Demethoxyviridiol
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| Category | Mycotoxins |
| Catalog number | BBF-04223 |
| CAS | 56617-66-4 |
| Molecular Weight | 324.33 |
| Molecular Formula | C19H16O5 |
| Purity | >95% by HPLC |
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Description
It is a mycotoxin produced by the strain of Nodulisporium hinnuleum. It is a fungal metabolite belonging to the wortmannin and viridin classes and an inhibitor of phosphatidylinositol 3-kinase. It affects phospholipid signalling and proliferation of swiss 3T3 cells.
Specification
| Synonyms | Desmethoxyviridiol; Cyclopenta(7,8)phenanthro(10,1-bc)furan-6,9-dione, 1,2,3,7,8,11b-hexahydro-1,3-dihydroxy-11b-methyl-, (1R-(1-alpha,3-alpha,11b-alpha))-; (1R,3S,11bR)-1,2,3,7,8,11b-Hexahydro-1,3-dihydroxy-11b-methylcyclopenta[7,8]phenanthro[10,1-bc]furan-6,9-dione; [1R-(1α,3α,11bα)]-1,2,3,7,8,11b-hexahydro-1,3-dihydroxy-11b-methylcyclopenta[7,8]phenanthro[10,1-bc]furan-6,9-dione |
| Storage | Store at -20°C |
| IUPAC Name | (1R,16S,18R)-16,18-dihydroxy-1-methyl-13-oxapentacyclo[10.6.1.02,10.05,9.015,19]nonadeca-2(10),3,5(9),12(19),14-pentaene-6,11-dione |
| Canonical SMILES | CC12C(CC(C3=COC(=C31)C(=O)C4=C2C=CC5=C4CCC5=O)O)O |
| InChI | InChI=1S/C19H16O5/c1-19-11-4-2-8-9(3-5-12(8)20)15(11)17(23)18-16(19)10(7-24-18)13(21)6-14(19)22/h2,4,7,13-14,21-22H,3,5-6H2,1H3/t13-,14+,19-/m0/s1 |
| InChI Key | OSSCBUARECIOCW-KSMMKXTCSA-N |
| Source | Nodulisporium sp. |
Properties
| Appearance | Crystal |
| Boiling Point | 486.7°C at 760 mmHg |
| Melting Point | 155-157°C |
| Density | 1.534 g/cm3 |
| Solubility | Soluble in Ethyl Acetate |
Reference Reading
1. Viridin-like steroids from Hymenoscyphus pseudoalbidus
Michelle Cleary, Stina Bengtsson, Pierre F Andersson, Jan Stenlid, Anders Broberg Phytochemistry . 2013 Feb;86:195-200. doi: 10.1016/j.phytochem.2012.09.012.
Three furanosteroids were isolated from the ash dieback causing fungus Hymenoscyphus pseudoalbidus along with the known compounds viridiol and demethoxyviridiol. The compounds were characterized by 1D and 2D NMR spectroscopy, LC-HRMS and polarimetry.
2. Hyfraxinic Acid, a Phytotoxic Tetrasubstituted Octanoic Acid, Produced by the Ash ( Fraxinus excelsior L.) Pathogen Hymenoscyphus fraxineus Together with Viridiol and Some of Its Analogues
Marco Masi, Benedetto Teodoro Linaldeddu, Roberta Di Lecce, Antonio Evidente, Lucia Maddau, Lucio Montecchio, Angela Tuzi J Agric Food Chem . 2019 Dec 11;67(49):13617-13623. doi: 10.1021/acs.jafc.9b06055.
A new tetrasubstituted octanoic acid, named hyfraxinic acid (1), was isolated together with known 1-deoxyviridiol (2), viridiol (3), nodulisporiviridin M (4), and demethoxyviridiol (5) from the organic extract ofHymenoscyphus fraxineusresponsible for ash (Fraxinus excelsiorL.) dieback in Europe. Hyfraxinic acid (1) was characterized, using spectroscopic methods, as 2,4-dihydroxy-7-methyl-6-methyleneoctanoic acid. Furthermore, the advanced Mosher method was used to determine the absolute configuration (3R) of 1-deoxyviridiol. Nodulisporiviridin M (4) was isolated for the first time fromH. fraxineus. The phytotoxicity of each compound was tested by a leaf puncture assay onCeltis australisL.,Quercus suberL.,Hedera elixL.,Juglans regiaL., andFraxinus angustifoliaL. leaves. Compounds1,3, and5exhibited remarkable phytotoxicity on all plants tested, inducing necrotic lesions at concentrations of 1.0 and 0.5 mg/mL, while compounds2and4were found to be inactive in this bioassay. These results could contribute to a deeper understanding of the pathogenicity ofH. fraxineus.
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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 ╳
