Sordariol and related compounds, hexaketides in the fungus Sordaria macrospora

Nine Constituents Including Six Xanthone-Related Compounds Isolated from Two Ascomycetes, Gelasinospora santi-florii and Emericella quadrilineata, Found in a Screening Study Focused on Immunomodulatory Activity

“…The 1 H-NMR spectrum in acetone-d 6 was identical with that of pinselin isolated from T. bacillosporus. 8) This compound was directly identified with authentic pinselin on a TLC plate (silica gel 60F 254 , Merck) with n-hexane-acetone Hydrogenation of GS-1 (1) A solution of 1 (3.0 mg) and NaBH 4 (3.0 mg) in EtOH (1.0 ml) was stirred at room temperature for 1 min to give a product mixture.…”

“…GS-3 was identified with 1-hydroxy-3-methylxanthone (3), a xanthone from an Ascomycete, Anixiella (ϭGelasinospora) micropertusa, 5) by the 1 H-and 13 C-NMR spectra. GS-5 was identified with sordarial (5), a hexaketide from some Ascomycetes, Sordaria macrospora, 6) Gelasinospora heterospora, and G. longispora, 7) by the 1 H-and 13 C-NMR spectra and the specific rotation. EQ-4 was identified with the racemic form of microperfuranone (6), a furanone from G. micropertusa, 5) by the 1 H-and 13 C-NMR spectra and the specific rotation (Ϯ0°).…”

Total Synthesis of the Putative Structure of Xylarinol B

“…The spectral data obtained for C(5) epimer was different from synthetic 2 and also deviated substantially from naturally occurring 2 . At this stage, Professor B.‐S Yun was contacted and he informed us that the structure of 2 was wrongly assigned and that its spectral data matched with previously isolated sordariol, with a dihydroisobenzofuran structure 16. Interestingly, there are several reports on the isolation of sordariols from different sources; however, the relative structure of these compounds has been not proposed.…”

HPLC‐SPE‐NMR Identification of a Novel Metabolite Containing the Benzo[c]oxepin Skeleton from the Endophytic FungusPestalotiopsis virgatulaCulture

“…The biosynthesis of 1 presumably involves aromatization of a polyketide and hydroxylation of the terminal methyl group. Phenol derivatives with an aliphatic chain at C-3 and an aldehyde or hydroxymethyl substituent at C-2 were previously isolated from Sor- [23,24], from an unidentified fungus probably belonging to Cladosporium [25], and from Ascomycetes [26].…”