The marine fungus Aspergillus versicolor was isolated from the inner tissue of the Red Sea green alga Halimeda opuntia. The fungus was identified by its morphology and 18s rDNA. Cultivation of this fungal strain led to a new metabolite named isorhodoptilometrin-1-methyl ether (1) along with the known compounds emodin (2), 1-methyl emodin (3), evariquinone (4), 7-hydroxyemodin 6,8-methyl ether (5), siderin (6), arugosin C (7), and variculanol (8). The structures were elucidated on the basis of NMR spectroscopic analysis and mass spectrometry. The biological properties of ethyl acetate extract and compounds 1-3 and 6-8 were explored for antimicrobial activity, anti-cancer activity and inhibition of Hepatitis C virus (HCV) protease.

Chemical investigations of the Egyptian soft coral Sarcophyton ehrenbergi have led to the isolation of compounds 1–3 as well as the previously reported marine cembranoid diterpene sarcophine (4). Structures were elucidated by comprehensive NMR and HRMS experimentation. Isolated compounds were in vitro assayed for cytotoxic activity against human hepatocarcinoma (HepG2) and breast adenocarcinoma (MCF-7) cell lines.

Four different Aspergilli (Aspergillus oryzae, A. parasiticus, A. terreus and A. versicolor) were grown on wheat grains underdifferent degrees of relative humidity 14, 50, 74, 80 and 90%. Samples of wheat grains were taken monthly for a period of six months and examined for mycotoxin production. A. oryzae was found to produce aflatoxins B1, B2, zearalenone, DON and T-2 toxins under elevated degrees of humidity and prolonged periods of storage. A. parasiticus produced aflatoxins B1, G1, NIV, DON and T-2 toxins in high concentrations during a period of not more than three months storage at 14% relative humidity; at an increased level of relative humidity of 74% ochratoxin A, zearalenone and sterigmatocystin were also produced at high levels. The isolate was drastic in toxin production. A. terrus produced toxins at 14% relative humidity (aflatoxin G2 and DON) at levels much higher than any other prevalent degrees of humidity. A. versicolor is highly sensitive to relative humidity and grain moisture content It produced aflatoxins B1, G1, NIV and DON at a relative humidity of 50% and another toxins (aflatoxin G2, ochratoxins A, B and zearalenone) at 74%. The microorganism can be considered a trichothecene producer under suitable relative humidity.

Cytochrome P450 (CYP) enzymes are responsible for metabolism of a wide range of endogeneous compounds and xenobiotics, e.g. drug molecules, pollutants, and environmental compounds. Among members of the CYP enzyme family, CYP3A4 is the most abundant enzyme in human liver microsomes and intestinal epithelium; approximately 30% of the total CYP was suggested to be CYP3A4, 1) and more than 50% of clinically used drugs are oxidized by CYP3A4.2,3) It is well known that concomitant oral administration of several foods and herbs affects drug metabolism in humans by inhibiting CYP3A4 activity. In the course of our study on CYP inhibitors from foods, we have reported the isolation and structure elucidation of CYP inhibitors from grapefruit (Citrus paradisii) juice, [4][5][6] white pepper, Piper nigrum, 7,8) strawberry fruit, Fragaria ananassa, 9) and the commercially available black cohosh, Cimicifuga racemosa. 10) Licorice is prescribed in many Chinese traditional medicines and has been reported to contain flavonoids and triterpenoids. [11][12][13][14][15][16][17][18][19] Recently, we found that the extract of licorice (Glycyrrhiza uralensis FISHER, Leguminosae) showed potent CYP3A4 inhibitory activity with the IC 50 value of 0.022 mg/ml. This paper reports the isolation, structure identification, and CYP inhibitory activity of the constituents of licorice. MATERIALS AND METHODS General ProceduresOptical rotations were determined with a Horiba SEPA-300 high sensitive polarimeter. NMR spectra were recorded on a JEOL GSX500 NMR spectrometer. Mass spectra were measured on a JEOL SX-102 mass spectrometer.Plant Materials The rhizomes of G. uralensis were purchased from Tochimoto Co., Ltd. (Osaka, Japan). A voucher specimen is deposited in the Laboratory of Pharmacognosy and Chemistry of Natural Products, Graduate School of Natural Science and Technology, Kanazawa University, Japan.Isolation of Compounds 1-9 The rhizomes (0.5 kg) of G. uralensis were extracted with methanol (MeOH) (3 lϫ3) at room temperature. The extract was evaporated in vacuo, and the residue was partitioned between ethyl acetate (EtOAc) and water (H 2 O). The aqueous fraction was then partitioned between butanol (BuOH) and water. The EtOAc soluble fraction (34.7 g) was subjected to column chromatography on silica gel with hexane/EtOAc followed by ODS column chromatography with MeOH/H 2 O to afford 1-4 (Fig. 1). The BuOH soluble fraction (34.9 g) was subjected to column chromatography on ODS with MeOH/H 2 O followed by ODS HPLC with MeOH/H 2 O to afford 6 and 8. The aqueous fraction (31.3 g) was subjected to column chromatography on ODS with MeOH/H 2 O followed by ODS HPLC with MeOH/H 2 O to afford 5, 7, and 9.Assay of CYP3A4 Inhibition CYP3A4 activity was measured based on nifedipine oxidation. Various amounts (0-10 mM, final concentration) of samples in 1 ml of dimethylsulfoxide (DMSO) were added to 192 ml of 100 mM phosphate buffer (pH 7.4) containing 50 mM nifedipine (Wako Pure Chemical Industries, Ltd., Osaka, Japan), 5 mM glucose-6-phosphate (Oriental...