Structure of rosein III: X-ray analysis without a heavy atom

Abstract

The structure (1) of rosein 111, indicated by chemical and spectroscopic evidence, has been confirmed by an X-ray analysis of the metabolite itself, using direct methods of phase determination. ROSEIX 111, a metabolite of Trichotheciwn yoseum, was ~~ -H c y 2 * @ b / C # * O 0 (11 0 (21 first described1 by Freeman and Morrison in 1948. We have re-isolated this compound [m.p. 221°, [a], (CHC1,)-124"] in minor amount, and on the basis of the limited evidence set out below were led to formulate it as 11-/?hydroxy rosenonolactone (1). More estensive investigations,2J also terminated by lack of material, established the part structure (2), but further suggested3 that this was incorporated in a rearranged rosane skeleton.

Endophytic fungus Trichothecium roseum LZ93 antagonizing pathogenic fungi in vitro and its secondary metabolites

“…11ȕ-hydroxyrosenonolactone (1) was previously identified by X-ray analysis (Guttormson et al, 1970;Kiriyama et al, 1971), but no NMR data were reported. Here 1 H and 13 C NMR data were assigned based on 2D-NMR experiments ( Table 2).…”

Cyclodepsipeptides, Sesquiterpenoids, and Other Cytotoxic Metabolites from the Filamentous Fungus Trichothecium sp. (MSX 51320)

“…Species of the genus Trichothecium have been a rich source of secondary metabolites . As just one example, at least 29 secondary metabolites have been described from T. roseum , − ranging from depsipeptides such as the destruxins, roseotoxins, and roseocardin, to terpenoids such as eremophilanes, rosenoic acids, and trichothecenes, indicative of the vast biosynthetic potential of this, and perhaps related, fungi.…”

Untitled

“…Although the theory of non-heavy atom structure determination was known, the majority of the terpenoid structures that were reported in the 1960's were based on heavy atom derivatives. One of the earliest terpenoid non-heavy atom structures to be reported 111 was that of rosein III (11β-hydroxyrosenonolactone) 72 in 1970.…”