Papyriflavonol A, a new prenylated flavonol from Broussonetia papyrifera

doi:10.1016/S0367-326X(00)00329-4

Fitoterapia

Volume 72, Issue 4, May 2001, Pages 456-458

https://doi.org/10.1016/S0367-326X(00)00329-4 Get rights and content

Abstract

A new prenylated flavonol, papyriflavonol A, was isolated from the root barks of Broussonetia papyrifera. The structure of this compound was elucidated as 5,7,3′,4′-tetrahydroxy-6,5′-di-(γ,γ-dimethylallyl)-flavonol (1) by spectroscopic analysis.

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Acknowledgements

This work was supported by the research from KOSEF (Project No. 98-0403-11-01-3).

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Flavanoids derivatives from the root bark of Broussonetia papyrifera as a tyrosinase inhibitor
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Citation Excerpt :
Therefore, the structure of compound 11 was established as broussocoumarin A. Compounds 5-9 were flavonoids (Fig. 1), which were identified as glycyrrhiza flavonol A (5) (Hatano et al., 1997), papyriflavonol A (6) (Son et al., 2001), broussoflavonol F (7) (Fang et al., 1995), broussoflavonol B (8) (Matsumoto et al., 1985), isolicofavonol (9) (Hatano et al., 1988), and one coumarin: 7,8-dihydroxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one (10) (Akihara et al., 2017), by comparison of their spectroscopic data with those reported in the literature. Among them, compound 8 was obtained from the Broussonetia genus for the first time.
Materials developed from Broussonetia papyrifera have been widely used in food and paper industries, but this root bark of the plant has been overlooked despiteits potentially economic values. Thus, the aim of the present study was to develop the root bark of B. papyrifera as a source of bioactive compounds. Chemical investigation of the bark of B. papyrifera led to the isolation of nine flavonoids derivatives (1-9) and two coumarins (10-11), which includes five new compounds (1–4 and 11). The structures of isolates were elucidated based on spectroscopic analyses. All the isolates were evaluated for their biological effects including tyrosinase inhibition, cytotoxicity, and anti-inflammatory activity. Compound 3 showed inhibition activity against tyrosinase with an IC₅₀ value of 9.29 μM (positive control, kojic acid: 30.56 μM). Molecular docking was used to support their inhibition activities which indicated that hydrogen bond formation played an important role in the ligand-enzyme complex. In addition, compound 4 exhibited cytotoxic activity against three cancer cell lines (NCI-H1975, HepG2, and MCF-7) and the structure-activity relationship of flavonoids (1-9) were established. Results from anti-inflammatory assay showed that compound 1 inhibited the production of IL-2 in Jurkat cells induced by phytohemagglutinin (PHA) and phorbol 12-myristate 13-acetate (PMA), with immunosuppressive activity. Overall, our study suggests that flavonoids from root bark of B. papyrifera can be used as a valuable source of bioactive compounds and support its use as a crop benefits to local economic.
Bioactive effects of quercetin in the central nervous system: Focusing on the mechanisms of actions
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Quercetin, a ubiquitous flavonoid that is widely distributed in plants is classified as a cognitive enhancer in traditional and oriental medicine. The protective effects of quercetin for the treatment of neurodegenerative disorders and cerebrovascular diseases have been demonstrated in both in vitro and in vivo studies. The free radical scavenging activity of quercetin has been well-documented, wherein quercetin has been observed to exhibit protective effects against oxidative stress mediated neuronal damage by modulating the expression of NRF-2 dependent antioxidant responsive elements, and attenuation of neuroinflammation by suppressing NF-κB signal transducer and activator of transcription-1 (STAT-1). Several in vitro and in vivo studies have also shown that quercetin destabilizes and enhances the clearance of abnormal protein such as beta- amyloid peptide and hyperphosphorlyated tau, the key pathological hallmarks of Alzheimer’s disease. Quercetin enhances neurogenesis and neuronal longevity by modulating a broad number of kinase signaling cascades such as phophoinositide 3- kinase (P13-kinase), AKT/PKB tyrosine kinase and Protein kinase C (PKC). Quercetin has also been well reported for its ability to reverse cognitive impairment and memory enhancement during aging. The current review focuses on summarizing the recent findings on the neuroprotective effect of quercetin, its mechanism of action and its possible roles in the prevention of neurological disorders.
New cytotoxic compounds of endophytic fungus Alternaria sp. isolated from Broussonetia papyrifera (L.) Vent
2016, Fitoterapia
Citation Excerpt :
Broussonetia papyrifera (L.) Vent., known as paper mulberry, is a highly valued plant in China. The leaves, roots, barks and fruits are used in traditional Chinese medicines with multiple bioacitivities [5–6]. So far there is no report on endophytic fungi of B. papyrifera.
