Anhydroophiobolin A
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| Category | Bioactive by-products |
| Catalog number | BBF-04280 |
| CAS | 6026-65-9 |
| Molecular Weight | 382.54 |
| Molecular Formula | C25H34O3 |
| Purity | >95% by HPLC |
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Description
It is the dehydrated analogue of ophiobolin A and a major member of the ophiobolin complex of phytotoxic metabolites produced by many species of the genus bipolaris. It possesses a broad biological profile with antibacterial, antifungal, antitumour, herbicidal and nematocidal activities.
Specification
| Synonyms | 14,17-Epoxy-5-oxo-3,7,18-ophiobolatrien-21-al; Anhydroophiobolin; (18R)-5-Oxo-14,18-epoxy-3,4-didehydroophiobola-7,19-diene-25-al; (2'S,3'S,3aR,5'R,6aS,9aS,10aR)-2,3a,4,4',5',6a,7,9a,10,10a-Decahydro-3',9,10a-trimethyl-5'-(2-methyl-1-propen-1-yl)-7-oxospiro[dicyclopenta[a,d]cyclooctene-3(1H),2'(3'H)-furan]-6-carboxaldehyde; [3S-[3α(3'R*,5'S*),3aα,6aβ,9aβ,10aβ]]-1,3a,4,4',5',6a,7,9a,10,10a-Decahydro-3',9,10a-trimethyl-5'-(2-methyl-1-propenyl)-7-oxo-spiro[dicyclopenta[a,d]cyclooctene-3(2H),2'(3'H)-furan]-6-carboxaldehyde; 3-Anhydro-cochliobolin; 3-Anhydroophiobolin A |
| Storage | Store at -20°C |
| IUPAC Name | (1'R,2S,3S,3'S,5R,7'S,8'E,11'R)-1',3,4'-trimethyl-5-(2-methylprop-1-enyl)-6'-oxospiro[oxolane-2,12'-tricyclo[9.3.0.03,7]tetradeca-4,8-diene]-8'-carbaldehyde |
| Canonical SMILES | CC1CC(OC12CCC3(C2CC=C(C4C(C3)C(=CC4=O)C)C=O)C)C=C(C)C |
| InChI | InChI=1S/C25H34O3/c1-15(2)10-19-12-17(4)25(28-19)9-8-24(5)13-20-16(3)11-21(27)23(20)18(14-26)6-7-22(24)25/h6,10-11,14,17,19-20,22-23H,7-9,12-13H2,1-5H3/b18-6-/t17-,19-,20+,22+,23+,24+,25-/m0/s1 |
| InChI Key | MDYSLOGZXCWLSL-CWPAWFJGSA-N |
| Source | Bipolaris sp. |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Fungi; Parasites; Bacterial |
| Boiling Point | 520.6±50.0°C (Predicted) |
| Melting Point | 136°C |
| Density | 1.10±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Microbial metabolites of ophiobolin A and antimicrobial evaluation of ophiobolins
D P Rotella, A M Clark, C D Hufford, E Li J Nat Prod . 1995 Jan;58(1):74-81. doi: 10.1021/np50115a009.
Ophiobolin A [1], 3-anhydroophiobolin A [2], ophiobolin B [3], and ophiobolin L [4] were isolated from fermentation broths of Cochliobolus heterostrophus. Preliminary screening showed that a number of organisms were capable of metabolizing the sesterterpene ophiobolin A [1]. Large-scale transformations of ophiobolin A [1] with Polyangium cellulosum produced 6 and 7 while Pseudomonas aeruginosa produced 8. Resting-cell preparations of Penicillium patulum afforded 9 and 10. The structures of these metabolites were established by spectroscopic methods and by comparison of the spectral data with those of the starting material. The antimicrobial activity of the ophiobolins was also evaluated.
2. Characterization of 6-epi-3-anhydroophiobolin B from Cochliobolus heterostrophus
D M Gibson, B G Turgeon, S W Lu, S B Krasnoff, C D Dunbar, J O'Neal, M T Hamann, O C Yoder, X Shen J Nat Prod . 1999 Jun;62(6):895-7. doi: 10.1021/np980462e.
The new sesterterpenoid 6-epi-3-anhydroophiobolin B (1) and six known ophiobolins were isolated from the extracts of the fungus Cochliobolus heterostrophus race O. The structure of 6-epi-3-anhydroophiobolin B was deduced from analysis of spectral data and the structural characterization of dehydration and dimerization products. Ophiobolin A (2) showed potent activity in cytotoxicity assays and marginal activity in antimalarial assays.
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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 ╳
