Recent advances in the synthesis of natural products containing the phloroglucinol motif

Phang, Yee Lin; Liu, Song; Zheng, Changwu; Hong, Xu

doi:10.1039/d1np00077b

Cited by 10 publications

(6 citation statements)

References 249 publications

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“…Therefore, preventing the growth of pathogenic bacteria in the wounds helps to promote wound healing. In some studies, phloroglucinol was found to exhibit anticancer [ 13 ], anti-inflammatory [ 14 ], and antibacterial activities [ 15 ]. Due to their potential antibacterial activity, some phloroglucinol has been synthesized, and its structure–activity relationships and mechanisms of action have also been studied further [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

Phloroglucinol Derivative Carbomer Hydrogel Accelerates MRSA-Infected Wounds’ Healing

Huang

Yang

Zhang

et al. 2022

IJMS

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Globally, wound infection is considered to be one of the major healthcare problems, with bacterial infections being the most critical threat, leading to poor and delayed wound healing, and even death. As a superbug, methicillin-resistant Staphylococcus aureus (MRSA) causes a profound hazard to public health safety, prompting us to search for alternative treatment approaches. Herein, the MTT test and Hoechst/propidium iodide (PI) staining demonstrated that PD was slightly less toxic to human fibroblasts including Human keratinocytes (HaCaT) cell line than Silver sulfadiazine (SSD), and Vancomycin (Van). In the MRSA-infected wound model, PD hydrogel (1%, 2.5%) was applied with for 14 days. The wound healing of PD hydrogel groups was superior to the SSD, Van, and control groups. Remarkably, the experimental results showed that PD reduced the number of skin bacteria, reduced inflammation, and upregulated the expression of PCNA (keratinocyte proliferation marker) and CD31 (angiogenesis manufacturer) at the wound site by histology (including hematoxylin–eosin (HE) staining, Masson staining) and immunohistochemistry. Additionally, no toxicity, hemocompatibility or histopathological changes to organs were observed. Altogether, these results suggested the potential of PD hydrogel as a safe, effective, and low toxicity hydrogel for the future clinical treatment of MRSA-infected wounds.

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Section: Introductionmentioning

confidence: 99%

Phloroglucinol Derivative Carbomer Hydrogel Accelerates MRSA-Infected Wounds’ Healing

Huang

Yang

Zhang

et al. 2022

IJMS

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“…Therefore, the presence or absence of FPCs in Eucalypt extracts offers interesting chemotaxonomic data that contribute to an ongoing taxonomic debate within the speciose genus Eucalyptus and the closely related Eucalypt genera, Corymbia and Angophora. The remarkable chemical diversity of Eucalyptus-derived phloroglucinol NPs, encompassing monomers, dimers, trimers, oligomers, polycyclics, meroterpenoids, xanthones, flavonoids, and coumarins, coupled with their demonstrated bioactivities against a broad range of diseases and infection targets, make them attractive targets for biodiscovery efforts [7,20]. Of particular note are the bioactivities demonstrated by FPCs against the pharmacologically relevant infective-disease-causing targets Staphylococcus aureus [21] and Plasmodium falciparum [22].…”

Section: Introductionmentioning

confidence: 99%

Structure Revision of Formyl Phloroglucinol Meroterpenoids: A Unified Approach Using NMR Fingerprinting and DFT NMR and ECD Analyses

Holland,

Carroll

2024

Molecules

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NMR fingerprints are valuable tools for analyzing complex natural product mixtures and identifying incorrectly assigned structures in the literature. Our diagnostic NMR fingerprints for formyl phloroglucinol meroterpenoids revealed discrepancies in the structures reported for eucalyprobusal C (1a) and eucalypcamal K (2a). NMR fingerprinting PCA analyses identified 1a as an oxepine-diformyl phloroglucinol and 2a as an oxepine 3-acyl-1-formyl phloroglucinol, contrary to their initial assignments as pyrano-diformyl and pyrano 3-acyl-1-formyl phloroglucinols, respectively. Extensive reinterpretation of their reported one- and two-dimensional NMR data, coupled with GIAO DFT-calculated 1H and 13C NMR chemical shift and DP4+ analyses, supported the unequivocal reassignment of eucalyprobusal C to 1b and eucalypcamal K to 2b. The absolute configurations of the revised oxepine-containing phloroglucinol meroterpenoids were confirmed via the reinterpretation of their reported ROESY and NOESY NMR data, along with comparative TDDFT-calculated and experimental ECD spectra.

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“…1–3 Notably, phloroglucinol-based meroterpenoids, characterized by the incorporation of terpenoid units with a phloroglucinol or triketone core through various coupling patterns, are garnering increasing attention from both organic chemists and pharmacologists. 4,5 In recent years, a series of phloroglucinol-based meroterpenoids with novel skeletons and biologically meaningful activities, including antiviral, antibacterial, anti-inflammatory, antioxidant, and insecticidal effects, were sequentially reported. 5,6…”

Section: Introductionmentioning

confidence: 99%

Xanthrysols A–D, novel meroterpenoids with antiviral activities from Xanthostemon chrysanthus

Liu,

Gu,

Zhang

et al. 2024

Org. Chem. Front.

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Recent advances in the synthesis of natural products containing the phloroglucinol motif

Abstract: Phloroglucinol-derived natural products possess notable bioactivities. This review summarizes the recent synthetic approaches to the natural products bearing a phloroglucinol motif, and demonstrates strategies to functionalize the phloroglucinols.

Cited by 10 publications

References 249 publications

Phloroglucinol Derivative Carbomer Hydrogel Accelerates MRSA-Infected Wounds’ Healing

Phloroglucinol Derivative Carbomer Hydrogel Accelerates MRSA-Infected Wounds’ Healing

Structure Revision of Formyl Phloroglucinol Meroterpenoids: A Unified Approach Using NMR Fingerprinting and DFT NMR and ECD Analyses

Xanthrysols A–D, novel meroterpenoids with antiviral activities from Xanthostemon chrysanthus

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