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This study represents the first comprehensive investigation into the phenolic profiles and biological properties of whole Hypericum japonicum and Hypericum sampsonii, two medicinal plant species within the genus Hypericum, revealing distinct chemical and bioactive properties of their extracts. Phenolic compounds, plant secondary metabolites widely recognized as bioactive, were extracted from the dried whole plant of each species and analysed by HPLC-DAD-MS/MS, and the bioactivities were assessed using in vitro methods. The predominant phenolic families differed between the two species, with flavonoids such as taxifolin-O-rhamnoside, isoquercitrin, and quercitrin being the major compounds found in H. japonicum. A total of 30 phenolic compounds were identified in this specie with a significantly higher total phenolic content (TPC = 184.51±0.2 mg/g extract dw) than H. sampsonii (TPC = 59.57±0.8 mg/g extract dw). In the latter species, 17 compounds were identified and quantified, being xanthones such as mangiferin, besides rutin, and hyperoside among the most prevalent compounds in H. sampsonii extract. Additionally, four different classes of previously unidentified anthocyanins were discovered in H. sampsonii, collectively amounting to 303.94±0.3 mg/g of extracted dw. The antioxidant activity assessed using the OxHLIA and TBARS methods yielded values of EC50 that were either equal to or superior to the positive control tested (Trolox). Additionally, the extracts exhibited promising antitumor effects, with particular significance attributed to the remarkable GI50 value of H. japonicum against the human gastric adenocarcinoma (AGS) cell line (69±2 μg/mL extract). While further research is warranted to generalize the cytotoxic activity, both extracts showed remarkable antimicrobial efficacy, with H. japonicum extract exhibiting minimum inhibitory concentration (MIC) values as low as 0.007 mg/mL against various clinical and food bacterial strains. Overall, the assessment of biological properties suggests that H. japonicum exhibits greater potential compared to H. sampsonii, likely due to its threefold higher TPC content. These findings suggest promising avenues for future research, including isolating key compounds and exploring these extracts as versatile functional foods and potent antioxidants across different sectors. Moreover, the possibility of developing pharmacological products based solely on concentrated herbal preparations or standardized extracts of Hypericum opens new horizons in natural product-based therapeutics.8,9- dehydrothymol methyl ether, 8,9-dehydrothymol and 8,9-dehydro-4-hydroxythymol dimethyl ether. [ABSTRACT FROM AUTHOR]

Two new phenolics, one xanthonoid (1) and one phloroglucinol derivative (2), together with eighteen known phenolics (3 – 20), were isolated from the aerial parts of Hypericum japonicum. Their structures were established by extensive spectral analysis, and the absolute configuration of compound 1 was determined by comparison of the calculated and experimental circular dichroism spectra. An anti-inflammatory activity assay revealed that compound 1 exhibited effective inhibitory effects on NO generation in LPS-stimulated RAW 264.7 macrophages, with an IC 50 value of 6.34 μg/mL. [Display omitted] • Two new phenolics were isolated from Hypericum japonicum. • Absolute configuration of compound 2 was assigned. • Compound 1 showed effective anti-inflammatory activity. [ABSTRACT FROM AUTHOR]

Porcine epidemic diarrhea virus (PEDV) infection causes lethal watery diarrhea and high mortality in neonatal piglets, leading to huge economic losses in the global swine industry. Currently, the existing commercial vaccines cannot fully control PEDV, so it is urgent to develop effective antiviral agents to complement vaccine therapy. In the present study, we investigated the antiviral effect of Hypericum japonicum extract (HJ) against PEDV in vivo and in vitro. In in vitro assays, HJ could directly inactivate PEDV strains; moreover, it inhibited the proliferation of PEDV strains in Vero or IPI-FX cells at its non-cytotoxic concentrations. Time of addition assays revealed that HJ mainly inhibited PEDV at the later stages of the viral life cycle. In in vivo, compared with the model group, HJ could reduce the viral titers in the intestines of infected piglets, and improve their intestinal pathological, indicating that HJ could protect the newborn piglets from highly pathogenic PEDV variant infection. Furthermore, this effect may be related to the fact that HJ can not only directly inhibit viruses, but also regulate the structure of intestinal microbiota. In conclusion, our results indicate that Hypericum japonicum could inhibit PEDV replication in vitro and in vivo and might possess the potential to develop as the anti-PEDV drug. [ABSTRACT FROM AUTHOR]

