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Harzianumnones A and B: two hydroxyanthraquinones from the coral-derived fungus Trichoderma harzianum.

ABSTRACT: Two new hydroxyanthraquinones, harzianumnones A (1) and B (2), together with seven known analogs (3-9), were isolated from the soft coral-derived fungus Trichoderma harzianum (XS-20090075). Their chemical structures were elucidated by extensive spectroscopic investigation. The absolute configurations of 1 and 2 were determined by ECD calculation and single-crystal X-ray diffraction. Compounds 1 and 2 were identified as a pair of epimers, which are the first example of hydroanthraquinones from T. harzianum. Compounds 7 and 8 exhibited cytotoxicity against hepatoma cell line HepG2 with IC₅₀ values of 2.10 and 9.39 μM, respectively. Compound 7 was still found to show cytotoxicity against cervical cancer cell line HeLa with an IC₅₀ value of 8.59 μM.

SUBMITTER: Shi T

PROVIDER: S-EPMC9083448 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Harzianumnones A and B: two hydroxyanthraquinones from the coral-derived fungus <i>Trichoderma harzianum</i>.

Shi Ting T Hou Xue-Mei XM Li Zhi-Yong ZY Cao Fei F Zhang Ya-Hui YH Yu Jia-Yin JY Zhao Dong-Lin DL Shao Chang-Lun CL Wang Chang-Yun CY

RSC advances 20180802 49

Two new hydroxyanthraquinones, harzianumnones A (1) and B (2), together with seven known analogs (3-9), were isolated from the soft coral-derived fungus <i>Trichoderma harzianum</i> (XS-20090075). Their chemical structures were elucidated by extensive spectroscopic investigation. The absolute configurations of 1 and 2 were determined by ECD calculation and single-crystal X-ray diffraction. Compounds 1 and 2 were identified as a pair of epimers, which are the first example of hydroanthraquinones ...[more]

PMID: 35542739

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Project description:Fungi have the capacity to assimilate a diverse range of both inorganic and organic sulfur compounds. It has been recognized that all sulfur sources taken up by fungi are in soluble forms. In this study, we present evidence that fungi can utilize gaseous carbonyl sulfide (COS) for the assimilation of a sulfur compound. We found that the filamentous fungus Trichoderma harzianum strain THIF08, which has constitutively high COS-degrading activity, was able to grow with COS as the sole sulfur source. Cultivation with 34S-labeled COS revealed that sulfur atom from COS was incorporated into intracellular metabolites such as glutathione and ergothioneine. COS degradation by strain THIF08, in which as much of the moisture derived from the agar medium as possible was removed, indicated that gaseous COS was taken up directly into the cell. Escherichia coli transformed with a COS hydrolase (COSase) gene, which is clade D of the β-class carbonic anhydrase subfamily enzyme with high specificity for COS but low activity for CO2 hydration, showed that the COSase is involved in COS assimilation. Comparison of sulfur metabolites of strain THIF08 revealed a higher relative abundance of reduced sulfur compounds under the COS-supplemented condition than the sulfate-supplemented condition, suggesting that sulfur assimilation is more energetically efficient with COS than with sulfate because there is no redox change of sulfur. Phylogenetic analysis of the genes encoding COSase, which are distributed in a wide range of fungal taxa, suggests that the common ancestor of Ascomycota, Basidiomycota, and Mucoromycota acquired COSase at about 790-670 Ma.IMPORTANCEThe biological assimilation of gaseous CO2 and N2 involves essential processes known as carbon fixation and nitrogen fixation, respectively. In this study, we found that the fungus Trichoderma harzianum strain THIF08 can grow with gaseous carbonyl sulfide (COS), the most abundant and ubiquitous gaseous sulfur compound, as a sulfur source. When the fungus grew in these conditions, COS was assimilated into sulfur metabolites, and the key enzyme of this assimilation process is COS hydrolase (COSase), which specifically degrades COS. Moreover, the pathway was more energy efficient than the typical sulfate assimilation pathway. COSase genes are widely distributed in Ascomycota, Basidiomycota, and Mucoromycota and also occur in some Chytridiomycota, indicating that COS assimilation is widespread in fungi. Phylogenetic analysis of these genes revealed that the acquisition of COSase in filamentous fungi was estimated to have occurred at about 790-670 Ma, around the time that filamentous fungi transitioned to a terrestrial environment.

Dataset Information

Harzianumnones A and B: two hydroxyanthraquinones from the coral-derived fungus Trichoderma harzianum.

Publications

Harzianumnones A and B: two hydroxyanthraquinones from the coral-derived fungus <i>Trichoderma harzianum</i>.

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