Altiloxin A
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| Category | Mycotoxins |
| Catalog number | BBF-00427 |
| CAS | 92675-11-1 |
| Molecular Weight | 268.35 |
| Molecular Formula | C15H24O4 |
| Purity | 95% |
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Description
It is produced by the strain of Phoma asparagi Sacc ALD-8. It is a plant toxin that can inhibit the growth of roots.
Specification
| Synonyms | (1as,3s,4r,4ar,8ar)-3-hydroxy-3,4a,8,8-tetramethyloctahydro-1ah-naphtho[1,8a-b]oxirene-4-carboxylic acid; (-)-Altiloxin A; CTK5H1580; DTXSID20896902; 3H-Naphth(1,8a-b)oxirene-4-carboxylic acid, octahydro-3-hydroxy-3,4a,8,8-tetramethyl-, (1aS,3R,4R,4aR,8aR)-; 3H-Naphth(1,8a-b)oxirene-4-carboxylic acid, octahydro-3-hydroxy-3,4a,8,8-tetramethyl-, (1aS-(1aalpha,3beta,4alpha,4aalpha,8aS*))- |
| IUPAC Name | (1aS,3S,4R,4aR,8aR)-3-hydroxy-3,4a,8,8-tetramethyl-1a,2,4,5,6,7-hexahydronaphtho[4,4a-b]oxirene-4-carboxylic acid |
| Canonical SMILES | CC1(CCCC2(C13C(O3)CC(C2C(=O)O)(C)O)C)C |
| InChI | InChI=1S/C15H24O4/c1-12(2)6-5-7-13(3)10(11(16)17)14(4,18)8-9-15(12,13)19-9/h9-10,18H,5-8H2,1-4H3,(H,16,17)/t9-,10+,13+,14-,15+/m0/s1 |
| InChI Key | LGLGMAPTXWEBIH-MGZPQWHJSA-N |
Properties
| Appearance | White Crystal |
| Boiling Point | 411.0 °C at 760 mmHg |
| Melting Point | 136-137 °C |
| Density | 1.210 g/cm3 |
| Solubility | Soluble in Chloroform |
Reference Reading
1. Pioneering Metabolomic Studies on Diaporthe eres Species Complex from Fruit Trees in the South-Eastern Poland
Barbara Abramczyk, Łukasz Pecio, Solomiia Kozachok, Mariusz Kowalczyk, Anna Marzec-Grządziel, Ewa Król, Anna Gałązka, Wiesław Oleszek Molecules. 2023 Jan 25;28(3):1175. doi: 10.3390/molecules28031175.
Fungi from the genus Diaporthe have been reported as plant pathogens, endophytes, and saprophytes on a wide range of host plants worldwide. Their precise identification is problematic since many Diaporthe species can colonize a single host plant, whereas the same Diaporthe species can inhabit many hosts. Recently, Diaporthe has been proven to be a rich source of bioactive secondary metabolites. In our initial study, 40 Diaporthe isolates were analyzed for their metabolite production. A total of 153 compounds were identified based on their spectroscopic properties-Ultraviolet-visible and mass spectrometry. From these, 43 fungal metabolites were recognized as potential chemotaxonomic markers, mostly belonging to the drimane sesquiterpenoid-phthalide hybrid class. This group included mainly phytotoxic compounds such as cyclopaldic acid, altiloxin A, B, and their derivatives. To the best of our knowledge, this is the first report on the metabolomic studies on Diaporthe eres species complex from fruit trees in the South-Eastern Poland. The results from our study may provide the basis for the future research on the isolation of identified metabolites and on their bioactive potential for agricultural applications as biopesticides or biofertilizers.
2. Secondary Metabolites Isolated from the Amazonian Endophytic Fungus Diaporthe sp. SNB-GSS10
Hugues Mandavid, Alice M S Rodrigues, Laila S Espindola, Véronique Eparvier, Didier Stien J Nat Prod. 2015 Jul 24;78(7):1735-9. doi: 10.1021/np501029s. Epub 2015 Jul 7.
We describe a Sabicea cinerea endophytic fungus closely related to Diaporthe pseudomangiferae that produces two known metabolites, mycoepoxydiene (1) and altiloxin A (2), as well as enamidin (3) and eremofortin F (4), two compounds not previously described in the literature. The structure of these four metabolites was elucidated using spectroscopic analysis, and their cytotoxic activities were measured against the human cell lines KB, MRC-5, and MDA-MB-435.
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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 ╳
