Metabolites of the higher fungi. Part 21. 3-Methyl-3,4-dihydroisocoumarins and related compounds from the ascomycete family xylariaceae

Anderson, John R.; Edwards, R. L.; Whalley, Anthony J. S.

doi:10.1039/p19830002185

Cited by 72 publications

(50 citation statements)

References 6 publications

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“…; [4] structures 10-13 were identified as 5-methylmellein, [5] 4-hydroxy-5-methylmellein, [6] 2-quinazolin-4(3H)-one, [7,8] and the mycotoxin alternariol, [9] by of the 13 C NMR spectroscopic data with those of compound 1, another biaryl ether isolated previously from a Phomopsis sp. by our group, [4] show the analogy of the chemical shifts, with the exception of that for C-2Јa.…”

Section: Resultsmentioning

confidence: 99%

Novel Highly Substituted Biraryl Ethers, Phomosines D–G, Isolated from the Endophytic Fungus Phomopsis sp. from Adenocarpus foliolosus

Dai¹,

Krohn²,

Flörke³

et al. 2005

Eur J Org Chem

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Six new metabolites, phomosines D–G (4–7), 6‐hydroxy‐6‐isopropylcyclohex‐1‐enecarboxylic acid (8) and(1aS,3R,4R,4aR,6S,7R,8aS)‐7‐chloro‐3,6‐dihydroxy‐3,4a,8,8‐tetramethyl‐octahydro‐1aH‐naphtho[1‐b]oxirene‐4‐carboxylic acid (9) were isolated together with seven known compounds (1–3, 10–13) from the endophytic fungus Phomopsis sp. The structures of 1–13 were determined by spectroscopic methods (mainly extensive 1D and 2D NMR experiments and by mass spectrometric measurements). The antibacterial, fungicidal, and herbicidal properties of the new compounds were evaluated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Resultsmentioning

confidence: 99%

Novel Highly Substituted Biraryl Ethers, Phomosines D–G, Isolated from the Endophytic Fungus Phomopsis sp. from Adenocarpus foliolosus

Dai¹,

Krohn²,

Flörke³

et al. 2005

Eur J Org Chem

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“…[18,19] (1S,2S,4S)-trihydroxy-p-menthane (8), [20] and 5-methylmellein (9) [21] by analysis of their NMR spectra and comparison with data reported in the literature.…”

Section: Resultsmentioning

confidence: 99%

Three New Antimicrobial Metabolites from the Endophytic Fungus Phomopsis sp.

et al. 2011

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Two new chromones, phomochromone A and B (1 and 2), and one new natural cyclopentenone derivative, phomotenone (3), together with six known compounds, phomosines A-D (4-7), (1S,2S,4S)-trihydroxy-p-menthane (8), and 5-methylmellein (9), have been isolated from the endophytic fungus Phomopsis sp. through a bioassay-guided procedure. The structures of the new compounds were assigned on the basis of the 1H and 13C NMR spectra, DEPT, and 2D COSY, HMQC, HMBC, and NOESY experiments, supported by molecular modelling. The absolute configurations of compounds 1-3 were assigned by TD-DFT CD calculations and, surprisingly, the two related phomochromones A and B have an opposite configuration at C-2. Compounds 1-3 show good antifungal (Microbotryum violaceum), antibacterial (Escherichia coli, Bacillus megaterium), and antialgal (Chlorella fusca) activities. Compound 8 shows good antialgal and antibacterial activity

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“…3) We describe herein the isolation and structural elucidation of one new methyl benzoate derivative (1), along with eleven known compounds, cytochalasin D (2), 4,5) desacetylcytochalasin D (3), 6) cytochalasin O (4), 5) (R)-(Ϫ)-mellein methyl ether (5), 7) 5-carboxymellein (6), 8,9) (R)-(Ϫ)-5-hydroxymellein (7), 10,11) 4-quinolinecarbonitrile (8), 12) 4-quinolinecarboxaldehyde oxime (9), 13) cyclo(L-Pro-L-Tyr) (10), 14,15) cerevisterol (11), 16) and uracil (12) (2) displayed higher toxicity than the standard drug, ellipticine. The remaining compounds were non-cytotoxic at the concentration of 50 mg/ml.…”

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confidence: 99%