Cytotoxic Tricycloalternarene Compounds from Endophyte Alternaria sp. W-1 Associated with Laminaria japonica

Shen, Li; Tian, Shujuan; Song, Hui-Liang; Chen, Xi; Guo, Hao; Wan, Dan; Wang, Yurou; Wang, Fengwu; Liu, Lijun

doi:10.3390/md16110402

Cited by 18 publications

(9 citation statements)

References 35 publications

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“…W-1, derived from Laminaria japonica, respectively. In the bioassay experiments, compound 317 and TCA-3a exhibited weak cytotoxicity against SMMC-7721 cells in a dose-dependent manner (IC 50 = 49.7, 45.8 µg/mL) [97]. Further studies revealed that the anticancer mechanism of TCA-3a is related to cell cycle arrest in the G1 phase, and that induction of apoptosis involved two pathways (mitochondrial and death receptor pathways) [97].…”

Section: Meroterpenesmentioning

confidence: 99%

“…Among them, compounds 307-310 possessed a rare tetrahydrofuran ring in TCAs [80]. Two new TCA acids (tricycloalternarenes K and L) (315 and 316) [96] and a new TCA ester (2H-(2E)-tricycloalternarene 12a, 317) [97] and six known derivatives were discovered from two fungal strains, Alternaria alternata ICD5-11, associated with marine isopod Ligia exotica, and Alternaria sp. W-1, derived from Laminaria japonica, respectively.…”

Section: Meroterpenesmentioning

confidence: 99%

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A Review of Terpenes from Marine-Derived Fungi: 2015–2019

Jiang

Guo

et al. 2020

Marine Drugs

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Marine-derived fungi are a significant source of pharmacologically active metabolites with interesting structural properties, especially terpenoids with biological and chemical diversity. In the past five years, there has been a tremendous increase in the rate of new terpenoids from marine-derived fungi being discovered. In this updated review, we examine the chemical structures and bioactive properties of new terpenes from marine-derived fungi, and the biodiversity of these fungi from 2015 to 2019. A total of 140 research papers describing 471 new terpenoids of six groups (monoterpenes, sesquiterpenes, diterpenes, sesterterpenes, triterpenes, and meroterpenes) from 133 marine fungal strains belonging to 34 genera were included. Among them, sesquiterpenes, meroterpenes, and diterpenes comprise the largest proportions of terpenes, and the fungi genera of Penicillium, Aspergillus, and Trichoderma are the dominant producers of terpenoids. The majority of the marine-derived fungi are isolated from live marine matter: marine animals and aquatic plants (including mangrove plants and algae). Moreover, many terpenoids display various bioactivities, including cytotoxicity, antibacterial activity, lethal toxicity, anti-inflammatory activity, enzyme inhibitor activity, etc. In our opinion, the chemical diversity and biological activities of these novel terpenoids will provide medical and chemical researchers with a plenty variety of promising lead compounds for the development of marine drugs.

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Section: Meroterpenesmentioning

confidence: 99%

Section: Meroterpenesmentioning

confidence: 99%

A Review of Terpenes from Marine-Derived Fungi: 2015–2019

Jiang

Guo

et al. 2020

Marine Drugs

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show abstract

“…However, the entomotoxic activity of the compounds is unknown, while their cytotoxic activity has not been sufficiently studied. For instance, weak cytotoxicity of tentoxin against HepG2 [38] and HeLa cell lines [39] as well as some TCAs for various tumor cell lines [40,41] have been reported. A relationship between the production of TCAs and the cytotoxic activity of A. tenuissima MFP253011 extracts against Sf9 cells is more likely (Figure 7).…”

Section: Detection Of Entomotoxic Metabolites In a Tenuissima Extractsmentioning

confidence: 99%

Entomotoxic Activity of the Extracts from the Fungus, Alternaria tenuissima and Its Major Metabolite, Tenuazonic Acid

