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. 2011 Apr 27;52(17):2206-2208.
doi: 10.1016/j.tetlet.2010.11.159.

New naphthoquinones and a new δ-lactone produced by endophytic fungi from Costa Rica

Shugeng Cao  1 , Jon Clardy
Affiliations

New naphthoquinones and a new δ-lactone produced by endophytic fungi from Costa Rica

Shugeng Cao et al. Tetrahedron Lett. .

Abstract

While searching for compounds with antimalarial activity, two new naphthoquinones, delitzchianones A (1) and B (2), were separated from Delitzchia winteri, an endophytic fungus from Costa Rica. The same search also led to a new 8-acetoxy pestalopyrone (3) and the known compound, pestalopyrone (4) from another Costa Rican endophytic fungus, Phomatospora bellaminuta. The structures of the three new compounds 1, 2 and 3 were established with extensive NMR and MS analyses. All four compounds were tested for activity in a growth / no growth Dd2 assay, but only compound 4 had measurable activity with an IC(50) value of 37 μM.

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Figures

Figure 1
Figure 1
HMBC Correlations of 1
Figure 2
Figure 2
Tautomerization of 2
See this image and copyright information in PMC

References

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    1. Sequencing and species identification. For identification by internal transcribed spacer (ITS) sequencing, CR237A and CR1092F were cultured in potato dextrose broth for 5 days. The mycelium was then retrieved by filtration and ground to a fine powder in liquid N2. Genomic DNA was extracted using the Wizard Genomic DNA Purification Kit (Promega), and large subunit rDNA was amplified by PCR using primers LR5 (5′-TCCTGAGGGAAACTTCG-3′) and LROR (5′-ACCCGCTGAACTTAAGC-3′). PCR products were transformed into E. coli TOP10 cells using a TOPO TA Cloning Kit (Invitrogen), according to manufacturer's protocols. Transformed plasmids were isolated and sequenced at Genewiz (http://www.genewiz.com/). The following consensus sequence were used in a BLAST search against deposited sequences: 237A:CCCCTATGCCCAAATTTGACGATCGATTTGCACGTCAGAACCGCTGCGAGCCTCCACCAGAGTTTCCTCTGGCTTCACCCTATTCAGGCATAGTTCACCATCTTTCGGGTCCCAACAGCTATGCTCTTACTCAAATCCATCCGAAGACATCAGGATCGGTCGATGGTGCGCCAGAGCTCGCGCCCTGGGTCCCACCTCCGTTCACTTTCATTCCGCGCCCGGGCTTGACACCCAAACACTCGCATAGATGTTAGACTCCTTGGTCCGTGTTTCAAGACGGGCCGCTTACGACCATTACGCCAGCATCCTAGCCGAAGCGCGGACCTCAGTCGGGGCTGGCTGCATGACGCCCTGGGCTATAACACTCCCCGAAGAGAGCTACATTCCCAAGGCCTTTCTCCAGCCGCCCCAACTGATGCTGGCCTGCCTGCCGCCGAGTGCACAGGGGACGGACCCCCGATGAACAGCGGCAGCCAAGTCTGGTTGCAAGCGCTTCCCTTTCAACAATTTCACGTGCTGTTTGACTCTCTTTCCAAAGTGCTTTTCATCTTTCGATCACTCTACTTGTGCGCTATCGGTCTCTGGCCAGTATTTAGCTTTAGAAGAAATATACCTCCCATTTAGAGCTGCATTCCCAAACAACTCGACTCGTCGAAGGGGGTTCACATGGCGCAGGCACCTGCCGCGTACGGGGTTCTCACCCTCTCTGACGTCCCGTTCCAAGGAACTTAGACAGGCGNCGTTGCCGAACCACCNTCTGCAAAGTACAACTCGGANCCCGCAAGGAGCCAGATTTCAAATTTGAGCTGTTGCCGCTTCACTCGCCGTTACTGAGGCAAT CR1092F:AGAGGTTGATAGTCTTTCGCCCCCATGCTCATGTTTGACGATCGATTTGCACGTCAGAACCGCTGCGAGCCTCCACCAGAGTTTCCTCTGGCTTCACCCTACACAAGCATAGTTCACCATCTTTCGGGTCCAAGCGGCAAGGCTCTTACTCAAATCCATCCGAAGACTTCAGGATCGGTCGATGGTGCGCCGAGGCTCCCACCTACGTTCACTTTCATTTCGCGTGCGGGTTTTACACCCAAACACTCGCCCTAATGCTTGACTCCTTGGTCCGTGTTTCAAGACGGGTCGCTGGTGACCATTACGCCAGCATCCTTGCAATGCGCGGTCCTCGGTCCCCGCGAGGGCATTGAGCAACGGGCTATAACACTCCCGGAGGAGCCACATTCCCGAGGCCTTTATCCCCCCGCGAGAACCGATGCTGGCCCGAGCCCGGCGGAGTGCACCGGCGAGAACGCCGGATGATCCGCCGGGCGCGAGTCTGGTCACAGGCGCTTCCCTTTCAACAATTTCACGTGCTTTTTAACTCTCTTTTCAAAGTGCTTTTCATCTTTCGATCACTCTACTTGTGCGCTATCGGTCTCTGGCCGGTATTTAGCTTTAGAAGAAATTTACCTCCCGCTTTGAGCAGCATTCCCAAACTACTCGACTCGTCGAAGGAGCTTTACAGAGGCTCGGCGTCCGCCTGTACGGGGCTCTCACCCTCTATGGCGTCCCGTTCCAGGGAACTCGGACGGCGCCTTGCCAAAAGCATCCTCTACAGATTACAACTCGGGCCCTGGGGACCAGATTTCAAATCTGAGCTGTTGCCGCTTCACTCGCCGTTACTGGGGCAATCCCTGTTGGTTTCTTTTCCTCCGCTTATTGATATGGTTAGTTTCAANCGGGGTAA

