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Keywords = phenylhexanoid

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12 pages, 685 KiB  
Article
Seven New Phenylhexanoids with Antioxidant Activity from Saxifraga umbellulata var. pectinata
by Jiao Huang, Donglin Chen, Mengying Liu, Yarui Yu, Yi Zhang and Jing Huang
Molecules 2023, 28(9), 3928; https://doi.org/10.3390/molecules28093928 - 6 May 2023
Cited by 2 | Viewed by 1404
Abstract
Seven new phenylhexanoids, (S)-(+)-3,4-dihydroxy-11-methoxyphenylhex-9-one (1), (E) 3,4-dihydroxy-phenylhex-10-en-9-one (2), (E)-4-hydroxyphenylhex-10-en-9-one (3), (R)-(−)-3,4,11-trihydroxyphenylhex-9-one 11-O-β-d-glucopyranoside (4), (R)-(−)-4,11-dihydroxyphenylhex-9-one 11-O-β- [...] Read more.
Seven new phenylhexanoids, (S)-(+)-3,4-dihydroxy-11-methoxyphenylhex-9-one (1), (E) 3,4-dihydroxy-phenylhex-10-en-9-one (2), (E)-4-hydroxyphenylhex-10-en-9-one (3), (R)-(−)-3,4,11-trihydroxyphenylhex-9-one 11-O-β-d-glucopyranoside (4), (R)-(−)-4,11-dihydroxyphenylhex-9-one 11-O-β-d-glucopyranoside (5), phenylhex-4,9,11-triol 11-O-β-d-glucopyranoside (6), and 9-O-acetyl-phenylhex-4,9,11-triol 11-O-β-d-glucopyranoside (7), were isolated and identified from Tibetan medicine Saxifraga umbellulata var. pectinate. The antioxidant activities of these compounds were evaluated using the DPPH and ABTS radical scavenging experiments. In the ABTS experiment, compounds 1 (IC50 13.99 ± 2.53 μM) and 2 (IC50 13.11 ± 0.94 μM) exhibited significantly better antioxidant activity than L-ascorbic acid (IC50 23.51 ± 0.44 μM). Full article
(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)
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23 pages, 1799 KiB  
Article
Anthelmintic A-Type Procyanidins and Further Characterization of the Phenolic Composition of a Root Extract from Paullinia pinnata
by Verena Spiegler
Molecules 2020, 25(10), 2287; https://doi.org/10.3390/molecules25102287 - 13 May 2020
Cited by 8 | Viewed by 4061
Abstract
Extracts from the roots of Paullinia pinnata L. are used in West Africa as traditional remedies for a variety of diseases including infestations with soil-transmitted helminths. Based on the results of an ethnopharmacological survey in Ghana, an aqueous acetone (70%) extract was investigated [...] Read more.
Extracts from the roots of Paullinia pinnata L. are used in West Africa as traditional remedies for a variety of diseases including infestations with soil-transmitted helminths. Based on the results of an ethnopharmacological survey in Ghana, an aqueous acetone (70%) extract was investigated for its anthelmintic and phytochemical properties. Partitioning of the crude extract followed by several fractionation steps of the ethyl acetate phase using Sephadex® LH-20, fast centrifugal partition chromatography, RP-18-MPLC and HPLC led to isolation of six oligomeric A-type procyanidins (1 to 6). To determine the anthelmintic activity, the crude extract, fractions and isolated compounds were tested in vitro against the model organism Caenorhabditis elegans. A significantly better activity was observed for the trimeric A-type procyanidin (1) compared to a B-type trimer. However, this effect could not be generalized for the tetrameric procyanidins, for which the type of the interflavan-linkage (4→6 vs. 4→8) had the greatest impact on the bioactivity. Besides the procyanidins, three novel compounds, isofraxidin-7-O-α-l-rhamnopyranosyl-(1″→6′)-β-d-glucopyranoside (17), 4-methoxycatechol-2-O-(5′′-O-vanilloyl-β-apiofuranosyl)-(1′′→2′)-β-glucopyranoside (18) and a 6-(3-methoxy-4-hydroxyphenyl)-hexane-2,4-diol-2-O-hexoside (19) were isolated together with further ten known compounds (7 to 16), mainly coumarins and coumarinolignans. Except for 3-β-d-glucopyranosyloxy-4-methyl-2(5H)-furanone (15), none of the isolated compounds has previously been described for P. pinnata. The anthelmintic activity was attributed to the presence of procyanidins, but not to any of the other compound classes. In summary, the findings rationalize the traditional use of P. pinnata root extracts as anthelmintic remedies. Full article
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