Ophiobolin A
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| Category | Antibiotics |
| Catalog number | BBF-02621 |
| CAS | 4611-05-6 |
| Molecular Weight | 400.55 |
| Molecular Formula | C25H36O4 |
| Purity | >95% by HPLC |
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Description
Ophiobolin A is the dominant member of a class of phytotoxic metabolites produced by plant pathogenic fungi. It is resistant to gram-positive bacteria, mycobacteria and fungi.
Specification
| Synonyms | Cochliobolin; NSC 114340; Spiro(dicyclopenta(a,d)cyclooctene-3(2H),2'(3'H)-furan)-6-carboxaldehyde, 1,3a,4,4',5',6a,7,8,9a,10,10a-dodecahydro-9-hydroxy-3',9,10a-trimethyl-5'-(2-methyl-1-propenyl)-7-oxo-, (2'S,3'S,3aR,5'R,6aS,9R,9aS,10aR)- |
| Storage | Store at -20°C |
| IUPAC Name | (1'R,2S,3S,3'S,4'R,5R,7'S,8'E,11'R)-4'-hydroxy-1',3,4'-trimethyl-5-(2-methylprop-1-enyl)-6'-oxospiro[oxolane-2,12'-tricyclo[9.3.0.03,7]tetradec-8-ene]-8'-carbaldehyde |
| Canonical SMILES | CC1CC(OC12CCC3(C2CC=C(C4C(C3)C(CC4=O)(C)O)C=O)C)C=C(C)C |
| InChI | InChI=1S/C25H36O4/c1-15(2)10-18-11-16(3)25(29-18)9-8-23(4)12-19-22(20(27)13-24(19,5)28)17(14-26)6-7-21(23)25/h6,10,14,16,18-19,21-22,28H,7-9,11-13H2,1-5H3/b17-6-/t16-,18-,19-,21+,22+,23+,24+,25-/m0/s1 |
| InChI Key | MWYYLZRWWNBROW-BDZRSQQBSA-N |
| Source | Bipolaris leersia |
Properties
| Appearance | Colorless Crystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria; fungi |
| Boiling Point | 443.19°C at 760 mmHg |
| Melting Point | 181°C |
| Density | 1.0278 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1. Ophiobolin A, a sesterterpenoid fungal phytotoxin, displays higher in vitro growth-inhibitory effects in mammalian than in plant cells and displays in vivo antitumor activity
Robert Kiss, Maria Chiara Zonno, Benjamin Lallemand, Marina Bury, Anna Andolfi, Vittoria Locato, Esther Novo-Uzal, Cédric Delporte, Pierre Van Antwerpen, Sara Cimini, Maurizio Vurro, Nathalie Wauthoz, Jacques Dubois, Alessio Cimmino, Walter Berger, Fabiana Avolio, Laura De Gara, Petra Heffeter, Antonio Evidente, Yves Poumay Int J Oncol . 2013 Aug;43(2):575-85. doi: 10.3892/ijo.2013.1979.
Ophiobolin A, a sesterterpenoid produced by plant pathogenic fungi, was purified from the culture extract of Drechslera gigantea and tested for its growth-inhibitory activity in both plant and mammalian cells. Ophiobolin A induced cell death in Nicotiana tabacum L. cv. Bright Yellow 2 (TBY-2) cells at concentrations ≥10 µM, with the TBY-2 cells showing typical features of apoptosis-like cell death. At a concentration of 5 µM, ophiobolin A did not affect plant cell viability but prevented cell proliferation. When tested on eight cancer cell lines, concentrations <1 µM of ophiobolin A inhibited growth by 50% after 3 days of culture irrespective of their multidrug resistance (MDR) phenotypes and their resistance levels to pro-apoptotic stimuli. It is, thus, unlikely that ophiobolin A exerts these in vitro growth-inhibitory effects in cancer cells by activating pro-apoptotic processes. Highly proliferative human keratinocytes appeared more sensitive to the growth-inhibitory effects of ophiobolin A than slowly proliferating ones. Ophiobolin A also displayed significant antitumor activity at the level of mouse survival when assayed at 10 mg/kg in the B16F10 mouse melanoma model with lung pseudometastases. Ophiobolin A could, thus, represent a novel scaffold to combat cancer types that display various levels of resistance to pro-apoptotic stimuli and/or various MDR phenotypes.
2. 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.
3. Augmented phytotoxic effect of nanoencapsulated ophiobolin A
Marco Masi, Helen E Townley, Maurizio Vurro, Antonio Evidente, Angela Boari, Rachel Morrison Nat Prod Res . 2022 Mar;36(5):1143-1150. doi: 10.1080/14786419.2020.1860975.
Ophiobolin A is a secondary phytotoxic metabolite produced by some pathogenic fungal species responsible for severe plant diseases, considered to play a role in disease development and symptom appearance. Herein we investigated whether the phytotoxic activities of ophiobolin A against weed species could be improved by nanoencapsulation. Given the rapid natural degradation of the compound, it was hoped that nanoencapsulation would prolong the phytotoxic effects or enhance the bioactivity, thus leading to improved weed control capabilities. This article presents an assessment of the effectiveness of encapsulated ophiobolin A on 11 commonly found weed species, compared to the pure ophiobolin, to the particle alone, and a combination of mixed particles and ophiobolin A, by applying the solution droplets to both intact or injured leaf surface, on the adaxial or abaxial side. The bioassays showed the improved efficacy of the encapsulated ophiobolin, and the need for leaf lesions to diffuse the particles into the tissues.[Formula: see text].
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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 ╳