Background: Plants possess various bioactive compounds with many biological activities. Antioxidant plays vital roles in initiating deleterious free scavenging radical reactions. Objectives: The present study was done to determine the presence of phytochemical properties of the plant along with its antioxidant analysis of four solvent fractions (hexane, diethyl ether, ethyl acetate and methanol) from Hypericum japonicum. Furthermore, five heavy metals-Zn, Cu, Cd, Pb and Cr were analyzed. Materials and Methods: All the experiments for phytochemical and antioxidants of different solvent extracts were investigated following standard protocols. The heavy metal content was analyzed using spectroscopy method. Results: Qualitative analysis revealed that almost all the phytochemicals were present on one or other solvents. The carbohydrate and protein content was highest in hexane and ethyl acetate extract. Ethyl acetate showed highest phenol content while diethyl ether showed highest in flavonoid content. Similarly, ethyl acetate extract showed strongest antioxidant activity. Heavy metals were found in very negligible amounts. Conclusion: The present study suggests that H. japonicum might have the potential to be a good source of phytochemicals and antioxidants. Further studies are required to analyze the pharmacological properties of the plant. [ABSTRACT FROM AUTHOR]

• OLE-HPLC-ABTS/Q-TOF-MS system was set up and applied in antioxidants analysis. • Nine antioxidants were found in Hypericum japonicum. • The antioxidant activity was validated by in vitro assay and molecular simulation. Hypericum japonicum is a traditional folk medicine with various bioactivities such as hepatoprotective, antioxidant, and anti-tumorous. The antioxidant effect of H. japonicum is one of the most prominent effects due to its responsibility for many of its activities. To clarify active natural substance, the antioxidant properties of H. japonicum were preliminarily assessed by ferric reducing–antioxidant power (FRAP), 2,2-azino-bis-3-ethylbenzothiazoline-6-sulphonic acid (ABTS) and Oxygen radical absorbance capacity (ORAC), as well as superoxide dismutase (SOD). Then, a straightforward and effective method named online liquid extraction-high performance liquid chromatography combined with ABTS antioxidant assay and mass spectrometry (OLE-HPLC-ABTS/Q-TOF-MS) was developed to swiftly and directly discover the antioxidants in H. japonicum. Using mobile phase as extraction and separation reagent, coupled with online activity analysis and compounds identification by high-resolution MS, the online system enables rapid screening of natural antioxidant bioactives from complex mixture. By using it, a total of 9 compounds including flavonoids and phenolic acids characterized by retention time, precise mass, and fragmentation ions in MS/MS spectra showed antioxidant action. Finally, the antioxidant and SOD activity of main found active compounds were validated by in vitro experiment assay and molecular docking. In summary, these results suggested that H. japonicum could be considered as a potential source of natural antioxidants, and the online integrated system might become a promising candidate for the natural antioxidants discovery in the future. [ABSTRACT FROM AUTHOR]

Comprehensive Summary: Unreported tautomeric/enantiomeric meroterpenoids, (±)‐hyperjaponols I—K (1—3), were discovered from Hypericum japonicum. Comprehensive chemical investigations established the absolute characteristics of these stereoisomers. The TS calculation demonstrated that 1a and 2a easily occur enol‐keto tautomerism with steady configurations individually. Amongst isolates, 1b showed the strongest neuroprotective activity with the concentration at 25 μmol/L on H2O2 insult SH‐SY5Y cells. In vitro molecular biological experiments manifested that 1b activated the Keap1‐Nrf2‐ARE pathway, leading to the promotion of Nrf2 nuclear translocation, downregulation of the expression level of Keap1, and upregulation of the levels of Nrf2, NQO‐1, and HO‐1. The results of in silico simulation showed that 1b possessed good binding features with Keap1 (5FNQ) via forming multiple typical hydrogen and hydrophobic bonds as well as less fluctuation of RMSD and RMSF during a natural physiological condition. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of the aerial part of Hypericum japonicum afforded two new xanthones (1 - 2), together with twelve known compounds (3 - 14). Their structures with absolute configurations were elucidated by analysis of MS NMR and their experimental and calculated electronic circular dichroism spectra. All of the isolated compounds were tested for their lipid-lowering activities. Compounds 10 , 11 , 13 exhibited potent lipid-lowering activities (with LDL-Uptake rates 3.02, 2.68 and 1.99, respectively, compared with vehicle control, which was designated as 1.00) and compounds 2 - 5 showed moderate activities (with LDL-Uptake rates 1.46, 1.41, 1.31 and 1.51, respectively). [Display omitted] • Two new xanthones were isolated from Hypericum japonicum. • Japoxanthone A-B possessed a novel carbon skeleton. • Compounds 10 , 11 , 13 exhibited potent lipid-lowering activities. [ABSTRACT FROM AUTHOR]

