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      Isolation of farnesylhydroquinones from the basidiomycete Ganoderma pfeifferi

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          Abstract

          Two farnesylhydroquinones were isolated from the fruiting bodies of Ganoderma pfeifferi, farnesylhydroquinone ( 1) and the new compound ganomycin K ( 2), (5 S)-3-[( E)-7,8-dihydroxy-4,8-dimethylnon-3-enyl]-5-(2,5-dihydroxyphenyl)-furan-2(5 H)-one. The structures of 1 and 2 were determined on the basis of mass spectrometric and NMR spectroscopic evidence. The antibacterial activity of the isolated compounds was neglectable.

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          Supplementary material is available for this article at 10.1007/s13659-013-0036-5 and is accessible for authorized users.

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          Ganoderma - a therapeutic fungal biofactory.

          Ganoderma is a basidiomycete white rot fungus which has been used for medicinal purposes for centuries particularly in China, Japan and Korea. A great deal of work has been carried out on Ganoderma lucidum. The common names for preparations include Lingzhi, Munnertake, Sachitake, Reishi and Youngzhi. This review collates the publications detailing activities and compounds by representative species whilst considering the most valid claims of effectiveness. The biological activities reported of preparations from Ganoderma are remarkable and given most emphasis herein as distinct from structure/activity information. The metabolites consist of mainly polysaccharides and terpenoids. Many are activities against the major diseases of our time and so the present review is of great importance. The list of effects is huge ranging from anti-cancer to relieving blockages of the bladder. However, the reports have not all been tested scientifically with the convincing evidence is reserved for assays of pure compounds. It is a prime example of an ancient remedy being of great relevance to the modern era. There does appear to be an assumption that the therapeutic effects attributed to the fungus have been proven. The next step is to produce some effective medicines which may be hampered by problems of mass production.
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            Natural products of the medicinal fungus Ganoderma lucidum: occurrence, biological activities, and pharmacological functions.

            Ganoderma lucidum, a fungus used in traditional Chinese medicine, produces polysaccharides and oxygenated triterpenoids with a very broad spectrum of biological activities and pharmacological functions. Among the Ganoderma triterpenoids, many pairs of C-3 alpha/beta stereoisomers and C-3/C-15 positional isomers have been identified. Biosynthetic study has indicated that the C-3alpha series of oxygenated triterpenoids is derived from the C-3beta series via an oxidation-reduction pathway. The interaction of Ganoderma triterpenoids with human platelets in the induction of aggregation and inhibition of agonist-induced aggregation and signal transduction has been elucidated. Reduction of cellular mevalonate content to a stage in which cholesterol synthesis is strongly inhibited and cell growth is marginally arrested sensitizes hepatoma cells to the oxygenated triterpenoids. A combination treatment of lovastatin and Ganoderma triterpenoids in animal studies has exhibited a potential anticancer effect. Copyright 2003 The Japan Chemical Journal Forum and Wiley Periodicals, Inc.
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              Antiviral Terpenoid Constituents of Ganoderma pfeifferi.

              Four sterols and 10 triterpenes were isolated from the fruiting bodies of Ganoderma pfeifferi, including the three new triterpenes 3,7,11-trioxo-5alpha-lanosta-8,24-diene-26-al (lucialdehyde D, 1), 5alpha-lanosta-8,24-diene-26-hydroxy-3,7-dione (ganoderone A, 2), and 5alpha-lanosta-8-ene-24,25-epoxy-26-hydroxy-3,7-dione (ganoderone C, 3). The structures of 1-3 were determined on the basis of spectroscopic evidence. Antibacterial, antifungal, and antiviral activity were studied for some of the isolated compounds. Ganoderone A (2), lucialdehyde B (4), and ergosta-7,22-dien-3beta-ol (7) were found to exhibit potent inhibitory activity against herpes simplex virus.
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                Author and article information

                Contributors
                timo.niedermeyer@uni-greifswald.de
                Journal
                Nat Prod Bioprospect
                Nat Prod Bioprospect
                Natural Products and Bioprospecting
                Springer Berlin Heidelberg (Berlin/Heidelberg )
                2192-2195
                2192-2209
                20 June 2013
                20 June 2013
                August 2013
                : 3
                : 4
                : 137-140
                Affiliations
                [ ]Institute of Pharmacy, Ernst-Moritz-Arndt-University, Friedrich-Ludwig-Jahn-Straße 17, 17487 Greifswald, Germany
                [ ]Institute of Biochemistry, Ernst-Moritz-Arndt-University, Felix-Hausdorffstraße 4, 17487 Greifswald, Germany
                Article
                36
                10.1007/s13659-013-0036-5
                4131579
                f96592f4-8ee0-43aa-879c-0d70ef27574a
                © The Author(s) 2013
                History
                : 30 April 2013
                : 2 June 2013
                Categories
                Regular Article
                Custom metadata
                © The Author(s) 2013

                ganoderma pfeifferi,farnesylhydroquinone,ganomycin
                ganoderma pfeifferi, farnesylhydroquinone, ganomycin

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