From the ethyl acetate extract of a culture of the endophytic fungus Alternaria species G7 in Broussonetia papyrifera, a new compound altertoxin IV (1) together with nine known compounds were isolated and identified by means of bioassay-guided fractionation. The structures of these compounds were established on the basis of spectroscopic methods, among which the absolute configuration of compound 1, a new tetrahydroperylenone derivative, was determined by means of X-Ray Crystallographic analysis. The isolated compounds were subjected to cytotoxic activity against three human cancer cell lines (A549, MG-63, and SMMC-7721). Compound 2 showed significant cytotoxic activities against tested cell lines, with IC₅₀ values of 1.47, 2.11 and 7.34 μg/mL, respectively. Additionally, compound 4 also exhibited significant cytotoxic activities against cell lines MG-63 and SMMC-7721, with IC₅₀ values of 0.53 and 2.92 μg/mL. Endophytic fungi Alternaria from B. papyrifera might be promising sources of natural bioactive and novel metabolites.
Tyrosinase inhibitors from paper mulberry (Broussonetia papyrifera)
2008, Food Chemistry
Fractionation of a chloroform-soluble extract from twigs of Broussonetia papyrifera, led to the isolation of one new compound, 3,5,7,4′-tetrahydroxy-3′-(2-hydroxy-3-methylbut-3-enyl)flavone (1), and 10 known compounds, uralenol (2), quercetin (3), isolicoflavonol (4), papyriflavonol A (5), broussoflavonol F (6), 5,7,3′,5′-tetrahydroxyflavanone (7), luteolin (8), isoliquiritigenin (9), broussochalcone A (10) and 5,7,3′,4′-tetrahydroxy-3-methoxyflavone (11). Their structures were identified by interpretation of MS, ¹H NMR, ¹³C NMR, HMQC and HMBC data. Their inhibitory activities on mushroom tyrosinase using l-tyrosine as substrate were investigated and the IC₅₀ values of 3,5,7,4′-tetrahydroxy-3′-(2-hydroxy-3-methylbut-3-enyl)flavone, uralenol, quercetin and broussoflavonol F were found to be 96.6, 49.5, 57.8, and 82.3 μM, respectively, better than arbutin, a well-known tyrosinase inhibitor.
Antimicrobial and cytotoxic activity of 18 prenylated flavonoids isolated from medicinal plants: Morus alba L., Morus mongolica Schneider, Broussnetia papyrifera (L.) Vent, Sophora flavescens Ait and Echinosophora koreensis Nakai
2004, Phytomedicine
Citation Excerpt :
To date, few reports of pharmacological activities of prenylated flavonoids are available as compared with conventional flavonoids. Our group has focused on the pharmacological activities of prenylated flavonoids linked with anti-inflammation (Kang et al., 2000; Chi et al., 2001; Son et al., 2001; Kim et al., 2002). During the screening of anti-inflammatory compounds, we have prepared 18 prenylated compounds (Fig. 1); kuraridin, kurarinone, 5-methylsophoraflavanone B, sophoraflavanone D and G, sophoraisoflavanone A, kenusanone A and C, isosophoranone, morusin, kuwanon C, sanggenon B and D, kazinol B, broussochalcone A, papyriflavonol A, mulberrofuran G and albanol B. Based on the literature survey, their various pharmacological activities, such as antioxidation, inhibition of COX-1, COX-2, 5-LOX, 12-LOX, suppression of iNOS, cytosolic protein kinase C, and inhibition of platelet aggregation, are summarized in Table 1.
Antimicrobial activity of the 18 prenylated flavonoids, which were purified from five different medicinal plants, was evaluated by determination of MIC using the broth microdilution methods against four bacterial and two fungal microorganisms (Candida albicans, Saccaromyces cerevisiae, Escherichia coli, Salmonella typhimurium, Staphylococcus epidermis and S. aureus). Papyriflavonol A, kuraridin, sophoraflavanone D and sophoraisoflavanone A exhibited a good antifungal activity with strong antibacterial activity. Kuwanon C, mulberrofuran G, albanol B, kenusanone A and sophoraflavanone G showed strong antibacterial activity with 5–30 μg/ml of MICs. Morusin, sanggenon B and D, kazinol B, kurarinone, kenusanone C and isosophoranone were effective to only gram positive bacteria, and broussochalcone A was effective to C. albicans. IC₅₀ values of papyriflavonol A, kuraridin, sophoraflavanone D, sophoraisoflavanone A and broussochalcone A in HepG2 cells were 20.9, 37.8, 39.1, 22.1, and 22.0 μg/ml, respectively. These results support the use of prenylated flavonoids in Asian traditional medicine to treat microbial infection and indicate a high potential for prenylated flavonoids as antimicrobial agents as well as anti-inflammatory agents.
Optimization of Ethanol Extraction Process for Active Components from Broussonetia papyrifera Root Bark and Its Antioxidant Activity
2023, Science and Technology of Food Industry

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Phytochemical communicationPapyriflavonol A, a new prenylated flavonol from Broussonetia papyrifera

Abstract

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Acknowledgements

Phytochemistry

Chem Pharm Bull

Phytochemical communication
Papyriflavonol A, a new prenylated flavonol from Broussonetia papyrifera