Metabolic Products of the Endophytic Fungus Microsphaeropsis sp. from Larix decidua

Abstract

Five new metabolites, palmarumycin M 1 (1a) and M 2 (3), papyracillic acid C (6) and the microsphaeropsins A (7) and B (8) were isolated from the fungus Microsphaeropsis sp. together with the known decaspirone (2) and the papyracillic acids A and B (4 and 5). Their structures were determined by means of spectroscopic data including HREIMS, 1 H NMR, 13 C NMR, 2D NMR (HMQC, HMBC, NOESY) and X-ray single crystal analysis. The absolute configuration of palmarumycin M 1 (1a) was determined by single-crystal X-ray

Relationships between the stereochemistry and biological activity of fungal phytotoxins

“…203 As expected, also the spectroscopic and physical properties 63 isolated from A. agropyrina var. nana were identical to those previously reported for papyracillic acid 202,204 as well as its AC determined in solid state CD spectra. 202 Papyracillic acid was also previously isolated from the ascomycete Lachum papyraceum.…”

“…nana were identical to those previously reported for papyracillic acid 202,204 as well as its AC determined in solid state CD spectra. 202 Papyracillic acid was also previously isolated from the ascomycete Lachum papyraceum. 204 Papyracillic acid is an analog of penicillic acid, a classical mycotoxin produced by various fungi including strains of the genera Penicillium and Aspergillus.…”

Flexible Route to Palmarumycin CP1 and CP2 and CJ‐12.371 Methyl Ether

“…The first representative, named bipendensin, was isolated from Afzelia bipendensis, an African plant. [1] However, it is most probable that the compound was produced by a fungus living in this plant, as later suggested by Prajoubklang et al [2] A few years later, a large number of these spiro compounds were isolated mostly from endophytic fungi, and they were named diepoxines, [3] "Sch-plus number", [4][5][6] "CJ-plus number", [7] cladosporins, [8][9][10] palmarumycins, [11][12][13][14][15] sphaerolones, [16] decaspirones, [17] and deoxypreussomerin (palmarumycin CP 1 ). [18] Almost 100 different compounds have been characterized in the meantime, and the "dimeric" 1,8-dihydroxynaphthalenes are amongst the polyketide natural products that show the greatest diversity (review: [19] ).…”

Bioactive Nitronaphthalenes from an Endophytic Fungus, Coniothyrium sp., and Their Chemical Synthesis

“…There are two major pathways for the biosynthesis of nitro compounds in nature: nitration, or oxygenation of amines. [1] During the past years, our research group has consistently isolated new biologically active secondary metabolites from diverse structural groups from endophytic fungi, [2][3][4][5] with 3-nitropropionic acid as the only nitro compound. [6] In connection with this work, we investigated the constituents of the endophytic fungus, Coniothyrium sp., internal strain number 7721, isolated from the shrub Sideritis chamaedryfolia, from an arid habitat near Alicante, Spain.…”