330. The structure of palitantin

Polyhydroxy Cyclohexanols from aDendrodochiumsp. Fungus Associated with the Sea CucumberHolothuria nobilisSelenka

“…This group of new metabolites is typical of fungal polyketide metabolites. The first example of such metabolites, palitantin, was obtained from culture filtrates of Penicillium palitans Westling in 1936, and its structure was determined in 1959 . Its structure closely resembled that of frequentin, an antifungal and antibiotic agent .…”

“…The first example of such metabolites, palitantin, was obtained from culture filtrates of Penicillium palitans Westling in 1936, 23 and its structure was determined in 1959. 24 Its structure closely resembled that of frequentin, an antifungal and antibiotic agent. 25 In 1997, a reinvestigation of a Penicillium sp.…”

Studies in the biosynthesis of fungal metabolites. The biosynthesis of palitantin

“…Palitantin, C14H2204, a metabolite of PeniciUlium palitans Westling and other species, was first isolated and characterized by Birkinshaw & Raistrick (1936). It was further investigated by Birkinshaw (1952) and by Bowden, Lythgoe & Marsden (1959), who proposed the structure (I) (Fig. 1).…”

“…Although acetate coupling is the pathway most readily visualized (Bowden et al 1959), the presence of three vicinal oxygen substituents is reminiscent of 5-dehydroshikimic acid (III), which is a known precursor of the aromatic amino acids and consequently an alternative source of benzenoid rings. Although the necessary additional modifications render this latter mechanism less probable, the possible operation of such a pathway added interest to the problem of palitantin biosynthesis.…”

“…The resulting extract was fractionated with sodium carbonate solution into crude palitantin and frequentin, ClJ12004, a related product of possible structure (IV) (Bowden et al 1959). Both fractions were highly labelled, as shown in Table 1.…”