Elucidation of an α-glucosidase inhibitor from the peel of Allium cepa by principal component analysis.

We conducted liquid chromatography-mass spectrometry measurements on hot-water extracts of peel from different varieties of Allium cepa. Some quercetin glycosides were identified as potential α-glucosidase inhibitors by principal component analysis of the liquid chromatography-mass spectrometry data. α-Glucosidase inhibitory activity assays identified quercetin-4'-O-glucoside as an α-glucosidase inhibitor.

Anti-Influenza Virus Activity of Adlay Tea Components.

Our previous study showed anti-influenza virus activity in adlay tea prepared from adlay seeds, naked barley seeds, soybean, and cassia seeds. In this study, we evaluated the anti-influenza virus activity of each component of this tea and analyzed their active ingredients. Each component was roasted and extracted in hot water; the extracts were tested for antiviral activity and their mechanisms of action were studied. All the tea components showed antiviral activity against the H1N1 and H3N2 influenza subtypes and against influenza B. The viral stages inhibited by the components were virus adsorption and replication in proliferative process, suggesting that the action mechanisms of the components might differ from those of oseltamivir acid. Of the tea components, soybean showed the strongest activity. Therefore, we analyzed its active ingredients by liquid chromatography quadruple time-of-flight mass spectrometry (LC/qTOF-MS) and daidzein and glycitein were detected as active ingredients. Here, anti-influenza virus action of glycitein was the first report.

Isomerization of feruloylputrescine in orange juice by light exposure.

Exposure to light may adversely affect the quality of foods. This investigation of how light exposure affects citrus (orange and mandarin blend) juice in polyethylene terephthalate (PET) bottles demonstrated that the isomeric form of a compound in the juice changed during storage. This compound was identified as feruloylputrescine (FP; CAS: 501-13-3; C14H20N2O3) using LC/MS (Q-TOF). LC/MS and NMR measurements showed that the content of the original form, trans-FP, decreased as it isomerized to cis-FP during storage. This phenomenon could be observed in citrus fruit juices containing FP, such orange and grapefruit juices. Therefore, determining the content of these two isomers of FP could be used to indicate the level of light exposure experienced by citrus fruit products.

Mode of Antifungal Action of Daito-Gettou (Alpinia zerumbet var. exelsa) Essential Oil against Aspergillus brasiliensis.

Plant-derived essential oils (EOs) are used in medicines, disinfectants, and aromatherapy products. Information on the antifungal activity of EO of Alpinia zerumbet var. exelsa (known as Daito-gettou) found in Kitadaito Island, Okinawa, is limited. Therefore, we aimed to evaluate the antifungal activity of EOs obtained via steam distillation of leaves of Daito-gettou, which is a hybrid of A. zerumbet and A. uraiensis. Daito-gettou EO showed antifungal activity (minimum inhibitory concentration = 0.4%) against Aspergillus brasiliensis NBRC 9455, which was comparable to that of A. zerumbet found in the Okinawa main island. Gas chromatography/mass spectrometry revealed that the main components of Daito-gettou EOs are γ-terpinene, terpinen-4-ol, 1,8-cineole, 3-carene, and p-cymene. Terpinen-4-ol content (MIC = 0.075%) was 17.24%, suggesting that the antifungal activity of Daito-gettou EO was mainly attributable to this component. Daito-gettou EO and terpinen-4-ol inhibited mycelial growth. Moreover, calorimetric observations of fungal growth in the presence of Daito-gettou EO showed a characteristic pattern with no change in the initial growth rate and only a delay in growth. As this pattern is similar to that of amphotericin B, it implies that the action mode of Daito-gettou EO and terpinen-4-ol may be fungicidal. Further studies on the molecular mechanisms of action are needed for validation.

Anti-influenza A virus activity of flavonoids in vitro: a structure-activity relationship.

Secondary plant metabolites from food extracts, namely daidzein, quercetin, and luteolin, exhibit anti-influenza virus effects, with IC50 values of 143.6, 274.8, and 8.0 µM, respectively. The activities of these metabolites differ depending on the functional groups. Therefore, in this study, we focused on members of the flavonoid group, and investigated the anti-influenza viral effects of different flavonoid classes (flavone, isoflavone, flavonol, flavanone, and flavan-3-ol) in vitro. The IC50 values were 4.9-82.8 µM, 143.6 µM, 62.9-477.8 µM, 290.4-881.1 µM, and 22.9-6717.2 µM, respectively, confirming their activity. The modifying group factors (number, position, type) in the flavonoid skeleton may be significantly related to the anti-influenza virus activity. Moreover, time-of-addition assay revealed that the mechanism of inhibition varied for the different classes; for example, flavonoids that inhibit virus adsorption or the early stage of viral growth. Interestingly, all the examined flavonoids inhibited the late stages of viral growth, suggesting that flavonoids mainly inhibit the late events in viral growth before the release of viral particles. Additionally, apigenin might be effective against oseltamivir-resistant strains. Our results may be important in the development of anti-influenza virus therapeutic strategies in the future.

