Sesquiterpenes from Omphalotus illudens

Draft Genome of Omphalotus olearius Provides a Predictive Framework for Sesquiterpenoid Natural Product Biosynthesis in Basidiomycota

“…Almost all of the reported O. olearius sesquiterpenoids appear to be derivatives of the Δ-6 protoilludene scaffold (McMorris, 1999; McMorris et al, 2002; McMorris et al, 2000; Morisaki, 1985) (Figure 1). To obtain an estimate of the mushroom’s capacity to create other sesquiterpene hydrocarbon scaffolds as well, we first determined its product profile of unmodified sesquiterpenes.…”

“…The following sesquiterpenoid compounds have been isolated from O. olearius and are proposed to be derived from the Δ-6 protoilludene scaffold: Illudin A and B, illudalenol (Arnone et al, 1991); illudin C,D,E (Arnone et al, 1991); illudosin (Arnone et al, 1991); dihydroilludin (Singh et al, 1971); 4α-Hydroxyilludin M (Bradshaw et al, 1982); neoilludol (Nair and Anchel, 1975); illudacetalic acid (Nair and Anchel, 1972); illudol (McMorris et al, 1971); illudalic acid and illudinine (Nair et al, 1969); illudosone hemiacetal, isoomphadione and illudiolone (McMorris et al, 2002), and omphadiol (McMorris et al, 2000). The sesquiterpene alcohol (+) torreyol (Nair and Anchel, 1973) (in square brackets) is not derived from Δ-6 protoilludene, instead it is proposed to be a derivative of α–muurolene.…”

Three new sesquiterpenoids from cultures of the basidiomyceteConocybe siliginea

“…IR absorption bands at 1716 and 3440 cm 21 revealed the existence of CvO and OH groups. The 1 H and 13 C NMR spectra of compound 3 (Table 1) Journal of Asian Natural Products Research 3 data indicated that 3 was a protoilludanetype sesquiterpenoid [6]. The carbon shift at d C 68.4 (s, C-7) was assigned to C-7, as evidenced by HMBC correlations (Figure 3) Figure 1.…”

Purification, crystallization and preliminary X-ray diffraction analysis of Omp6, a protoilludene synthase fromOmphalotus olearius

“…We recently described the genome sequencing, genome mining and subsequent discovery of a suite of novel sesquiterpene synthases from Omphalotus olearius, a Basidiomycete which had previously been shown to produce the anticancer sesquiterpene scaffold illudin (McMorris et al, 1990(McMorris et al, , 2002Wawrzyn et al, 2012). Two of these novel sesquiterpene synthases, Omp6 and Omp7, have been shown to be highly active and product-specific protoilludene synthases, producing Á-6 protoilludene via a likely 1,11 ring closure of FPP to create a trans-humulyl cation intermediate followed by two cyclization steps to yield the final volatile sesquiterpene ( Fig.…”