Gianluca Nasini

Spirolaxine and sporotricale: Two long-chain phthalides produced by Sporotrichum laxum

Abstract Spirolaxine and sporotricale were isolated from cultures of Sporotrichum laxum . The structure of the two metabolites was determined by means of NMR, mass spectrometry and chemical evidence.

Stereochemistry of cercosporin

Abstract The absolute configuration of the asymmetric carbons and the axial chirality of the natural mold metabolite cercosporin (from Cercospora sp .) have been established on the basis of X-ray analysis and chemical reactions. The results confirm the inherent dissymmetry of the perylenequinone ring, the twisting of which gives rise to the diastereoisomer isocercosporin. The energy barrier for the conversion of cercosporin into isocercosporin has been evaluated.

Isolation and structure elucidation of tsugicolines A-D, novel protoilludane sesquiterpenes from Laurilia tsugicola1

Abstract Four novel Sesquiterpenes, tsugicolines A-D ( 1a, 2, 3a, 4 ), have been isolated from still cultures of the fungus Laurilia tsugicola (Basidiomycetae) Their structures were elucidated by means of chemical correlations and NMR studies and the relative configurations were established through a series of NOE difference spectra. The absolute configuration of tsugicoline A 1a (3- epi -illudol-5-one) was determined as 3S,6S,7R,9R,13S by the ‘partial resolution’ method of Horeau Treatment of tsugicoline A 1a with triethylamine in MeOH gave the metabolite 4; a possible mechanism is reported. Tsugicoline A is inactive on bacteria and fungi but inhibits the germination of the water cress Lepidium sativum .

Comparative evaluation of photodynamic efficiency of some natural quinonoid fungal toxins

Abstract A scale of photodynamic efficiency of some quinonoid fungal metabolises measured in vitro as amount of hydroperoxides produced by methyl oleate est

Isoflavonoid constituents of the west african red wood Baphia nitida

Abstract The red heartwood of the West African tree Baphia nitida (camwood) contains the new pigment santarubin C and a dimethoxytrihydroxyisoflavene; both compounds have been identified on the basis of spectroscopic analysis of derivatives.

Cyathiformines A–D, new chorismate-derived metabolites from the fungus clitocybe cyathiformis☆

Abstract Cyathiformines A–D, 1, 4a, 5and6a, have been isolated from the Basidiomycetous fungus Clitocybe cyathiformis. Structural determination was based on NMR studies and chemical evidence.

A new strain of Streptomyces: An anthracycline containing a C-glucoside moiety and a chiral decanol

Abstract Two new metabolites have been isolated from strain C57 of Streptomyces and their structure determined on the basis of chemical and NMR evidence.

Isolation and structure elucidation of tsugicolines F-H, novel furosesquiterpenes, and tsugicoline I from the fungus Laurilia tsugicola☆

Abstract Three novel sesquiterpenes of protoilludane origin, tsugicolines F-H (4a–6a), have been isolated from solid cultures of the Basidiomycetae Laurilia tsugicola. Their structures were elucidated by means of chemical correlation and NMR studies; a possible pathway for the formation from the protoilludane derivative tsugicoline A is reported. The furosesquiterpenes 4a and 5a are weakly active on bacteria but inhibited the germination of the water cress Lepidium sativum. A fourth metabolite, the norsesquiterpene tsugicoline I 7, was also isolated from the same fungus.

Eleganthol, a sesquiterpene from Clitocybe elegans

Abstract The structure and relative configuration of eleganthol, a new amorphane sesquiterpene, have been elucidated on the basis of single crystal X-ray analysis and NMR data.

Phanerosporic acid, a β-resorcylate obtained from Phanerochaete chrysosporium☆

Abstract The structure of phanerosporic acid, a β-resorcylate isolated from cultures of Phanerochaete chrysosporium , has been assigned on the basis of its 1 H and 13 C NMR data and chemical transformations. Its use as a synthon for macrolide synthesis is also described.