Botryodiplodin
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| Category | Antibiotics |
| Catalog number | BBF-00164 |
| CAS | 27098-03-9 |
| Molecular Weight | 144.17 |
| Molecular Formula | C7H12O3 |
| Purity | >98% |
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Description
Botryodiplodin is an antibiotic mycotoxin produced by Botryodiplodia theobromae. It has activity against gram-positive bacteria.
Specification
| Synonyms | Cytostipin; Antibiotic PSX 1; Botryodipolodin |
| Storage | Store at -20°C |
| IUPAC Name | 1-(5-hydroxy-4-methyloxolan-3-yl)ethanone |
| Canonical SMILES | CC1C(COC1O)C(=O)C |
| InChI | InChI=1S/C7H12O3/c1-4-6(5(2)8)3-10-7(4)9/h4,6-7,9H,3H2,1-2H3 |
| InChI Key | CLYSZQBIUYRLNX-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 249.4°C at 760 mmHg |
| Melting Point | 42°C |
| Density | 1.126 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Phytotoxic Responses of Soybean ( Glycine max L.) to Botryodiplodin, a Toxin Produced by the Charcoal Rot Disease Fungus, Macrophomina phaseolina
Hamed K Abbas, Nacer Bellaloui, Alemah M Butler, Justin L Nelson, Mohamed Abou-Karam, W Thomas Shier Toxins (Basel). 2020 Jan 1;12(1):25. doi: 10.3390/toxins12010025.
Toxins have been proposed to facilitate fungal root infection by creating regions of readily-penetrated necrotic tissue when applied externally to intact roots. Isolates of the charcoal rot disease fungus, Macrophomina phaseolina, from soybean plants in Mississippi produced a phytotoxic toxin, (-)-botryodiplodin, but no detectable phaseolinone, a toxin previously proposed to play a role in the root infection mechanism. This study was undertaken to determine if (-)-botryodiplodin induces toxic responses of the types that could facilitate root infection. (±)-Botryodiplodin prepared by chemical synthesis caused phytotoxic effects identical to those observed with (-)-botryodiplodin preparations from M. phaseolina culture filtrates, consistent with fungus-induced phytotoxicity being due to (-)-botryodiplodin, not phaseolinone or other unknown impurities. Soybean leaf disc cultures of Saline cultivar were more susceptible to (±)-botryodiplodin phytotoxicity than were cultures of two charcoal rot-resistant genotypes, DS97-84-1 and DT97-4290. (±)-Botryodiplodin caused similar phytotoxicity in actively growing duckweed (Lemna pausicostata) plantlet cultures, but at much lower concentrations. In soybean seedlings growing in hydroponic culture, (±)-botryodiplodin added to culture medium inhibited lateral and tap root growth, and caused loss of root caps and normal root tip cellular structure. Thus, botryodiplodin applied externally to undisturbed soybean roots induced phytotoxic responses of types expected to facilitate fungal root infection.
2. Pigment Produced by Glycine-Stimulated Macrophomina Phaseolina Is a (-)-Botryodiplodin Reaction Product and the Basis for an In-Culture Assay for (-)-Botryodiplodin Production
Sahib Alam, Hamed K Abbas, Michael Sulyok, Vivek H Khambhati, Wahab O Okunowo, Wayne Thomas Shier Pathogens. 2022 Feb 22;11(3):280. doi: 10.3390/pathogens11030280.
An isolate of Macrophomina phaseolina from muskmelons (Cucumis melo)was reported by Dunlap and Bruton to produce red pigment(s) in melons and in culture in the presence of added glycine, alanine, leucine, or asparagine in the medium, but not with some other amino acids and nitrogen-containing compounds. We explored the generality and mechanism of this pigment production response using pathogenic M. phaseolina isolates from soybean plants expressing symptoms of charcoal rot disease. A survey of 42 M. phaseolina isolates growing on Czapek-Dox agar medium supplemented with glycine confirmed pigment production by 71% of isolates at the optimal glycine concentration (10 g/L). Studies in this laboratory have demonstrated that some pathogenic isolates of M. phaseolina produce the mycotoxin (-)-botryodiplodin, which has been reported to react with amino acids, proteins, and other amines to produce red pigments. Time course studies showed a significant positive correlation between pigment and (-)-botryodiplodin production by selected M. phaseolina isolates with maximum production at seven to eight days. Pigments produced in agar culture medium supplemented with glycine, beta-alanine, or other amines exhibited similar UV-vis adsorption spectra as did pigments produced by (±)-botryodiplodin reacting in the same agar medium. In a separate study of 39 M. phaseolina isolates, red pigment production (OD520) on 10 g/L glycine-supplemented Czapek-Dox agar medium correlated significantly with (-)-botryodiplodin production (LC/MS analysis of culture filtrates) in parallel cultures on un-supplemented medium. These results support pigment production on glycine-supplemented agar medium as a simple and inexpensive in-culture method for detecting (-)-botryodiplodin production by M. phaseolina isolates.
3. First Report of the Production of Mycotoxins and Other Secondary Metabolites by Macrophomina phaseolina (Tassi) Goid. Isolates from Soybeans ( Glycine max L.) Symptomatic with Charcoal Rot Disease
Vivek H Khambhati, Hamed K Abbas, Michael Sulyok, Maria Tomaso-Peterson, W Thomas Shier J Fungi (Basel). 2020 Dec 3;6(4):332. doi: 10.3390/jof6040332.
Macrophomina phaseolina (Tassi) Goid., the causal agent of charcoal rot disease of soybean, is capable of causing disease in more than 500 other commercially important plants. This fungus produces several secondary metabolites in culture, including (-)-botryodiplodin, phaseolinone and mellein. Given that independent fungal isolates may differ in mycotoxin and secondary metabolite production, we examined a collection of 89 independent M. phaseolina isolates from soybean plants with charcoal rot disease using LC-MS/MS analysis of culture filtrates. In addition to (-)-botryodiplodin and mellein, four previously unreported metabolites were observed in >19% of cultures, including kojic acid (84.3% of cultures at 0.57-79.9 µg/L), moniliformin (61.8% of cultures at 0.011-12.9 µg/L), orsellinic acid (49.4% of cultures at 5.71-1960 µg/L) and cyclo[L-proline-L-tyrosine] (19.1% of cultures at 0.012-0.082 µg/L). In addition, nine previously unreported metabolites were observed at a substantially lower frequency (<5% of cultures), including cordycepin, emodin, endocrocin, citrinin, gliocladic acid, infectopyron, methylorsellinic acid, monocerin and N-benzoyl-L-phenylalanine. Further studies are needed to investigate the possible effects of these mycotoxins and metabolites on pathogenesis by M. phaseolina and on food and feed safety, if any of them contaminate the seeds of infected soybean plants.
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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 ╳
