ABSTRACT
Objective: To study the phenylpropanoids from Daphne aurantiaca. Methods: The constituents were separated by column chromatography, their structures were elucidated by spectral data analyses. Results: Thirteen phenylpropanoids were isolated from the EtOAc extract and were identified as caffeic acid tricosyl ester (1), caffeic acid eicosanyl ester (2), caffeic acid nonadecyl ester (3), caffeic acid octadecyl ester (4), caffeic acid heptadecyl ester (5), caffeic acid hexadecyl ester (6), caffeic acid tetradecyl ester (7), caffeic acid dodecyl ester (8), caffeic acid undecyl ester (9), caffeic acid isopentyl ester (10), ferulic acid (11), 3, 4-dimethoxy-cinnamaldehyde (12), and caffeic alcohol (13). Conclusion: The compounds are obtained from this plant for the first time.
ABSTRACT
AIM@#To evaluate the anti-HIV activity and mechanism of action of wikstroelide M, a daphnane diterpene from Daphne acutiloba Rehder (Thymelaeaceae).@*METHODS@#The anti-HIV activities of wikstroelide M against different HIV strains were evaluated by cytopathic effect assay and p24 quantification assay with ELISA. The inhibitory effect of wikstroelide M on HIV reverse transcription was analyzed by real-time PCR and ELISA. The effect of wikstroelide M on HIV-1 integrase nuclear translocation was observed with a cell-based imaging assay. The effect of wikstroelide M on LEDGF/p75-IN interaction was assayed by molecular docking.@*RESULTS@#Wikstroelide M potently inhibited different HIV-1 strains, including HIV-1IIIB, HIV-1A17, and HIV-19495, induced a cytopathic effect, with EC50 values ranging from 3.81 to 15.65 ng·mL⁻¹. Wikstroelide M also had high inhibitory activities against HIV-2ROD and HIV-2CBL-20-induced cytopathic effects with EC50 values of 18.88 and 31.90 ng·mL⁻¹. The inhibitory activities of wikstroelide M on the three HIV-1 strains were further confirmed by p24 quantification assay, with EC50 values ranging from 15.16 to 35.57 ng·mL⁻¹. Wikstroelide M also potently inhibited HIV-1IIIB induced cytolysis in MT-4 cells, with an EC50 value of 9.60 ng·mL⁻¹. The mechanistic assay showed that wikstroelide M targeted HIV-1 reverse transcriptase and nuclear translocation of integrase through disrupting the interaction between integrase and LEDGF/p75.@*CONCLUSION@#Wikstroelide M may be a potent HIV-1 and HIV-2 inhibitor, the mechanisms of action may include inhibition of reverse trascriptase activity and inhibition of integrase nuclear translocation through disrupting the interaction between integrase and LEDGF/p75.
Subject(s)
Humans , Anti-HIV Agents , Pharmacology , Therapeutic Uses , Cell Line , Daphne , Chemistry , Diterpenes , Pharmacology , HIV Infections , Drug Therapy , Virology , HIV Integrase , Metabolism , HIV Integrase Inhibitors , Pharmacology , Therapeutic Uses , HIV Reverse Transcriptase , HIV-1 , HIV-2 , Intercellular Signaling Peptides and Proteins , Metabolism , Phytotherapy , Plant Extracts , Pharmacology , Therapeutic Uses , Virus Integration , Virus ReplicationABSTRACT
The chemical investigation on Ganoderma philippii led to the isolation of sixteen compounds by silica gel and Sephadex LH-20 column chromatography. On the basis of spectroscopic data analyses, their structures were elucidated as 2, 5-dihydroxyacetophenone (1), methyl gentisate (2), (S) -dimethyl malate (3), muurola-4, 10 (14) -dien-11beta-ol (4), dihydroepicubenol (5), 5-hydroxymethylfuran carboxaldehyde (6), ergosta-7, 22E-dien-3beta-ol (7), ergosta-7, 22E-dien-3-one (8), ergosta-7, 22E-diene-2beta, 3alpha, 9alpha-triol (9), 6/beta-methoxyergo-sta-7, 22E-dien-3beta, 5alpha-diol (10), ergosta-4, 6, 8(14), 22E-tetraen-3-one (11), ergosta4, 6, 8-(14), 22E-etetraen-3beta-ol (12), 5alpha, 8alpha-epidioxy-ergosta-6, 22E-dien-3beta-ol (13), 7alpha-methoxy-5alpha, 6alpha-epoxyergosta-8-(14), 22E-dien-3beta-ol (14), ergosta-8, 22E-diene-3beta, 5alpha, 6beta, 7alpha-tetraol (15), and ergosta-5, 23-dien-3beta-ol, acetate (16). All the compounds were obtained from this fungus for the first time, and compounds 4 and 5 were isolated from the Ganoderma genus for the first time.
Subject(s)
Ganoderma , Chemistry , Medicine, Chinese Traditional , Organic ChemicalsABSTRACT
<p><b>OBJECTIVE</b>To study the chemical constituents from Daphne acutiloba.</p><p><b>METHOD</b>The constituents were separated by column chromatography, and their structures were elucidated by spectroscopic data analyses.</p><p><b>RESULT</b>Fifteen compounds were isolated from the EtOAc extract and identified as wikstroelide M (1), vesiculosin (2), prostratin (3), 7-hydroxy-coumarin (4), 7,8-di-hydroxy-coumarin (5), isodaphnoside (6), daphnorine (7), rutamontine (8), daphnolin (9), daphneticin (10), (+)-pinoresinol-beta-D-glucoside (11), oleodapnone (12), oleodaphnal (13), ergosterol peroxide (14) and cholest-5-en-3beta-ol (15).</p><p><b>CONCLUSION</b>All the compounds except for 4, 5 and 14 were obtained from the stems of this plant for the first time.</p>
Subject(s)
Coumarins , Chemistry , Daphne , Chemistry , Drugs, Chinese Herbal , Chemistry , Furans , Chemistry , Lignans , Chemistry , Mass SpectrometryABSTRACT
Objective: To study the chemical constituents from the stems of Daphne acutiloba. Methods: The constituents were separated by column chromatography and their structures were elucidated by spectral data analyses. Results: Fourteen biflavans or biflavons were isolated from the EtOAc fraction of 95% ethanol reflux extract in the stems of D. acutiloba and were identified as daphnodorin A (1), daphnodorin C (2), daphnodorin C' (3), daphnodorin F (4), daphnodorin E (5), wikstrol A (6), daphnodorin K (7), iso-chamaejasmin (8), (+)-chamaejasmin (9), daphnodorin D1 (10), daphnodorin H (11), 3-methoxyl daphnodorin H (12), daphnodorin K' (13), and daphnodorin B (14). Conclusion: All the compounds except 14 are obtained from the stems of this plant for the first time.