Coronavirus disease 2019 (COVID-19) is an acute respiratory infection caused by the Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2). However, there are still no specific treatments. Recently, traditional Chinese medicine (TCM) was proposed as a potential therapeutic strategy for the prevention and treatment of COVID-19. The present study aims to explore the potential of Hypericum japonicum Thunb. ex Murray against COVID-19 based on network pharmacology and molecular docking methods. Potential targets of H. japonicum were collected from available databases for protein–protein interaction analysis. Further GO and KEGG pathway analysis were performed to reveal the corresponding mechanism. Molecular docking was employed to evaluate the binding energy between the components in H. japonicum and three target proteins (ACE2, Mpro and PLP). Finally, a total of 45 core targets were screened. GO and KEGG pathway analysis revealed that several key pathways were involved in the potential beneficial effects of H. japonicum against COVID-19. Molecular docking results showed that most components in H. japonicum have a binding affinity to ACE2, Mpro and PLP molecules less than −5 kcal/mol, indicating good binding capacity to these target proteins. Vincetoxicoside B, bijaponicaxanthone and quercetin possess the top binding activity to ACE2, Mpro and PLP, respectively. The molecular docking results and the traditionally known possible functions of H. japonicum, including stabilizing blood oxygen environment, preventing inflammatory storms, regulating immune response and inhibiting viral infections, hereby indicate the potential of H. japonicum against COVID-19.

Eight nonaromatic acylphloroglucinol-terpenoid adducts including 7 new compounds were isolated from H. japonicum. Among them, compounds 1 – 4 showed significant PXR agonistic activity. [Display omitted] • Seven novel nonaromatic acylphloroglucinol-terpenoid adducts were isolated. • Compounds 1 − 4 showed significant PXR agonistic activity in dual-luciferase reporter gene model. • Compounds 1 − 4 can upregulate the expression of PXR-targeted gene in mice primary hepatocyte model. • Compounds 1 − 4 efficiently promoted PXR nuclear translocation at 10 μM. • The binding models of active compounds and PXR were elucidated. Pregnane X receptor (PXR) has been considered as a promising therapeutic target for cholestasis due to its crucial regulation in bile acid biosynthesis and metabolism. To search promising natural PXR agonists, the PXR agonistic activities of five traditional Chinese medicines (TCMs) with hepatoprotective efficacy were assayed, and Hypericum japonicum as the most active one was selected for subsequent phytochemical investigation, which led to the isolation of eight nonaromatic acylphloroglucinol-terpenoid adducts including seven new compounds (1 − 4 , 5a , 5b and 6). Their structures including absolute configurations were determined by comprehensive spectroscopic, computational and X-ray diffraction analysis. Meanwhile, the PXR agonistic activities of aplenty compounds were evaluated via dual-luciferase reporter assay, RT-qPCR and immunofluorescence. Among them, compounds 1 − 4 showed more potent activity than the positive drug rifampicin. Furthermore, the molecular docking revealed that 1 − 4 were docked well on the PXR ligand binding domain and formed hydrogen bonds with amino acid residues Gln285, Ser247 and His409. This investigation revealed that H. japonicum may serve as a rich source of natural PXR agonists. [ABSTRACT FROM AUTHOR]

