Ophiobolin B
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| Category | Antibiotics |
| Catalog number | BBF-02622 |
| CAS | 5601-74-1 |
| Molecular Weight | 402.57 |
| Molecular Formula | C25H38O4 |
| Purity | >95% by HPLC |
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Description
A minor member of a class of phytotoxic metabolites produced by bipolaris and other genera of plant pathogenic fungi; acts by inhibiting calmodulin action in calcium regulation.
Specification
| Synonyms | Zizanin B; 3,14-Dihydroxy-5-oxoophiobola-7,19-dien-25-al |
| Storage | Store at -20°C |
| IUPAC Name | (1R,3S,4R,7S,8E,11R,12S)-4,12-dihydroxy-1,4-dimethyl-12-[(2S)-6-methylhept-5-en-2-yl]-6-oxotricyclo[9.3.0.03,7]tetradec-8-ene-8-carbaldehyde |
| Canonical SMILES | CC(CCC=C(C)C)C1(CCC2(C1CC=C(C3C(C2)C(CC3=O)(C)O)C=O)C)O |
| InChI | InChI=1S/C25H38O4/c1-16(2)7-6-8-17(3)25(29)12-11-23(4)13-19-22(20(27)14-24(19,5)28)18(15-26)9-10-21(23)25/h7,9,15,17,19,21-22,28-29H,6,8,10-14H2,1-5H3/b18-9-/t17-,19-,21+,22+,23+,24+,25-/m0/s1 |
| InChI Key | SXRLPRKYTRWOES-PCQMDVLKSA-N |
| Source | Bipolaris leersia |
Properties
| Appearance | Colorless Crystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria; fungi |
| Boiling Point | 543.41°C at 760 mmHg (Predicted) |
| Melting Point | 175°C |
| Density | 1.12 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1. Influence of light on the biosynthesis of ophiobolin A by Bipolaris maydis
Francesca Fanelli, Marco Masi, Pierluigi Reveglia, Maurizio Vurro, Maria Chiara Zonno, Giuseppina Mulè, Antonio Evidente, Alessio Cimmino Nat Prod Res . 2017 Apr;31(8):909-917. doi: 10.1080/14786419.2016.1253084.
Ophiobolin A (O-A) is a sesterpenoid with numerous biological activities, including potential anticancer effects. Its production at an industrial level is hampered due to inability of fungus Bipolaris maydis to biosynthesise it in vitro in large amount. Among the environmental factors regulating fungal metabolism, light plays a crucial role. In this study, the use of different light wavelength (light emitting diodes (LEDs)) was evaluated to increase the O-A production. The white light allowed the highest production of the metabolite. The blue and green lights showed an inhibitory effect, reducing the production to 50%, as well as red and yellow but at a lower level. No correlation between fungal growth and metabolite production was found in relation to the light type. A novel application of LED technologies, which can be optimised to foster specific pathways and promote the production of metabolites having scientific and industrial interest was proposed.
2. Ophiobolin E and 8-epi-ophiobolin J produced by Drechslera gigantea, a potential mycoherbicide of weedy grasses
Andrea Motta, Raghavan Charudattan, Maurizio Vurro, Antonio Evidente, Alessio Cimmino, Mariano Fracchiolla, Anna Andolfi Phytochemistry . 2006 Oct;67(20):2281-7. doi: 10.1016/j.phytochem.2006.07.016.
Drechslera gigantea, a fungal pathogen isolated from large crabgrass (Digitaria sanguinalis) and proposed as a potential mycoherbicide of grass weeds, produces phytotoxic metabolites in liquid and solid cultures. Ophiobolin A and three minor ophiobolins i.e., 6-epi-ophiobolin A, 3-anhydro-6-epi-ophiobolin A and ophiobolin I were obtained from the liquid culture broths. Interestingly and unexpectedly, ophiobolins also appeared in cultures of this fungus and they were isolated together with the known ophiobolins B and J, and designed as ophiobolin E and 8-epi-ophiobolin J. They were characterized using essentially spectroscopic methods. It is noteworthy that D. gigantea produces such a plethora of bioactive organic substances. Some structure-activity relationship results are also discussed in this report.
3. Low concentrations of the toxin ophiobolin A lead to an arrest of the cell cycle and alter the intracellular partitioning of glutathione between the nuclei and cytoplasm
Sara Cimini, Laura De Gara, Vittoria Locato, Antonio Evidente, Maria Chiara Zonno, Esther Novo Uzal, Alessandra Micera, Christine H Foyer J Exp Bot . 2015 May;66(10):2991-3000. doi: 10.1093/jxb/erv110.
Ophiobolin A, a tetracyclic sesterpenoid produced by phytopathogenic fungi, is responsible for catastrophic losses in crop yield but its mechanism of action is not understood. The effects of ophiobolin A were therefore investigated on the growth and redox metabolism of Tobacco Bright Yellow-2 (TBY-2) cell cultures by applying concentrations of the toxin that did not promote cell death. At concentrations between 2 and 5 μM, ophiobolin A inhibited growth and proliferation of the TBY-2 cells, which remained viable. Microscopic and cytofluorimetric analyses showed that ophiobolin A treatment caused a rapid decrease in mitotic index, with a lower percentage of the cells at G1 and increased numbers of cells at the S/G2 phases. Cell size was not changed following treatment suggesting that the arrest of cell cycle progression was not the result of a block on cell growth. The characteristic glutathione redox state and the localization of glutathione in the nucleus during cell proliferation were not changed by ophiobolin A. However, subsequent decreases in glutathione and the re-distribution of glutathione between the cytoplasm and nuclei after mitosis occurring in control cells, as well as the profile of glutathionylated proteins, were changed in the presence of the toxin. The profile of poly ADP-ribosylated proteins were also modified by ophiobolin A. Taken together, these data provide evidence of the mechanism of ophiobolin A action as a cell cycle inhibitor and further demonstrate the link between nuclear glutathione and the cell cycle regulation, suggesting that glutathione-dependent redox controls in the nuclei prior to cell division are of pivotal importance.
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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 ╳
