Sakyomicin B

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Category Antibiotics
Catalog number BBF-02851
CAS 86470-27-1
Molecular Weight 372.33
Molecular Formula C19H16O8

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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.

Specification

Synonyms (2S)-3,4,4a,12b-Tetrahydro-2β,3α,4aβ,8,12bβ-pentahydroxy-3-methylbenz[a]anthracene-1,7,12(2H)-trione; Benz(a)anthracene-1,7,12(2H)-trione,3,4,4a,12b-tetrahydro-2,3,4a,8,12b-pentahydroxy-3-methyl-, (2S-(2-alpha,3-beta,4a-alpha,12b-alpha))-; Antibiotic SEN 136A; Antibiotic WP 3688-1; Antibiotic PD 116198; (+)-Sakyomicin B
IUPAC Name (2S,3R,4aS,12bR)-2,3,4a,8,12b-pentahydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione
Canonical SMILES CC1(CC2(C=CC3=C(C2(C(=O)C1O)O)C(=O)C4=C(C3=O)C(=CC=C4)O)O)O
InChI InChI=1S/C19H16O8/c1-17(25)7-18(26)6-5-9-12(19(18,27)16(24)15(17)23)14(22)8-3-2-4-10(20)11(8)13(9)21/h2-6,15,20,23,25-27H,7H2,1H3/t15-,17-,18-,19+/m1/s1
InChI Key TVRZORMBTKRMAO-OWYHZJEWSA-N

Properties

Appearance Yellow Fine Needle Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Mycobacteria
Boiling Point 717.4°C at 760 mmHg
Density 1.75 g/cm3
Solubility Soluble in Ethanol, Dioxan

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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