Sterol Constituents from the Fruit Bodies of Grifola frondosa (FR.) S. F. GRAY.

Antitubercular Activity and Inhibitory Effect on Epstein-Barr Virus Activation of Sterols and Polyisoprenepolyols from an Edible Mushroom, Hypsizigus marmoreus

“…Reversed-phase preparative HPLC (HPLC I; 25 cmϫ10 mm i.d., Pegasil ODS II (Senshu Scientific Co., Ltd., Tokyo, Japan) column; mobile phase: MeOH-H 2 O-acetic acid (AcOH), 19 : 1 : 1, 2.0 ml/min) of purified fraction A (0.39 g) gave compound 1 (60 mg; retention time (t R ) 28.3 min) and ergosterol peroxide (2) 2) (12 mg; t R 27.8 min). HPLC (HPLC II; column used was the same as that of HPLC I; mobile phase: MeOH-H 2 O-AcOH, 9 : 1 : 1, 2.0 ml/min) of purified fraction B (0.38 g) gave five compounds, cerevisterol (3) 8) (40 mg; t R 23.6 min), 6-epicerevisterol (4) 9) (1.7 mg; t R 38.6 min), 22,23-dihydrocerevisterol (5) 10) (6.7 mg; t R 28.6 min), 6-O-methylcerevisterol (6) 11) (2.4 mg; t R 37.1 min), and (22E,24R)-5a,6a-epoxyergosta-8,22-diene3b,7b-diol (7) 12 Identification of sterols 1-7 was done by 1 H-NMR (400 MHz) and EI-MS spectral comparison with the corresponding compounds in the literature, 2,[8][9][10][11][12] and identification of hypsiziprenols 8-15 by 1 H-NMR and FAB-MS spectral comparison with the corresponding or relevant compounds in the literature. 4) Determination of Antitubercular Activity The antitubercular activity of compounds in DMSO was determined against Mycobacterium tuberculosis H 37 Rv (ATCC 27294) in Middlebrook 7H12 medium using the Microplate Alamar Blue Assay (MABA), as previously described.…”

“…From the limited data set, it appears that C6a,8a-epidioxidation (2), hydroxylation at both C-5a and C6a/b (3-6), or hydroxylation at C-7b accompanied with C5a,6a-epoxidation (7) gives rise to higher activity for the 3b-hydroxy sterols. On the other hand, two compounds, hypsizprenol A 9 (8; MIC 15 mg/ml) and hypsiziprenol BA 10 (12; 44 mg/ml), showed potent antitubercular activity among the eight hypsiziprenols (8)(9)(10)(11)(12)(13)(14)(15) tested. There was no apparent correlation between the structures and antitubercular activity for the hypsiziprenols.…”

“…4) In the course of our studies on the bioactive principles of natural medicines and foodstuffs, 5,6) we evaluated the constituents of H. marmoreus for their antitubercular activity 7) as well as their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). 5,6) In this paper, we describe the antitubercular activity against Mycobacterium tuberculosis of seven sterols (1-7) and eight polyisoprenepolyols, hypsiziprenols (8)(9)(10)(11)(12)(13)(14)(15), and inhibitory effects on the induction of EBV-EA by the TPA of seven sterols (1-7) and three hypsiziprenols (8, 10, 12) isolated from the non-saponifiable lipid (NSL) fraction of the extract of H. marmoreus.…”

Inhibition of human neutrophil elastase by ergosterol derivatives from the mycelium of Phellinus linteus

“…The stereochemistry of the side chain was determined by comparison of the 1 H and 13 C NMR data of 1 with those of a (22E,24R)-methyl-D 22 -sterol side chain. 19 On the basis of the above data, the structure of 1 was established as (22E,24R)-ergosta-7,22-dien-2a,3a,9a-triol.…”

“…In addition, 14 known compounds were identified as ergosterol (2), 20 ergosterol peroxide (3), 20 ergosterol peroxide glycoside (4), 21 5a,6a-epoxy-ergosta-8(14),22-dien-3b,7a-diol (5), 20 5a,6a-epoxyergosta-8(9),22-dien-7-on-3b-ol (6), 22 5a,6a;8a,9a-diepoxy-ergost-22-en-3b,7a-diol (7), 23 3b-hydroxy-ergosta-7,22-dien-6-one (8), 24 3b,5a-dihydroxy-ergosta-7,22-dien-6-one (9), 24 3b,5a,9a-triydroxyergosta-7,22-dien-6-one (10), 21 14a-hydroxy-ergosta-4,7,9(11),22-tetraen-3,6-dione (11), 24 ergosta-4,7,22-trien-3,6-dione (12), 25 3b,5a-dihydroxy-6b-methoxyergosta-7,22-diene (13), 26 ergosta-7,22-dien-3b,5a,6b-triol (14) 26 and ergosta-7,22-dien-2b,3a,9a-triol (15) 18 by comparing their physicochemical and spectral data to those in the literature.…”