Coronavirus disease 2019 (COVID-19) is an acute respiratory infection caused by the Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2). However, there are still no specific treatments. Recently, traditional Chinese medicine (TCM) was proposed as a potential therapeutic strategy for the prevention and treatment of COVID-19. The present study aims to explore the potential of Hypericum japonicum Thunb. ex Murray against COVID-19 based on network pharmacology and molecular docking methods. Potential targets of H. japonicum were collected from available databases for protein–protein interaction analysis. Further GO and KEGG pathway analysis were performed to reveal the corresponding mechanism. Molecular docking was employed to evaluate the binding energy between the components in H. japonicum and three target proteins (ACE2, Mpro and PLP). Finally, a total of 45 core targets were screened. GO and KEGG pathway analysis revealed that several key pathways were involved in the potential beneficial effects of H. japonicum against COVID-19. Molecular docking results showed that most components in H. japonicum have a binding affinity to ACE2, Mpro and PLP molecules less than −5 kcal/mol, indicating good binding capacity to these target proteins. Vincetoxicoside B, bijaponicaxanthone and quercetin possess the top binding activity to ACE2, Mpro and PLP, respectively. The molecular docking results and the traditionally known possible functions of H. japonicum, including stabilizing blood oxygen environment, preventing inflammatory storms, regulating immune response and inhibiting viral infections, hereby indicate the potential of H. japonicum against COVID-19. [ABSTRACT FROM AUTHOR]

• 57 secondary metabolites of HJME were characterized by LC–MSn and UPLC-QTOF. • Flavonoids, phloroglucinols, phenolic acids and xanthones are the main constituents. • HJME exerts a significant anti-NF-κB/AP-1 activity on human cell lines. • HJME exerts a significant cytotoxic activity on human cell lines. • HJME could be a potential source of anti-inflammatory and cytotoxic compounds. Hypericum japonicum Thunb. ex Murray is traditionally used in Nepal to treat several diseases, among whom inflammation and acute pain. Although several secondary metabolites from the same Hypericum species have been already characterized and considered for their pharmacological use, an exhaustive phytochemical characterization of H. japonicum from Nepal is lacking, as well as the assessment of its potential pharmacological properties. Hence, the aims of this study were the characterization of a methanolic extract of H. japonicum (HJME) collected from the Northern region of Nepal by LC–MSn and UPLC-QTOF. The assessment of in vitro inhibition of nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) and activator protein 1 (AP-1) transcription factors and HJME's cytotoxic effect on human cell lines was performed to evaluate the potential use of this herb as a source of anti-inflammatory and cytotoxic lead compounds. Fifty-seven phytoconstituents were identified, being mainly flavonoids, phloroglucinols, phenolic acids and xanthones. Although compounds characteristic of H. japonicum were detected (quercetin, quercetin-7-O-α-l-rhamnoside, quercitrin and hyperoside), several others are here reported for the first time in this species. The results from bioassays indicated that HJME could significantly reduce the viability of human THP-1 cells (IC 50 = 5.4 ± 1.1 μg mL−1), showing the promising potential of HJME as anti-tumor agent. Furthermore, HJME significantly decreased the activation of both NF-κB and AP-1 at the concentration of 2 μg mL−1. Overall, these data suggest that H. japonicum from Nepal could be used as a source of potential natural anti-inflammatory and anti-tumor lead compounds. [ABSTRACT FROM AUTHOR]

Phloroglucinols are characteristic constituents of Hypericumjaponicum that are claimed to exert several bioactivities, such as anti-inflammatory, anti-depressant and anti-viral ones. Phloroglucinols are unstable compounds and their synthesis is challenging; thus, isolation from natural sources is still one of the main strategies for obtaining these constituents in purified form. Assessing the presence of phloroglucinols in plant materials can be of interest for compound isolation, and LC-MS approaches afford sensitivity and specificity in this regard. In this work, we combined data from quadrupole-time of flight (QTOF) and ion trap (IT) mass spectrometers in order to assess the presence of the phloroglucinols characteristic of H. japonicum and to elucidate their MS fragmentation pathways. The identified compounds present similar structures bearing the 1,3,5-trihydroxybenzene core with different substitutions, which, in constituents at higher MW, is linked to 3′,3′-dimethyl-6′-oxo-phlorisobutyrophenone by a methylene bridge. Differences in MS2 spectra of the considered phloroglucinols are useful for compound identification and differentiation, and to perform dereplication studies. Overall, the proposed approach could be useful for the analysis of phloroglucinols in H. japonicum and other plant species.

