2. Academic Validation
  3. Haenamindole, an unusual diketopiperazine derivative from a marine-derived Penicillium sp. KCB12F005

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

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: jangjh@kribb.re.kr.
  • 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: jsahn@kribb.re.kr.
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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