]-, [3R-[3a,4ab,12bb(2R*,5R*,6R*)]]-
IUPAC Name (3R,4aS,12bR)-3,4a,8-trihydroxy-12b-[(2R,5R,6R)-5-hydroxy-6-methyloxan-2-yl]oxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione
Canonical SMILES CC1C(CCC(O1)OC23C(=O)CC(CC2(C=CC4=C3C(=O)C5=C(C4=O)C(=CC=C5)O)O)(C)O)O
InChI InChI=1S/C25H26O9/c1-12-15(26)6-7-18(33-12)34-25-17(28)10-23(2,31)11-24(25,32)9-8-14-20(25)22(30)13-4-3-5-16(27)19(13)21(14)29/h3-5,8-9,12,15,18,26-27,31-32H,6-7,10-11H2,1-2H3/t12-,15-,18-,23+,24-,25-/m1/s1
InChI Key DSMQDARJKCLOPP-PKASFQQMSA-N

Properties

Appearance Orange Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Mycobacteria
Boiling Point 782.1°C at 760 mmHg
Melting Point 143-145°C
Density 1.54 g/cm3
Solubility Soluble in Methanol, Chloroform

Reference Reading

1. Sakyomicins A, B, C and D: new quinone-type antibiotics produced by a strain of Nocardia. Taxonomy, production, isolation and biological properties
T Nagasawa, H Fukao, H Irie, H Yamada J Antibiot (Tokyo). 1984 Jul;37(7):693-9. doi: 10.7164/antibiotics.37.693.
Actinomycete strain M-53, a new soil isolate, was found to produce four quinone-type antibiotics. Antibiotic sakyomicin components, A, B, C and D were isolated from the fermentation broth of strain M-53 by XAD-2 column chromatography, silica gel column chromatography and Sephadex LH-20 column chromatography. The components are active against Gram-positive bacteria. Strain M-53 was identified as a strain of genus Nocardia.

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