3-Propyl-8-Hydroxy-6-Methoxyisocumarin aus<i>Solidago multiradiata</i>

Bohlmann, Ferdinand; Banerjee, S.; Jakupovic, J.

doi:10.1055/s-2007-969676

Cited by 5 publications

(3 citation statements)

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“…The 1 H NMR spectrum was in agreement with the published data for 3,4-dihydro-8-hydroxy-6-methoxy-(3R)-propylisocoumarin. 22,23 The chirality at the C-3 position was determined to be R ([R] D negative) by comparison to the published data for both the R and S synthetic compounds. 23 The 13 C NMR chemical shift assignments are reported for the first time (Table 2).…”

Section: Resultsmentioning

confidence: 99%

“…This evidence proves that treatment of the extract with diazomethane had no effect on the isolated compound 4, which is identical to the natural product produced by the endophyte. Compound 4 was previously isolated from the roots of Solidago multiradiata 22 with no reported configuration at C-3 and was later synthesized as both enantiomers. 23 It is reported here for the first time as a fungal metabolite and is of unknown toxicity.…”

Section: Resultsmentioning

confidence: 99%

“…Tyrosol. p-Hydroxyphenethyl alcohol (10): 1 H NMR (CDCl3, 400 MHz) δ 7.08 (d, J ) 8.4 Hz, 2H), 6.77 (d, J ) 8.8 Hz, 2H), 3.81 (t, J ) 6.4 Hz, 2H), 2.79 (t, J ) 6.6 Hz, 2H); EIMS m/z 138 [M] + (25), 124 (16), 107 (100), 91 (10), 77 (14), 69 (11), 55 (14), 43 (22), 41 (17); HRMS m/z 138.0681 (calcd for C 8H10O2, 138.0681).…”

Section: Methodsmentioning

confidence: 99%

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Characterization of Polyketide Metabolites from Foliar Endophytes of Picea glauca

et al. 2008

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A collection of 250 foliar endophytes of Picea glauca (white spruce) yielded several isolates that produced metabolites toxic to Choristoneura fumiferana (spruce budworm). Three of these strains were selected for further study based on their ability to be cultured and produce secondary metabolites under laboratory conditions. The culture filtrate of each was extracted and analyzed by LC-MS and LC-NMR, and the major metabolites were isolated and characterized. Structures were elucidated by spectroscopic analyses including 2D NMR and HRMS and by comparison to literature data. In some cases the extract was methylated in order to facilitate separation, but the original natural structure was determined by comparing the NMR data of the isolated methylated product with that of the stop-flow NMR of the underivatized extract (i.e., 2a, 2b, and 4). Two of these metabolites, 1 and 2a, are new structures, 3 and 4 are reported here for the first time as fungal metabolites, and 5- 10 as known fungal metabolites from other species. Tyrosol (10) was the only common metabolite found in all three extracts but did not account for the observed toxicity to C. fumiferana.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%