Fungal metabolites. Part 5. Uvidins, new drimane sesquiterpenes from Lactarius uvidus Fries

Bioaktywne związki grzybów z rodzaju Lactarius

“…Związki o szkielecie kariofylenu wyizolowano z grzybów Lactarius camphoratus [15]. Szkielet guajanu jest specyficzny dla seskwiterpenów pochodzących z Lactarius sanguiflus [16], Lactarius deterrimus [17], Lactarius indigo [18], Lactarius deliciosus [19, 20, ], zaś szkielet drimanu dla związków wydzielonych z Lactarius uvidus [21,22]. Seskwiterpeny o szkielecie guajanu izolowano głównie z gatunków o intensywnym zabarwieniu mleczka, np.…”

Fungal metabolites. Part 15. Structure and chemical correlations of uvidin C, D, and E, new drimane sesquiterpenes from Lactarius uvidus Fries

“…analysis of an acetone extract indicated, in addition to (1) and (2), some minor sesquiterpenes of L. uuidus with intermediate polarity. 6 Thus, from the column chromatography fractions between those of (I) and (2) we could isolate three new sesquiterpenes in very small amounts.…”

“…In this paper. we describe the isolation and structure elucidation of these new metabolites, namely uvidin C (3), uvidin D (6), and uvidin E (10). A few more related sesquiterpenes were also partially purified, but their structures could not be established because of the poor amounts available.…”

“…In the 'H n.m.r. spectrum of (6), in fact, the signal for 8-CH3 appeared as a doublet (J 7.2 Hz) at 6 0.81, and that of 7-H again as a doublet (J 7.5 Hz) at 6 4.31, being geminal to a secondary OH group and coupled to 8-H.t From these data the structure of 7-hydroxy-6-oxodrimanol was assigned to compound (6). Moreover the magnitude of coupling constants observed (J 4-7.5 Hz) for the hydrogens at C-7, C-8, and C-9 indicated that these protons are all involved in axial-equatorial interactions, in agreement with the stereochemistry shown in structure (6).…”

Total Synthesis of 3‐Hydroxydrimanes Mediated by Titanocene(III) – Evaluation of Their Antifeedant Activity

“…Among natural sesquiterpenoids, [1] 3-hydroxydrimanes are intriguing metabolites that occur in organisms such as plants, fungi, and nudibranchs, [2][3][4][5][6][7][8][9][10][11][12] which are philogenetically very distant but share the common feature of having an appetizing and apparently vulnerable appearance for predators. We therefore speculated that, as occurs with other closely related sesquiterpenoids, [13,14] these metabolites might act as chemical deterrents against insects and other parasites.…”