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Morchella fluvialis, a morel mushroom, is one of the most famous edible mushrooms all over the world. Interest in this mushroom is steadily increasing due to its organoleptic properties and nutritional value. The methanolic extract of M. fluvialis showed α-glucosidase inhibitory and antioxidant activities in an assay system. Therefore, the purification and characterisation of bioactive metabolites and evaluation of biological activity were conducted. Fractionation of the M. fluvialis extract resulted in the isolation of nine compounds, namely, three fatty acids, (9Z,12Z)-octadecadienoic acid (linoleic acid, 1), (9Z,12Z)-3-hydroxyoctadecadienoic acid (2) and (6Z,9Z)-13-hydroxyoctadecadienoic acid (3); four sterols, stellasterol (4), ergosterol peroxide (5), ergosterol (6) and brassicasterol (7); one sugar alcohol, arabitol (8); and nicotinamide (9). Among them, compounds 2–3 and 7 were first reported from Morchella. In addition, compound 1 exhibited potent α-glucosidase inhibition, with an IC50 value of 14.8 μM. The content of compound 1, the major compound, was 1.2 mg · g–1 extract, as quantitated by HPLC analysis, which was lower than the IC50 value of compound 1. Therefore, M. fluvialis can benefit from diabetes and related diseases through the synergistic effect of linoleic acid (1) and other ingredients.

Cratoxylum formosum ssp. pruniflorum (Kurz.) Gogel (Guttiferae), called kuding tea, is widely distributed in Southeast Asia. In this study, the constituents and biological activity of C. formosum ssp. pruniflorum were investigated. Extract of its leaves, roots and stems showed antioxidant and α-glucosidase inhibitory activity. Interestingly, comparison of the metabolite profiles of leaves, roots and stems of C. formosum ssp. pruniflorum by LC-MS analysis showed a great difference between the roots and leaves, whereas the roots and stems were quite similar. Purification of the roots and leaves of C. formosum ssp. pruniflorum through various chromatographic techniques resulted in the isolation of 25 compounds. The structures of isolated compounds were elucidated on the basis of spectroscopic analysis as 18 xanthones, 5 flavonoids, a benzophenone and a phenolic compound. Among them, a xanthone (16) and a benzophenone (19) were first reported from nature. Evaluation of biological activity revealed that xanthones had a potent α-glucosidase inhibitory activity, while flavonoids were responsible for the antioxidant activity. To maximize the biological activity, yield and total phenolic content of C. formosum ssp. pruniflorum, extraction conditions such as extraction solvent, time and temperature were optimized using response surface methodology with Box–Behnken Design (BBD). Regression analysis showed a good fit of the experimental data, and the optimal condition was obtained as MeOH concentration in EtOAc, 88.1%; extraction time, 6.02 h; and extraction temperature 60.0 °C. α-Glucosidase inhibitory activity, yield and total phenolic content under the optimal condition were found to be 72.2% inhibition, 10.3% and 163.9 mg GAE/g extract, respectively. These results provide useful information about C. formosum ssp. pruniflorum as functional foods for oxidative stress–related metabolic diseases. [ABSTRACT FROM AUTHOR]

As the leaf of Actinidia arguta has shown antioxidant activity, a study was conducted to identify the active ingredients. Forty-eight compounds were isolated from the leaves of A. arguta through various chromatographic techniques. Further characterization of the structures on the basis of 1D and 2D NMR and MS data identified several aromatic compounds, including phenylpropanoid derivatives, phenolics, coumarins, flavonoids and lignans. Among them, five compounds were newly reported, naturally occurring, and named argutosides A–D (1–4), which consist of phenylpropanoid glycosides that are conjugated with a phenolic moiety, and argutoside E (5), which is a coumarin glycoside that is conjugated with a phenylpropanoid unit. The isolated compounds showed good antioxidant and α-glucosidase inhibitory activity with differences in activity depending on the structures. Molecular docking analysis demonstrated the interaction between the hydroxyl and carbonyl groups of compounds 1 and 5 with α-glucosidase. Taken together, the leaves of A. arguta are rich in aromatic compounds with diverse structures. Therefore, the leaves of A. arguta and their aromatic components might be beneficial for oxidative stress and glucose-related diseases. [ABSTRACT FROM AUTHOR]

