Trichosordarin A, a norditerpene glycoside from the marine-derived fungus <i>Trichoderma harzianum</i> R5

Liang, Xiujuan; Ma, Xinyue; Ji, Nai‐Yun

doi:10.1080/14786419.2019.1574782

Cited by 19 publications

(20 citation statements)

References 17 publications

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“…One of the mechanism of these bioactivities of T. harzianum is considered to be its ability to produce metabolites with various activities, such as antifungal harzianopyridone (Ahluwalia et al, 2015) and 6-pentyl-α-pyrone (Chen et al, 2012), plant growth promoter harzianic acid (Vinale et al, 2013), and plant growth regulator harzianolide (Cai et al, 2013). Marine-derived T. harzianum can also produce substantial active secondary metabolites (Liang et al, 2019;Yamada et al, 2019;Zhao et al, 2019). More than 60 compounds have been isolated from marine-derived T. harzianum that further demonstrated the potential ability of this fungus to produce natural products with diverse structures.…”

Section: Introductionmentioning

confidence: 99%

Terpenoids From the Coral-Derived Fungus Trichoderma harzianum (XS-20090075) Induced by Chemical Epigenetic Manipulation

et al. 2020

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The soft coral-derived fungus Trichoderma harzianum (XS-20090075) was found to be a potential strain to produce substantial new compounds in our previous study. In order to explore its potential to produce more metabolites, chemical epigenetic manipulation was used on this fungus to wake its sleeping genes, leading to the significant changes of its secondary metabolites by using a histone deacetylase (HDAC) inhibitor. The most obvious difference was the original main products harziane diterpenoids were changed into cyclonerane sesquiterpenoids. Three new terpenoids were isolated from the fungal culture treated with 10 µM sodium butyrate, including cleistanthane diterpenoid, harzianolic acid A (1), harziane diterpenoid, harzianone E (2), and cyclonerane sesquiterpenoid, 3,7,11-trihydroxy-cycloneran (3), together with 11 known sesquiterpenoids (4-14). The absolute configurations of 1-3 were determined by single-crystal X-ray diffraction, ECD and OR calculations, and biogenetic considerations. This was the first time to obtain cleistanthane diterpenoid and africane sesquiterpenoid from genus Trichoderma, and this was the first chlorinated cleistanthane diterpenoid. These results demonstrated that the chemical epigenetic manipulation should be an efficient technique for the discovery of new secondary metabolites from marinederived fungi.

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Section: Introductionmentioning

confidence: 99%

Terpenoids From the Coral-Derived Fungus Trichoderma harzianum (XS-20090075) Induced by Chemical Epigenetic Manipulation

et al. 2020

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“…Four verrucosidin derivatives, penicyrone (52), norpenicyrone (53), methyl norpenicyrone (54), and methyl penicyrone (55) were isolated from the hydrothermal vent sulfurderived fungus Penicillium sp. Y-50-10 (Kueishantao, Taiwan, the East China Sea).…”

Section: Antifungal Activitymentioning

confidence: 99%

“…A new sordarin derivative, trichosordarin A (80), with a unique norditerpene aglycone, was isolated from Trichoderma harzianum R5 (the Bohai Sea). Compound 80 ( Figure 7) was toxic to Artemia salina, but it appeared to only weakly inhibit Amphidinium carterae and Phaeocystis globosa [53]. Later, a large number of drimane sesquiterpenoids were isolated from this fungal strain and one of them, ustusol A (72), exhibited activity against a panel of plant pathogenic fungi, including Thielaviopsis paradoxa, Pestalotia calabae, and Gloeosporium musarum [51].…”

Section: Plankton Toxicitymentioning

confidence: 99%

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Metabolites of Marine Sediment-Derived Fungi: Actual Trends of Biological Activity Studies

2021

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Marine sediments are characterized by intense degradation of sedimenting organic matter in the water column and near surface sediments, combined with characteristically low temperatures and elevated pressures. Fungi are less represented in the microbial communities of sediments than bacteria and archaea and their relationships are competitive. This results in wide variety of secondary metabolites produced by marine sediment-derived fungi both for environmental adaptation and for interspecies interactions. Earlier marine fungal metabolites were investigated mainly for their antibacterial and antifungal activities, but now also as anticancer and cytoprotective drug candidates. This review aims to describe low-molecular-weight secondary metabolites of marine sediment-derived fungi in the context of their biological activity and covers research articles published between January 2016 and November 2020.

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“…It has been discovered that Trichoderma fungi are almost ubiquitous in terrestrial and aquatic environments. To date, more than one hundred new terpenes, steroids, polyketides, alkaloids, and peptides with antimicroalgal, antibacterial, antifungal, cytotoxic, and enzyme-inhibitory properties have been obtained from the marine-derived Trichoderma species Liang et al 2016Liang et al , 2019Miao et al 2012;Pang et al 2018;Shi et al 2018Shi et al , 2019Song et al 2018a, b, c, d;Su et al 2018). Among them, T. asperellum is one of the most productive species, and its isolates from marine algae and sediments have contributed a number of new terpenes and nitrogen-bearing compounds that mainly comprise menthane, bisabolane, cyclonerane, harziane, ergostane, oxazole, diketopiperazine, and peptaibol derivatives (Ren et al 2009;Shi et al 2019;Song et al 2018b, c, d).…”

Section: Introductionmentioning

confidence: 99%

Three nitrogen-containing metabolites from an algicolous isolate of Trichoderma asperellum

Song

Miao

Yin

et al. 2020

Mar Life Sci Technol

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As one of the most productive species, Trichoderma asperellum, especially isolated from marine algae, has contributed a number of new terpenes and nitrogen-bearing compounds, encouraging our continuous efforts to further explore them. Consequently, three new nitrogen-containing secondary metabolites, including cyclo(L-5-MeO-Pro-L-5-MeO-Pro) (1), 5′-acetoxy-deoxycyclonerin B (2), and 5′-acetoxy-deoxycyclonerin D (3) were isolated from the marine alga-derived endophytic fungus Trichoderma asperellum A-YMD-9-2. Their structures and relative configurations were fully elucidated through spectroscopic techniques, mainly including 1D/2D NMR and MS. The absolute configurations of 1 and 2 were ascertained on the basis of X-ray diffraction (Cu Kα radiation) and ECD data, respectively. The isolation of these new nitrogen-bearing compounds adds to the structural diversity of marine algicolous Trichoderma spp., and they display potent inhibition against some marine phytoplankton species.

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Trichosordarin A, a norditerpene glycoside from the marine-derived fungus Trichoderma harzianum R5

Cited by 19 publications

References 17 publications

Terpenoids From the Coral-Derived Fungus Trichoderma harzianum (XS-20090075) Induced by Chemical Epigenetic Manipulation

Terpenoids From the Coral-Derived Fungus Trichoderma harzianum (XS-20090075) Induced by Chemical Epigenetic Manipulation

Metabolites of Marine Sediment-Derived Fungi: Actual Trends of Biological Activity Studies

Three nitrogen-containing metabolites from an algicolous isolate of Trichoderma asperellum

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