Bafilomycin D

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Bafilomycin D
Category Antibiotics
Catalog number BBF-03927
CAS 98813-13-9
Molecular Weight 604.81
Molecular Formula C35H56O8
Purity >99% by HPLC

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Description

Bafilomycin D is a macrolide antibiotic produced by Streptomyces. Bafilomycin D is an inhibitor that is more selective than Balifomycin A.

Specification

Synonyms Tubaymycin, 3D5
Storage Store at -20°C
IUPAC Name 16-(3,9-dihydroxy-4,8,10-trimethyl-5-oxoundec-6-en-2-yl)-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyl-1-oxacyclohexadeca-3,5,11,13-tetraen-2-one
Canonical SMILES CC1CC(=CC=CC(C(OC(=O)C(=CC(=CC(C1O)C)C)OC)C(C)C(C(C)C(=O)C=CC(C)C(C(C)C)O)O)OC)C
InChI InChI=1S/C35H56O8/c1-20(2)31(37)23(5)15-16-28(36)26(8)33(39)27(9)34-29(41-10)14-12-13-21(3)17-24(6)32(38)25(7)18-22(4)19-30(42-11)35(40)43-34/h12-16,18-20,23-27,29,31-34,37-39H,17H2,1-11H3
InChI Key ZKOTUWJMGBWBEO-UHFFFAOYSA-N
Source Streptomyces sp.

Properties

Appearance White Powder
Antibiotic Activity Spectrum Gram-positive bacteria; fungi
Solubility Soluble in ethanol, methanol, DMF, DMSO

Reference Reading

1. Exploration of Chemical Diversity and Antitrypanosomal Activity of Some Red Sea-Derived Actinomycetes Using the OSMAC Approach Supported by LC-MS-Based Metabolomics and Molecular Modelling
Ahmed O El-Gendy, Yara I Shamikh, Usama Ramadan Abdelmohsen, Noha M Gamaleldin, Hossam M Hassan, Walid Bakeer, Ahmed M Sayed, Hannes Horn, Wael N Hozzein Antibiotics (Basel) . 2020 Sep 22;9(9):629. doi: 10.3390/antibiotics9090629.
In the present study, we investigated the actinomycetes associated with the Red Sea-derived soft coralSarcophyton glaucumin terms of biological and chemical diversity. Three strains were cultivated and identified to be members of generaMicromonospora,Streptomyces, andNocardiopsis; out of them,Micromonosporasp. UR17 was putatively characterized as a new species. In order to explore the chemical diversity of these actinobacteria as far as possible, they were subjected to a series of fermentation experiments under altering conditions, that is, solid and liquid fermentation along with co-fermentation with a mycolic acid-containing strain, namelyNocardiasp. UR23. Each treatment was found to affect these actinomycetes differently in terms of biological activity (i.e., antitrypanosomal activity) and chemical profiles evidenced by LC-HRES-MS-based metabolomics and multivariate analysis. Thereafter, orthogonal projections to latent structures discriminant analysis (OPLS-DA) suggested a number of metabolites to be associated with the antitrypanosomal activity of the active extracts. The subsequent in silico screenings (neural networking-based and docking-based) further supported the OPLS-DA results and prioritized desferrioxamine B (3), bafilomycin D (10), and bafilomycin A1 (11) as possible antitrypanosomal agents. Our approach in this study can be applied as a primary step in the exploration of bioactive natural products, particularly those from actinomycetes.
2. A unique indolizinium alkaloid streptopertusacin A and bioactive bafilomycins from marine-derived Streptomyces sp. HZP-2216E
Zhizhen Zhang, Weiyun Chai, Xiao-Yuan Lian, Xiufang Zhang, Lu Chen Phytochemistry . 2017 Dec;144:119-126. doi: 10.1016/j.phytochem.2017.09.010.
Streptopertusacin A, a unique indolizinium alkaloid existing as a zwitterion, and six bafilomycins including two previously undescribed ones of 21,22-en-bafilomycin D and 21,22-en-9-hydroxybafilomycin D were isolated from a culture of the seaweed-derived Streptomyces sp. HZP-2216E. Structures of these isolated compounds were determined based on extensive NMR spectroscopic analyses, HRESIMS and MS-MS data. The stereochemical assignments were achieved by NOE information, chemical degradation, Marfey's method, and electronic circular dichroism (ECD) calculation. Streptopertusacin A is the first example of this type of indolizinium alkaloid from microorganisms and showed moderate activity against the growth of methicillin-resistant Staphylococcus aureus (MRSA). 21,22-en-bafilomycin D and 21,22-en-9-hydroxybafilomycin D had potent activities in inhibiting the proliferation of glioma cells and the growth of MRSA.
3. Hygrobafilomycin, a cytotoxic and antifungal macrolide bearing a unique monoalkylmaleic anhydride moiety, from Streptomyces varsoviensis
Heinz-Herbert Fiebig, Christian Hertweck, Klaus-Dieter Menzel, Isabel Sattler, Armin Maier, Basile Le S Tchize Ndejouong, Gerhard Kelter J Antibiot (Tokyo) . 2010 Jul;63(7):359-63. doi: 10.1038/ja.2010.52.
A new bafilomycin-type macrolide, named hygrobafilomycin (6), was isolated by a bioassay-guided selection and fractionation from a terrestrial actinomycete, Streptomyces varsoviensis, along with three known derivatives, bafilomycin D (3), C1 (4) and C2 (5). The structure of hygrobafilomycin was fully established by MS and NMR analyses, revealing a hygrolidin-bafilomycin hybrid with an unusual monoalkylmaleic anhydride moiety. Hygrobafilomycin (6) shows strong antifungal, antiproliferative and cytotoxic activities. In a panel of 40 tumor cell lines, compound 6 shows high cytotoxic potency (mean IC(50)=5.3 n).

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