Four novel phloroglucinol derivatives (1-4) featuring a 2,4-dimethyl-cinnamyl-phloroglucinol moiety, along with their putative biosynthetic precursors 5 and 6, were isolated from the leaves of Cleistocalyx operculatus. Compounds 1 and 2 are two pairs of new enantiomeric phloroglucinol dimers possessing an unprecedented polycyclic skeleton with a highly functionalized dihydropyrano[3,2- d]xanthene tetracyclic core. Compounds 3 and 4 are two new phloroglucinol-terpene adducts (PTAs) with a novel carbon skeleton. The structures of 1-4 including their absolute configurations were unambiguously accomplished by combination of extensive spectroscopic analyses, X-ray crystallography, and quantum chemical ECD calculations. A hypothetical biosynthetic pathway for 1-4 was also proposed. Compound 1 exhibited a promising in vitro antiherpes simplex virus type-1 (HSV-1) effect.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.8b01050 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Construction and Optimization of Engineered for Synthesis of Phloretin and Its Derivatives.
J Agric Food Chem
January 2025
Frontiers Science Center for Synthetic Biology and Key Laboratory of Systems Bioengineering (Ministry of Education), School of Chemical Engineering and Technology, Tianjin University, Yaguan Road 135, Jinnan District, Tianjin 300350, China.
Phloretin and its derivatives are dihydrochalcone compounds with diverse pharmacological properties and biological activities, offering significant potential for applications in the food and pharmaceutical industries. Due to their structural similarity to flavonoids, their extraction and isolation were highly challenging. Although the biosynthesis of phloretin via three distinct pathways has been reported, a systematic comparison within the same host has yet to be conducted.
View Article and Find Full Text PDFThe microbiota metabolite, phloroglucinol, confers long-term protection against inflammation.
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.
View Article and Find Full Text PDFIsolation and Biomimetic Semisynthesis of Hyperzrones A and B, Two Nor-Polycyclic Polyprenylated Acylphloroglucinols with a Characteristic Cyclobutane Moiety, from .
Org Lett
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.
Article Synopsis
- Two new compounds, Hyperzrones A and B, are unique polycyclic polyprenylated acylphloroglucinols with a cyclobutane structure.
- Their structures were confirmed using a combination of spectroscopic analysis, X-ray crystallography, and quantum chemical calculations.
- A bioinspired method was developed to synthesize these compounds from hypercalin B, along with creating various derivatives for further biological research.
POCOP-Ni(II) pincer compounds derived from phloroglucinol. Cytotoxic and antioxidant evaluation.
Front Chem
November 2024
Instituto de Química, Universidad Nacional Autónoma de México, Ciudad de México, Mexico.
Article Synopsis
- POCOP-Ni(II) pincer compounds, initially studied for their catalytic properties, were evaluated for their anticancer and antioxidant activities in this research.
- Four specific POCOP-Ni(II) complexes derived from phloroglucinol showed significant cytotoxicity against various cancer cell lines, with IC values between 2.43 and 7.85 μM.
- The study also employed techniques like single-crystal X-ray diffraction to analyze molecular structures and suggested that these complexes can intercalate with DNA, indicating potential mechanisms for their therapeutic effects.
Polyprenylated Benzoylphloroglucinols Isolated from Species and Their Cytotoxic Effects on Cancer Cell Lines.
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.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!