Comments on ‘Piperidone derivative from <i>Dalbergia sympathetica</i>’

Winkler, Tammo

doi:10.1002/mrc.1783

Cited by 5 publications

(4 citation statements)

References 17 publications

(5 reference statements)

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“…HPLC-MS/MSn analysis of the extract in the positive ion mode allowed the identification of nitrogen-containing compounds. The occurrence of compound I was confirmed by the MS analysis, in full agreement with the literature [17,18,35]. The compound has been previously reported in Sideroxylon obtusifolium (Sapoteaceae), a medicinal species from Northeast Brazil with anti-inflammatory [36] and wound healing properties [37].…”

Section: Amino Acids and Derivativessupporting

confidence: 87%

“…The tandem mass spectrometry (MS 2 ) fragmentation showed the same pattern as theviridoside dihexoside or hexoside, suggesting derivatives of theviridoside. The [M − H] − ions of compounds 3, 4, 6, and 9 showed two peaks separated by two atomic mass units in a 3:1 ratio, in agreement with the isotopic peaks of 35 Cl (75.8%) and 37 Cl (24.2%), supporting the presence of a chlorine atom in the compounds.…”

Section: Iridoid Glycosidessupporting

confidence: 72%

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Iridoids and Amino Acid Derivatives from the Paraguayan Crude Drug Adenocalymma marginatum (ysypó hû)

et al. 2020

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The crude drug ysypó hû (Adenocalymma marginatum DC., Bignoniaceae) is used traditionally by the Guarani of Eastern Paraguayan as a male sexual enhancer. The aim of the present study was to identify the main constituents of the crude drug and to evaluate the in vitro inhibitory activity towards the enzyme phosphodiesterase-5 (PDE-5). The main compounds were isolated by counter-current chromatography (CCC). The metabolites were identified by spectroscopic and spectrometric means. The chemical profiling of the extracts was assessed by high-performance liquid chromatography coupled to mass spectrometry (HPLC-MS/MS). The crude extract and main isolated compounds were tested for their PDE-5 inhibitory activity using commercial kits. The iridoid theviridoside and 4-hydroxy-1-methylproline were isolated as the main constituent of the crude drug. Four chlortheviridoside hexoside derivatives were detected for the first time as natural products. Chemical profiling by HPLC-MS/MS led to the tentative identification of nine iridoids, six phenolics, and five amino acids. The crude extracts and main compounds were inactive towards PDE-5 at concentrations up to 500 µg/mL. Iridoids and amino acid derivatives were the main compounds occurring in the Paraguayan crude drug. The potential of ysypó hû as a male sexual enhancer cannot be discarded, since other mechanisms may be involved.

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Section: Amino Acids and Derivativessupporting

confidence: 87%

Section: Iridoid Glycosidessupporting

confidence: 72%

Iridoids and Amino Acid Derivatives from the Paraguayan Crude Drug Adenocalymma marginatum (ysypó hû)

et al. 2020

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“…Fraction F 7 (70 g) was further subjected to column chromatography over silica gel and eluting with n-hexane/EtOAc mixture in increasing polarity to yield 28,29-dinorcycloart-24-ene-3β,4α,6α-triol (4) (Brader et al, 1998) (60 mg). Fraction F 8 (85 g) was also separated in a similar manner to give sitosterol-3β-O-glucopyranoside (100 mg) while fraction F 9 (30 g) afforded 4-hydroxy-N-methyl-L-proline (Winkler, 2006) (50 mg) unusually isolated from a member of the Meliaceae family. The structures of the isolated compounds were established by analysis of their spectroscopic and spectrometric data and comparison with values reported in the literature as referenced.…”

Section: Present Studymentioning

confidence: 99%

Limonoids from the West African Trichilia welwitschii (Meliaceae)

Tsamo

Langat

Nkounga

et al. 2013

Biochemical Systematics and Ecology

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“…The spectral data for the synthetic product are practically identical to those of compound 1 (Table ). The NMR chemical shift data for the C-5 and C-7 positions differ slightly from each other due to the strong pH dependence of the chemical shifts of amino acids in D 2 O solution …”

mentioning

confidence: 94%

Isolation and Synthesis of (−)-(5S)-2-Imino-1-methylpyrrolidine-5- carboxylic Acid from Cliona tenuis: Structure Revision of Pyrostatins

et al. 2006

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[reaction: see text] (-)-(5S)-2-Imino-1-methylpyrrolidine-5-carboxylic acid (1), previously reported as the N-acetyl-beta-d-glucosaminidase inhibitor pyrostatin B, has been isolated from the organic extracts of the burrowing sponge Cliona tenuis. The structure of 1, including its absolute stereochemistry, was characterized from its spectral data and chemical transformations and confirmed by total synthesis. The synthesis of 1 reveals that the structure of pyrostatin B has been incorrectly assigned. Comparison of NMR spectral data strongly suggests that pyrostatins A and B are identical to 5-hydroxyectoine and ectoine, respectively.

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Comments on ‘Piperidone derivative from Dalbergia sympathetica’

Cited by 5 publications

References 17 publications

Iridoids and Amino Acid Derivatives from the Paraguayan Crude Drug Adenocalymma marginatum (ysypó hû)

Iridoids and Amino Acid Derivatives from the Paraguayan Crude Drug Adenocalymma marginatum (ysypó hû)

Limonoids from the West African Trichilia welwitschii (Meliaceae)

Isolation and Synthesis of (−)-(5S)-2-Imino-1-methylpyrrolidine-5- carboxylic Acid from Cliona tenuis: Structure Revision of Pyrostatins

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