Deoxyfusapyrone
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| Category | Antibiotics |
| Catalog number | BBF-04252 |
| CAS | 156856-32-5 |
| Molecular Weight | 590.79 |
| Molecular Formula | C34H54O8 |
| Purity | >98% by HPLC |
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Description
It is a broad spectrum antifungal metabolite isolated from several fusarium species. It exhibits low zoo-toxicity as evidenced by a lack of toxicity against artemia salina. It is a useful candidate for control of postharvest crop diseases.
Specification
| Synonyms | Deoxyneofusapyrone; 3-(4-deoxy-β-xylo-hexopyranosyl)-2-hydroxy-6-[(3E,5E,8Z)-2-hydroxy-1,1,5,7,9,11-hexamethyl-3,5,8-heptadecatrien-1-yl]-4H-pyran-4-one |
| Storage | Store at -20°C |
| IUPAC Name | 3-[(2S,3R,4S,6S)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-4-hydroxy-6-[(4E,6E,9Z)-3-hydroxy-2,6,8,10,12-pentamethyloctadeca-4,6,9-trien-2-yl]pyran-2-one |
| Canonical SMILES | CCCCCCC(C)CC(=CC(C)C=C(C)C=CC(C(C)(C)C1=CC(=C(C(=O)O1)C2C(C(CC(O2)CO)O)O)O)O)C |
| InChI | InChI=1S/C34H54O8/c1-8-9-10-11-12-21(2)15-23(4)17-24(5)16-22(3)13-14-28(38)34(6,7)29-19-26(36)30(33(40)42-29)32-31(39)27(37)18-25(20-35)41-32/h13-14,16-17,19,21,24-25,27-28,31-32,35-39H,8-12,15,18,20H2,1-7H3/b14-13+,22-16+,23-17-/t21?,24?,25-,27-,28?,31+,32-/m0/s1 |
| InChI Key | MRMMGDLQIQYRDA-PWVYRXAXSA-N |
| Source | Fusarium sp. |
Properties
| Appearance | Oily Matter |
| Antibiotic Activity Spectrum | Fungi |
| Boiling Point | 765.9±60.0°C at 760 mmHg |
| Density | 1.1±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Structure-activity relationships of derivatives of fusapyrone, an antifungal metabolite of Fusarium semitectum
Antonio Evidente, Mara Favilla, Raffaele Pengue, Angelo Visconti, Claudio Altomare J Agric Food Chem . 2004 May 19;52(10):2997-3001. doi: 10.1021/jf035233z.
Fusapyrone (1) and deoxyfusapyrone (2) are two 3-substituted-4-hydroxy-6-alkyl-2-pyrones isolated from Fusarium semitectum that have considerable antifungal activity against molds. Because of their low zootoxicity and selective action they are potentially utilizable along with biocontrol yeasts for control of postharvest crop diseases. Seven derivatives of 1 (3 and 5-10) and one derivative of 2 (4) were obtained by chemical modifications of the glycosyl residue, the 2-pyrone ring, the aliphatic chain, or a combination thereof, and a structure-activity correlation study was carried out with regard to their zootoxicity and antifungal activity. Derivatives 7-10, as well as 1, were slightly zootoxic in Artemia salina (brine shrimp) bioassays, whereas pentaacetylation of 1 into 3, 5, and 6 resulted in a strong increase in toxicity. Compound 4, the tetraacetyl derivative of 2, was as toxic as 2. Because the structural changes of 1 that resulted in an increase of biological activity in A. salina bioassay were those that affected mainly the water solubility of the molecule, it appears that toxicity is related to hydrophobicity. Compounds 1 and 2 showed strong antifungal activity toward Botrytis cinerea, Aspergillus parasiticus, and Penicilliun brevi-compactum (minimum inhibitory concentration at 24 h = 0.78-6.25 microg/mL). Among derivatives 3-10, only compounds 7, 9, and 10 retained some activity, limited to B. cinerea and at high concentration (25-50 microg/mL). None of the compounds 1-10 inhibited the growth of the biocontrol yeasts Pichia guilliermondii and Rhodotorula glutinis at the highest concentration tested (50 microg/mL).
2. High performance liquid chromatography for the analysis of fusapyrone and deoxyfusapyrone, two antifungal alpha-pyrones from Fusarium semitectum
R Pengue, C Altomare, C Amalfitano, A Evidente Nat Toxins . 1999;7(4):133-7. doi: 10.1002/(sici)1522-7189(199907/08)7:43.0.co;2-i.
A simple, very sensitive and rapid HPLC method was developed for the simultaneous quantitative analysis of both fusapyrone (FP) and deoxyfusapyrone (DFP), the two antifungal 3-substituted-4-hydroxy-6-alkyl-2-pyrones isolated from rice culture of Fusarium semitectum, in crude extracts. Such method was optimized on C-18 reverse phase column, using the isolated metabolites as standards, with a sequence of linear elution steps with a MeOH-H(2)O mixture and using an ultraviolet detector fixed at 285 nm, where both alpha-pyrones showed a characteristic absorption maximum. This method was used to quantify the bioactive metabolites in crude organic extracts from two F. semitectum strains. The recovery of FP and DFP was measured in a crude extract from a poor metabolite producer F. semitectum strain. The recovery values ranged from 84% to 99% for FP and from 99% to 101% for DFP, indicating that the method was close to quantitative recovery. Furthermore, an efficient medium pressure column chromatography and TLC combined method was developed for the isolation and purification of FP and DFP from fungal culture extracts.
3. Isolation and characterization of bioactive metabolites from marine-derived filamentous fungi collected from tropical and sub-tropical coral reefs
S Meguro, M Namikoshi, H Kobayashi, K Akano, T Yoshimoto Chem Pharm Bull (Tokyo) . 2000 Oct;48(10):1452-7. doi: 10.1248/cpb.48.1452.
Two new compounds, paecilospirone (1) and phomopsidin (2), and seven known compounds, chaetoglobosin A (3), griseofulvin (4), fusarielin A (5), fusapyrone (6), deoxyfusapyrone (7), and verrucarins J (8) and L acetate (9), have been isolated and characterized from marine-derived fungi collected in tropical and sub-tropical coral reef environments. The utility of marine-derived fungi as a source of bioactive secondary metabolites is discussed.
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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 ╳
