Abstract
Two pairs of geometrical isomers – cuevaenes A (1) and C (3) as well as cuevaenes D (4) and E (5) – and cuevaene B (2) were isolated from gdmAI-disrupted Streptomyces sp. LZ35. The constitution of cuevaene C (3) was found to be identical to cuevaene A (1) by means of NMR spectroscopy and high resolution mass spectrometry. However, the relative configurations of the triene side chain moieties were determined to be different. It was established on the basis of spectroscopic data that cuevaenes D (4) and E (5) are amides and geometrical isomers. Cuevaenes A–C (1–3) displayed moderate activity against Gram-positive bacteria (e.g., Bacillus subtilis strain ATCC 11060) and modest activity against fungi (e.g., Fusarium verticillioides strain S68 and Rhizoctonia solani strain GXE4). However, cuevaenes D (4) and E (5) showed no inhibitory activity against any of the tested microbes.
Highlights
Cuevaenes are polyketides containing 3-hydroxybenzoic acid (3-HBA)
Cuevaenes A and B were isolated from Streptomyces sp
All of these natural products have a tricyclic core and a polyene side chain with an enolmethyl ether inside. This type of triene structural moiety is rarely found in natural products
Summary
Cuevaenes are polyketides containing 3-hydroxybenzoic acid (3-HBA). Only 4 naturally occurring cuevaenes are described. Cuevaenes A and B were isolated from Streptomyces sp. We present the isolation and structural characterization of three new 3-HBA-containing polyketides, namely cuevaenes C–E (3–5), along with cuevaenes A and B (1 and 2) from the metabolites of the strain LZ35ΔgdmAI (Figure 1).
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