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    1. Culturing and extraction. Agar plugs of CR237A and CR1092F were initially grown at 25°C on yeast malt agar plates supplemented with 30 μg/ml streptomycin and 12 μg/ml chlortetracycline. After one week, agar plugs of this plate were placed in 150 ml of rich seed media in 1 L flasks. They were grown at 25 °C and 150 rpm for 7 days. 450 ml of 0.66% (w/v) malt extract and 10 g HP-20 resin were then added to each flask, and the fungi were cultured under the same conditions for 21 days. The fungal cultures were then held at 25 °C without shaking for 5 days. Extraction of the mycelium was accomplished by three rounds of sonication in ethanol. Rich seed media: 5 g peptone, 10 g dextrose, 3 g yeast extract, 10 g malt extract per 1 L water (pH 6.2). Separation. Extract CR237A was loaded on C-18 SPE and three fractions were collected. Compounds 1 (tR: 33.0 min, 1.5 mg) and 2 (tR: 28.5 min, 1.0 mg) were collected after a C-18 HPLC column (250 × 21.2 mm, 5 μ, 10 ml/min, 80% MeOH for 20 min then to 100% MeOH in 10 min) from fraction 3. Extract CR1092F was was suspended in aqueous MeOH (MeOH-H2O, 9:1, 100 mL) and extracted with hexanes (3 × 100 mL portions). The aqueous layer was then diluted to 70 % MeOH with H2O and extracted with CH2Cl2 (3 × 100 mL portions). After C-18 SPE, the hexanes extract was separated using HPLC to yield compound 3 (tR: 8 min, ~0.1 mg; C-18, Phemonenex, Luna, 250 × 10 mm, 5 μ, 4 ml/min, 45% MeOH) and compound 4 (tR: 9.5 min, 2.0 mg; C-18, Phemonenex, Luna, 250 × 10 mm, 5 μ, 2 ml/min, 60~100% MeOH in 20 min).