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10-Dihydrosteffimycin A

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Category Antibiotics
Catalog number BBF-01416
CAS 75086-96-3
Molecular Weight 576.54
Molecular Formula C28H32O13

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Product Description

It is produced by the strain of Actinoplanes utahensis. 10-Dihydrosteffimycin A has anti-gram-positive bacterial activity.

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Synonyms 3,4,10,12-tetrahydroxy-2,8-dimethoxy-3-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 6-deoxy-2-O-methylhexopyranoside
IUPAC Name 7-(4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl)oxy-4,6,9,10-tetrahydroxy-2,8-dimethoxy-9-methyl-8,10-dihydro-7H-tetracene-5,12-dione
Canonical SMILES CC1C(C(C(C(O1)OC2C(C(C(C3=CC4=C(C(=C23)O)C(=O)C5=C(C4=O)C=C(C=C5O)OC)O)(C)O)OC)OC)O)O
InChI InChI=1S/C28H32O13/c1-9-18(30)22(34)24(38-4)27(40-9)41-23-17-13(25(35)28(2,36)26(23)39-5)8-12-16(21(17)33)20(32)15-11(19(12)31)6-10(37-3)7-14(15)29/h6-9,18,22-27,29-30,33-36H,1-5H3
InChI Key UNKIHGIMHCGUGS-UHFFFAOYSA-N
Appearance Crystalline
Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 780.9°C at 760 mmHg
Melting Point 245-248°C
Density 1.58 g/cm3
1. Microbial conversion of steffimycin and steffimycin B to 10-dihydrosteffimycin and 10-dihydrosteffimycin B
P F Wiley, D W Elrod, J M Slavicek, V P Marshall J Antibiot (Tokyo). 1980 Aug;33(8):819-23. doi: 10.7164/antibiotics.33.819.
It has been shown that steffimycin (1) and steffmycin B (2) are reduced at the C-10 carbonyl by Actinoplanes utahensis, UC-5885 and Chaetomium sp., UC-4634, respectively. Using cell-free extracts of the latter organism, the optimum conversion time, pH, and enzyme concentration have been determined for the conversion of 2 to 4. The biochemical conversion of 2 has been found to be TPNH linked.
2. Steffimycin E, a new anti-mycobacterial agent against Mycobacterium avium complex, produced by Streptomyces sp. OPMA02852
Nobuhiro Koyama, Satoru Shigeno, Akihiko Kanamoto, Hiroshi Tomoda J Antibiot (Tokyo). 2020 Aug;73(8):581-584. doi: 10.1038/s41429-020-0290-9. Epub 2020 Mar 4.
The marine actinomycete strain OPMA02852, identified as the genus Streptomyces, was found to produce anti-mycobacterial compounds against Mycobacterium avium complex (MAC). One new compound, designated as steffimycin E (1), was isolated together with three known steffimycins (steffimycin (2), 10-dihydrosteffimycin (3), and 8-demethoxysteffimycin (4)) from the culture broth of this producing microorganism by solvent extraction, ODS column chromatography, and preparative HPLC. Compound 1 has a tetracyclic quinone structure with a sugar moiety. Compound 1 exhibited anti-mycobacterial activity against M. intracellulare, M. bovis BCG, and M. smegmatis.

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