Mosquito control with naturally derived herbal insecticides has gained much momentum, with the increased insecticide resistance of vectors and the multiple infectious diseases spread by them. Yet, recent studies also suggest that mosquitoes could probably transmit some cancerous cells or cancer-causing viruses from one individual to another between their blood meals. The current research thus focused on the screening and characterization of novel plants with both mosquitocidal and anticancerous properties. Accordingly, different solvent extracts of Hypericum japonicum, a key plant in Chinese medicine, were screened for its larvicidal efficacy using the fourth instar larvae of Aedes aegypti (major vector of Dengue and chikungunya). Methanolic extracts of the plant showed effective larvicidal property with LC50 7.37 ppm and LC9011.59 ppm values. The anticancerous property of the plant extract was also evaluated by in vitro cytotoxicity assay against Daltons Lymphoma Ascites (DLA) cells. The results indicated that H. japonicum plant extracts at very low concentrations of LC500.95 ppm and LC901.85 ppm were potent cytotoxic agents. To the best of our knowledge, this is the first and the foremost report of Hypericum japonicum as a potent mosquitocidal and anticancerous agent. Identification and characterization of such plant-derived bioactive plants thus could serve as a double-headed sword against the spread of infectious diseases and cancer. [ABSTRACT FROM AUTHOR]

Hyperjaponol H (1), a new filicinic acid-based meroterpenoid, with a 6/6/10 ring system trans-fused by hetero-Diels–Alder cycloaddition between a germacrane sesquiterpenoid and a filicinic acid moiety, was isolated from aerial parts of Hypericum japonicum. The elucidation of its structure and absolute configuration were accomplished by the analyses of extensive spectroscopic data and the comparison of Cotton effects of electron circular dichroism (ECD) with previously reported ones. The bioactivity assay showed that hyperjaponol H exhibited a moderate inhibitory efficacy on lytic Epstein-Barr virus (EBV) DNA replication in B95-8 cells. [ABSTRACT FROM AUTHOR]

Hypericum japonicum Thunb. ex Murray is mainly distributed throughout Asia, Oceania and North America and is used as an important herbal medicine. H. japonicum contains many valuable secondary metabolites, such as flavonoids, phloroglucinols and xanthones and has hepatoprotective, anti-tumor, antibacterial, antiviral, and antioxidant activities and effects on the cardiovascular system and immunity. Coupled with phytochemical and pharmacological research, a series of analytical methods have been developed to evaluate the quality of H. japonicum based on its bioactive components. A pharmacokinetics study involved the absorption of two main flavonoids of H. japonicum in rats. This review aims to present an up-to-date and comprehensive overview of the phytochemistry, pharmacology, quality control and pharmacokinetics of H. japonicum, which should be useful for the greater development of H. japonicum, especially in the development of new drugs and therapeutics for various diseases.

Porcine epidemic diarrhea virus (PEDV) infection causes lethal watery diarrhea and high mortality in neonatal piglets, leading to huge economic losses in the global swine industry. Currently, the existing commercial vaccines cannot fully control PEDV, so it is urgent to develop effective antiviral agents to complement vaccine therapy. In the present study, we investigated the antiviral effect of Hypericum japonicum extract (HJ) against PEDV in vivo and in vitro . In in vitro assays, HJ could directly inactivate PEDV strains; moreover, it inhibited the proliferation of PEDV strains in Vero or IPI-FX cells at its non-cytotoxic concentrations. Time of addition assays revealed that HJ mainly inhibited PEDV at the later stages of the viral life cycle. In in vivo , compared with the model group, HJ could reduce the viral titers in the intestines of infected piglets, and improve their intestinal pathological, indicating that HJ could protect the newborn piglets from highly pathogenic PEDV variant infection. Furthermore, this effect may be related to the fact that HJ can not only directly inhibit viruses, but also regulate the structure of intestinal microbiota. In conclusion, our results indicate that Hypericum japonicum could inhibit PEDV replication in vitro and in vivo and might possess the potential to develop as the anti-PEDV drug., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2023 Rao, Su, Zhang, Wang, Li, Li, Zeng and Li.)

