Solorinic acid

Certain other anthraquinones of this pathway begin with more complex starter units. The CoA derivative of hexanoic acid (n-CsHiiCO-SCoA) is utilized to produce the somewhat unusual anthraquinone solorinic acid (61) (Fig. 6.14). 

MS, m/z 384 (M+), 366,341, 313 Deriv Triacetylsolorinic acid, yellow crystals (benzene-n-hexane), mp 147 °C, by acetylation of solorinic acid with AC20-pyridine StL Solorina crocea (L.) Ach. 

Anderson HA, Thomson RH, Wells JW (1966) Naturally occurring quinones. Part VIII. Solorinic acid and norsolorinic acid. J Chem Soc (C) 1727-1729 Andres WW, Kunstmann MP, Mitscher LA (1967) Isolation and structure of 2,4-dihydroxy-3,5,6-trimethylbenzoic acid from Mortierella ramanniana. Experientia 23 703-704... 

The novel bisanthraquinone disolorinic acid (176) was isolated from the lichen Solorina crocea 306). This metabolite co-occurred with its monomeric precursor, solorinic acid, which facilitated structural elucidation. 

Solorinic acid (15) from Solorina crocea was characterized by Roller and Russ (1937). The demethyl compound, norsolorinic acid (14), was produced by A. versicolor (Hamasaki et aL, 1967b) and S. crocea L. (Anderson et aL, 1966). Aspergillus versicolor furthermore yielded both averantin (16) (Birkinshaw et aL, 1966) and T-O-methylaverantin (17) (Aucamp and Holzapfel, 1970). Drastic acid treatment converted these two compounds into averythrin (18), a metabolite of A. versicolor (RobQvts and Rofiey, 1965). 

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