Trichothecenes from an Endophytic Fungus Alternaria sp. sb23

Abstract

Three new (alterchothecenes A – C, 1 –3) and 3 known (4 –6) trichothecenes, along with 9 known compounds (7 –15), were isolated from the culture of Alternaria sp. sb23, an endophytic fungus separated from the root of Schisandra sphenanthera Rehd. et Wils. Their structures were elucidated by spectroscopic analyses, and the absolute configurations of 1–3 were determined through comparison of the experimental electronic circular dichroism (ECD) spectra and optical rotations with similar analogues. In vitro cytotoxicity tests of compounds 1–6 against human HT-29 colon carcinoma and human MCF-7 breast cancer cell lines indicated that 4–6 exhibited significant cytotoxic effects, with IC50 values ranging from 0.89 to 9.38 µM. And the potential of compounds 1–6 as tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL) sensitizers in HT-29 cells was evaluated. The results revealed that combination treatment of TRAIL with compounds 1–6 synergistically decreased cell viability compared with the sole treatment with those compounds.

Bioactive compounds and biomedical applications of endophytic fungi: a recent review

“…SZMC 23772 Hypericum perforatum Antimicrobial activity [ 60 ] Alternaria sp. sb23 Schisandra sphenanthera Anticancer activity [ 223 ] Alternaria sp. LV52: Cystoseira tamariscifolia Anticancer activity [ 224 ] A. alternata Paeonia lactiflora Anticancer activity [ 225 ] A. alternata MGTMMP031 Vitex negundo Anticancer activity [ 226 ] A. altenata Lithospermum Officinale Antioxidant activity [ 227 ] A.alternata Picrorhiza kurroa Antioxidant and antimicrobial activities [ 185 ] A.alternata Melissa officinalis Anticancer activity [ 228 ] A.alternata Ziziphus spina-christi Antimicrobial and antioxidant activities [ 186 ] A. brassicicola Terminalia arjuna Anticancer activity [ 229 ] A.Destruens Calotropis gigantean Antimicrobial, antibiofilm, antidiabetic activities [ 230 ] …”

Secondary metabolites of Alternaria: A comprehensive review of chemical diversity and pharmacological properties

“…New trichothecene derivatives with a 1, 2-diol moiety at C-12 and C-13, alterchothecenes A-C (166-168), were isolated from Alternaria sp. sb23 bearing a 12, 13epoxytrichothec-9-ene ring moiety (Gao et al, 2020). Spectra data analysis of NMR, DEPT, and HSQC suggested that 167 is 8-dihydrogeneated derivatives and 168 is 13-acetylated derivatives of 166 respectively (Gao et al, 2020).…”

“…sb23 bearing a 12, 13epoxytrichothec-9-ene ring moiety (Gao et al, 2020). Spectra data analysis of NMR, DEPT, and HSQC suggested that 167 is 8-dihydrogeneated derivatives and 168 is 13-acetylated derivatives of 166 respectively (Gao et al, 2020). Similarly, (1R,5R,6R,7R,10S)-1,6-Dihroxyeudesm-4(15)-ene ( 169) is a new sesquiterpenoid isolated from Alternaria alternate .…”

Structure Elucidation and Anti-Tumor Activities of Trichothecenes from Endophytic Fungus Fusariumsporotrichioides

“…Currently, approximately 200 members of the trichothecene family have been identified [ 8 ]. Trichothecenes are also a source of contamination in food, which could induce a series of acute and chronic symptoms, such as hypotension, anemia and so on [ 9 ]. Nevertheless, some trichothecenes have also been reported to exhibit antifungal, antimalarial, antiviral and phytotoxic activities [ 9 , 10 , 11 ].…”

“…Trichothecenes are also a source of contamination in food, which could induce a series of acute and chronic symptoms, such as hypotension, anemia and so on [ 9 ]. Nevertheless, some trichothecenes have also been reported to exhibit antifungal, antimalarial, antiviral and phytotoxic activities [ 9 , 10 , 11 ]. The biological investigation of the five compounds suggested that all of them exhibited cytotoxicities against Huh-7 cells and MRMT-1 cells.…”