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Planta Med 2025; 91(06/07): 371-381
DOI: 10.1055/a-2536-8292
Original Papers

Pseudopeptides of Marine Vibrio spp. from Taiwan and Their Combined Treatment Effects with Commercial Antibiotics

Mao-Xuan Hong
1   Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung, Taiwan
,
Bo-Wei Wang
2   Doctoral Degree Program in Marine Biotechnology, National Sun Yat-sen University/Academia Sinica, Kaohsiung, Taiwan
3   Agricultural Biotechnology Research Center, Academia Sinica, Taipei, Taiwan
,
Li-Hua Lo
1   Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung, Taiwan
,
Gamaralalage Eranga Dilshan Jayalath
1   Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung, Taiwan
,
Wei-Tsen Lin
1   Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung, Taiwan
,
Yu-Liang Yang
3   Agricultural Biotechnology Research Center, Academia Sinica, Taipei, Taiwan
,
Sung-Pin Tseng
4   Department of Medical Laboratory Science and Biotechnology, College of Health Science, Kaohsiung Medical University, Kaohsiung, Taiwan
,
Yen-Hsu Chen
5   Institute of Medical Science and Technology, National Sun Yat-sen University, Kaohsiung, Taiwan
,
Wan-Chi Tsai
6   Medical Laboratory Science and Biotechnology, Kaohsiung Medical University, Kaohsiung, Taiwan
,
Wei-Chieh Cheng
7   Genomics Research Center, Academia Sinica, Taipei, Taiwan
,
Chih-Chuang Liaw 
1   Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung, Taiwan
3   Agricultural Biotechnology Research Center, Academia Sinica, Taipei, Taiwan
8   Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan
9   Graduate Institute of Pharmacognosy, Taiwan Medical University, Taipei, Taiwan
› Author Affiliations
This work was supported by grants from the Ministry of Science and Technology of Taiwan (MOST 110 – 2320-B-110-002-MY3) and the National Sun Yat-sen University–Kaohsiung Medical University Joint Research Project (NSYSU–KMU 111-I006) awarded to C. C. Liaw and a grant from Academia Sinica (AS-IDR-113 – 03) awarded to W. C. Cheng. The authors also express gratitude for the financial support received from the Innovation Center for Drug Development and Optimization, National Sun Yat-sen University, Kaohsiung, Taiwan.
› Further Information
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Abstract

Vibrio strains, identified by 16S rDNA, were isolated from the marine environment surrounding Taiwan, revealing diverse bioactive effects, such as iron-chelating and antimicrobial activities. Notably, the hierarchical clustering dendrogram of mass spectrum profiles of the Vibrio strains using matrix-assisted laser desorption ionization time-of-flight, in contrast to the phylogenetic tree based on 16S rDNA sequencing analysis, exhibited a strong correlation with their observed bioactivities. Within this set, global natural products social molecular network analysis by LC-HRMS/MS highlighted that three strains, Vibrio tubiashii DJW05 – 1, Vibrio japonicus DJW05 – 8, and Vibrio fortis DJW21 – 4, shared similar bioactive pseudopeptides in the same cluster. Subsequent chromatographical isolation and purification yielded an unprecedented unsaturated diketopiperazine, (Z)-3-(2-methylpropylidene)-2,3-dihydropyrrolo[1,2-a]pyrazine-1,4-dione (1), along with a series of diketopiperazines, and a potential new annotated pseudopeptide (2), as well as three pseudopeptides, including andrimid (10), moiramide B (11), and moiramide C (12), and several alkaloids from V. tubiashii DJW05 – 1. Further investigation into the combined applications of the major antimicrobial compound and commercial antibiotics revealed that andrimid (10) displayed significant inhibitory effects against gram-positive Staphylococcus aureus, and gram-negative Escherichia coli, Salmonella typhimurium, and Acinetobacter baumannii, but not Pseudomonas aeruginosa. Nevertheless, the potential for synergistic and additive effects of andrimid (10) with certain antibiotics remains, presenting valuable prospects for medicinal applications.

Keywords

Vibrio spp. - Biotyper - molecular network analysis - pseudopeptides - andrimid - combination treatments - antibiotics - synergism - antagonism

Supporting Information

    MS and 1H and 13C NMR spectra of compounds 1 – 17 and the fully assigned NMR data of the known compounds are available as Supporting Information.

  • Supporting Information


Publication History

Received: 27 June 2024

Accepted after revision: 10 February 2025

Accepted Manuscript online:
11 February 2025

Article published online:
14 March 2025

© 2025. Thieme. All rights reserved.

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