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S19159, a modulator of neurite outgrowth produced by the ascomycete Preussia aemulans. II. Structure elucidation.

High resolution FAB-MS data indicated the molecular formula C30H44O5, which is consistent with the 13C NMR data. The 13C NMR spectrum exhibited thirty signals which were assigned as shown in Table 1 by analyses of DEPT and 2D PFG-HMQC2) and HMBC3) spectra. The 13C NMR spectrum indicated the presence of one ketone group (C-1, 211.63ppm), one carboxyl group (C-28, 181.15ppm), a tri-substituted double bond at C-7 (117.82 and 142.48ppm) and an exomethylene at C-24 (157.72 and 106.89ppm) and also included five methyls, eight methylenes, seven aliphatic methines (including two oxygenated methines) and four sp3 quaternary carbons. The molecular formula and hydrogen deficient index together with the 13C NMR data suggested that S19159 consists of a pentacyclic structure. The presence of the partial structures shown in Fig. 2 as bold lines was revealed by analyses of DQF-COSY and spin-decoupling experiments. Assignments of 1H NMR signals for the D ring and side chain portions, which were severely overlapped, were supported by 1D selective PFG-TOCSY4) experiments, using well separated signals of H-14 at 3.04ppm, Me-21 at 0.97ppm, H-23 at 2.14ppm and also H-7 at 5.24ppm which had long range coupling with the H-14 methine proton. One remaining isolated methylene group at 1.38 and 1.51ppm (Hs-19) had a small geminal coupling constant value of 4.2Hz, indicating the presence of