Hyperjapones F–I ( 1 – 4 ), novel terpenoid polymethylated acylphloroglucinols (TPAPs) with three unusual carbon skeletons, were characterized from Hypericum japonicum . Their structures were determined on the basis of comprehensive MS and NMR spectroscopic data. Compounds 1 and 2 could be formed by hybridization of a trimethylated acylphloroglucinol core with a sabinene-type monoterpenoid unit, while compounds 3 and 4 contained a pinene-type monoterpenoid unit in their molecules. Biosynthetically, a key hetero-Diels–Alder mechanism was proposed for the generation of compounds 1 – 4 . [ABSTRACT FROM AUTHOR]

Hypericum japonicum (Guttiferae), a type of annual or perennial herb, has been historically applied to cure infectious hepatitis, acute and chronic hepatitis, gastrointestinal disorder, and internal hemorrhage. In our successive studies on the genus Hypericum, two new α-pyrones termed japopyrones A and B (1 and 2) were isolated from H. japonicum. Their structures and absolute configurations were established by the comprehensive analyses of spectroscopic data, the application of the Single-crystal X-ray diffraction structural analysis, and the experimental electronic circular dichroism (ECD) spectra. Bioactivity screenings suggested that compound 2 possessed the potential inhibition efficacy on lytic replication of Kaposi’s sarcoma associated herpesvirus (KSHV) with an IC50 29.46 μM and a selective index of higher than 6.79, respectively. [ABSTRACT FROM AUTHOR]

Four undescribed trimethylated acylphloroglucinol meroterpenoids, hyjapones A−D, along with seven known analogues, were isolated from Hypericum japonicum Thunb. Hyjapone A represents the first example of a double norflavesones-caryophyllene hybrid featuring a rare 6/6/9/4/6/6 hexacyclic frame. Hyjapone D was isolated as a natural product for the first time. Their structures and absolute configurations were established by comprehensive spectroscopic data analyses and electronic circular dichroism (ECD) calculations. The anti-inflammatory activities of all compounds were evaluated using lipopolysaccharide-induced RAW264.7 cells. Hyperjapone A showed more pronounced anti-inflammatory effect through reducing the production of nitric oxide (IC 50 value of 11.32 ± 2.10 μM) and proinflammatory cytokines. In addition, the mechanistic studies revealed hyperjapone A inhibited LPS-induced activation of nuclear factor-κB. Four undescribed meroterpenoids along with seven known analogues were isolated from Hypericum japonicum Thunb. The anti-inflammatory activities of all compounds were evaluated using lipopolysaccharide-induced RAW264.7 cells. [Display omitted] • Four undescribed meroterpenoids along with seven known analogues were isolated from Hypericum japonicum Thunb. • Hyjapone A represents the first example of a double norflavesones-caryophyllene hybrid. • Hyperjapone A showed significant anti-inflammatory effect through suppressing NF-κB signaling pathway. [ABSTRACT FROM AUTHOR]

The widely-used Chinese medicinal herb Hypericum japonicum, also known as Hypericum japonicum Thunb or Tianjihuang, displays potent anti-carcinogenic effects against liver cancer. However, the molecular mechanism underlying the therapeutic effects of Hypericum japonicum remains to be elucidated. The present study investigated the in vivo efficacy of ethyl acetate extract of Hypericum japonicum (EAEHJ) against tumor growth in an H22 cell-bearing liver cancer mouse model. Treatment with EAEHJ significantly reduced tumor weight, but had no effect on murine body weight. The results of the present study also showed that EAEHJ induced H22 cell apoptosis in vivo. In addition, the anti-carcinogenic effects of EAEHJ were investigated in vitro. The results of the present study demonstrate that both phospholipid asymmetry in the plasma membrane and mitochondrial membrane potential were deregulated in HepG2 human hepatoma cells, following treatment with EAEHJ. Treatment with EAEHJ also increased the ratio of pro-apoptotic B-cell lymphoma 2 (Bcl-2)-associated X protein (Bax) to anti-apoptotic Bcl-2, and activated the caspase-9 signaling pathway. These results suggest that EAEHJ is able to trigger the apoptosis of liver cancer cells via the mitochondria-dependent pathway. [ABSTRACT FROM AUTHOR]

Hydro-distilled essential oil of the aerial parts ofHypericum japonicumThunb. ex Murray (Hypericaceae), grown in northern India was analyzed by gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). A total of seventy constituents representing 93.6% of the total composition have been identified. Major constituents of the essential oil were 2-methyl octane (24.9%),n-nonane (21.4%), (2Z)-nonenol (16.5%),n-decanal (8.2%) and allo-aromadendrene epoxide (3.3%). The characteristic of theH. japonicumessential oil was the presence of higher amount of aliphatic compounds (82.5%) compared with terpenoids. [ABSTRACT FROM PUBLISHER]

