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Sarubicin B

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Sarubicin B
Category Antibiotics
Catalog number BBF-02886
CAS 84745-01-7
Molecular Weight 258.23
Molecular Formula C13H10N2O4

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is produced by the strain of Str. violaceoruber sp. JA 2861. It has anti-gram-positive bacteria effect, but no anti-gram-negative bacteria, fungi and yeast effects.

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Synonyms 2-Naphthalenecarboxamide, 5-acetyl-3-amino-1,4-dihydro-1,4-dioxo-
IUPAC Name 5-acetyl-1-hydroxy-3-imino-4-oxonaphthalene-2-carboxamide
Canonical SMILES CC(=O)C1=CC=CC2=C1C(=O)C(=N)C(=C2O)C(=O)N
InChI InChI=1S/C13H10N2O4/c1-5(16)6-3-2-4-7-8(6)12(18)10(14)9(11(7)17)13(15)19/h2-4,14,17H,1H3,(H2,15,19)
InChI Key YKJQUOFKMCKKGM-UHFFFAOYSA-N
Appearance Orange Crystal
Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 540.6°C at 760 mmHg
Melting Point 282-284°C
Density 1.466 g/cm3
Solubility Soluble in Methanol, DMSO, Benzene
1. Sarubicin b, a new quinone antibiotic, isolated from the fermentation broth of a streptomyces strain
K Eckardt, D Tresselt, W Ihn, G Bradler, G Reinhardt J Antibiot (Tokyo). 1982 Dec;35(12):1638-40. doi: 10.7164/antibiotics.35.1638.
Sarubicin B, isolated from the culture filtrate of a Streptomyces strain JA 2861, is a new quinone antibiotic. The compound was isolated as an orange crystalline powder, mp 282 approximately 284 degrees C. In vitro sarubicin B was found to inhibit Gram-positive bacteria. It was not active against Gram-negative microorganisms.
2. Sarubicinols A-C, Cytotoxic Benzoxazoles from a Streptomyces
Han Wang, Huan Qi, Shao-Yong Zhang, Wen-Shuai Song, Li-Qin Zhang, Wen-Sheng Xiang, Ji-Dong Wang J Nat Prod. 2022 Apr 22;85(4):1167-1173. doi: 10.1021/acs.jnatprod.1c00820. Epub 2022 Feb 25.
A chemical investigation of Streptomyces sp. Hu186 afforded two known quinone antibiotics, sarubicin A (1) and sarubicin B (2), together with three unusual variants, sarubicinols A-C (3-5), and two new 1,4-naphthoquinone metabolites, sarubicin B1 (6) and sarubicin B2 (7). Compounds 3-5 possess a rare 2-oxabicyclo [2.2.2] substructure and a benzoxazole ring system. Their structures were elucidated using 1D and 2D nuclear magnetic resonance and high-resolution electrospray ionization mass spectrometry data. The absolute configurations of the side-chain moieties in 4 and 5 were solved by electronic circular dichroism calculations. Compounds 1-7 showed moderate cytotoxic activity against four tumor cell lines.

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