Abstract
Three new eremophilane sesquiterpenes (1–3) were isolated from the mangrove endophytic fungus Xylaria sp. BL321 together with 07H239-A (4), a known analogue of the new compounds. The structures of these compounds were elucidated by analysis of their MS, 1D and 2D NMR spectroscopic data. Compound 4 showed activation activity on α-glucosidase at 0.15 μM (146%), and then, 4 gradually produced inhibitory activity on α-glucosidase with increasing concentration, and the IC50 value is 6.54 μM.
Highlights
Many structurally novel and biologically active metabolites have been isolated and characterized from the fungal genus Xylaria, including cytochalasins [1–3], phytotoxins [2], xyloketals [4–7], cyclopeptides [8–10], lactones [11,12], xanthones [13,14], sesquiterpenes [15,16], and aromatic derivatives [17,18]
Its IR spectrum indicated the presence of a hydroxyl group at 3300~2700 cm−1 and carbonyl, together with conjugated carbonyl absorptions at 1728, 1705, 1682 and
Analysis of the COSY spectrum disclosed three spin systems of H-1–H-4, H-6–H-7, and H-2'–H-10' and H-8'–H-11', which led to the establishment of the structure fragments C-1–C-4, C-6–C-7, and the long side chain incorporated a 1,3-diene, respectively
Summary
Many structurally novel and biologically active metabolites have been isolated and characterized from the fungal genus Xylaria, including cytochalasins [1–3], phytotoxins [2], xyloketals [4–7], cyclopeptides [8–10], lactones [11,12], xanthones [13,14], sesquiterpenes [15,16], and aromatic derivatives [17,18]. 2508 had led to the isolation of a series of the above mentioned compounds [5–10,17,18]. Our previous studies on the mangrove endophytic fungus Xylaria sp. 2508 encouraged chemical research resulting in the isolation of two new lactones from a endophytic fungus Xylaria sp. BL321 that led to the discovery of three new eremophilane sesquiterpenes [1,2,3] and a known analogue 07H239-A [4] [15] isolated by extensive silica gel column chromatography and semipreparative HPLC. We report the isolation, structure elucidation and enzyme-based biological assays against α-glucosidase of the four eremophilane sesquiterpenes
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