Die Struktur von Panepoxydon und verwandten Pilzmetaboliten

Abstract

in 50 ml Aceton wurden mit 0,3 ml 3~ Salzsaure 4 Std. untcr Ruckfluss gekocht. Das Losungsmittel wurde im Vakuum weitgehend abgedampft. Nach Zusatz von Natriumhydrogencarbonat extrahierte man mit Chloroform. Der Chloroformauszug wurde ahgedampft und der Ruckstand mit Chloroform/Methanol = 5/1 dunnschichtchromatographisch gereinigt. Ausheute : 10 mg, die nicht kristallisierten, aher sich in allen anderen untersuchten Eigenschaften als identisch mit der in Versuch 13.1. beschriebenen Base erwiesen (UV.-, 1R.-, Massenspektrum, CR. und Rf-Werte; 1R.-Spektrum (CHC1,) : 3367, 1675, 1610). LITERATURVERZEICHNIS [l] H .Summary. The structure of panepoxydone (1) and some related products, produced by two species of Panus (basidiomycetes), are proposed on the basis of chemical transformations and physical measurements.The absolute configurations of the main products are deduced b y the interpretation of CD.studies and compared with those of the structurally related compounds epoxydone (lo), terreic acid (11) and terremutin (12).Die Gattung P a w s gehort zur Klasse der Basidiomyceten, Familie Agaricaleae, Unterfamilie Leukosporae. Unseres Wissens sind bisher keine antibiotisch oder cytostatisch wirksamen Metaboliten bei dieser Gattung gefunden worden.

A potent trypanocidal component from the fungus Lentinus strigosus inhibits trypanothione reductase and modulates PBMC proliferation

“…Hypnophilin (4) (Kis et al 1970), while panepoxydone was isolated with hypnophilin from cultures of the L. connatus (Rukachaisirikul et al 2005) and L. crinitus (Erkel et al 1996).…”

“…Dihydrohypnophilin (3) was isolated from a culture of L. crinitus (Abate & Abraham 1994) and L. conatus (Rukachaisirikul et al 2005). Panepoxydone and neopanepoxydol were obtained from fermentations of Panus rudis and Panus conchatus (Kis et al 1970), while panepoxydone was isolated with hypnophilin from cultures of the L. connatus (Rukachaisirikul et al 2005) and L. crinitus (Erkel et al 1996).…”

Lentinulactam, a hirsutane sesquiterpene with an unprecedented lactam modification

“…The modifications are manifested in oxygenation, unsaturation, degradation or rearrangement to form different ring skeletons. In our efforts to discover new natural products from Thai Basidiomycota, 9 we report in this paper on the isolation, structure determination and the biological evaluation of novel hirsutane compounds with unprecedented modification named lentinulactam (1), along with four known compounds, connatusin A (2), 8 connatusin B (3), 8 6-hydroxy-2,2-dimethylchroman-4-one (4), 10 and 6-methoxy-2,2-dimethylchroman-4-ol (5) 11 from the basidiomycete Lentinus cf. fasciatus collected in Thailand.…”

“…12,13 Our findings supported the previously reported configuration for connatusins and confirmed that lentinulactam (1) Compounds 4 and 5 were assigned as 6-hydroxy-2,2-dimethylchroman-4-one (4), and 6-methoxy-2,2-dimethylchroman-4-ol (5) (Figure 1) by comparison of their HRESIMS and NMR data with those in the literature. 10,11 The nomenclature of compound 5 was incorrectly published by Rukachaisirikul et al 8 as 2,2-dimethyl-3-hydroxy-6-methoxy-4-chromanone. The correct nomenclature is 6-methoxy-2,2-dimethylchroman-4-ol.…”

“…Compounds 2 to 5 are known from fungi, and were first isolated from Lentinus species and species of the closely related species genus Panus. 8,10,11 To the best of our knowledge none of the compounds has been isolated from Lentinus fasciatus before. Furthermore, compounds 2, 3 and 5 were already tested for their cytotoxic properties 8 and showed only weak or no activity; our study confirms the analysis (compound 5 was not tested due to limited material).…”