Salimova

Dalinova

Dubovik

et al. 2021

JoF

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The study of fungal antibiotics in their competitive interactions with arthropods may lead to the development of novel biorational insecticides. Extracts of Alternaria tenuissima MFP253011 obtained using various methods showed a wide range of biological activities, including entomotoxic properties. Analysis of their composition and bioactivity allowed us to reveal several known mycotoxins and unidentified compounds that may be involved in the entomotoxic activity of the extracts. Among them, tenuazonic acid (TeA), which was the major component of the A. tenuissima extracts, was found the most likely to have larvicidal activity against Galleria mellonella. In the intrahaemocoel injection bioassay, TeA was toxic to G. mellonella and of Zophobas morio with an LT50 of 6 and 2 days, respectively, at the level of 50 µg/larva. Administered orally, TeA inhibited the growth of G. mellonella larvae and caused mortality of Acheta domesticus adults (LT50 7 days) at a concentration of 250 µg/g of feed. TeA showed weak contact intestinal activity against the two phytophages, Tetranychus urticae and Schizaphis graminum, causing 15% and 27% mortality at a concentration of 1 mg/mL, respectively. TeA was cytotoxic to the Sf9 cell line (IC50 25 µg/mL). Thus, model insects such as G. mellonella could be used for further toxicological characterization of TeA.

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“…However, entomotoxic activity of the compounds is unknown while their cytotoxic activity has not been sufficiently studied. For instance, weak cytotoxicity of tentoxin against HepG2 [38] and HeLa cell lines [39] as well as some TCAs for various tumor cell lines [40,41] was reported. Relation between the production of TCAs and cytotoxic activity of A. tenuissima MFP253011 extracts against Sf9 cells is more likely (Figure 7).…”

Section: Detection Of Entomotoxic Metabolites In a Tenuissima Extractsmentioning

confidence: 99%

Entomotoxic Activity of the Extracts from the Fungus, <em>Alternaria tenuissima</em> and Its Major Metabolite, Tenuazonic Acid

Salimova¹,

Dalinova²,

Dubovik³

et al. 2021

Preprint

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Study of fungal antibiotics in their competitive interactions with arthropods may lead to development novel biorational insecticides. Extracts of Alternaria tenuissima MFP253011 obtained by various methods showed a wide range of biological activity, including entomotoxic properties. Analysis of their composition and bioactivity allowed to reveal several known mycotoxins and unidentified compounds that may be involved in entomotoxic activity of the extracts. Among them, tenuazonic acid (TeA), which was the major component of the A. tenuissima extracts, was found the most likely to have larvicidal activity against Galleria mellonella. In the intrahaemocoel injection bioassay, TeA was toxic to G. mellonella and of Zophobas morio with LT50 6 and 2 days, respectively, at the level of 50 µg/larva. Administered orally, TeA inhibited growth of G. mellonella larvae and caused mortality of Acheta domesticus imagines (LT50 7 days) at a concentration of 250 µg/g of feed. TeA showed weak contact-intestinal activity against the two phytophages, Tetranychus urticae and Schizaphis graminum, causing the 12 and 40% of mortality at a concentration of 1 mg/mL. TeA was cytotoxic to Sf9 cell line (IC50 25 µg/mL). Thus, model insect G. mellonella and cell line Sf9 could be used for a further toxicological characterization of TeA.

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Cytotoxic Tricycloalternarene Compounds from Endophyte Alternaria sp. W-1 Associated with Laminaria japonica

Cited by 18 publications

References 35 publications

A Review of Terpenes from Marine-Derived Fungi: 2015–2019

A Review of Terpenes from Marine-Derived Fungi: 2015–2019

Entomotoxic Activity of the Extracts from the Fungus, Alternaria tenuissima and Its Major Metabolite, Tenuazonic Acid

Entomotoxic Activity of the Extracts from the Fungus, <em>Alternaria tenuissima</em> and Its Major Metabolite, Tenuazonic Acid

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