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Article in Chinese | WPRIM | ID: wpr-879092


Chemical constituents were isolated and purified from fruiting bodies of Ganoderma calidophilum by various column chromatographic techniques, and their chemical structures were identified through combined analysis of physicochemical properties and spectral data. As a result, 11 compounds were isolated and identified as(24E)-lanosta-8,24-dien-3,11-dione-26-al(1), ganoderone A(2), 3-oxo-15α-acetoxy-lanosta-7,9(11), 24-trien-26-oleic acid(3),(23E)-27-nor-lanosta-8,23-diene-3,7,25-trione(4), ganodecanone B(5), ganoderic aldehyde A(6), 11β-hydroxy-lucidadiol(7), 3,4-dihydroxyacetophenone(8), methyl gentiate(9), ganoleucin C(10), ganotheaecolumol H(11). Among them, compound 1 is a new triterpenoid. The cytotoxic activities of all of the compounds against tumor cell lines were evaluated. The results showed that compounds 1, 3, 4 and 6 showed cytotoxic activity against BEL-7402, with IC_(50) values of 26.55, 11.35, 23.23, 18.66 μmol·L~(-1); compounds 1 and 3-6 showed cytotoxic activity against K562, with IC_(50) values of 5.79, 22.16, 12.16, 35.32, and 5.59 μmol·L~(-1), and compound 4 showed cytotoxic activity against A549, with IC_(50) value of 42.50 μmol·L~(-1).

Cell Line, Tumor , Fruiting Bodies, Fungal , Ganoderma , Molecular Structure , Triterpenes/pharmacology
Article in Chinese | WPRIM | ID: wpr-777474


Chemical constituents were isolated from the fruiting bodies of Ganoderma australe by various column chromatographic techniques and HPLC method, and their chemical structures were identified through the combined analysis of physicochemical properties and spectral data. Meanwhile, their α-glucosidase inhibitory activity and anti-oxidative ability were evaluated. Seven compounds were isolated from G. australe and were identified as 6-methoxyl-cyclo-(Phe-Ile)(1), applanoxidic acid A methyl ester(2), ergosta-7,22 E-dien-3β-ol(3), cinnamic acid(4), 5α,8α-epidioxy-(20S,22E,24R)-ergosta-6,22-diene-3β-ol(5), 1-(3, 4-dihydroxyphenyl) ethanone(6), salicylic acid(7) and benzoic acid(8). Among the compounds, compound 1 was a new cyclic dipeptide. Compound 2 was a new lanosta natural product, and compounds 4, 6, 7 and 8 were obtained from G. australe for the first time. Moreover, compounds 4 and 8 exhibited α-glucosidase inhibitory activity with inhibition rates of 36.8% and 34.7%, and compounds 4, 7 and 8 had a certain activity in DPPH free radical scavenging activity with IC_(50) values of 0.168, 0.458 and 0.170 g·L~(-1), respectively. The DPPH radical scavenging rate of compound 1 was 41.1%.

Free Radical Scavengers , Fruiting Bodies, Fungal , Chemistry , Ganoderma , Chemistry , Glycoside Hydrolase Inhibitors , Molecular Structure
Article in Chinese | WPRIM | ID: wpr-321371


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.

Ganoderma , Chemistry , Medicine, Chinese Traditional , Organic Chemicals
Article in English | WPRIM | ID: wpr-812288


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.

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 , Humans , Intercellular Signaling Peptides and Proteins , Metabolism , Phytotherapy , Plant Extracts , Pharmacology , Therapeutic Uses , Virus Integration , Virus Replication
Article in Chinese | WPRIM | ID: wpr-346870


<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>

Coumarins , Chemistry , Daphne , Chemistry , Drugs, Chinese Herbal , Chemistry , Furans , Chemistry , Lignans , Chemistry , Mass Spectrometry
Article in Chinese | WPRIM | ID: wpr-855573


Objective: To investigate the chemical constituents from Osbeckia chinensis. Methods: The constituents were separated by column chromatography and their structures were elucidated by spectral data analyses. Results Sixteen compounds were isolated from O. chinensis and identified as 4-0-β-D- glucopyranosyl-3-O-methylellagic acid (1), 4-O-β-D-glucopyranosyl-3, 3′-di-O-methylellagic acid (2), 4-O-β-D-glucopyranosyl-3,3′, 4′-tri-O-methylellagic acid (3), kaempferol-3-O-β-L-ramnopyranoside (4), quercetin-3-O-β-D-galactopyranoside (5), quercetin-3-O-β-D- rhamnopyranoside (6), kaempferol-6-C-β-D-glucopyranoside (7), quercetin-3-O-β-D-rhamnopyranosyl-2″-acetyl (8), kaempferol-3-O- β-D-glucopyranosyl-2″,6″-bis-O-E-(4-hydroxy)-cinnamoyl (9) 4′-hydroxyflavone-3-O-(6-O-trans-p-coumaroyl)-β-D-glucopyranoside (10), kaempferol-3-O-β-D-glucopyranosyl-6‴-O-E-(4-hydroxy)-cinnamoyl (11), 3β-hydroxy-9(11)-fernen-23-oic acid (12), 1,2-dihydroxy-9(11)- arborinen-3-one (13), cholest-5-ene-2,3,21-triol (14), β-sitosterol (15), and daucosterol (16). Conclusion: Except for compounds 5 and 16, all compounds are obtained from O. chinensis for the first time.