Piperapeptins A and B, Cyclic Hexapeptides Containing the Rare Amino Acid Piperazic Acid, Produced by a Combined-Culture of Amycolatopsis sp. and Tsukamurella pulmonis
Abstract The novel cyclic hexapeptides, piperapeptins A (1) and B (2) with rare N−OH-Leu and piperazic acid moieties, were discovered in the combined-culture broth of Amycolatopsis sp. 26-11 and Tsukamurella pulmonis TP-B0596. The planar structures were elucidated by HR-MS and 1D/2D NMR analyses. The stereochemistry of Ala and Phe was determined using our highly sensitive advanced Marfey’s method. The structures of N-OH-Leu, piperazic acids, and 4-OH-piperazic acids were confirmed by single-crystal X-ray diffraction analysis. Piperapeptins A (1) and B (2) exhibited weak antibacterial activity against Bacillus subtilis, and 1 showed an IC50 value of 14.9 ± 3.9 μM against HeLa S3 cells.
Authors
- Kotaro Kiga (ORCID: https://orcid.org/0000-0002-0248-6951)
- Naoya Shinzato (ORCID: https://orcid.org/0000-0002-0555-9183)
- Aa Haeruman Azam (ORCID: https://orcid.org/0000-0001-6350-7683)
- Chengqian Pan (ORCID: https://orcid.org/0000-0001-9306-2419)
- Hideaki Kakeya (ORCID: https://orcid.org/0000-0002-4293-7331)
- Hiroyasu Onaka (ORCID: https://orcid.org/0000-0003-4536-1881)
- Hidehiro Uekusa (ORCID: https://orcid.org/0000-0001-9809-1411)
- Takefumi Kuranaga (ORCID: https://orcid.org/0000-0003-2566-2038)
- Mai Taniguchi (ORCID: https://orcid.org/0009-0002-0140-8406)
- Yuko Kishida
- Koichi Watashi
- Maki Kurimura
Institutions
- Jiangsu University (CN)
- Kyoto University (JP)
- University of the Ryukyus (JP)
- Institute of Science Tokyo (JP)
- Japan Institute for Health Security (JP)
- Gakushuin University (JP)
Publication Details
- Journal
- Journal of Natural Products
- Published
- 2026-10-26
- DOI
- https://doi.org/10.1021/acs.jnatprod.6c01093
- Primary Topic
- Microbial Natural Products and Biosynthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Japan Agency for Medical Research and Development
- Ministry of Education, Culture, Sports, Science and Technology
- National Natural Science Foundation of China
- Senior Talent Foundation of Jiangsu University