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Phytochemistry Letters
Elsevier B.V.
Phytochemistry Letters

Elsevier B.V.

1874-3900

Phytochemistry Letters/Journal Phytochemistry LettersSCIISTP
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    Three new compounds from Artemisia anomala and their antitumor activities

    Xia P.S.Li L.Y.Li Y.K.Chen F....
    7页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeThree new compounds were isolated from Artemisia anomala, and their structures were determined using HR-ESI-MS, IR, UV, and NMR. The antitumor activities of the three compounds were evaluated in the human lung cancer cell line A549 and the human colorectal cancer cell line HCT116. The results showed that compound 2 significantly inhibited cell viability and proliferation and promoted apoptosis of HCT116 and A549 cells, suggesting that compound 2 may be used for colon and lung cancer treatments in clinical practice.
      原文链接:
    • NSTL
    • Elsevier

    Amino ether analogues of 4,4′-dihydroxy-3-methoxy-6,7′-cyclolignan and their activity against drug-resistant bacteria

    Nunez-Mojica G.Hernandez-Carrillo M.L.Avalos-Alanis F.G.Camacho-Corona M.D.R....
    4页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeLarrea tridentata antibacterial lignan 4,4′-dihydroxy-3-methoxy-6,7′-cyclolignan (1) was derivatized to obtain eleven new amino ether derivatives (2 A-12 C). The structural elucidation of compounds was performed by analysis of 1D- and 2D NMR spectral data and HRESIMS. The antibacterial activity of compounds was determined against nine drug-resistant bacteria and two strains of Mycobacterium tuberculosis (sensitive ATCC 27294 H37Rv and drug-resistant G122). Results showed that all derivatives were devoid of activity towards six gram-negative clinical isolates assayed. However, seven derivatives displayed antibacterial activity against three gram-positive drug-resistant bacteria. Further, enhancement of antibacterial activity was only observed for the compounds 2 A and 10 C-12 C (MIC of 12.5 μg/mL) which were two-fold more active than the starting material 1 against vancomycin-resistant Enterococcus faecium. All derivatives, except compound 9 B, showed antitubercular activity against both M. tuberculosis strains. Interestingly, all the compounds, except for 2 A and 11 A, were more active than the starting material 1 (MIC of 50 μg/mL). Compound 4 C was the only compound as active as the positive control ethambutol against the drug-resistant strain M. tuberculosis G122 (MIC of 6.25 μg/mL). In addition, the derivative 7 C was the most active compound against the sensitive strain M. tuberculosis H37Rv (MIC of 6.25 μg/mL)
      原文链接:
    • NSTL
    • Elsevier

    Antioxidant activity-guided isolation of flavonoids from Silene gallica aerial parts

    Bechkri S.Khalfallah A.Kabouche A.Kabouche Z....
    6页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeA bio-guided fractionation of the 80% aqueous ethanolic extract of the aerial parts of Silene gallica L. (Caryophyllaceae), growing in North-Eastern Algeria, was performed to evaluate its antioxidant activity using DPPH, hydroxyl radical scavenging and CUPRAC assays. Successive chromatographic separations of the most antioxidant n-BuOH soluble fraction yielded four acylated flavone C-glycosides, vitexin 2''-O-β-D-(4''',6'''-di-acetyl)-glucopyranoside (1), orientin-2''-O-β-D-(4''',6'''-di-acetyl)-glucopyranoside (2), orientin-2''-O-β-D-(6'''-feruloyl)-glucopyranoside (3), and orientin-2''-O-β-D-(6'''-sinapoyl)-glucopyranoside (4), as well as six known compounds including four flavonoids (5-8), a phenylpropanoid glycerolglucoside (regaloside A) (9), and a phytoecdysteroide (20-hydroxyecdysone) (10). Their structures were established by UV, 1D, 2D NMR, and HR-ESI-MS spectral data, in addition to comparison with literature data. The antioxidant activity of the crude extracts, fractions and compounds 1-8 was evaluated. Two acylated orientin glycosides (3 and 4) displayed the strongest antioxidant activity.
      原文链接:
    • NSTL
    • Elsevier

    Predicting medicinal resources in Ranunculaceae family by a combined approach using DNA barcodes and chemical metabolites

