Eutyscoparols A-G, polyketide derivatives from endophytic fungus Eutypella scoparia SCBG-8

Zhang, Wenge; Wang, Miaomiao; Zhang, Sha; Xu, Kang‐Ping; Tan, Gui‐Shan; Qiu, Shaofu; Zou, Zhen‐Xing; Tan, Haibo

doi:10.1016/j.fitote.2020.104681

Cited by 13 publications

(10 citation statements)

References 20 publications

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“…In this study, phomolides A and B were characterized with a natural, rarely occurring ester-acetal skeleton, which is constructed by a carboxylic acid and a phenol hydroxyl functionality ( Chen et al., 2021 ) together with an aldehyde fragment ( Ahmed Laskar and Younus, 2019 ), giving rise to a distinctive difference with the common acetal moiety formatted with two alcoholic hydroxyl groups and an aldehyde. To our knowledge, there were only four examples of natural products sharing this skeleton reported in previous literatures ( Zhang et al., 2020 ; Choi et al., 2021 ). The discovery of phomolides A and B further enriches the structural types and the members of these ester-acetal compounds.…”

Section: Resultsmentioning

confidence: 93%

Five new secondary metabolites from an endophytic fungus Phomopsis sp. SZSJ-7B

et al. 2022

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Two previously undescribed lactones, phomolides A and B (1 and 2), and three new sesquiterpenoids, phomenes A–C (3–5), together with one known compound, colletotricholide A (6), were isolated from the endophytic fungus Phomopsis sp. SZSJ-7B. Their chemical structures, including the absolute configurations, were comprehensively established by extensive analyses of NMR, high-resolution electrospray ionization mass spectrometry, electronic circular dichroism powered by theoretical calculations, and X-ray diffractions. Moreover, the cytotoxic and antibacterial activities of compounds 1–6 were also evaluated, and the results demonstrated that compound 2 showed significant antibacterial effects towards methicillin-resistant Staphylococcus aureus and S. aureus strains with minimum inhibitory concentration as low as 6.25 μg/ml, which was comparable to that of the clinical drug vancomycin. Moreover, all compounds showed no cytotoxic activity.

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Section: Resultsmentioning

confidence: 93%

Five new secondary metabolites from an endophytic fungus Phomopsis sp. SZSJ-7B

et al. 2022

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“…In recent years, a variety of compounds have been isolated from Eutypella species, mainly including terpenoids, cytochalasins, steroids, lactones, etc. ( Sun et al, 2013 ; Zhou et al, 2017 ; Zhang et al, 2020 , 2021a ), and it has been found that the secondary metabolites of Eutypella species have good antibacterial, antitumor activities ( Wang et al, 2018 ; Zhang et al, 2021b ). The diterpenoids Libertellenone H showed moderate cytotoxic activity against SW-1990, SG7901, and HeLa tumor cells ( Zhang et al, 2021b ).…”

Section: Introductionmentioning

confidence: 99%

Optimization of Protoplast Preparation and Establishment of Genetic Transformation System of an Arctic-Derived Fungus Eutypella sp.

Ning¹,

Hu²,

Yu³

et al. 2022

Front. Microbiol.

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Arctic-derived fungus Eutypella sp. D-1 has attracted wide attention due to its huge ability to synthesize secondary metabolites. However, current studies only focus on stimulating its production of new secondary metabolites by OSMAC strategies, and the relationship between secondary metabolites and biosynthetic gene clusters (BGCs) has not been explored. In this study, the preparation and regeneration conditions of Eutypella sp. D-1 protoplasts were explored to lay a foundation for the study of genetic transformation of this fungus. Orthogonal experiment showed that the optimal preparation conditions were 0.75 M NaCl, 20 g/L of lysing enzyme, and 20 g/L of driselase, 28°C for 6 h. The maximum yield of Eutypella sp. D-1 protoplasts could reach 6.15 × 106 cells·ml−1, and the concentration of osmotic stabilizer NaCl was the most important factor for Eutypella sp. D-1 protoplasts. The results of FDA staining showed that the prepared protoplasts had good activity. Besides, the best protoplasts regeneration medium was YEPS, whose maximum regeneration rate is 36%. The mediums with nitrogen sources, such as SR and RM, also had good effects on the Eutypella sp. D-1 protoplast regeneration, indicating that nitrogen sources played an important role on the Eutypella sp. D-1 protoplast regeneration. Subsequent transformation experiments showed that hygromycin resistance genes (hrg) could be successfully transferred into the genome of Eutypella sp. D-1, indicating that the prepared protoplasts could meet the needs of subsequent gene manipulation and research. This study lays a foundation for the genetic transformation of Eutypella sp. D-1.

