Studies in the biochemistry of micro-organisms. 96. The colouring matters of Penicillium herquei Bainier & Sartory

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Abstract
The dried mycelium of laboratory cultures of a typical strain of Penicillium herquei yields by solvent extraction, about 17% of its weight of a complex mixture of crude coloring matters. Minor constituents of this mixture are physcion (4,5-dihydroxy-7-methoxy-2-methylanthraquinone) and the colorless tetrahydric alcohol, mesoerythritol. Two of the major constituents are the hitherto undescribed norherqueinone, C19H18O7, dark-red needles, m.p. 279[degree], and its monomethyl ether, herqueinone, C20H20O7, brick-red needles, m.p. 226[degree]. Both substances are strongly dextro-rotatory. A number of functional derivatives of herqueinone and norherqueinone are described. Acid hydrolysis of herqueinone gives one molecule each of methyl isopropyl ketone, C5H10O, and xanthoherquein, C15H12O7, golden-yellow needles m.p. 295-296[degree]. Similar hydrolysis of norherqueinone gives the same ketone and norxanthoherquein, C14H10O7, orange-yellow plates, m.p. above 360[degree]. Norxanthoherquein and xanthoherquein give the same pentamethyl ether, C14H5O2(OCH3)5. Hence xanthoherquein is the monomethyl ether of norxanthoherquein.