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  • 1
    Electronic Resource
    Electronic Resource
    Antibiotics from basidiomycetes (1981)
    Springer
    Archives of microbiology 130 (1981), S. 223-227 
    Details
    ISSN: 1432-072X
    Keywords: Antibiotics ; Basidiomycetes ; Pleurotellus hypnophilus ; Galerina cephalotricha ; Hypnophilin ; Pleurotellol ; Pleurotellic acid ; Complicatic acid
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract Three new antibiotically active metabolites were isolated from cultures of the fungus Pleurotellus hypnophilus. The structures which are closely related to the coriolins were elucidated by spectroscopic methods. Hypnophilin (1) has a hirsutane sceleton whereas pleurotellol (2) and pleurotellic acid (3) are sesquiterpenoids with novel hirsutane skeletons. The common structural feature of all three metabolites is an α-methylene ketone moiety. The antibiotics inhibited the growth of several bacteria as well as of some fungi. In cells of the ascitic form of Ehrlich carcinoma RNA and DNA syntheses were more affected than protein synthesis. The mode of action was compared with the antimicrobial and cytotoxic effects of complicatic acid (4) and other α-methylene ketones and lactones from higher plants. All the compounds tested reacted rapidly with cysteine to form adducts which were almost devoid of biological activity.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00459523
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  • 2
    Electronic Resource
    Electronic Resource
    Antibiotics from basidiomycetes XVI. Antimicrobial and cytotoxic polyines from Mycena viridimarginata karst (1982)
    Springer
    Archives of microbiology 132 (1982), S. 194-196 
    Details
    ISSN: 1432-072X
    Keywords: Antibiotics ; Polyines ; Basidiomycetes ; Mycena viridimarginata ; 10-Hydroxy-undeca-2,4,6,8-tetraynamide ; 3,4,13-Trihydroxy-tetradeca-5,7,9,11-tetraynoic acid-γ-lactone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract Two new biologically active polyines were isolated from cultures of the fungus Mycena viridimarginata. Their structures were elucidated by spectroscopic and chemical methods as 10-hydroxy-undeca-2,4,6,8-tetraynamide (1) and 3,4,13-trihydroxy-tetradeca-5,7,9,11-tetraynoic acid-γ-lactone (2). The main component (1) is highly antibiotically active and cytotoxic.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00508730
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  • 3
    Electronic Resource
    Electronic Resource
    Antibiotika aus Basidiomyceten, XII. Cristatsäure, ein modifiziertes Farnesylphenol aus Fruchtkörpern von Albatrellus cristatus (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 2099-2105 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Antibiotics from Basidiomycetes, XII.  -  Cristatic Acid, a Modified Farnesylphenol from Fruiting Bodies of Albatrellus cristatusFruiting bodies of Albatrellus cristatus contain high concentrations of cristatic acid (3), a farnesylphenol modified by incorporation of a furan ring in its side chain. A closely related American Albatrellus species contains grifolic acid (6) instead of 3. Biological screening of 3, 6 and related meroterpenoids revealed remarkable cytotoxic activities especially for dimethylcristatic acid methyl ester (4).
    Notes: Fruchtkörper von Albatrellus cristatus enthalten in hoher Konzentration Cristatsäure (3), ein Farnesylphenol, dessen Seitenkette durch Einbau eines Furanringes modifiziert ist. In einer nahe verwandten amerikanischen Albatrellus-Art kommt anstelle von 3 Grifolsäure (6) vor. Die biologische Aktivität von 3, 6 und verwandten Meroterpenoiden wird untersucht, wobei besonders die cytotoxische Wirkung von Dimethylcristatsäure-methylester (4) bemerkenswert ist.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119811203
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  • 4
    Electronic Resource
    Electronic Resource
    Antibiotika aus Basidiomyceten, XIX Naematolin und Naematolon, zwei Caryophyllan-Derivate aus Kulturen von Hypholoma-Arten (Agaricales) (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 1332-1342 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Antibiotics from Basidiomycetes, XIX. - Naematolin and Naematolone, Two Caryophyllane Derivatives from Cultures of Hypholoma Species (Agaricales)The isolation, structural elucidation, and biological activity of naematolin (1) and naematolone (9), two sesquiterpenoids with caryophyllane skeleton from cultures of several Hypholoma species, is described.
    Notes: Die Isolierung, Strukturaufklärung und biologische Aktivität von Naematolin (1) und Naematolon (9), zweier Sesquiterpenoide vom Caryophyllan-Typ aus Kulturen verschiedener Hypholoma-Arten, werden beschrieben.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840709
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  • 5
    Electronic Resource
    Electronic Resource
    Antibiotika aus Basidiomyceten, XX Synthese von Strobilurin A und Revision der Stereochemie der natürlichen Strobilurine (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 1616-1625 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Antibiotics from Basidiomycetes, XX. - Synthesis of Strobilurin A and Revision of the Stereochemistry of Natural StrobilurinsCondensation of cinnamaldehyde (5) with 2-oxobutyric acid (6) leads to the (E,E)-keto acid 7 which is converted into (9E)-strobilurin (1a) via methyl ester 9 and Wittig reaction of the latter with (methoxymethylene)triphenylphosphorane. On irradiation 1a undergoes inversion at the double bond in position 9 and yields strobilurin A (1b) which is identical with the natural product. Due to this result the (9Z) stereochemistry has to be assigned to all natural strobilurins 1b-4b, contrary to former formulations. This assignment is further supported by spectral comparison of 1a and 1b as well as by thermal cyclization of 1b to the biphenyl derivative 11. The latter can also be obtained by condensation of methyl 2-(methoxymethylene)acetoacetate (13) with cinnamylidenetriphenylphosphorane (12). Base-catalyzed condensation of 13 yields dimethyl 4-hydroxyisophthalate (14).
    Notes: Kondensation von Zimtaldehyd (5) mit 2-Oxobuttersäure (6) liefert die (E,E)-Ketosäure 7, die nach Überführung in den Methylester 9 und Wittig-Reaktion mit (Methoxymethylen)triphenylphosphoran (9E)-Strobilurin A (1a) ergibt. Inversion der 9-Doppelbindung durch Belichten führt zu Strobilurin A (1b), das mit dem Naturprodukt identisch ist. Danach besitzen alle natürlichen Strobilurine 1b-4b im Gegensatz zu früheren Angaben die (9Z)-Konfiguration. Diese Zuordnung wird durch den spektroskopischen Vergleich von 1a und 1b sowie durch thermische Cyclisierung von 1b zum Biphenyl-Derivat 11 gesichert. 11 kann auch durch Reaktion von 2-(Methoxymethylen)acetessigsäure-methylester (13) mit Cinnamylidentriphenylphosphoran (12) erhalten werden. Kondensation von 13 unter basischen Bedingungen liefert 4-Hydroxyisophthalsäure-dimethylester (14).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840910
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