Haenamindole, an unusual diketopiperazine derivative from a marine-derived Penicillium sp. KCB12F005

  • Bioorg Med Chem Lett. 2015 Nov 15;25(22):5398-401. doi: 10.1016/j.bmcl.2015.09.026.
Jong Won Kim  1 ,  Sung-Kyun Ko  2 ,  Sangkeun Son  2 ,  Kee-Sun Shin  3 ,  In-Ja Ryoo  3 ,  Young-Soo Hong  2 ,  Hyuncheol Oh  4 ,  Bang Yeon Hwang  5 ,  Hiroshi Hirota  6 ,  Shunji Takahashi  6 ,  Bo Yeon Kim  2 ,  Hiroyuki Osada  7 ,  Jae-Hyuk Jang  8 ,  Jong Seog Ahn  9
Affiliations
  • 1. Korea Research Institute of Bioscience and Biotechnology, Chungbuk 363-883, Republic of Korea; College of Pharmacy, Chungbuk National University, Chungbuk 362-763, Republic of Korea.
  • 2. Korea Research Institute of Bioscience and Biotechnology, Chungbuk 363-883, Republic of Korea; Department of Biomolecular Science, University of Science and Technology, Daejeon 305-333, Republic of Korea.
  • 3. Korea Research Institute of Bioscience and Biotechnology, Chungbuk 363-883, Republic of Korea.
  • 4. College of Pharmacy, Wonkwang University, Jeonbuk 570-749, Republic of Korea.
  • 5. College of Pharmacy, Chungbuk National University, Chungbuk 362-763, Republic of Korea.
  • 6. RIKEN-KRIBB Joint Research Unit, Global Research Cluster, RIKEN, Saitama 351-0198, Japan.
  • 7. Chemical Biology Research Group, RIKEN CSRS, Saitama 351-0198, Japan.
  • 8. Korea Research Institute of Bioscience and Biotechnology, Chungbuk 363-883, Republic of Korea; Department of Biomolecular Science, University of Science and Technology, Daejeon 305-333, Republic of Korea. Electronic address: [email protected].
  • 9. Korea Research Institute of Bioscience and Biotechnology, Chungbuk 363-883, Republic of Korea; Department of Biomolecular Science, University of Science and Technology, Daejeon 305-333, Republic of Korea. Electronic address: [email protected].
PMID: 26403931 DOI: 10.1016/j.bmcl.2015.09.026
Abstract

During the chemical investigation of marine-derived fungus, an unusual diketopiperazine (DKP) alkaloid, haenamindole (1), was isolated from a culture of the marine-derived fungus Penicillium sp. KCB12F005. The structure of 1, which possesses benzyl-hydroxypiperazindione and phenyl-pyrimidoindole rings system in the molecule, was elucidated by analysis of NMR and MS data. The stereochemistry of 1 was determined by ROESY and advanced Marfey's method.

Keywords
Diketopiperazine alkaloid; Marine-derived fungus; Penicillium sp.; Pyrimidoindole; β-Phenylalanine.
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