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

Jong Won Kim; Sung-Kyun Ko; Sangkeun Son; Kee-Sun Shin; In-Ja Ryoo; Young-Soo Hong; Hyuncheol Oh; Bang Yeon Hwang; Hiroshi Hirota; Shunji Takahashi; Bo Yeon Kim; Hiroyuki Osada; Jae-Hyuk Jang; Jong Seog Ahn

doi:10.1016/j.bmcl.2015.09.026

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. Epub 2015 Sep 10.

Authors

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aquatic Organisms / chemistry*
Diketopiperazines / chemistry*
Diketopiperazines / isolation & purification
Diketopiperazines / pharmacology
Magnetic Resonance Spectroscopy
Molecular Structure
Penicillium / chemistry*
Stereoisomerism

Substances

Diketopiperazines
haenamindole