    An Q.Chen J.Tan G.Ren Y....
    10页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropePlant taxonomy based on molecular phylogenetic study and/or chemosystematics study has become increasingly important in exploring and utilizing medicinal resources due to the advent of big data era. In this study, we proposed a classifying approach combining DNA and chemical metabolites for the prediction of new medicinal resources. Specifically, we obtained 104 ITS2 barcodes and 847 chemical metabolites from 104 species in Ranunculaceae. Then, phylogenetic tree based on the ITS2 barcode and clustering tree based on structural similarity of metabolites were separately constructed. In addition, we tested the classifying accuracy of the two methods by Baker‘s correlation coefficient and the result showed that phylogenetic tree based on the ITS2 barcode was more accurate, giving a higher score of 0.627, whereas clustering tree based on chemical metabolites obtained a lower score of 0.301. Therefore, the natural products of plants might be described using these clades found by ITS2-based methods, and thus new metabolites of plants might be predicted due to the close relationships in a given clade. Using this combined method, 53 plants with structurally similar metabolites were included in 9 plant groups and currently unknown species-metabolite relations were predicted. Finally, 26.92% species in Ranunculaceae were found to contain the predicted metabolites after verification using two alternative KNApSAcKCore and ChEBI databases. As a whole, the combined approach can successfully classify plants and predict specialized natural products based on plant taxa.
      原文链接:
    • NSTL
    • Elsevier

    Oleanane-type glycosides from Weigela x Styriaca and two cultivars of W. florida: “Minor black” and “Brigela”

    Hobloss S.Bruguiere A.Champy-Tixier A.-S.Dessertaine S....
    8页
    查看更多>>摘要：? 2022Sixteen oleanane-type glycosides were extracted from three Weigela hybrids and cultivars: W. x Styriaca, W. florida “Minor black” and W. florida “Brigela”, and four of them were previously undescribed ones: 3-O-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyloleanolic acid, 3-O-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyloleanolic acid, 3-O-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyloleanolic acid, and 3-O-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyloleanolic acid. Their full structural elucidation required extensive 1D and 2D NMR experiments, as well as mass spectrometry analysis. Six compounds among the known ones were in sufficient amount to be tested for their antifungal activity against Candida albicans, and their antibacterial activity against Staphylococcus aureus and Pseudomonas aeruginosa.
      原文链接:
    • NSTL
    • Elsevier

    Two new alliacane sesquiterpenes from the fruiting bodies of edible mushroom Gomphus purpuraceus

    He Y.Wan Y.Guo Z.Hu F....
    4页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeTwo new alliacane sesquiterpenes, named purpuracolide B (1) and purpuracolide C (2), have been isolated from the fruiting bodies of edible mushroom Gomphus purpuraceus. Their structures were elucidated based on spectroscopic studies including electronic circular dichroism calculation. Furthermore, their antiproliferative effects were evaluated in breast cancer cells MCF7, MDA-MB-231 and 4T1.
      原文链接:
    • NSTL
    • Elsevier

    Intracellular oxidation of methyl p-coumarate is involved in anti-melanogenic and cytotoxic activities against melanoma cells

    Satooka H.Nihei K.-I.Kubo I.
    6页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeTyrosinase-catalyzed L-tyrosine oxidation is a key step in melanogenesis, and intense melanin formation is often a problem in chemotherapies or food preservation. Methyl p-coumarate is isolated from fresh flower of medicinal plant, Trixis michuacana var longifolia (D. Dow) C., and it suppressed melanogenesis in cultured murine B16-F10 melanoma cells while p-coumaric acid did not show anti-melanogenic activity. Methyl p-coumarate exhibited cytotoxicity with an IC50 of 130 μM (23.2 μg/mL), and p-coumaric acid showed similar activity, but to a lesser extent, suggesting that the anti-melanogenic activity of methyl p-coumarate is at least due to the melanocytotoxicity. This cytotoxicity of methyl p-coumarate was reduced in a dose-dependent manner by ascorbic acid but not with butylated hydroxyanisole. Moreover, methyl 4-methoxycinnamate, which lacks the oxidizable phenolic hydroxyl group, still exhibited comparable cytotoxicity to methyl p-coumarate. In addition, anethole did not show noticeable cytotoxicity, indicating that the enone moiety is an essential element in eliciting melanocytotoxicity. Thus, the enone moiety in methyl p-coumarate is a biologically critical nucleophilic group as a Michael reaction acceptor contributing to the anti-melanogenic activity and cytotoxicity against melanoma cells.
      原文链接:
    • NSTL
    • Elsevier

    Two new lignans with their biological activities in Portulaca oleracea L.

