2. Academic Validation
  3. Herqueilenone A, a unique rearranged benzoquinone-chromanone from the Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729

Herqueilenone A, a unique rearranged benzoquinone-chromanone from the Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729

  • Bioorg Chem. 2020 Dec;105:104397. doi: 10.1016/j.bioorg.2020.104397.
Jae Sik Yu 1,  Chunshun Li 2,  Mincheol Kwon 3,  Taehoon Oh 4,  Tae Hyun Lee 1,  Dong Hyun Kim 1,  Jong Seog Ahn 3,  Sung-Kyun Ko 4,  Chung Sub Kim 1,  Shugeng Cao 5,  Ki Hyun Kim 6
Affiliations

Affiliations

  • 1 School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
  • 2 Daniel K. Inouye College of Pharmacy, University of Hawaii at Hilo, Hilo, HI 96720, United States.
  • 3 Anticancer Agent Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB), Cheongju 28116, Republic of Korea.
  • 4 Natural Medicine Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB), Cheongju 28116, Republic of Korea.
  • 5 Daniel K. Inouye College of Pharmacy, University of Hawaii at Hilo, Hilo, HI 96720, United States. Electronic address: scao@hawaii.edu.
  • 6 School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea. Electronic address: khkim83@skku.edu.
PMID: 33130348 DOI: 10.1016/j.bioorg.2020.104397
Abstract

The study of a Hawaiian volcanic soil-associated Fungal strain Penicillium herquei FT729 led to the isolation of one unprecedented benzoquinone-chromanone, herqueilenone A (1) and two phenalenone derivatives (2 and 3). Their structures were determined through extensive analysis of NMR spectroscopic data and gauge-including atomic orbital (GIAO) NMR chemical shifts and ECD calculations. Herqueilenone A (1) contains a chroman-4-one core flanked by a tetrahydrofuran and a benzoquinone with an acetophenone moiety. Plausible pathways for the biosynthesis of 1-3 are proposed. Compounds 2 and 3 inhibited IDO1 activity with IC50 values of 14.38 and 13.69 μM, respectively. Compounds 2 and 3 also demonstrated a protective effect against acetaldehyde-induced damage in PC-12 cells.

Keywords

Acetaldehyde-induced damage; Benzoquinone-chromanone; Indoleamine 2,3-dioxygenase 1; Penicillium herquei FT729; Phenalenone derivative; Soil-associated fungus.

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