Sarcodonins and Sarcoviolins, Bioactive Polyhydroxy‐p‐terphenyl Pyrazinediol Dioxide Conjugates from Fruiting Bodies of the Basidiomycete Sarcodon leucopus

Abstract

Six new polyhydroxy‐p‐terphenyl pyrazinediol dioxide conjugates (4−9) related to sarcodonin (3) have been isolated from the EtOAc extract of the fruiting bodies of the basidiomycete Sarcodon leucopus and we established their structures by spectral analysis and chemical conversions. Three of them, named sarcodonins α (4), β (5), and γ (6), afforded the same peracetate 12 upon acetylation. Compounds 7, 8, and 9 gave peracetate 13 and were characterized as the N‐oxide epimers of 3−5, respectively, and are named, accordingly, episarcodonin, episarcodonin α, and episarcodonin β. From the EtOH extract, we obtained a mixture of two violet pigments. Chemical and spectroscopic data allowed their structures to be established as the p‐terphenyl ortho‐quinones related to the sarcodonins, namely sarcoviolin α (10) and episarcoviolin α (11). Compounds 3, 4, 6, and 7 and the mixture of 10 and 11 were found to be active in assays against tumor cell cultures. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

Cyathane Diterpenoids and Nitrogenous Terphenyl Derivative from the Fruiting Bodies of Basidiomycete Phellodon niger

“…The stereochemistry of 1 was elucidated by the ROESY correlations (Fig. 3) (Table 2), as well as IR and UV data, showed features very similar to those of p-terphenyl derivatives sarcodonin b (5) and the other related compounds sarcodonin a, g and d, 14,15) suggesting that they were analogues. Particularly, in the NMR spectrum of 3, the typical low-field signals of the p-terphenyl core and the majority of the signals of the side chain in the aliphatic moiety closely resemble the related compounds.…”

“…In addition, no HMBC correlations of aromatic quaternary carbons with the protons of methoxy were observed, so the methoxy was connected directly with N-1a. The relative stereochemistry of four chiral centers at N-1b, C-2b, C-4a and C-4b of 3 was the same as that of sarcodonin b (5) 14) and sarcodonin 13) by comparison of their 1 H-and 13 C-NMR spectral data. (Table 2).…”

“…From comparison of the 1 H-and 13 C-NMR spectral data of 3 with those of sarcodonin b (5), 14) (Table 2) it was apparent that 3 contained a p-terphenyl core bearing oxygenated functions at the same positions. In addition to the p-terphenyl resonances, it also revealed the presence of two aliphatic side chains, four acetoxyl groups, and a methoxyl group in compound 3 on the basis of the DEPT and 2D NMR experiments.…”

“…All these cyathanetype diterpenoids consisting of angularly condensed five-, six-, and seven-membered rings, and were mainly isolated from a diverse variety of fungi and few sponges. 12) Recently, a series of unusual nitrogenous terphenyl derivatives were isolated from the fruiting bodies of Sarcodon leucopus, 13,14) S. scabrosus, 15) Hydnellum suaveolens, and H. geogerirum. 16) These compounds were found to have cytotoxity in tumor cell lines, and antioxidant activity.…”

Pigments of higher fungi - a review

“…Karst., Bankeraceae) contain a range of compounds related to terphenylquinones. The main pigments are the unusual nitrogenous violet terphenylquinols sarcoviolins, exemplified by sarcoviolon α (82), which are accompanied by their colourless precursors sarcodonins (83) and structurally related compounds (Geraci et al 2000;Cali et al 2004). …”