Altiloxin B

Altiloxin B

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Category Mycotoxins
Catalog number BBF-00428
CAS 92675-14-4
Molecular Weight 302.79
Molecular Formula C15H23O4Cl

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Description

It is produced by the strain of Phoma asparagi Sacc ALD-8. Plant toxin.

Specification

Synonyms (1aS,8aS)-7α-Chlorooctahydro-3β-hydroxy-3,4aα,8,8-tetramethyl-3H-naphth[1,8a-b]oxirene-4α-carboxylic acid
IUPAC Name (1aS,3R,4R,4aR,7S,8aS)-7-chloro-3-hydroxy-3,4a,8,8-tetramethyl-1a,2,4,5,6,7-hexahydronaphtho[4,4a-b]oxirene-4-carboxylic acid
Canonical SMILES CC1(C(CCC2(C13C(O3)CC(C2C(=O)O)(C)O)C)Cl)C
InChI InChI=1S/C15H23ClO4/c1-12(2)8(16)5-6-13(3)10(11(17)18)14(4,19)7-9-15(12,13)20-9/h8-10,19H,5-7H2,1-4H3,(H,17,18)/t8-,9-,10+,13+,14+,15+/m0/s1
InChI Key FZDLFIRMAQCUGH-MSKJFZEMSA-N

Properties

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. Pestalotiopens A and B: stereochemically challenging flexible sesquiterpene-cyclopaldic acid hybrids from Pestalotiopsis sp
Yasmin Hemberger, Jing Xu, Victor Wray, Peter Proksch, Jun Wu, Gerhard Bringmann Chemistry. 2013 Nov 11;19(46):15556-64. doi: 10.1002/chem.201302204. Epub 2013 Oct 2.
From the endophytic fungus Pestalotiopsis sp. isolated from the leaves of the Chinese mangrove, Rhizophora mucronata, two novel hybrid sesquiterpene-cyclopaldic acid metabolites with an unusual carbon skeleton, named pestalotiopens A and B, were obtained, together with the already known phytotoxin altiloxin B. Pestalotiopen B even contains a third, triketide-derived module. The constitutions and the absolute configurations of the new metabolites and of altiloxin B were unambiguously determined by a combination of spectroscopic methods and quantum-chemical optical-rotatory dispersion (ORD) and circular dichroism (CD) calculations. A biosynthetic pathway to pestalotiopens A and B is proposed with altiloxin B as one of the suggested precursors. Pestalotiopen A shows moderate antimicrobial activity against Enterococcus faecalis.

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