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Secondary Metabolites by Chemical Screening, 23. Waraterpols, New Penicillium Metabolites and Their Derivatives
Author(s) -
Henne Petra,
Thiericke Ralf,
Grabley Susanne,
Hütter Klaus,
Wink Joachim,
Jurkiewicz Elke,
Zeeck Axel
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199319930192
Subject(s) - chemistry , derivatization , hydroquinone , phenols , hydroxymethyl , moiety , metabolite , penicillium , stereochemistry , quinone , organic chemistry , high performance liquid chromatography , biochemistry , food science
Abstract Substituted phenols can easily be recognized by using the chemical screening method, whereby they are found to be widely spread secondary metabolites of microorganisms. In the culture filtrate of Penicillium sp. (strain FH‐A 6260) new phenols named waraterpols were detected by a striking purple coloration by using anisaldehyde/sulfuric acid. These secondary metabolites ( 1 to 3 and 6 to 8 ) exhibit a C 15 ‐carbon skeleton and can be characterized as hydroxylated branched‐chain sesquiterpenoids with a benzoide moiety. The minor compounds were O ‐acetyl ( 2 and 3 ) and dehydrated derivatives ( 6 to 8 ) of the parent compound waraterpol ( 1 ), which was shown to be 6‐[2‐hydroxy‐4‐(hydroxymethyl)phenyl]‐2‐methylheptane‐1,6‐diol. Derivatization of 1 resulted in the quinone and hydroquinone compounds 10 and 5 as well as in the cyclic derivatives 11 and 12 . The waraterpols exhibit distinct antibacterial and antifungal activities whereas an inhibition of HIV‐1 in a MT‐4 cell assay was found for 11 .