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Three new meroterpenoids from Sargassum macrocarpum and their inhibitory activity against amyloid β aggregation

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Abstract

Amyloid β (Aβ) is thought to be involved in the pathogenesis of Alzheimer’s disease (AD). Aβ aggregation in the brain is considered the cause of AD. Therefore, inhibiting Aβ aggregation and degrading existing Aβ aggregates is a promising approach for the treatment and prevention of the disease. In searching for inhibitors of Aβ42 aggregation, we found that meroterpenoids isolated from Sargassum macrocarpum possess potent inhibitory activities. Therefore, we searched for active compounds from this brown alga and isolated 16 meroterpenoids, which contain three new compounds. The structures of these new compounds were elucidated using two-dimensional nuclear magnetic resonance techniques. Thioflavin-T assay and transmission electron microscopy were used to reveal the inhibitory activity of these compounds against Aβ42 aggregation. All the isolated meroterpenoids were found to be active, and compounds with a hydroquinone structure tended to have stronger activity than those with a quinone structure.

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Acknowledgements

The authors thank Mr. Takahiko Ikemori, Ishikawa Prefecture Fisheries Research Center, for his assistance with collection and classification of the alga.

Funding

This work was partially supported by Grants-in-Aids for Scientific Research from the Japan Society for the Promotion of Science (JSPS) KAKENHI under grant number 22K06664.

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Authors and Affiliations

  1. Faculty of Bioresources and Environmental Science, Ishikawa Prefectural University, 1-308 Suematsu, Nonoichi, Ishikawa, 921-8836, Japan

    Seiya Shinoda & Mitsuhiro Sekiguchi

  2. Graduate School of Science and Technology, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki, 305-8572, Japan

    Yuta Tozawa

  3. School of Pharmacy, Showa University, 1-5-8, Hatanodai, Shinagawa-ku, Tokyo, 142-8555, Japan

    Shin-ichiro Kurimoto

  4. Institute of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki, 305-8572, Japan

    Hideyuki Shigemori

  5. Microbiology Research Center for Sustainability (MiCS), University of Tsukuba, Tsukuba, Ibaraki, 305-8572, Japan

    Hideyuki Shigemori

Authors
  1. Seiya Shinoda
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  2. Yuta Tozawa
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  3. Shin-ichiro Kurimoto
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  4. Hideyuki Shigemori
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  5. Mitsuhiro Sekiguchi
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Contributions

MS and HS designed experiments and wrote the manuscript. SS isolated compounds. SS and SK measured physicochemical data including NMR and MS and elucidated the structures. YT conducted Th-T assay and TEM measurement. All authors have been read and approved the manuscript.

Corresponding author

Correspondence to Mitsuhiro Sekiguchi.

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The authors declare that they have no conflict of interest related to this report or the study it describes.

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Shinoda, S., Tozawa, Y., Kurimoto, Si. et al. Three new meroterpenoids from Sargassum macrocarpum and their inhibitory activity against amyloid β aggregation. J Nat Med 77, 508–515 (2023). https://doi.org/10.1007/s11418-023-01693-y

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  • DOI: https://doi.org/10.1007/s11418-023-01693-y

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