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New secondary metabolites produced by Paraphoma radicina FB55 as potential antifungal agents

The Journal of Antibiotics volume 76, pages 474–480 (2023)Cite this article

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Abstract

Microorganisms in specific environments are rich sources of bioactive natural products as they produce compounds that can aid their survival in harsh environments. In an effort to investigate antifungal compounds produced by microorganisms, the fungal strain Paraphoma radicia FB55, isolated from a marine sediment of the Beaufort Sea, north of Alaska, was subjected to chemical investigation. Chromatography of the culture extracts yielded two new compounds (1 and 2) and eight known compounds (3–10). Their structures were determined using spectroscopic and chemical methods. Compound 1 was a new analog of the known compound (3) with an isobenzofuranone skeleton. The absolute configuration of the chiral center in 1 was established by comparison of its ECD and specific rotation values with those for a known analogue. Compound 2 is a polyketide-amino acid hybrid. Comprehensive Nuclear Magnetic Resonance (NMR) analysis indicated that 2 consisted of two substructures:5-methyl-6-oxo-2,4-heptadienoic acid and isoleucinol. The absolute configuration of the isoleucinol moiety in 2 was determined to be D using Marfey’s method. All the isolated compounds were evaluated for antifungal activities. Although the antifungal activity of the isolated compounds was not potent, co-treatment of compounds 7 and 8 with a clinically available amphotericin B (AmB) lowered the IC50 values of AmB by synergism against human pathogenic yeast.

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Funding

This research was supported by the National Research Foundation of Korea (grant numbers NRF-2021R1A2C1004958, 2022R1A4A3022401, and 2022R1C1C2003274). This research was partially supported by the “Research Base Construction Fund Support Program,” funded by Jeonbuk National University in 2022. We acknowledge Professor Jongheon Shin for providing the fungal strain, Paraphoma radicina FB55.

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Author notes

  1. These authors contributed equally: Yeongwoon Jin, Kyung-Tae Lee

Authors and Affiliations

  1. Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul, 01369, Republic of Korea

    Yeongwoon Jin, Taeyeon Kim, Jaekyeong Kim & Sang Hee Shim

  2. Korea Zoonosis Research Institute, Jeonbuk National University, Iksan, 54531, Jeonbuk, Republic of Korea

    Kyung-Tae Lee

  3. College of Pharmacy, Duksung Women’s University, Seoul, 01369, Republic of Korea

    Jin Woo Lee

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  1. Yeongwoon Jin
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Correspondence to Sang Hee Shim.

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Jin, Y., Lee, KT., Kim, T. et al. New secondary metabolites produced by Paraphoma radicina FB55 as potential antifungal agents. J Antibiot 76, 474–480 (2023). https://doi.org/10.1038/s41429-023-00626-x

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