Through bioassay-guided fractionation of the extracts from the aerial parts of the Chinese herb Hypericum japonicum Thunb. Murray, Isojacareubin (ISJ) was characterized as a potent antibacterial compound against the clinical methicillin-resistant Staphylococcus aureus (MRSA). The broth microdilution assay was used to determine the minimal inhibitory concentrations (MICs) and minimal bactericidal concentrations (MBCs) of ISJ alone. The results showed that its MICs/MBCs ranged from 4/16 to 16/64 µg/mL, with the concentrations required to inhibit or kill 50% of the strains (MIC50/MBC50) at 8/16 µg/mL. Synergistic evaluations of this compound with four conventional antibacterial agents representing different types were performed by the chequerboard and time-kill tests. The chequerboard method showed significant synergy effects when ISJ was combined with Ceftazidime (CAZ), Levofloxacin (LEV) and Ampicillin (AMP), with the values of 50% of the fractional inhibitory concentration indices (FICI50) at 0.25, 0.37 and 0.37, respectively. Combined bactericidal activities were also observed in the time-kill dynamic assay. The results showed the ability of ISJ to reduce MRSA viable counts by log10CFU/mL at 24 h of incubation at a concentration of 1 × MIC were 1.5 (LEV, additivity), 0.92 (CAZ, indifference) and 0.82 (AMP, indifference), respectively. These in vitro anti-MRSA activities of ISJ alone and its synergy with conventional antibacterial agents demonstrated that ISJ enhanced their efficacy, which is of potential use for single and combinatory therapy of patients infected with MRSA. [ABSTRACT FROM AUTHOR]

Antioxidants contents and antioxidative enzymes and their activities in fresh aerial tissues of Hypericum sampsonii (Sampson’s St John’s Wort), Hypericum japonicum (Japanese St John’s Wort) and Hypericum perforatum were investigated. Hypericum sampsonii contained more total ascorbate [34.33 μmol g−1 fresh weight (FW)] than H. perforatum (57% less) and H. japonicum (82% less). It also contained more thiol and phenolics than two other species. Hypericum japonicum had highest superoxide dismutase (SOD) activity (8.74 mmol min−1 g−1 FW), followed by H. sampsonii (2% less) and H. perforatum (37% less). Hot-air dried H. perforatum materials contained more thiol [208.7 μmol g−1 dry weight (DW)] and phenolics (352.82 mg g−1 DW) than freeze-dried and fresh materials. Both drying treatments decreased the activities of antioxidative enzymes in aerial tissues of H. perforatum. However, freeze-dried H. perforatum contained the highest SOD activity (5.42 mmol min−1 g−1 DW) among the antioxidative enzymes measured from both freeze-dried and hot-air dried tissues (ranged from 0.02 to 2.65 μmol min−1 g−1 DW). [ABSTRACT FROM AUTHOR]

Abstract: Objective: To investigate the hepatoprotective activity of different parts of Hypericum japonicum against carbon tetrachloride(CCl4)-induced hepatitis and α-naphthyl-isothiocyanate (ANIT)-induced cholestasis. Materials and Methods: Mice were divided into groups and then administrated orally with solutions extracted from herbs before they were modeled in the experiments. Levels of alanine aminotransferase (ALT), aspartate aminotransferase (AST) and total bilirubin (T-BIL) in serum were evaluated. HPLC fingerprint was used for phytochemical analysis of the extracts. Results: The total aqueous extract of Hypericum japonicum had an obvious effect on the decreasing of AST, ALT and T-BIL levels in serum. The isolated fraction IV (F4) exhibited a preferable activity of ameliorating cholestasis, while Fraction V (F5) was more efficacious in protecting liver from injury. Chemical fingerprint indicated that F5 contained several flavonoids which might be the active chemicals against hepatotoxicity. Conclusion: Different fractions of Hypericum japonicum manifest different effect, indicating their different potentials as candidacies of new drugs. [Copyright &y& Elsevier]

