Nitrogenous cyclonerane sesquiterpenes from an algicolous strain of <i>Trichoderma asperellum</i>

Song, Yongxiang; Miao, Fang; Yin, Xiuli; Ji, Nai‐Yun

doi:10.1039/c9qo00942f

Cited by 9 publications

(12 citation statements)

References 32 publications

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“…Twentythree signals appeared in the 13 C NMR spectrum (Table 1), ascribed to six methyls, seven methylenes, four methines, and six nonprotonated carbons by DEPT and HSQC data. The above NMR data were very similar to those of deoxycyclonerin B (Song et al 2019), except for the existence of an extra acetyl group, confirmed by the HMBC correlations from H 3 -8′ and H 2 -5′ to C-7′ (Fig. 1).…”

Section: Resultssupporting

confidence: 71%

“…1). On account of the NOE correlation between H-2′ and H 2 -4′ and the similar NMR data with those of deoxycyclonerins (Song et al 2019), the E-geometry was appointed to the vinyl group at C-2′. The relative configurations at C-2, C-3, C-6, and C-7 were certified by the identical 1 H and 13 C NMR data with those of cyclonerane derivatives (Langhanki et al 2014;Laurent et al 1990;Song et al 2018b).…”

Section: Resultsmentioning

confidence: 60%

“…The relative configurations at C-2, C-3, C-6, and C-7 were certified by the identical 1 H and 13 C NMR data with those of cyclonerane derivatives (Langhanki et al 2014;Laurent et al 1990;Song et al 2018b). The absolute configurations at C-2, C-3, C-6, and C-7 were deduced to be uniform with its analogues according to biogenic consideration (Song et al 2019). To corroborate the absolute configuration of C-10, the electronic circular dichroism (ECD) spectrum of 1 was measured in methanol, which showed a negative Cotton effect at 225 nm (Fig.…”

Section: Resultsmentioning

confidence: 98%

“…3). In light of the biosynthetic origin and agreements of experimental ECD spectra between 2 and deoxycyclonerin B (Song et al 2019), the stereogenic centers of 5′-acetoxydeoxycyclonerin B were determined to be 2S, 3R, 6R, 7R, and 10R.…”

Section: Resultsmentioning

confidence: 99%

“…The fungal strain (GenBank no. MH819724), fermentation, extraction, and inceptive isolation were described in previous work (Song et al 2019). The third fraction was chromatographed on a Si gel column with petroleum ether/ethyl acetate (2:1) and was further isolated by column chromatography on RP-18 (methanol/water, 3:7) and preparative thinlayer chromatography (dichloromethane/methanol, 50:1) to afford 1 (118 mg).…”

Section: Fungal Material Fermentation Extraction and Isolationmentioning

confidence: 99%

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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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Section: Resultssupporting

confidence: 71%

Section: Resultsmentioning

confidence: 60%

Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Section: Fungal Material Fermentation Extraction and Isolationmentioning

confidence: 99%

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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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Structural and Biological Insights into the Hot‐Spot Marine Natural Products Reported from 2012 to 2021

Zhang

2022

Chin. J. Chem.

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Comprehensive Summary The vast marine ecosystem contains a sea of natural products, which are potential model molecules for new drug development. With more than one thousand new structures been discovered each year, the past decade has become the golden time for marine natural product discovery, leading to a valuable but extra‐large chemical database. Serving as an epitome of the most promising compounds, which take the ultra‐new skeletons and/or excellent bioactivities, this review covers 243 hot‐spot marine natural products reported from 2012 to 2021, to abstract some important chemical and/or biological inspirations for marine natural product study and marine drug development in the future. In addition, some general rules regarding to the source organism, structure‐specialty, organism‐structure specificity, and organism‐bioactivity relationship of these outstanding compounds will also be presented.

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Chemistry and biology of marine-derived Trichoderma metabolites

Song,

2024

Nat. Prod. Bioprospect.

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Marine-derived fungi of the genus Trichoderma have been surveyed for pharmaceuticals and agrochemicals since 1993, with various new secondary metabolites being characterized from the strains of marine animal, plant, sediment, and water origin. Chemical structures and biological activities of these metabolites are comprehensively reviewed herein up to the end of 2022 (covering 30 years). More than 70 strains that belong to at least 18 known Trichoderma species have been chemically investigated during this period. As a result, 445 new metabolites, including terpenes, steroids, polyketides, peptides, alkaloids, and others, have been identified, with over a half possessing antimicroalgal, zooplankton-toxic, antibacterial, antifungal, cytotoxic, anti-inflammatory, and other activities. The research is highlighted by the molecular diversity and antimicroalgal potency of terpenes and steroids. In addition, metabolic relevance along with co-culture induction in the production of new compounds is also concluded. Trichoderma strains of marine origin can transform and degrade heterogeneous molecules, but these functions need further exploration. Graphical Abstract

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Nitrogenous cyclonerane sesquiterpenes from an algicolous strain of Trichoderma asperellum

Abstract: Eight new nitrogenous cyclonerance derivatives (1–8) including two unprecedented hydroxamic acids (1 and 2) with potent algicidal activity were characterized from the algicolous fungus Trichoderma asperellum.

Cited by 9 publications

References 32 publications

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

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

Structural and Biological Insights into the Hot‐Spot Marine Natural Products Reported from 2012 to 2021

Chemistry and biology of marine-derived Trichoderma metabolites

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