Ascosteroside
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| Category | Antibiotics |
| Catalog number | BBF-00100 |
| CAS | |
| Molecular Weight | 646.85 |
| Molecular Formula | C37H58O9 |
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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
Ascosteroside is an antifungal antibiotic produced by Ascotricha amphitricha. It has activity against yeasts (such as Candida albicans, Saccharomyces cerevisiae, etc.) and filamentous fungi, but has no antibacterial effect.
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| Synonyms | (3S,5R,10S,13R,14S,15R,17R)-3-[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxy-tetrahydropyran-2-yl]oxy-17-[(1R)-1,5-dimethyl-4-methylene-hexyl]-15-hydroxy-10,13-dimethyl-4-methylene-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-14-carboxylic acid; (3S,5R,10S,13R,14S,15R,17R)-3-[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy-15-hydroxy-10,13-dimethyl-4-methylidene-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-14-carboxylic acid |
| IUPAC Name | (3S,5R,10S,13R,14S,15R,17R)-3-[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy-15-hydroxy-10,13-dimethyl-4-methylidene-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-14-carboxylic acid |
| Canonical SMILES | CC(C)C(=C)CCC(C)C1CC(C2(C1(CCC3=C2CCC4C3(CCC(C4=C)OC5C(C(C(C(O5)CO)OC)O)O)C)C)C(=O)O)O |
| InChI | InChI=1S/C37H58O9/c1-19(2)20(3)9-10-21(4)26-17-29(39)37(34(42)43)25-12-11-23-22(5)27(14-15-35(23,6)24(25)13-16-36(26,37)7)45-33-31(41)30(40)32(44-8)28(18-38)46-33/h19,21,23,26-33,38-41H,3,5,9-18H2,1-2,4,6-8H3,(H,42,43)/t21-,23+,26-,27+,28+,29-,30+,31+,32+,33-,35+,36-,37-/m1/s1 |
| InChI Key | VWTJLWBUAZAHKW-VFKIOILVSA-N |
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | fungi; yeast |
| Melting Point | 123-130°C |
1. Ascosteroside D, a new mitochondrial respiration inhibitor discovered by pesticidal screening using insect ADP/ATP carrier protein-expressing Saccharomyces cerevisiae
Yoshihiro Watanabe, Yukihiro Asami, Satomi Narusawa, Shohei Hashimoto, Masato Iwatsuki, Kenichi Nonaka, Yasuo Shinohara, Takahiro Shiotsuki, Naoya Ichimaru, Hideto Miyoshi, Satoshi Ōmura, Kazuro Shiomi J Antibiot (Tokyo). 2017 Oct 11. doi: 10.1038/ja.2017.118. Online ahead of print.
A new lanostane-type triterpenoid, ascosteroside D, was isolated from a fungus, Aspergillus sp. FKI-6682. It inhibited insect ADP/ATP carrier protein (AAC)-expressing Saccharomyces cerevisiae in glycerol-containing medium, but did not inhibit Δaac S. cerevisiae in glucose-containing medium. It is hypothesized that ascosteroside D inhibits ATP production in mitochondria.The Journal of Antibiotics advance online publication, 11 October 2017; doi:10.1038/ja.2017.118.
2. Anti-Candida metabolites from endophytic fungi
Roland W S Weber, Reinhard Kappe, Thomas Paululat, Eva Mösker, Heidrun Anke Phytochemistry. 2007 Mar;68(6):886-92. doi: 10.1016/j.phytochem.2006.12.017. Epub 2007 Feb 6.
Submerged cultures of some 1500 Ascomycota and Basidiomycota isolated from their fruit-bodies or as soil-borne, coprophilous or endophytic fungi were screened for activity against Candida albicans and a range of other pathogenic and saprotrophic fungi. Considerably more Ascomycota (11-16%) than Basidiomycota (3.5%) produced metabolites with activity against C. albicans. From five species of endophytes, six bioactive compounds were isolated and identified, viz. cerulenin (1), arundifungin (2), sphaeropsidin A (3), 5-(1,3-butadiene-1-yl)-3-(propene-1-yl)-2-(5H)-furanone (4), ascosteroside A (formerly called ascosteroside; 5) and a derivative of 5, ascosteroside B (6). 1, 3 and 5 were isolated from fungi belonging to different orders than previously described producers. Antifungal activities of 2 and 4-6 in the agar diffusion test were comparable with those of amphotericin B. Compound 6 exhibited a similar antifungal activity as 5 but its cytotoxicity towards Hep G2 cells was considerably lower. This study points to endophytic fungi related to hemibiotrophic or latent plant pathogens as an important source of bio- and chemodiversity.
3. The effect of carbon source, temperature and aeration on the production of ascosteroside, a novel antifungal agent, by Ascotricha amphitricha
S E Lowe, D R Gustavson, D S Meyers, J A Veitch, S Forenza, K S Lam J Antibiot (Tokyo). 1997 May;50(5):412-7. doi: 10.7164/antibiotics.50.412.
This paper describes the optimization of production of ascosteroside, a novel antifungal agent with an alpha-linked glycoside of a lanosterone-type triterpenoid structure. Glucose, sorbose and inositol were determined to be the best carbon sources for the production of ascosteroside. Temperature affected levels of ascosteroside, with production being highest at 16 degrees C with 1% glucose, and lowest at 32 degrees C. Dissolved oxygen levels were found to be critical in the production of ascosteroside in fermenter cultures. In order for production of ascosteroside to occur in fermenter cultures, the threshold level of dissolved oxygen was found to be above 26%.
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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 ╳