Abstract: A novel and sensitive HPLC-UV method has been developed for the simultaneous determination of five major flavonoids in Hypericum japonicum hydroalcoholic extract. The chemical profile of five flavonoids, including taxfolin-7-O-α-l-rhamnoside (1), isoquercitrin (2), quercitrin (3), quercetin-7-O-α-l-rhamnoside (4) and quercetin (5) was acquired by using high-performance liquid chromatography-diode array detector coupled to an electrospray tandem mass spectrometer (HPLC-DAD–ESI/MS). The analysis was performed on a ZORBAX SB-C18 analytical column (5μm, 250mm×4.6mm, i.d.) with a gradient solvent system of acetonitrile-0.5% aqueous formic acid. The validation was carried out and the linearities (r 2 >0.9997) and recoveries (ranged from 98.4% to 99.8%) were acceptable. The limits of detection (LOD) of these flavonoids ranged from 0.5 to 7.5ng. The results indicated that the contents of investigated flavonoids in H. japonicum varied significantly from habitat to habitat with contents ranging from 2.00 to 34.18mg/g. The proposed method is simple, effective and suitable for the quality control of this traditional Chinese medicine (TCM). [Copyright &y& Elsevier]

Two new xanthones, 1,6-dihydroxyisojacereubin-5-O-β-D-glucoside (1) and 3,6,7-tri-hydroxy-1-methoxy-xanthone (2), were isolated from Hypericum japonicum. The structural elucidation of the isolated compounds were primarily based on HREIMS, EIMS, UV, IR, 1D-, and 2D-NMR analyses, including COSY, HMQC, HMBC, and NOESY correlations. [ABSTRACT FROM AUTHOR]

Ferroptosis is a new type of cell death, which involves central neuronal system. Inhibition of ferroptosis is a promising strategy to prevent and treat neurological diseases. Thirteen phloroglucinols (1 − 13) were obtained from the whole plants of Hypericum japonicum. Of them, compounds 1 – 3 are new ones. Their structures were elucidated by extensive analysis of spectroscopic data and X-ray diffraction. All the isolates were evaluated for their inhibitory effect on RSL3-induced ferroptosis. Two new compounds 2 – 3 showed significant inhibitory effect with EC 50 of 0.48 ± 0.14 μM and 0.94 ± 0.14 μM, respectively. DPPH free radical scavenging abilities of all compounds were assessed to evaluate their antioxidant effect. This work first reports the anti-ferroptosis activity of phloroglucinols. [Display omitted] • Thirteen phloroglucinols including three new ones were isolated. • Phloroglucinols exhibited significant anti-ferroptosis activity. • Compound 2 exhibited most potent anti-ferroptosis activity with EC 50 value of 0.48 μM. [ABSTRACT FROM AUTHOR]

Phloroglucinols are characteristic constituents of Hypericumjaponicum that are claimed to exert several bioactivities, such as anti-inflammatory, anti-depressant and anti-viral ones. Phloroglucinols are unstable compounds and their synthesis is challenging; thus, isolation from natural sources is still one of the main strategies for obtaining these constituents in purified form. Assessing the presence of phloroglucinols in plant materials can be of interest for compound isolation, and LC-MS approaches afford sensitivity and specificity in this regard. In this work, we combined data from quadrupole-time of flight (QTOF) and ion trap (IT) mass spectrometers in order to assess the presence of the phloroglucinols characteristic of H. japonicum and to elucidate their MS fragmentation pathways. The identified compounds present similar structures bearing the 1,3,5-trihydroxybenzene core with different substitutions, which, in constituents at higher MW, is linked to 3′,3′-dimethyl-6′-oxo-phlorisobutyrophenone by a methylene bridge. Differences in MS2 spectra of the considered phloroglucinols are useful for compound identification and differentiation, and to perform dereplication studies. Overall, the proposed approach could be useful for the analysis of phloroglucinols in H. japonicum and other plant species. [ABSTRACT FROM AUTHOR]

Fractions from a partition of a total extract of Hypericum ascyron L. and Hypericum japonicum Thunb. ex Murray were investigated for their antibacterial activity against a strain of multidrug-resistant (MDR) Staphylococcus aureus possessing the NorA multidrug-efflux transporter, the major characterized MDR pump in this species. The hexane fraction of Hypericum ascyron and the n -BuOH fraction of H. japonicum both showed appreciable antibacterial activities with minimum inhibitory concentration (MIC) values of 128 µg/ml for both fractions. Given the complexity of these extracts and the relevance of the NorA efflux mechanism in clinical isolates of Staphylococcus aureus , these results highlight the potential of the genus Hypericum as a source of new antibacterial drug-leads. [ABSTRACT FROM AUTHOR]