Revised absolute configurations of natural khellactone esters

Lemmich, John; Pedersen, Peter Alsted; Nielsen, B.

doi:10.1016/s0040-4039(00)99764-8

Cited by 25 publications

(40 citation statements)

References 7 publications

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“…The identity of the purified coumarins, confirmed by HPLC-ESI-QTOF-MS/MS, 1D-and 2D-NMR, was established as follows: devenyol (1), cis-khellactone (2), d-laserpitin (3), isolaserpitin (4) and octanoyllomatin (5) (Figure 1). The spectroscopic data (Supplementary Materials-Part B) were in agreement with those available in spectral libraries and literature (14,19,20). Next, the yields of the isolated compounds obtained by liquid-liquid chromatography were compared with those obtained by conventional solid-liquid chromatography (open column chromatography and preparative HPLC) [14].…”

Section: Hexane/ethyl Acetate/methanol/watersupporting

confidence: 63%

“…The column preparation times (column filling, column equilibration, column cleaning) were not included in these calculations. * data for the solid-liquid chromatography separations were extracted from [14,19,20]; § the yields were calculated by dividing the mass of each individual coumarin obtained to the mass of sample (extract) processed; $ the total separation time was calculated by summing up the duration of the three liquid-liquid chromatography separations; # the total solvent consumption was calculated by multiplying the total separation time with the flow-rate; ns, not specified.…”

Section: Hexane/ethyl Acetate/methanol/watermentioning

confidence: 99%

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Coumarins from Seseli devenyense Simonk.: Isolation by Liquid–Liquid Chromatography and Potential Anxiolytic Activity Using an In Vivo Zebrafish Larvae Model

Widelski

Luca

Skiba

et al. 2021

IJMS

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Different types of anxiety disorders have become the number one mental health issue in developed countries. The search for new, safer and effective drug-like molecules among naturally derived substances faces two difficulties: an efficient method of isolation compounds with a high-purity and high-throughput animal model for activity assay. Thus, the aim of the present study was to isolate by liquid–liquid chromatography high-purity rare coumarins from the fruits of Seseli devenyense Simonk. and evaluate their anxiolytic effect (defined as reversed thimotaxis) using a 5-days post-fertilization (dpf) Danio rerio larvae model. Liquid–liquid chromatography enabled the isolation of one simple hydroxycoumarin (devenyol) and four pyranocoumarins (cis-khellactone, d-laserpitin, isolaserpitin and octanoyllomatin). The anxiolytic effect was defined as a decrease in the time spent in the boundaries of the living space (also described as reversed thigmotaxis). Our results show that all isolated courmarins exerted a significant influence on the anxiety behavior (anxiolytic activity) in the zebrafish larvae model. According to our knowledge, this is the first report of anxiolytic activity of pyranocoumarins and devenyol.

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Section: Hexane/ethyl Acetate/methanol/watersupporting

confidence: 63%

Section: Hexane/ethyl Acetate/methanol/watermentioning

confidence: 99%

Coumarins from Seseli devenyense Simonk.: Isolation by Liquid–Liquid Chromatography and Potential Anxiolytic Activity Using an In Vivo Zebrafish Larvae Model

Widelski

Luca

Skiba

et al. 2021

IJMS

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“…The compounds were identified by spectral analysis and optical activity as (þ )-cis-khellactone (7) and (2 )-trans-khellactone (8) as a minor artefact arising from epimerization at C-4 0 because of the benzyl effect and S N 2 reaction mechanism [4]. The absolute configurations of 7 and 8 were described previously as 3 0 R, 4 0 R and 3 0 R, 4 0 S by chemical methods and X-ray diffraction analysis [5,6] and, accordingly, the absolute configuration of 1 was established as 3 0 R, 4 0 R. The chemical structure of 1 was finally elucidated as 3 0 (R)-angeloyloxy-4 0 (R)-isovarloyloxy-3 0 ,4 0 -dihydroseselin. Its enantiomer, named Pd-III ([a ] D þ 25.9), was isolated from the root of same genus, Peucedanum praeruptorum [7].…”

Section: Resultsmentioning

confidence: 99%

Coumarins fromPeucedanum wulongense

Kong

Zhi²

2003

Journal of Asian Natural Products Research

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A new angular dihydropyrancoumarin named wulongensin A, along with five known coumarins, (-)-anomalin, umbelliferone, (-)-smyrinol, 3'(S),4'(S)-disenecioyloxy-3',4'-dihydroseselin, (+)-trans-khellactone, was isolated from the root of Peucedanum wulongense. The structure of wulongensin A was established as 3'(R)-angeloyloxy-4'(R)-isovaleryloxy-3',4'-dihydroseselin by spectroscopic methods and the absolute configurations were deduced by chemical correlations with known compounds.

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“…(-)-trans-Diacetylkhellactone (35) was found to undergo a partial deacetylation under hydrogenation conditions with perchloric acid as activator (Scheme 6). 42…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Chroman-2-ones by Reduction of Coumarins

Semeniuchenko¹,

Groth²,

Khilya³

2009

Synthesis

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C h r o m a n -2 -o n e s b y R e d u c t i o n o f C o u m a r i n sAbstract: The scientific literature detailing the synthesis of chroman-2-ones by hydrogenation/reduction of the corresponding coumarins is reviewed. The following methods are described: hydrogenation on palladium, platinum, nickel, catalytic transfer hydrogenation, homogeneous hydrogenation, reduction by complex hydrides, reduction by metals, and electrochemical reduction. For each appropriate reaction, the yield, duration and some additional information is given (if available). Moreover, many exceptions and interesting transformations are described.

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Revised absolute configurations of natural khellactone esters

Cited by 25 publications

References 7 publications

Coumarins from Seseli devenyense Simonk.: Isolation by Liquid–Liquid Chromatography and Potential Anxiolytic Activity Using an In Vivo Zebrafish Larvae Model

Coumarins from Seseli devenyense Simonk.: Isolation by Liquid–Liquid Chromatography and Potential Anxiolytic Activity Using an In Vivo Zebrafish Larvae Model

Coumarins fromPeucedanum wulongense

Synthesis of Chroman-2-ones by Reduction of Coumarins

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