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Bioactive polyketides from the pathogenic fungus of Epicoccum sorghinum
- Source :
- Planta. 253(6)
- Publication Year :
- 2021
-
Abstract
- We discovered and identified a series of characteristic substances, including one new polyketide, epicorepoxydon B, of the important pathogenic fungus, Epicoccum sorghinum, of sorghum. The fungal extract and some isolated polyketides are sensitive to a malignant triple-negative breast cancer cell line, MDA-MB-231. Sorghum (Kaoliang) grain is an important crop with high economic value and several applications. In Taiwan, sorghum has been used in the wine industry, and “Kinmen Kaoliang Liquor” is a well-known Asian brand. Fungal contamination is one of the major threats affecting the production of sorghum grain resulting in economic losses as well as human and animal health problems. Several fungal species can infect sorghum grain and generate some toxic secondary metabolites. Epicoccum sorghinum is one of the major fungal contaminants of sorghum grains and a potent producer of mycotoxins such as tenuazonic acid (TeA). However, except for TeA, few studies focused on chemical compounds produced by this fungus. To explore the potential biological and toxic effects of E. sorghinum, a chemical investigation was carried out on the ethyl acetate extract of the fungus because it showed cytotoxic activity against a triple-negative breast cancer cell line, MDA-MB-231 (54.82% inhibition at 20 µg/mL). One new polyketide, epicorepoxydon B (1), along with six known compounds including 4,5-dihydroxy-6-(6′-methylsalicyloxy)-2-hydroxymethyl-2-cyclohexenl-one (2), epicorepoxydon A (3), 3-hydroxybenzyl alcohol (4), 6-methylsalicylic acid (5), gentisyl alcohol (6), and 6-(hydroxymethyl)benzene-1,2,4-triol (7) were obtained, and their structures were established by the interpretation of their MS and NMR spectroscopic data. The cytotoxic activity of all isolated polyketides 1–7 was evaluated, and compounds 2, 6, and 7 exhibited potent activities against A549, HepG2, and MDA-MB-231 human cancer cell lines with IC50 value ranging from 1.86 to 18.31 μM. The structure–activity relationship of the isolated compounds was proposed.
- Subjects :
- 0106 biological sciences
0301 basic medicine
Ethyl acetate
Plant Science
Fungus
01 natural sciences
03 medical and health sciences
chemistry.chemical_compound
Polyketide
Ascomycota
Genetics
Tenuazonic acid
Structure–activity relationship
Food science
Mycotoxin
Sorghum
biology
Molecular Structure
food and beverages
Pathogenic fungus
biology.organism_classification
030104 developmental biology
chemistry
Polyketides
Edible Grain
010606 plant biology & botany
Subjects
Details
- ISSN :
- 14322048
- Volume :
- 253
- Issue :
- 6
- Database :
- OpenAIRE
- Journal :
- Planta
- Accession number :
- edsair.doi.dedup.....714aa14be4d0fe75a6a2185a6018cea7