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Inositol Derivatives with Anti-Inflammatory Activity from Leaves of Solanum capsicoides Allioni.

ABSTRACT: Eight new inositol derivatives, solsurinositols A-H (1-8), were isolated from the 70% EtOH extract of the leaves of Solanum capsicoides Allioni. Careful isolation by silica gel column chromatography followed by preparative high-performance liquid chromatography (HPLC) allowed us to obtain analytically pure compounds 1-8. They shared the same relative stereochemistry on the ring but have different acyl groups attached to various hydroxyl groups. This was the first time that inositol derivatives have been isolated from this plant. The chemical structures of compounds 1-8 were characterized by extensive 1D nuclear magnetic resonance (NMR) and 2D NMR and mass analyses. Meanwhile, the in vitro anti-inflammatory activity of all compounds was determined using lipopolysaccharide (LPS)-induced BV2 microglia, and among the isolates, compounds 5 (IC₅₀ = 11.21 ± 0.14 µM) and 7 (IC₅₀ = 14.5 ± 1.22 µM) were shown to have potential anti-inflammatory activity.

SUBMITTER: Liu Y

PROVIDER: S-EPMC9503535 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Inositol Derivatives with Anti-Inflammatory Activity from Leaves of Solanum capsicoides Allioni

Liu Yan Y Meng Xin X Wang Han H Sun Yan Y Wang Si-Yi SY Jiang Yi-Kai YK Algradi Adnan Mohammed AM Naseem Anam A Kuang Hai-Xue HX Yang Bing-You BY

Molecules (Basel, Switzerland) 20220916 18

Eight new inositol derivatives, solsurinositols A-H (1-8), were isolated from the 70% EtOH extract of the leaves of Solanum capsicoides Allioni. Careful isolation by silica gel column chromatography followed by preparative high-performance liquid chromatography (HPLC) allowed us to obtain analytically pure compounds 1-8. They shared the same relative stereochemistry on the ring but have different acyl groups attached to various hydroxyl groups. This was the fir ...[more]

PMID: 36144793

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Project description:Persistent inflammation contributes to a number of diseases; therefore, control of the inflammatory response is an important therapeutic goal. In an effort to identify novel anti-inflammatory compounds, we screened a library of pyridazinones and structurally related derivatives that were used previously to identify N-formyl peptide receptor (FPR) agonists. Screening of the compounds for their ability to inhibit lipopolysaccharide (LPS)-induced nuclear factor κB (NF-κB) transcriptional activity in human THP1-Blue monocytic cells identified 48 compounds with anti-inflammatory activity. Interestingly, 34 compounds were FPR agonists, whereas 14 inhibitors of LPS-induced NF-κB activity were not FPR agonists, indicating that they inhibited different signaling pathways. Further analysis of the most potent inhibitors showed that they also inhibited LPS-induced production of interleukin 6 (IL-6) by human MonoMac-6 monocytic cells, again verifying their anti-inflammatory properties. Structure-activity relationship (SAR) classification models based on atom pair descriptors and physicochemical ADME parameters were developed to achieve better insight into the relationships between chemical structures of the compounds and their biological activities, and we found that there was little correlation between FPR agonist activity and inhibition of LPS-induced NF-κB activity. Indeed, Cmpd43, a well-known pyrazolone-based FPR agonist, as well as FPR1 and FPR2 peptide agonists had no effect on the LPS-induced NF-κB activity in THP1-Blue cells. Thus, some FPR agonists reported to have anti-inflammatory activity may actually mediate their effects through FPR-independent pathways, as it is suggested by our results with this series of compounds. This could explain how treatment with some agonists known to be inflammatory (i.e., FPR1 agonists) could result in anti-inflammatory effects. Further research is clearly needed to define the molecular targets of pyridazinones and structurally related compounds with anti-inflammatory activity and to define their relationships (if any) to FPR signaling events.

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Inositol Derivatives with Anti-Inflammatory Activity from Leaves of Solanum capsicoides Allioni.

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Inositol Derivatives with Anti-Inflammatory Activity from Leaves of Solanum capsicoides Allioni

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Inositol Derivatives with Anti-Inflammatory Activity from Leaves of Solanum&nbsp;capsicoides Allioni.

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Inositol Derivatives with Anti-Inflammatory Activity from Leaves of Solanum capsicoides Allioni

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Inositol Derivatives with Anti-Inflammatory Activity from Leaves of Solanum capsicoides Allioni.