Further Meroterpenes Produced by Penicillium sp., an Endophyte Obtained from Melia azedarach

Abstract

From the methanolextract of Penicillium sp. cultivated on sterilized rice for three weeks we isolated three new meroterpenes preaustinoid A1, A2 and B1. The fungus was isolated from the root bark of Melia azedarach after surface sterilization. The structures of these compounds were identified by intensive spectroscopic studies.

3,5‐Dimethylorsellinic Acid Derived Meroterpenoids from Eupenicillium sp. 6A‐9, a Fungus Isolated from the Marine Sponge Plakortis simplex

“…[9] The 1 H and 13 C NMR spectra of 3 are almost identical to those of 7 (Table 1 and Figure S9 in the Supporting Information), with the exception of the appearance of the signals of the methoxy (δ C = 51.2 ppm, δ H = 3.55 ppm) and hydroxy group (δ H = 4.06 ppm). These data suggest that the B, C, and D rings are intact, including the C-20 methyl ester, which accounts for eight indices of unsaturation, the A ring lactone in 7 is hydrolyzed in 3, one of the three hydroxy groups is methylated, and this methylation site is pinpointed by the long-range HMBC correlation of the 1-OCH 3 protons to C-1 (δ C = 173.4 ppm).…”

“…By comparing the spectroscopic and specific rotation data with literature values, the remaining four known compounds were identified as preaustinoid A1 (7), [9] berkeleyone C (8), [10] berkeleyacetal A (9), [11] and preaustinoid A3 (10) [12] (see Tables S9 and S10 in the Supporting Information), among which only the absolute configuration of preaustinoid A1 (7) was reported previously as shown. [19] In this work, we also clarified the absolute configurations of compounds 8-10.…”

“…zsq2 (FJ545752), isolated from the marine sponge Plakortis simplex, aroused our interest as its EtOAc extract had numerous derivatives showing MS peaks at m/z = 400-500 in the medium polarity area and had a plethora of split 1 H NMR peaks in the aromatic region (see Figures S1 and S2 in the Supporting Information). Next, large-scale fermentation and separation by preparative medium-pressure liquid chromatography (MPLC) and HPLC led to the isolation of the previously reported 22-deoxyminiolutelide B (6), [8] preaustinoid A1 (7), [9] berkeleyone C (8), [10] berkeleyacetal A (9), [11] and preaustinoid A3 (10) [12] as well as five new meroterpenoids, eupeniacetal A (1), eupeniacetal B (2), 1-methoxy-hydropreaustinoid A1 (3), hydroberkeleyone B (4), and 22-deoxy-10-oxominiolutelide B (5; Figure 1). The structures and absolute configurations of these compounds were illuminated by virtue of detailed spectroscopic analysis, single-crystal X-ray diffraction, and TDDFT/ECD and [α] D calculations on solution conformers.…”

Penicillium species endophytic in coffee plants and ochratoxin A production

“…Both phenotypic and molecular identification methods found some of the same species living as endophytes. For example, dos Santos et al (2003) isolated seven Penicillium species (P. citrinum, P. herquei Bainier & Sartory, P. janthinellum, P. rubrum Stoll, P. rugulosum Thom, P. simplicissimum [Oudemans] Thom and P. implicatum Biorgue) from roots, stems, leaves and fruits of Melia azedarach L. while Yong et al (2003) reported P. citrinum as an endophyte in the bark of Taxus cuspidata and Singh et al (2003) reported P. chrysogenum Thom as an endophyte in the leaves of an unidentified plant in Peru. Evans et al (2003) isolated P. aculeatum Raper & Fennell, P. glabrum (Wehmer) Westling and P. sp.1 as endophytes in stems of the cacao relative Theobroma gileri in Ecuador.…”

Biologically active polyketides produced by Penicillium janthinellum isolated as an endophytic fungus from fruits of Melia azedarach

“…4 Species of Penicillium isolated from this host plant have shown the ability to produce chemically interesting and biologically active compounds. [5][6][7] Herein we report our chemical investigations of another Penicillium, identified as P. janthinellum, cultivated on sterilized white corn. This fungus produced polyketides, basically hydroxyanthraquinones, ergosterol and poliols.…”