Low-molecular-mass metabolites of fungi I. Stachybotrin fromStachybotrys alternans

Abstract

Stachybotrys alternaus produces a series of low-molecular-mass compounds. By their column chromatography we have isolated the nitrogen-containing compound stachybotrin. The structure of stachybotrin has been determined on the basis of chemical transformations together with the results of l H and 13C NMR spectroscopy, 2M NMR 1H-1H and ]H-lsc chemical shift correlation (COSY), correlation of long-range 1H-]sC interactions (HMBC), measurements of NOEs in a rotating coordinate system (ROESY), and IR and electronimpact mass spectra.Stachybotrys alternans damages cellulose-containing fodders, producing mycotoxins causing toxicoses in animals [1]. The chemical nature of these mycotoxius has not been elucidated. In view of this, we have studied the low-molecular-mass metabolites of Stachybotrys alternans. By column chromatography of the total products of the vital activity of the organism grown under laboratory conditions we isolated the quantitatively predominant component, which we have called stachybotrin (1, Scheme 1). In the present paper we report the establishment of the structure of this compound.

Fungal phthalimidines-chemodiversity, bioactivity and biosynthesis of a unique class of natural products

“…In 1997, Kamalov et al isolated a nitrogencontaining compound from cultures of S. chartarum, established the structure and named as stachybotrin (Kamalov et al 1997), which in fact was incorrectly assigned, however, a year later the structure was revised and confirmed by single X-ray crystallography, revealing it possessed the same structure and stereochemistry as compound 45 (Kamalov et al 1998). The same fungus also produces a methylated analogue of 45, which was coined stachybotrin A (49), not to be confused with the precedent stachybotrin A (32) (Kamalov et al 1999).…”

Low Molecular Metabolites of Fungi. 13, 3-Dimetoxystachibotrinis Stachybotrys Chartarum

“…2. The alicyclic part of the molecule consists of 15 carbon atoms and resembles the skeleton of the dryman sesquiterpenoid [14][15][16][17][18][19][20][21][22].…”

Natural sesquiterpenoids

“…39,40 The structure of stachybotrin has been determined as 32. This compound has been isolated from Stachybotrys alternans, 41 whilst kampanols A-C 33-35 are novel Ras farnesyl-protein transferase inhibitors, which have been isolated from Stachybotrys kampalensis. 42 Four new sesquiterpene nitrobenzoyl esters 36-39 with cytotoxic properties have been obtained from the fungus Aspergillus versicolor, which grows on the surface of the Caribbean green alga Penicillus capitatus.…”