    Wang C.Guo S.Tian J.Liu P....
    5页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeTwo new lignans, identified as 6,7-dihydroxy-4-(4′’-hydroxy-3′’-methoxyphenyl)-2-naphthoic acid, named Oleralignan C (1), and 4-(3,4-dihydroxyphenyl)-6-hydroxy-7-methoxy-2-naphthoic acid, named Oleralignan D (2), were obtained from Portulaca oleracea L. The structures were determined by spectroscopic methods, including UHPLC-ESI-QTOFMS, 1D and 2D NMR. Both Oleralignan C (1) and Oleralignan D (2) inhibited the inflammatory factors, IL-1β and TNF-α in RAW 264.7 cells induced by lipopolysaccharide (LPS). Both compounds also could clear 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radicals indicating their antioxidant potential.
      原文链接:
    • NSTL
    • Elsevier

    Constituents of Desmodium salicifolium (Poir.) DC (Fabaceae) with antifungal activity

    Donkia A.P.T.Tsafack B.T.Teponno R.B.Tapondjou L.A....
    6页
    查看更多>>摘要：? 2022Phytochemical investigation of the roots of Desmodium salicifolium led to the isolation of two new compounds (Desmoflavanone A: 5,2',4'-trihydroxy-4'',4''-dimethyl-2H-dihydropyranoisoflavanone (1) and desmodioside A: (22R)-3β,22,23-trihydroxyolean-12-en-3-O-α- L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranoside (2)) together with nine known secondary metabolites including kaikasaponin III (3), spinosin (4), isovitexin (5), β-sitosterol 3-O-β-D-glucopyranoside (6), neorautenol (7), kaempferol (8), oleanolic acid (9), betulinic acid (10), and lupeol (11). The structures of these compounds were elucidated mainly by extensive spectroscopic analysis, particularly 1D and 2D NMR spectroscopy, electrospray ionization-mass spectrometry and by comparison of their spectroscopic data with those of related compounds reported in the literature. The methanolic extract, EtOAc and n-BuOH fractions as well as some isolated compounds were assessed for their antifungal activities against two fungi using microdilution method. The methanolic extract displayed weak activity against Candida albicans (MIC = 512 μg/mL). The EtOAc fraction also exhibited weak inhibitory effect with MIC of 256 μg/mL against Candida albicans and Candida glabrata. Compound 3 showed moderate effect against Candida glabrata with MIC value of 16 μg/mL while 1 was inactive against both fungi.
      原文链接:
    • NSTL
    • Elsevier

    Tricyclic diterpenes from the resin of Daemonorops draco and their activities on oxidative stress-induced mesenchymal stromal cells

    Paudel S.B.Nguyen T.T.Kil Y.-S.Choi H....
    6页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeA bioassay-guided chemical investigation of the resin exudates from Daemonorops draco (dragon's blood, Palmaceae) has resulted in the isolation of two new trinorditerpenes, 7β-13-dihydroxypodocarpa-8,11,13-trien-15-oic acid (1) and 7α-13-dihydroxypodocarpa-8,11,13-trien-15-oic acid (2), along with ten previously described abietane diterpenes, 7β-15-dihydroxydehydroabietic acid (3), 7α-15-dihydroxydehydroabietic acid (4), 15-hydroxydehydroabietic acid (5), 7-oxodehydroabietic acid (6), dehydroabietic acid (7), 15-hydroxyabietic acid (8), 12α-hydroxyabietic acid (9), abietic acid (10), 7,13,15-abietatrien-18-oic acid (11), and cephasinene B (12). The structures of 1 and 2 were elucidated using spectroscopic techniques, including HR-ESIMS and 1D/2D NMR. The absolute configurations were determined by comparing the experimental electronic circular dichroism (ECD) spectra with the calculated ECD data based on time-dependent density functional theory. The bioactivity of the extracts, fractions, and isolated compounds was assessed in oxidative stress-induced mesenchymal stromal cells (MSCs). The crude extract and the hexanes, ethyl acetate, and aqueous fractions exhibited high potency against oxidative stress-induced apoptosis of MSCs. Among the isolated compounds, compounds 1 (3 μM) and 10 (100 μM) demonstrated good recovery of MSCs against oxidative stress.
      原文链接:
    • NSTL
    • Elsevier