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New diketopiperazine alkaloid and polyketides from marine-derived fungus Penicillium sp. TW58-16 with antibacterial activity against Helicobacter pylori.
Fitoterapia. 2022 Jan; 156:105095.F

Abstract

Marine-derived fungi can usually produce structurally novel and biologically potent metabolites. In this study, a new diketopiperazine alkaloid (1) and two new polyketides (10 and 11), along with 8 known diketopiperazine alkaloids (2-9) were isolated from marine-derived fungus Penicillium sp. TW58-16. Their structures were fully elucidated by analyzing UV, IR, HR-ESI-MS, 1D, and 2D NMR spectroscopic data. The absolute configurations of the new compounds 1, 10 and 11 were ascertained by X-ray diffraction (Cu Kα radiation) and comparing their CD data with those reported. In addition, the antibacterial activities of these compounds against Helicobacter pylori in vitro were assessed. Results showed that compounds 3, 6, 8 and 9 displayed moderate antibacterial activity against standard strains and drug-resistant clinical isolates of H. pylori in vitro. This result demonstrates that diketopiperazine alkaloids could be lead compounds to be explored for the treatment of H. pylori infection.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Tian D
Institute of Traditional Chinese Medicine and Natural Products, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drug Research, College of Pharmacy, Jinan University, Guangzhou 510632, China.
Gou X
Institute of Traditional Chinese Medicine and Natural Products, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drug Research, College of Pharmacy, Jinan University, Guangzhou 510632, China.
Jia J
Department of Pathogen Biology, Jiangsu Key Laboratory of Pathogen Biology, Helicobacter pylori Research Centre, Nanjing Medical University, Nanjing 211166, China.
Wei J
Ocean College, Zhejiang University, Zhoushan Campus, Zhoushan 316021, China.
Zheng M
Department of Pathogen Biology, Jiangsu Key Laboratory of Pathogen Biology, Helicobacter pylori Research Centre, Nanjing Medical University, Nanjing 211166, China.
Ding W
Institute of Traditional Chinese Medicine and Natural Products, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drug Research, College of Pharmacy, Jinan University, Guangzhou 510632, China.
Bi H
Department of Pathogen Biology, Jiangsu Key Laboratory of Pathogen Biology, Helicobacter pylori Research Centre, Nanjing Medical University, Nanjing 211166, China. Electronic address: hkbi@njmu.edu.cn.
Wu B
Ocean College, Zhejiang University, Zhoushan Campus, Zhoushan 316021, China. Electronic address: wubin@zju.edu.cn.
Tang J
Institute of Traditional Chinese Medicine and Natural Products, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drug Research, College of Pharmacy, Jinan University, Guangzhou 510632, China. Electronic address: jstang0615@jnu.edu.cn.

MeSH

AlkaloidsAnti-Bacterial AgentsChromatography, GelChromatography, LiquidCrystallography, X-RayDiketopiperazinesHelicobacter pyloriMagnetic Resonance SpectroscopyOptical RotationPenicilliumPolyketidesSeawaterSpectrophotometry, InfraredSpectrophotometry, UltravioletSpectroscopy, Fourier Transform InfraredTaiwan

Pub Type(s)

Journal Article

Language

eng

PubMed ID

34896204

Citation

Tian, Danmei, et al. "New Diketopiperazine Alkaloid and Polyketides From Marine-derived Fungus Penicillium Sp. TW58-16 With Antibacterial Activity Against Helicobacter Pylori." Fitoterapia, vol. 156, 2022, p. 105095.
Tian D, Gou X, Jia J, et al. New diketopiperazine alkaloid and polyketides from marine-derived fungus Penicillium sp. TW58-16 with antibacterial activity against Helicobacter pylori. Fitoterapia. 2022;156:105095.
Tian, D., Gou, X., Jia, J., Wei, J., Zheng, M., Ding, W., Bi, H., Wu, B., & Tang, J. (2022). New diketopiperazine alkaloid and polyketides from marine-derived fungus Penicillium sp. TW58-16 with antibacterial activity against Helicobacter pylori. Fitoterapia, 156, 105095. https://doi.org/10.1016/j.fitote.2021.105095
Tian D, et al. New Diketopiperazine Alkaloid and Polyketides From Marine-derived Fungus Penicillium Sp. TW58-16 With Antibacterial Activity Against Helicobacter Pylori. Fitoterapia. 2022;156:105095. PubMed PMID: 34896204.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - New diketopiperazine alkaloid and polyketides from marine-derived fungus Penicillium sp. TW58-16 with antibacterial activity against Helicobacter pylori. AU - Tian,Danmei, AU - Gou,Xiaoshuang, AU - Jia,Jia, AU - Wei,Jihua, AU - Zheng,Mingxin, AU - Ding,Wenjuan, AU - Bi,Hongkai, AU - Wu,Bin, AU - Tang,Jinshan, Y1 - 2021/12/08/ PY - 2021/11/10/received PY - 2021/11/30/revised PY - 2021/11/30/accepted PY - 2021/12/14/pubmed PY - 2022/3/11/medline PY - 2021/12/13/entrez KW - Antibacterial activity KW - Diketopiperazine alkaloid KW - H. pylori KW - Penicillium sp. KW - Polyketide SP - 105095 EP - 105095 JF - Fitoterapia JO - Fitoterapia VL - 156 N2 - Marine-derived fungi can usually produce structurally novel and biologically potent metabolites. In this study, a new diketopiperazine alkaloid (1) and two new polyketides (10 and 11), along with 8 known diketopiperazine alkaloids (2-9) were isolated from marine-derived fungus Penicillium sp. TW58-16. Their structures were fully elucidated by analyzing UV, IR, HR-ESI-MS, 1D, and 2D NMR spectroscopic data. The absolute configurations of the new compounds 1, 10 and 11 were ascertained by X-ray diffraction (Cu Kα radiation) and comparing their CD data with those reported. In addition, the antibacterial activities of these compounds against Helicobacter pylori in vitro were assessed. Results showed that compounds 3, 6, 8 and 9 displayed moderate antibacterial activity against standard strains and drug-resistant clinical isolates of H. pylori in vitro. This result demonstrates that diketopiperazine alkaloids could be lead compounds to be explored for the treatment of H. pylori infection. SN - 1873-6971 UR - https://www.unboundmedicine.com/medline/citation/34896204/New_diketopiperazine_alkaloid_and_polyketides_from_marine_derived_fungus_Penicillium_sp__TW58_16_with_antibacterial_activity_against_Helicobacter_pylori_ DB - PRIME DP - Unbound Medicine ER -