Hericium erinaceus, commonly called lion's mane mushroom , is an edible and medicinal mushroom that has been traditionally used for the treatment of metabolic disorders, gastrointestinal diseases and memory impairment. In this study, potential anti-hyperglycemic constituents were identified to support the traditional usage of H. erinaceus. The components of H. erinaceus were purified using various column chromatography techniques. The structure of the separated compounds was determined based on spectroscopic data analysis, i.e., 1D and 2D NMR analysis. The anti-hyperglycemic activity of the isolated compounds was evaluated by measuring the inhibitory effects on α-glucosidase activity. Molecular docking analysis was also conducted for elucidation of α-glucosidase inhibitory activity of isolated compounds. Ten compounds including four new compounds, erinacenols A-D (1 – 4), were isolated from the fruiting bodies of H. erinaceus. Investigation of the anti-hyperglycemic effect of isolated compounds demonstrated that erinacenol D (4), 4-[3′,7′–dimethyl-2′,6′-octadienyl]-2-formyl-3-hydroxy-5-methyoxybenzylalcohol (6), hericene A (7), hericene D (8) and hericenone D (9) strongly inhibited α-glucosidase activity with IC 50 values of <20 μM. The structure activity relationship suggested the importance of long side chain for α-glucosidase inhibitory activity. Further analysis by molecular docking demonstrated the interaction of α-glucosidase and isolated compounds, which supported the inhibitory activity of α-glucosidase. Our present study demonstrated the beneficial effect of H. erinaceus by characterization of α-glucosidase inhibitory compounds, including four new compounds. This approach can be valuable support for the traditional use of H. erinaceus for the treatment of diabetes and metabolic diseases, which needs to be clarified by further in-vivo study. Image 1 • Lion's mane mushroom (Hericium erinaceus) inhibited α-glucosidase activity. • Ten compounds were isolated from the fruiting bodies of H. erinaceus. • Four compounds, erinacenols A-D, were newly reported. • Long side chain was suggested to be important for the α-glucosidase inhibitory activity. • Interaction of α-glucosidase and compounds by molecular docking analysis. [ABSTRACT FROM AUTHOR]

The composition of a plant, together with its efficacy, vary depending on its maturity and plant parts. In this study, the chemical constituents of immature fruits of Maclura tricuspidata (Moraceae) were investigated together with their anti-diabetic and antioxidant effects. A total of 34 compounds were isolated from the immature fruits of M. tricuspidata using various chromatographic methods. Structure elucidation using extensive spectroscopic analysis led to the characterization of isolated compounds as isoflavonoids with prenyl substituents. Among them, macluraisoflavones A-O were first isolated from nature. The anti-diabetic and antioxidant activity of the isolated compounds were also suggested by α-glucosidase inhibitory activity and DPPH radical scavenging activity, respectively. In particular, macluraisoflavone I, an isoflavonoid with 2,2-dimethylpyran and 2-hydroperoxy-3-methylbut-3-enyl moieties, showed potent α-glucosidase inhibitory activity and DPPH radical scavenging activity. Further molecular docking analysis suggested hydrogen bond and alkyl interactions between α-glucosidase and macluraisoflavone I. Therefore, the immature fruits of M. tricuspidata can be used as an important natural product with antioxidant and anti-diabetic properties. Fifteen undescribed isoflavonoids, macluraisoflavones A-O, and 19 known compounds were isolated from the immature fruits of Maclura tricuspidata, which showed anti-α-glucosidase and anti-oxidative activity. [Display omitted] • Thirty-four compounds were isolated from the immature fruits of Maclura tricuspidata. • They were isoflavonoid with different numbers and types of prenyl moieties. • Fifteen compounds, macluraisoflavones A-O, were undescribed. • Macluraisoflavone I showed α-glucosidase inhibitory and antioxidant activity. • The interaction with α-glucosidase was analyzed by molecular docking analysis. [ABSTRACT FROM AUTHOR]

[Display omitted] • Forty-seven prenylated isoflavonoids were isolated from Masclura tricuspidata leaves. • Sixteen compounds, cudracusisoflavones A-P, were newly reported. • Prenylated isoflavonoids inhibited α-glucosidase activity and AGE formations. • Structure activity relationship was suggested using molecular docking analysis. Investigation of chemical constituents of Masclura tricuspidata leaves resulted in the isolation of 47 isoflavonoids possessing prenyl groups with different numbers and structures. Among them, sixteen compounds named cudracusisoflavones A-P (1 – 16) were first isolated from nature. The isoflavonoids isolated from M. tricuspidata leaves showed anti-diabetic effects as measured by inhibition on α-glucosidase activity and advanced glycation end-products (AGEs) formations. Especially, cudracusisoflavone L (12), a new compound, together with gancaonin M (27), erysenegalensein E (41) and millewanin G (44) showed strong α-glucosidase inhibition with IC 50 values <10.0 μM. In addition, cudracusisoflavones A (1), D (4), M (13) and N (14), together with known prenylated isoflavonoids efficiently inhibited methylglyoxal (MGO)- or glyoxal (GO)-induced AGE formations. Structure activity relationship together with molecular docking analysis suggested the importance of hydroxy group and linear type of prenyl moiety for α-glucosidase inhibition. Conclusively, diverse prenylated isoflavonoids in M. tricuspidata leaves might ameliorate glycotoxicity-induced metabolic diseases. [ABSTRACT FROM AUTHOR]