2′-, 4′-, and 6′-O-substituted 1,5,9-epideoxyloganic acids from Nepeta grandiflora

Nagy, Tamás Milán; Kocsis, Ákos; Morvai, Miklós; Szabó, László; Podányi, Benjamin; Gergely, András; Jerkovich, Gyula

doi:10.1016/s0031-9422(98)80074-5

Cited by 12 publications

(10 citation statements)

References 5 publications

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“…The positive value of specific rotation of compound 1 was in agreement with a (1 S ,5 S ,9 R ) stereostructure. Analogously, the CD spectrum of 1 displayed a positive Cotton effect, as reported for iridoids from Nepeta [31]. Moreover, the enzymatic hydrolysis of 1 led to a C-1 epimeric mixture of aglycones, whose 1 H-NMR data were superimposable to those reported for the aglycone of penstemonoside [25].…”

Section: Resultsmentioning

confidence: 55%

Phytochemical and Biological Studies of Nepeta asterotricha Rech. f. (Lamiaceae): Isolation of Nepetamoside

et al. 2019

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The n-butanolic extract, from an Iranian specimen of Nepeta asterotricha Rech. f. (NABE), displayed anti-inflammatory effects on lipopolysaccharide (LPS)-stimulated J774A.1 macrophages, which reduced nitrites and cytokines production. Bioassay guided fractionation of the extract led to the isolation of four iridoid glycosides, including a new one known as nepetamoside (1), one hexenyl-diglycoside, and some polyphenol and flavonoid components. None of the isolated iridoid components displayed significant effects on nitrites formation in an in vitro LPS-induced model of inflammation, thus suggesting that the plant anti-inflammatory effect is probably due to a synergistic action among its constituents.

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Section: Resultsmentioning

confidence: 55%

Phytochemical and Biological Studies of Nepeta asterotricha Rech. f. (Lamiaceae): Isolation of Nepetamoside

et al. 2019

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“…The structure of the new isolated compound (C 41 H 74 O 5 ) was determined on the basis of proton and carbon (1D and 2D) magnetic experiments, LC‐MS/MS, IR, and UV spectra. The assignment of all signals of the 1 H and 13 C NMR spectra was based on 1 H and 13 C spectral information and comparison with data published for typical iridoid compounds (Nacy and others 1998; Muhammad and others 2001; Perez‐Bonilla and others 2006). The LC‐MS/MS spectrum showed a predominated [M‐H] − signal at m / z 645 and fragment ions at m / z (%) 580 (59), 544 (13), 419 (8), 335 (13), 297(17), 280(13), 253 (67), 227 (32) (Figure 4).…”

Section: Resultsmentioning

confidence: 99%

Phenolic Composition, Isolation, and Structure of a New Deoxyloganic Acid Derivative from Dhokar and Gemri‐Dhokar Olive Cultivars

Rigane¹,

Salem²,

Sayadi³

et al. 2011

Journal of Food Science

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Two rare olive cultivars, Dhokar and Gemri-Dhokar, growing in the south of Tunisia were investigated to identify their phenolic profile and evaluate their sugar content and antioxidant activity. The highest value of phenolic content was detected in Gemri-Dhokar cultivar extract (6.97 g gallic acid equivalents/kg of fresh olive). In addition, sugar content was quantified; glucose (45.17 g/kg of fresh olive) was the predominant sugar in Dhokar cultivar, followed by fructose (40.83 g/kg of fresh olive). The identification of phenolic compounds was based on separation by high-performance liquid chromatography equipped with a diode array detector followed by liquid chromatography-mass spectrometry analysis. In both cultivars, Oleuropein aglycon derivatives and elenolic acid were the main phenolic components. Oleuropeins were the major compounds quantified in the Gemri-Dhokar drupes olives (61.04 mg/100 g of fresh olive), while 0.25 mg/100 g were found in fresh Dhokar. A new iridoid compound, isolated as pure compound, was not previously reported in the literature. Its structure was established by spectroscopic analyses (NMR, UV, MS, and IR). DPPH, ABTS, and FRAP assays showed that the most important antioxidant capacity of olive extracts was found in with Gemri-Dhokar cultivar.

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“…Several iridoid glucosides (compounds 1-12, Scheme 1) have been isolated from Physostegia virginiana L. and their configurations have been determined. 5 Since proton-proton coupling constants and NOE interactions confirmed their dominant conformations, they are informative model compounds for examining the role of carbon-proton coupling constants in the structure elucidation of iridoids, where the basic question is the configuration of the chiral carbon atoms of the aglycone. They can also serve as model compounds to study the relationship between structural parameters and carbon-proton coupling constants.…”

Section: Introductionmentioning

confidence: 99%

Effect of oxygen substituents on two- and three-bond carbon-proton spin-spin coupling constants

et al. 2000

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2′-, 4′-, and 6′-O-substituted 1,5,9-epideoxyloganic acids from Nepeta grandiflora

Cited by 12 publications

References 5 publications

Phytochemical and Biological Studies of Nepeta asterotricha Rech. f. (Lamiaceae): Isolation of Nepetamoside

Phytochemical and Biological Studies of Nepeta asterotricha Rech. f. (Lamiaceae): Isolation of Nepetamoside

Phenolic Composition, Isolation, and Structure of a New Deoxyloganic Acid Derivative from Dhokar and Gemri‐Dhokar Olive Cultivars

Effect of oxygen substituents on two- and three-bond carbon-proton spin-spin coupling constants

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