Chrysospermins, New Peptaibol Antibiotics from Apiocrea chrysosperma Ap101.

Abstract

Four new membersofpeptaibol antibiotics, designated as chrysospermins A, B, C, and D, were isolated from the mycelium of Apiocrea chrysosperma AplOl by solvent extraction, silica gel chromatographyand preparative recycling HPLC. Their structures as newnonadecapeptides were settled by detailed spectroscopic analysis and chemical degradation experiments. The chrysospermins display antibacterial and antifungal activity, and induce pigment formation by the fungus Phoma destructiva.

The occurrence of peptaibols and structurally related peptaibiotics in fungi and their mass spectrometric identification via diagnostic fragment ions

“…The authors making this claim pointed out the obvious structural homologies with the even coisolated chrysospermins A-D [32], but they did not mention whether the fresh (in the case of boletusin) or dried material (in the case of the tylopeptins), used for extraction, showed any sign of decay or infection by mycophilic fungi.…”

“…Examples are harzianin HC I, III, XI, XII, and XIII [72]; trichorzin PA II, IV, V, VI, VII, VII and XI; PA U 4 and PC U 4 [73,74]; trichokindins I-VII [75]; chrysospermins [32] and tylopeptins [30,31].…”

Isolation and sequence analysis of new peptaibol, boletusin, fromBoletus spp.

“…(Boletaceae), boletusin, which is composed of 19 residue amino acids, together with four known peptaibols. The four known peptaibols, compounds 2, 3, 4 and 5, are identical with chrysospermins previously reported from Apiocrea chrysosperma [6] and the new peptaibol, boletusin, is also structurally related to chrysospermins.…”

“…The residue eluted with 4:1 CHCl 3 /MeOH was purified by a semi-preparative HPLC [MAXSIL 5 m C 18 , Phenomenex, 10 ×250 ml, 80:20 MeOH/H 2 O] to yield compounds 1 (t R = 45 min, 4 mg), mixtures 2/3 (t R =23 min, 7 mg), and 4/5 (t R =30 min, 15 mg). The structural elucidation of peptaibols 2, 3, 4, and 5 was performed by using the FAB MS/MS technique and by direct comparison with previously published data [6].…”

Cephaibols, New Peptaibol Antibiotics with Anthelmintic Properties from Acremonium tubakii DSM 12774.

“…6.23 (6) 1.74 (2) 0.93 (1) 1.10 (1) 1.06 (1) 0.77 (1) 0.92 (1) 1.08 (1) 2.17 (2) 5.21 (5) 6.87 (7) 2.48 (3) 1.03 (1) 0.90 (1) 1.04 (1) 1.28 (1) 1.24 (1) 1.06 (1) 1.03 (1) 0.75 (1) 0.78 (1) 0.99 (1) 0.90 (1) 1. 16 (1) 1.…”