Abierixin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Animal Health |
| Catalog number | BBF-00002 |
| CAS | 100634-16-0 |
| Molecular Weight | 724.96 |
| Molecular Formula | C40H68O11 |
Online Inquiry
Description
Abierixin is a polyether antibiotic isolated from Streptomyces albus NRRL B-1865. Abierixin exhibited weak antimicrobial and ionophorous activities, low toxicity but good anticoccidial activity.
Specification
| Synonyms | Nigericin, 3,7-deepoxy-2,3-didehydro-7-hydroxy-; (2E)-7-hydroxy-8-(2-{5'-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl]-2,3'-dimethyloctahydro-2,2'-bifuran-5-yl}-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]dec-7-yl)-2,4-dimethyloct-2-enoic acid |
| IUPAC Name | (E)-7-hydroxy-8-[2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2,4-dimethyloct-2-enoic acid |
| Canonical SMILES | CC1CC(C(OC1C2CC(C(O2)C3(CCC(O3)C4(CC(C5(O4)C(C(CC(O5)CC(CCC(C)C=C(C)C(=O)O)O)OC)C)C)C)C)C)(CO)O)C |
| InChI | InChI=1S/C40H68O11/c1-22(15-25(4)36(43)44)11-12-29(42)18-30-19-31(46-10)28(7)40(48-30)27(6)20-38(9,51-40)33-13-14-37(8,49-33)35-24(3)17-32(47-35)34-23(2)16-26(5)39(45,21-41)50-34/h15,22-24,26-35,41-42,45H,11-14,16-21H2,1-10H3,(H,43,44)/b25-15+ |
| InChI Key | JQESXHYTUWEFCM-MFKUBSTISA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | parasites |
| Boiling Point | 801.3°C at 760 mmHg |
| Melting Point | 83-85°C |
| Density | 1.18 g/cm3 |
Reference Reading
1. Nigericin and grisorixin methyl ester from the Algerian soil-living Streptomyces youssoufiensis SF10 strain: a computational study on their epimeric structures and evaluation of glioblastoma stem cells growth inhibition
Nassima Leulmi, Denise Sighel, Andrea Defant, Karima Khenaka, Abderrahmane Boulahrouf, Ines Mancini Nat Prod Res. 2019 Jan;33(2):266-273. doi: 10.1080/14786419.2018.1446014. Epub 2018 Mar 7.
The present work describes the metabolites produced by a strain identified as Streptomyces youssoufiensis, whose secondary metabolites profile has not been studied so far. The crude ethyl acetate extract was analyzed by high performance liquid chromatography-electrospray ionization mass spectrometry, leading to the detection of the ionophoric polyethers nigericin, epinigericin, abierixin and the newly isolated grisorixin methyl ester. The presence of epimeric forms of nigericin/epinigericin and grisorixin/epigrisorixin has spurred density functional theory computational calculations. This analysis was able to provide the relative stability of the most favored epimers, setting the basis for general structural considerations applicable to several other polyethers. Both nigericin sodium salt and grisorixin methyl ester showed to affect glioblastoma stem cells proliferation in a dose-dependent manner, with a higher activity for the more lipophilic grisorixin methyl ester (GI50 values of 3.85 and 3.05 μM for VIPI and COMI human glioblastoma stem cells, respectively).
2. Investigation on antimicrobial agents of the terrestrial Streptomyces sp. BCC71188
Khomsan Supong, Paranee Sripreechasak, Somboon Tanasupawat, Kannawat Danwisetkanjana, Pranee Rachtawee, Pattama Pittayakhajonwut Appl Microbiol Biotechnol. 2017 Jan;101(2):533-543. doi: 10.1007/s00253-016-7804-1. Epub 2016 Aug 23.
The terrestrial actinomycete strain BCC71188 was identified as Streptomyces by its morphology (having spiral chain spore on the aerial mycelium), chemotaxonomy (containing LL-diaminopimelic acid in the cell wall), and 16S rRNA gene sequence analysis [showing high similarity values compared with Streptomyces samsunensis M1463T (99.85 %) and Streptomyces malaysiensis NBRC 16446T (99.40 %)]. The crude extract exhibited antimalarial against Plasmodium falciparum (IC50 0.19 μg/ml), anti-TB against Mycobacterial tuberculosis (MIC 6.25 μg/ml), and antibacterial against Bacillus cereus (MIC 1.56 μg/ml) activities. Therefore, chemical investigation was conducted by employing bioassay-guided method and led to the isolation of 19 compounds including two cyclic peptides (1-2), five macrolides (3-7), new naphthoquinone (8), nahuoic acid C (9), geldanamycin derivatives (10-13), cyclooctatin (14), germicidins A (15) and C (16), actinoramide A (17), abierixin, and 29-O-methylabierixin. These isolated compounds were evaluated for antimicrobial activity, such as antimalarial, anti-TB, and antibacterial activities, and for cytotoxicity against both cancerous (MCF-7, KB, NCI-H187) and non-cancerous (Vero) cells. Compounds 1-7, 10-14 exhibited antimalarial (IC50 0.22-7.14 μg/ml), and elaiophylin analogs (4-6) displayed anti-TB (MIC 0.78-12.00 μg/ml) and B. cereus (MIC 0.78-3.13 μg/ml) activities. Compounds 1, 2, 14, and abierixin displayed weak cytotoxicity, indicating a potential for antimicrobial agents.
3. Antimicrobial compounds from endophytic Streptomyces sp. BCC72023 isolated from rice (Oryza sativa L.)
Khomsan Supong, Chitti Thawai, Wilunda Choowong, Chokchai Kittiwongwattana, Dusanee Thanaboripat, Chamroon Laosinwattana, Prommart Koohakan, Nonglak Parinthawong, Pattama Pittayakhajonwut Res Microbiol. 2016 May;167(4):290-298. doi: 10.1016/j.resmic.2016.01.004. Epub 2016 Jan 22.
An endophytic actinomycete strain BCC72023 was isolated from rice (Oryza sativa L.) and identified as the genus Streptomyces, based on phenotypic, chemotaxonomic and 16S rRNA gene sequence analyses. The strain showed 99.80% similarity compared with Streptomyces samsunensis M1463(T). Chemical investigation led to the isolation of three macrolides, efomycins M (1), G (2) and oxohygrolidin (3), along with two polyethers, abierixin (4) and 29-O-methylabierixin (5). To our knowledge, this is the first report of efomycin M being isolated from a natural source. The compounds were identified using spectroscopic techniques and comparison with previously published data. All compounds exhibited antimalarial activity against the Plasmodium falciparum, K-1 strain, a multidrug-resistant strain, with IC50 values in a range of 1.40-5.23 μg/ml. In addition, these compounds were evaluated for biological activity against Mycobacterium tuberculosis, Bacillus cereus, Colletotrichum gloeosporioides and Colletotrichum capsici, as well as cytotoxicity against both cancerous (MCF-7, KB, NCI-H187) and non-cancerous (Vero) cells.
Recommended Products
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
