“…273 751-757, methylhydroheptelidate 758 and carotane derivatives 759 and 760. 274 Cultivation of Trichoderma erinaceum supplemented with L-phenylalanine yielded a different suite of metabolites to those produced without supplementation. In the absence of L-phenylalanine, terpenoids, including new metabolites 761-764 were produced but with supplementation, aromatic compounds including 765-771 were produced (the last a known synthetic compound but a new MNP).…”
Section: Cyanobacteriamentioning
confidence: 99%
“…268 A number of metabolites were isolated from Trichoderma strains, including epipolythiodiketopiperazines 725 and 726 , 269 trichothecene sesquiterpenoids 727–729 , 269 730–739 , 270 740 and 741 , 271 cyclonerane sesquiterpenoids 742 and 743 and isocoumarin 744 , 272 cadinane sesquiterpenoids 745 , 746 and 747 (as a new MNP), rhinomilisin E, 748 , trichrodermaloid C, 749 , rhinomilisin G, 750 (absolute configurations established for rhinomilisin E and G), 273 751–757 , methylhydroheptelidate 758 and carotane derivatives 759 and 760 . 274 Cultivation of Trichoderma erinaceum supplemented with l -phenylalanine yielded a different suite of metabolites to those produced without supplementation. In the absence of l -phenylalanine, terpenoids, including new metabolites 761–764 were produced but with supplementation, aromatic compounds including 765–771 were produced (the last a known synthetic compound but a new MNP).…”
Section: Marine Microorganisms and Phytoplanktonmentioning
“…273 751-757, methylhydroheptelidate 758 and carotane derivatives 759 and 760. 274 Cultivation of Trichoderma erinaceum supplemented with L-phenylalanine yielded a different suite of metabolites to those produced without supplementation. In the absence of L-phenylalanine, terpenoids, including new metabolites 761-764 were produced but with supplementation, aromatic compounds including 765-771 were produced (the last a known synthetic compound but a new MNP).…”
Section: Cyanobacteriamentioning
confidence: 99%
“…268 A number of metabolites were isolated from Trichoderma strains, including epipolythiodiketopiperazines 725 and 726 , 269 trichothecene sesquiterpenoids 727–729 , 269 730–739 , 270 740 and 741 , 271 cyclonerane sesquiterpenoids 742 and 743 and isocoumarin 744 , 272 cadinane sesquiterpenoids 745 , 746 and 747 (as a new MNP), rhinomilisin E, 748 , trichrodermaloid C, 749 , rhinomilisin G, 750 (absolute configurations established for rhinomilisin E and G), 273 751–757 , methylhydroheptelidate 758 and carotane derivatives 759 and 760 . 274 Cultivation of Trichoderma erinaceum supplemented with l -phenylalanine yielded a different suite of metabolites to those produced without supplementation. In the absence of l -phenylalanine, terpenoids, including new metabolites 761–764 were produced but with supplementation, aromatic compounds including 765–771 were produced (the last a known synthetic compound but a new MNP).…”
Section: Marine Microorganisms and Phytoplanktonmentioning
“…A new cadinane derivative trichocadinin H ( 99 ), was isolated from the culture of Trichoderma virens RR‐dl‐6‐8 associated with the organohalogen‐enriched marine red alga Rhodomela confervoides , which showed inhibition activity against Amphidinium carterae and Heterosigma akashiwo , with IC 50 values of 1.5 and 0.87 μg/mL, respectively. [ 59 ] …”
Section: Marine Habitats For Microorganisms Producing Halogenated Com...mentioning
Comprehensive Summary
Natural products derived from marine microorganisms have been received great attention as a potential source of new compound entities for drug discovery. The unique marine environment brings us a large group of halogen‐containing natural products with abundant biological functionality and good drugability. Meanwhile, biosynthetically halogenated reactions are known as a significant strategy used to increase the pharmacological activities and pharmacokinetic properties of compounds. Given that a tremendous increase in the number of new halogenated compounds from marine microorganisms in the last five years, it is necessary to summarize these compounds with their diverse structures and promising bioactivities. In this review, we have summarized the chemistry, biosynthesis (related halogenases), and biological activity of a total of 316 naturally halogenated compounds from marine microorganisms covering the period of 2015 to May 2021. Those reviewed chlorinated and brominated compounds with the ratio of 9 : 1 were predominantly originated from 36 genera of fungi (62%) and 9 bacterial strains (38%) with cytotoxic, antibacterial, and enzyme inhibitory activities, structural types of which are polyketides (38%), alkaloids (27%), phenols (11%), and others. This review would provide a plenty variety of promising lead halogenated compounds for drug discovery and inspire the development of new pharmaceutical agents.
“…Sesquiterpenes are almost ubiquitous in Trichoderma species, such as T. asperellum (Shi et al, 2019;Song et al, 2019), T. brevicompactum (Klaiklay et al, 2019;Shi et al, 2020), T. citrinoviride (Liu et al, 2020), T. harzianum (Song et al, 2018), T. polysporum (Fujita et al, 1984), and T. virens (Song et al, 2020), and they contain at least ten kinds of frameworks (Reino et al, 2008). Although T. hamatum has proven to produce a series of simple isonitrile (isocyanide) and cyclopentanone derivatives as well as a pentacyclic polyketide (Baldwin et al, 1985;Boyd et al, 1991;Brewer et al, 1979;Matsumoto et al, 1999;Sakuno et al, 2000), no sesquiterpenes and other terpenes have previously been discovered from this species.…”
Section: Introductionmentioning
confidence: 99%
“…Although T. hamatum has proven to produce a series of simple isonitrile (isocyanide) and cyclopentanone derivatives as well as a pentacyclic polyketide (Baldwin et al, 1985;Boyd et al, 1991;Brewer et al, 1979;Matsumoto et al, 1999;Sakuno et al, 2000), no sesquiterpenes and other terpenes have previously been discovered from this species. During our continuing investigation toward the structural diversity of secondary metabolites from marine-derived Trichoderma (Liu et al, 2020;Shi et al, 2020;Song et al, 2020), an epiphytic isolate Trichoderma hamatum Z36-7 obtained from the marine red alga Grateloupia sp. was chemically examined.…”
Two new cyclonerane sesquiterpenes, 5-hydroxyepicyclonerodiol oxide (1) and 4-hydroxyepicyclonerodiol oxide (2), and one new naturally occurring halogenated trichothecane derivative, trichodermol chlorohydrin (3), were isolated from Trichoderma hamatum Z36− 7, an epiphytic fungal strain obtained from the marine red alga Grateloupia sp. Their structures and relative configurations were assigned on the basis of spectroscopic techniques, including 1D/2D NMR and IR as well as MS. Compound 2 features an unusual 4-hydroxy group on the five-membered ring of cycloneranes, and 3 is the first natural isolate of halogenated trichothecanes. These isolates represent the first occurrence of terpenes in T. hamatum and exhibit growth inhibition of several bacteria and phytoplankton species.
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