Configuration of kellerin and samarkandin

Perel'son, M. E.; Шейченко, В. И.; Sklyar, Yu. E.; Andrianova, V. B.

doi:10.1007/bf00778177

Cited by 4 publications

(7 citation statements)

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“…The structures of compounds 2 and 3 could be assigned to farnesiferols C and B, respectively, which are known as main constituents from F. assafetida . , The constitution of 4 was deduced from its 1D- and 2D-NMR spectra. 1 H NMR data of this compound (labeled as kellerin) have been published by Perel’son et al and are consistent with ours. Furthermore, the relative configuration could be proven by a series of 1D-NOESY experiments.…”

Section: Resultssupporting

confidence: 91%

“…mode: m/z 441.7 [M + H] + ) and extensive 1D-and 2D-NMR experiments (see Supporting Information) and assigned to kellerin by comparison with literature. 42 Compounds 1-4 showed HPLC and 1 H NMR purities of >95% with spectroscopic and spectrometric parameters (UV, MS, NMR) identical with the literature.…”

Section: Methodssupporting

confidence: 60%

“…40,41 The constitution of 4 was deduced from its 1D-and 2D-NMR spectra. 1 H NMR data of this compound (labeled as kellerin) have been published by Perel'son et al 42 and are consistent with ours. Furthermore, the relative configuration could be proven by a series of 1D-NOESY experiments.…”

Section: Resultsmentioning

confidence: 99%

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Structure-Based Virtual Screening for the Discovery of Natural Inhibitors for Human Rhinovirus Coat Protein

et al. 2008

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Inhibitors of the human rhinovirus (HRV) coat protein are promising candidates to treat and prevent a number of upper respiratory diseases. The aim of this study was to find antiviral compounds from nature, focusing on the HRV coat protein. Through computational structure-based screening of an in-house 3D database containing 9676 individual plant metabolites from ancient herbal medicines, combined with knowledge from traditional use, we selected sesquiterpene coumarins from the gum resin asafetida as promising natural products. Chromatographic separation steps resulted in the isolation of microlobidene (1), farnesiferol C (2), farnesiferol B (3), and kellerin (4). Determination of the inhibition of the HRV-induced cytopathic effect for serotypes 1A, 2, 14, and 16 revealed a dose-dependent and selective antirhinoviral activity against serotype 2 for asafetida (IC50 = 11.0 microg/mL) and its virtually predicted constituents 2 (IC50 = 2.5 microM) and 3 (IC50 = 2.6 microM). Modeling studies helped to rationalize the retrieved results.

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Section: Resultssupporting

confidence: 91%

Section: Methodssupporting

confidence: 60%

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Structure-Based Virtual Screening for the Discovery of Natural Inhibitors for Human Rhinovirus Coat Protein

et al. 2008

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“…We analyzed the stereochemistry by 2D NMR, ECD, and single-crystal X-ray analysis. The results established the absolute configurations of compounds 1-5 and 10, and for the first time clarified the absolute configurations of compounds 2, 4, and 5, which had been reported in the literature only with their relative configurations [22,23]. Moreover, a detailed analysis of the 2D-NMR spectra produced a systematic assignment of compounds 2-6 for the first time.…”

Section: Resultssupporting

confidence: 73%

Sesquiterpene Coumarins from Ferula sinkiangensis Act as Neuroinflammation Inhibitors

Xing

Zhou

et al. 2016

Planta Med

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Neuroinflammation mediated by microglia cells plays a critical role in the development of Alzheimer's disease. To identify novel natural neuroinflammation inhibitors, a bioactivity-guided phytochemical research was performed on the traditional Chinese medicine "Awei", that exhibited a significant inhibitory effect on nitric oxide production in over-activated microglia cells. The research identified sixteen bioactive sesquiterpene coumarins (two new and fourteen known ones) in the effective extract of . Further, the anti-neuroinflammatory activities in BV-2 microglial cells were evaluated by monitoring LPS-induced nitric oxide production. In conclusion, the major constituent, (3', 5', 8', 9', 10')-kellerin (1.5 %, w/w), should be responsible for the anti-neuroinflammatory effect exhibited by Awei. Furthermore, it might be a potential natural therapeutic agent for Alzheimer's disease. The research indicated moreover, that its primary mechanism is the inhibition of mRNA expression of the inflammatory cytokines nitric oxide, tumor necrosis factor-α, cyclooxygenase-2, interleukin-6 and interleukin-1.

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“…The relative configurations of compound 1 at the two adjacent carbons C-2 and C-1′ were assigned using selective gradient NO-ESY experiment and comparison of their NMR spectroscopic data with those found in literature. The H-2 proton was determined to be axially configured, as its double doublet multiplicity at δ H 4.69 dd (J = 9.2, 8.3 Hz) was typically resulting from vicinal interaction constants with nonequivalent H 2 -3 geminal protons to H-2 [21]. Selective gradient NOESY excitation of a proton resonance at δ Η 3.03 m, assigned as H-3a, showed enhanced signals on the axial H-2 (δ Η 4.69), which in turn showed an enhanced signal on the H 3 -8′ (δ Η 1.24).…”

mentioning

confidence: 99%

Antimicrobial Prenylated Acetophenones from Berries ofHarrisonia abyssinica

Mayaka

Langat

Omolo³

et al. 2012

Planta Med

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The ripe berries of Harrisonia abyssinica yielded two new prenylated acetophenones, namely 5-(ethan-1'''-one)-4,6-dihydroxy-7-(3'',3''-dimethylallyl)-2 S-(1' S-hydroxy-1',5'-dimethylhex-4'-enyl)-2,3-dihydrobenzofuran (1) and 5-(2'''-hydroxyethan-1'''-one)-4,6-dihydroxy-7-(3'',3''-dimethylallyl)-2 S-(1' S-hydroxy-1',5'-dimethylhex-4'-enyl)-2,3-dihydrobenzofuran (2), herein named harronin I and harronin II, respectively. The compounds were isolated following activity guided fractionation and the structures were determined using 1D, 2D NMR spectroscopic, CD and MS spectrometric techniques. The methanol-dichloromethane mixture (1 : 1 v/v) crude extract exhibited strong antimicrobial activity against Candida albicans, Bacillus cereus, Escherichia coli, Salmonella typhimurium, Staphylococcus aureus, and Lactobacillus casei. Harronin I (1) showed a MIC of 5 µg/mL against C. albicans, 6 µg/mL against B. cereus, and more than 20 µg/mL against other tested microorganisms. Harronin II (2) showed much weaker MIC values (> 100 µg/mL) against all the tested microorganisms.

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Configuration of kellerin and samarkandin

Cited by 4 publications

References 0 publications

Structure-Based Virtual Screening for the Discovery of Natural Inhibitors for Human Rhinovirus Coat Protein

Structure-Based Virtual Screening for the Discovery of Natural Inhibitors for Human Rhinovirus Coat Protein

Sesquiterpene Coumarins from Ferula sinkiangensis Act as Neuroinflammation Inhibitors

Antimicrobial Prenylated Acetophenones from Berries ofHarrisonia abyssinica

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