Two new phloroglucinol derivatives, mallotophilippen A (1). and B (2). were isolated from the fruits of Mallotus philippensis. These compounds were identified, using chemical and spectral data, as 1-[5,7-dihydroxy-2,2-dimethyl-6-(2,4,6-trihydroxy-3-isobutyryl-5-methyl-benzyl)-2H-chromen-8-yl]-2-methyl-butan-1-one and 1-[6-(3-Acetyl-2,4,6-trihydroxy-5-methyl-benzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-2-methyl-butan-1-one, respectively. They inhibited nitric oxide (NO) production and inducible NO synthase (iNOS) gene expression by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-gamma (IFN-gamma). Furthermore, they inhibited histamine release from rat peritoneal mast cells induced by Compound 48/80. These results suggest that the novel phloroglucinol derivatives have anti-inflammatory effects.
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http://dx.doi.org/10.1248/cpb.50.1566 | DOI Listing |
Gut Microbes
December 2024
CIC bioGUNE, Basque Research and Technology Alliance (BRTA), Derio, Spain.
Phloroglucinol is a key byproduct of gut microbial metabolism that has been widely used as a treatment for irritable bowel syndrome. Here, we demonstrate that phloroglucinol tempers macrophage responses to pro-inflammatory pathogens and stimuli. , phloroglucinol administration decreases gut and extraintestinal inflammation in murine models of inflammatory bowel disease and systemic infection.
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December 2024
Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 210009, People's Republic of China.
Front Chem
November 2024
Instituto de Química, Universidad Nacional Autónoma de México, Ciudad de México, Mexico.
ACS Omega
October 2024
Department of Agro-Industrial, Food, and Environmental Technology, Faculty of Applied Science, King Mongkut's University of Technology North Bangkok (KMUTNB), Bangkok 10800, Thailand.
Polyprenylated benzoylphloroglucinols (PPBPs) make up a group of complex natural products with anticancer potentials that are mainly distributed in plants. As part of our intensive exploration on new bioactive substances from this genus, we report two undescribed PPBPs, picrorhizones I () and J (), along with four known analogues (-) from the stem bark of and . The new structures were elucidated on the basis of spectroscopic analysis, particularly 1D and 2D NMR and HRESIMS, whereas the absolute configurations were determined by a combination of ECD and NMR calculations coupled with a DP4+ probability analysis.
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December 2024
Science and Technology Innovation Center, Guangzhou University of Chinese Medicine, Guangzhou 510405, People's Republic of China. Electronic address:
Fifteen undescribed phenylpropanoyl phloroglucinol derivatives featuring modified isoprenyl and/or geranyl units (1-15), in conjunction with thirteen known analogues (16-28), were obtained from the glandular hairs of the fruit of Mallotus philippensis. Meanwhile, fourteen pairs of new enantiomers [(±)-1-9, (±)-11-15] were further resolved by chiral purification. Their structures were determined by comprehensive spectroscopic analyses, single-crystal X-ray diffraction experiments and quantum chemical calculations.
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