Confirmation of the stereochemistry of two naturally occurring epimeric phenylpropanoids via synthesis: Elucidation of hitherto unknown full stereostructures

Chakraborty, Ipsita; Chatterjee, Shankar; Manna, Avrajit; Bhaumik, Tanurima

doi:10.1016/j.tetlet.2019.05.022

Cited by 3 publications

(1 citation statement)

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“…Chakraborty et al recently stereoselectively synthesized the related compounds, threo - and erythro -1-(4-hydroxyphenyl)-1-methoxy-2,3-propanediol, and the coupling constants of H-1′ of threo - and erythro - forms were 7.0 and 6.4 Hz, respectively. According to this report, compound 5 showing the coupling constant of H-1′ ( J = 7.3 Hz) can be concluded as a threo isomer, 4-[ threo -2-hydroxy-1,3-dimethoxypropyl]phenol [ 39 ].…”

Section: Resultsmentioning

confidence: 99%

Six New Phenylpropanoid Derivatives from Chemically Converted Extract of Alpinia galanga (L.) and Their Antiparasitic Activities

et al. 2021

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Chemical conversion of the extract of natural resources is a very attractive way to expand the chemical space to discover bioactive compounds. In order to search for new medicines to treat parasitic diseases that cause high morbidity and mortality in affected countries in the world, the ethyl acetate extract from the rhizome of Alpinia galanga (L.) has been chemically converted by epoxidation using dioxirane generated in situ. The biological activity of chemically converted extract (CCE) of A. galanga (L.) significantly increased the activity against Leishmania major up to 82.6 ± 6.2 % at 25 μg/mL (whereas 2.7 ± 0.8% for the original extract). By bioassay-guided fractionation, new phenylpropanoids (1–6) and four known compounds, hydroquinone (7), 4-hydroxy(4-hydroxyphenyl)methoxy)benzaldehyde (8), isocoumarin cis 4-hydroxymelein (9), and (2S,3S,6R,7R,9S,10S)-humulene triepoxide (10) were isolated from CCE. The structures of isolated compounds were determined by spectroscopic analyses of 1D and 2D NMR, IR, and MS spectra. The most active compound was hydroquinone (7) with IC50 = 0.37 ± 1.37 μg/mL as a substantial active principle of CCE. In addition, the new phenylpropanoid 2 (IC50 = 27.8 ± 0.34 μg/mL) also showed significant activity against L. major compared to the positive control miltefosine (IC50 = 7.47 ± 0.3 μg/mL). The activities of the isolated compounds were also evaluated against Plasmodium falciparum, Trypanosoma brucei gambisense and Trypanosoma brucei rhodeisense. Interestingly, compound 2 was selectively active against trypanosomes with potent activity. To the best of our knowledge, this is the first report on the bioactive “unnatural” natural products from the crude extract of A. galanga (L.) by chemical conversion and on its activities against causal pathogens of leishmaniasis, trypanosomiasis, and malaria.

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Section: Resultsmentioning

confidence: 99%