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“…They are commonly isolated from various terrestrial and marine environments (Da Silva et al, 2008;Moyo et al, 2016;Zhang, 2019) and play an important ecological role as a decomposer (Lee et al, 2011;Deng et al, 2019;Brglez et al, 2020). Meanwhile, the fungi Eutypella are reported to be valuable biological resources due to their ability to produce bioactive secondary metabolites such as terpenoids, alkaloids, and polyketides (Sun et al, 2011;Liu et al, 2014b;Niu et al, 2017a;Zhang et al, 2020;Zhang et al, 2021b). Accumulated reports suggest that the secondary metabolites represent a wide range of biological activities including antiproliferative, anti-inflammatory, antibacterial, and antiviral activities (Palem et al, 2015;Kuriakose et al, 2016;Liao et al, 2017;Niu et al, 2018;Mao et al, 2021).…”

Section: Introductionmentioning

confidence: 99%

“…BCC 13199 (Isaka et al, 2011), E. scoparia PSU-D44 (Pongcharoen et al, 2006), E. scoparia FS46 (Liu et al, 2017b), E. scoparia FS26 (Sun et al, 2012a), E. scoparia PSU-H267 (Kongprapan et al, 2015), E. sp. D-1 (Lu et al, 2014), E. scoparia ICB-OBX (Ciavatta et al, 2008), E. scoparia 1-15 (Qi et al, 2015), E. scoparia SCBG-8 (Zhang et al, 2020), and E. sp. MCCC 3A00281 (Niu et al, 2017a)] for their secondary metabolites.…”

Section: Introductionmentioning

confidence: 99%

Terpenoids and other secondary metabolites produced by the Eutypella fungi and their bioactivities

Zhou

He²,

Chen³

2022

Front. Mar. Sci.

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The fungi Eutypella could metabolize a myriad of natural products with unique structures and diverse bioactivities, which were deemed as key sources for lead compounds in drug discovery. Since the first research on the genus Eutypella in 2009, a myriad of secondary metabolites including terpenoids, alkaloids, and polyketides have been discovered in this genus, and most of them exhibited significant pharmacological activities. However, there are no systematic reviews that reported about the structures and bioactivities of Eutypella up to now. In this review, a total of 153 secondary metabolites and 42 references have been systematically summarized, and we found that the terpenoids (68.09%) and alkaloids (19.15%) were the new main components of this fungi, and the primary antiproliferative activity (64.89%) was mainly derived from the terpenoids and alkaloids. Thus, this review about the chemical diversity and biological activities of the metabolites from the fungus Eutypella provided a new perspective for the development of new drugs for pharmacologists.

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Eutyscoparols A-G, polyketide derivatives from endophytic fungus Eutypella scoparia SCBG-8

Cited by 13 publications

References 20 publications

Five new secondary metabolites from an endophytic fungus Phomopsis sp. SZSJ-7B

Five new secondary metabolites from an endophytic fungus Phomopsis sp. SZSJ-7B

Optimization of Protoplast Preparation and Establishment of Genetic Transformation System of an Arctic-Derived Fungus Eutypella sp.

Terpenoids and other secondary metabolites produced by the Eutypella fungi and their bioactivities

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