Ring B Aromatic Norpimarane Glucoside from a Xylaria sp.

Abstract

A novel 20-norpimarane glucoside, xylopimarane (1), together with the known sphaeropsidin C (2) and clonostachydiol (3), was isolated from the fungus Xylaria sp. BCC 4297. Compound 1 exhibited cytotoxicity to cancer cell lines KB, MCF-7, and NCI-H187 with respective IC(50) values of 1.0, 13, and 65 μM.

Isolation and Identification of Algicidal Compound from Streptomyces and Algicidal Mechanism to Microcystis aeruginosa

“…Several bacteria can convert ginsenoside to saponins [40,41]. Diterpene glucosides are parts of terpene glucoside compounds and produced by a fungus [42–44]. In contrast to the structures of known triterpenoid saponins, triterpenoid saponin found in this study may be a new type of saponin from actinobacteria.…”

ChemInform Abstract: Secondary Metabolites from the Genus Xylaria and Their Bioactivities

“…Xylarenolide (47) was isolated from Xylaria sp. BCC 4297 [17]. Compounds 48 and 49 were isolated from the fungus Xylaria sp.…”

“…Compounds 9, 10, and 33 exhibited moderate antitumor activities against HeLa cells [7]. Xylopimarane (51) exhibited cytotoxicity against cancer cell lines KB, MCF-7, and NCI-H187 with IC 50 values of 1.0, 13, and 65 mm, respectively [17]. Chlorine heptelidic acid (45) showed slight cytotoxicities against two cell lines, A549 and SGC7901 [16].…”

Chemical investigation on the cultures of the fungus Xylaria carpophila

“…The culture broth (21 L) was filtered, and the filtrate was extracted three times with EtOAc while the mycelium was extracted three times with CH 3 ClMeOH (1:1). The EtOAc layer together with the mycelium extraction was concentrated under reduced pressure to give a crude extract (4.5 g), and this residue was subjected to CC over silica gel (200-300 mesh) eluted with a gradient of CH 3 Cl-MeOH (1:0 → 0:1) to obtain eight fractions (1)(2)(3)(4)(5)(6)(7)(8). Fraction 2 (570 mg) applied to MPLC (MeOH-H 2 O, eluting from 50:50 to 100:0 for 100 mins with a flow of 20 mL/min) then isolated and purified by repeated silica gel chromatography, eluted with petroleum ether/EtOAc (2:1), followed by Sephadex LH-20 (Me 2 CO) to afford 2 (2.5 mg), 3 (0.7 mg), 5 (1.4 mg) and 7 (1.0 mg).…”

“…Previous studies revealed that isopimarane diterpene glycosides, 1 xylopimarane, 2 4,6,8 (14),22-tetraen-3-one, 3 xylarisin, 4 coloratin A, 5 kolokoside A, 6 cytochalasins, 7 clonostachydiol, 7 xylobovide, 7 07H239-A, 8 cytochalasin D, 9 multiplolides A and B, 10 sordaricin, 11 mellisol, 12 1,8-dihydroxynaphthol 1-O-α-glucopyranoside, 12 benzoquinones, 13 and integric acid 14 from some species of this genus showed diverse pharmacological properties, including cytotoxic, antimicrobial, antifungal, anthelmintic, antivirus, and antimalarial activities. But the chemical constituents of Xylaria carpophila have received little attention.…”