Synthesis and biological activity of (±)-7,3′,4′-trihydroxyhomoisoflavan and its analogs

Noshita, Toshiro; Fujita, Katsuzo; Koga, Takeru; Ouchi, Hidekazu; Tai, Akihiro

doi:10.1016/j.bmcl.2020.127674

Cited by 3 publications

(2 citation statements)

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“…To investigate the practical utility of this photocatalytic acylarylation process, several illustrative examples of simple derivatization of 3-(arylmethyl)chroman-4-ones were provided ( Figure 4 ). For example, I 2 -mediated dehydrogenation of the resulting 3-(arylmethyl)chroman-4-ones ( 3aa and 3cm ) proceeded well to provide the extensively studied and medicinally important chromones [ 4 ( Zheng et al, 2015 ; Gobbi et al, 2016 ) and 5 ( Kirkiacharian et al, 1989 ; Cavalli et al, 2005 ; Kirkiacharian and Gomis, 2005 ; Rao et al, 2008 ; Kupcewicz et al, 2013 ; Noshita et al, 2021 )] with 86% and 75% yields, respectively. 3-Benzylchroman-4-one 3cm was treated with H 2 O 2 in the presence of K 2 CO 3 to obtain the corresponding amide 6 in 92% yield.…”

Section: Resultsmentioning

confidence: 99%

Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation

Ding

Yu²,

Ren³

et al. 2022

Front. Chem.

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A metal- and aldehyde-free visible-light-driven photoredox-neutral alkene acylarylation with readily available cyanoarenes is described. A variety of 3-(arylmethyl)chroman-4-ones (i.e., homoisoflavonoids) and analogs are efficiently synthesized with good functional group tolerance. This mild protocol relies on a phosphoranyl radical-mediated acyl radical-initiated cyclization and selective radical-radical coupling sequence, and is also further highlighted by subsequent derivatization to chromone and 2H-chromene as well as its application in the three-component alkene acylarylation.

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Section: Resultsmentioning

confidence: 99%

Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation

Ding

Yu²,

Ren³

et al. 2022

Front. Chem.

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“…7,3′,4′-Trihydroxy-3-benzyl-2H-chromene is a homoisoflavan [ 18 ]. Noshita et al's study evaluated homoisoflavonoids as AChE inhibitors and neurite growth promoters, and the results showed that some of the homoisoflavonoids significantly promoted neurite outgrowth induced by nerve growth factor (NGF) [ 19 ]. Studies have shown that homoisoflavan had a good α -glucosidase and COX-II inhibitory activity [ 20 ].…”

Section: Discussionmentioning

confidence: 99%

Systematic Elucidation of the Mechanism of Sappan Lignum in the Treatment of Diabetic Peripheral Neuropathy Based on Network Pharmacology

Kang

Jin

Zhang

et al. 2021

Evidence-Based Complementary and Alternative Medicine

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Background. Diabetic peripheral neuropathy (DPN) is one of the most common chronic complications of diabetes, which seriously affects the physical and mental health of patients. Sappan Lignum (SL) is effective in treating DPN. Previous reports have shown that SL has a clear hypoglycemic and anti-inflammatory effect. However, the study of SL in the treatment of DPN is still limited and rare. Objective. To investigate the mechanism of SL in the treatment of DPN based on network pharmacology. Methods. The active ingredients of SL were screened by related databases. The compound targets were collected by the target prediction platforms. The DPN-related targets were gathered through disease databases. The intersection targets were obtained by uploading the compound targets and disease targets to Venny 2.1.0, and a compound-target network was constructed by Cytoscape3.7.2. The protein-protein interaction (PPI) relationships were obtained by the STRING11.0 database. Genome Ontology (GO) and Kyoto Encyclopedia of Genes and Genomes (KEGG) analyses were performed using the DAVID6.8 database. Molecular docking of key compounds and core targets was performed by DockThor. Results. A total of 29 compounds and 51 intersection targets with potential therapeutic effects on DPN were obtained. The compound-target network construction resulted in four key compounds: protostemonine, 3-deoxysappanchalcone, 7,3′,4′-trihydroxy-3-benzyl-2H-chromene, and o-12′-methylergocornine. PPI network analysis yielded 10 core targets: AKT1, MAPK3, CXCL8, TNF, OPRM1, MTOR, STAT3, MAPK8, SIRT1, and HSP90AA1. KEGG analysis resulted in 82 signaling pathways ( P < 0.05 ), including insulin resistance, HIF-1 signaling pathway, and type II diabetes. The docking results indicated that the main active compounds could stably bind to core targets. Conclusion. SL had the mechanism of multiple ingredients, multiple targets, and multiple pathways in the treatment of DPN. This study provided a scientific basis for further research on the treatment of DPN with SL and its extracts.

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Syringin: a naturally occurring compound with medicinal properties

Qian,

Pan,

Yang

et al. 2024

Front. Pharmacol.

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Syringin, a phenylpropanoid glycoside, is widely distributed in various plants, such as Acanthopanax senticosus (Rupr. et Maxim.) Harms, Syringa reticulata (BL) Hara var. mandshurica (Maxim.) Hara, and Ilex rotunda Thumb. It serves as the main ingredient in numerous listed medicines, health products, and foods with immunomodulatory, anti-tumor, antihyperglycemic, and antihyperlipidemic effects. This review aims to systematically summarize syringin, including its physicochemical properties, plant sources, extraction and separation methods, total synthesis approaches, pharmacological activities, drug safety profiles, and preparations and applications. It will also cover the pharmacokinetics of syringin, followed by suggestions for future application prospects. The information on syringin was obtained from internationally recognized scientific databases through the Internet (PubMed, CNKI, Google Scholar, Baidu Scholar, Web of Science, Medline Plus, ACS Elsevier, and Flora of China) and libraries. Syringin, extraction and separation, pharmacological activities, preparations and applications, and pharmacokinetics were chosen as the keywords. According to statistics, syringin can be found in 23 families more than 60 genera, and over 100 species of plants. As a key component in many Chinese herbal medicines, syringin holds significant research value due to its unique sinapyl alcohol structure. Its diverse pharmacological effects include immunomodulatory activity, tumor suppression, hypoglycemic action, and hypolipidemic effects. Additionally, it has been shown to provide neuroprotection, liver protection, radiation protection, cardioprotection, and bone protection. Related preparations such as Aidi injection, compound cantharidin capsule, and Tanreqing injection have been widely used in clinical settings. Other studies on syringin such as extraction and isolation, total synthesis, safety profile assessment, and pharmacokinetics have also made progress. It is crucial for medical research to deeply explore its mechanism of action, especially regarding immunity and tumor therapy. Meanwhile, more robust support is needed to improve the utilization of plant resources and to develop extraction means adapted to the needs of industrial biochemistry to further promote economic development while protecting people’s health.

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Synthesis and biological activity of (±)-7,3′,4′-trihydroxyhomoisoflavan and its analogs

Cited by 3 publications

References 9 publications

Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation

Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation

Systematic Elucidation of the Mechanism of Sappan Lignum in the Treatment of Diabetic Peripheral Neuropathy Based on Network Pharmacology

Syringin: a naturally occurring compound with medicinal properties

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