Inhibition of influenza virus replication by Apiaceae plants, with special reference to Peucedanum japonicum (Sacna) constituents.

ETHNOPHARMACOLOGICAL RELEVANCE: Apiaceae plants possess various pharmacological properties, such as antimicrobial, antioxidant, hypoglycemic, hypolipidemic, anxiolytic, analgesic, anti-inflammatory, anti-convulsant, and anti-cancer activities; however, data on their antiviral activity are limited. Peucedanum japonicum, also known as Sacna, is a plant used as food and as a traditional folk medicine for treating coughs. However, the active components in the leaves of this plant are yet unexplored. AIM OF THE STUDY: To assess Apiaceae plants, especially Peucedanum japonicum, with anti-viral activity, and the function and antiviral potential of Sacna constituents, considering the emergence of influenza virus strains resistant to the currently available drugs. MATERIALS AND METHODS: We prepared grinds of the freeze-dried leaves and roots of the Apiaceae family and the hot water extracts. The antiviral activities of the extracts were determined by focus formation reduction assay. In the time-of-addition assay, the test medium containing Sacna extract at 2 mg/mL was added at -1 to 0 h (adsorption) or from 0 to 4, 4 to 8, or 0 to 8 h (replication). The Sacna extract was separated by reversed-phase flash column chromatography using an Isolera Spektra system. The antiviral activity of each fraction was then determined using the focus formation reduction assay. The active fraction was analyzed using an LC20ADXR high performance liquid chromatography system equipped with a microTOF-QII quadrupole time-of-flight tandem mass spectrometer. RESULTS: All examined extracts of Apiaceae plants showed anti-influenza activity. Sacna extract most strongly inhibited the replication of influenza viruses. Individual components of Sacna possess antiviral activities against the influenza A/PR/8/34 virus. Sacna was found to inhibit the multiplication of A (H1N1 and H3N2) types and B types of influenza viruses, including amantadine-resistant and oseltamivir-resistant viruses. Sacna also inhibited influenza infection during viral replication. However, Sacna did not inhibit influenza infection during cell adsorption and did not suppress hemagglutination inhibition or cell fusion. Further, our findings suggest that the antiviral compounds in Sacna include flavonoids (quercetin and luteolin) and other polyphenols (caffeic acid, hymecromone, and umbelliferone). Although several effective compounds in Sacna inhibit multiple steps of viral replication, caffeic acid, which was increased by heat treatment at the time of extraction, significantly inhibited only the late period of viral growth, similar to the Sacna extract, indicating that it is the major component responsible for the antiviral activity of Sacna. CONCLUSIONS: Apiaceae plants possess antiviral activity. Caffeic acid is the major component responsible for the antiviral activity of Sacna. To our knowledge, this is the first report regarding the anti-influenza virus activity of Sacna. Overall, these results indicate that Sacna has potential as a novel treatment against influenza A and B viruses.

Influenza virus entry and replication inhibited by 8-prenylnaringenin from Citrullus lanatus var. citroides (wild watermelon).

We previously demonstrated the anti-influenza activity of Citrullus lanatus var. citroides (wild watermelon, WWM); however, the active ingredient was unknown. Here, we performed metabolomic analysis to evaluate the ingredients of WWM associated with antiviral activity. Many low-molecular weight compounds were identified, with flavonoids accounting for 35% of all the compounds in WWM juice. Prenylated flavonoids accounted for 30% of the flavonoids. Among the measurable components of phytoestrogens in WWM juice, 8-prenylnaringenin showed the highest antiviral activity. We synthesized 8-prenylnaringenin and used liquid chromatography-mass spectrometry to quantitate the active ingredient in WWM. The antiviral activities of 8-prenylnaringenin were observed against H1N1 and H3N2 influenza A subtypes and influenza B viruses. Moreover, 8-prenylnaringenin was found to inhibit virus adsorption and late-stage virus replication, suggesting that the mechanisms of action of 8-prenylnaringenin may differ from those of amantadine and oseltamivir. We confirmed that 8-prenylnaringenin strongly inhibited the viral entry of all the influenza virus strains that were examined, including those resistant to the anti-influenza drugs oseltamivir and amantadine. This result indicates that 8-prenylnaringenin may activate the host cell's defense mechanisms, rather than directly acting on the influenza virus. Since 8-prenylnaringenin did not inhibit late-stage virus replication of oseltamivir-resistant strains, 8-prenylnaringenin may interact directly with viral neuraminidase. These results are the first report on the anti-influenza virus activity of 8-prenylnaringenin. Our results highlight the potential of WWM and phytoestrogens to develop effective prophylactic and therapeutic approaches to the influenza virus.