ABSTRACT
Four new lignans, strebluslignanol F (1), (7'R,8'S,7â³R,8â³S)-erythro-strebluslignanol G (2), isomagnaldehyde (3) and isostrebluslignanaldehyde (4), along with 12 known lignans (5-16) were isolated from the ethyl acetate-soluble part of MeOH extract of the root of Streblus asper. Their structures were elucidated through various spectroscopic methods, including 1D NMR ((1)H NMR, (13)C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centers was determined using CD spectra, as well as analyses of coupling constants and optical rotation data. The isolated lignans were evaluated for their anti-HBV activities in vitro using the HBV transfected HepG2.2.15 cell line. The most active lignans, (7'R,8'S,7â³R,8â³S)-erythro-strebluslignanol G, magnolol, isomagnolol and isolariciresinol, exhibited significant anti-HBV activities with IC50 values of 1.58, 2.03, 10.34 and 3.67 µM, respectively, for HBsAg with no cytotoxicity, and of 3.24, 3.76, 8.83 and 14.67 µM, respectively, for HBeAg with no cytotoxicity. (7'R,8'S,7â³R,8â³S)-erythro-Strebluslignanol G and magnolol showed significant anti-HBV activities to inhibit the replication of HBV DNA with the IC50 values of 9.02 and 8.67 µM, respectively.
Subject(s)
Antiviral Agents/pharmacology , Hepatitis B virus/drug effects , Lignans/pharmacology , Moraceae/chemistry , Plant Extracts/pharmacology , Plant Roots/chemistry , Antiviral Agents/chemistry , Antiviral Agents/isolation & purification , Dose-Response Relationship, Drug , Hep G2 Cells , Humans , Lignans/chemistry , Lignans/isolation & purification , Microbial Sensitivity Tests , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Structure-Activity RelationshipABSTRACT
Seven compounds, (7'S,8'S)-trans-streblusol A, (7'R,8'S)-erythro-streblusol B, (7'S,8'S)-threo-streblusol B, 8'R-streblusol C, streblusquinone, (8R,8'R)-streblusol D, and streblusol E, along with 15 known compounds (8-22) were isolated from the n-butanol-soluble part of the MeOH extract of stem bark of Streblus asper. Their structures were elucidated through application of extensive spectroscopic methods, including ESI-MS and 2D NMR spectroscopy (HMQC and HMBC). The stereochemistry at the chiral centers was determined using CD spectra, as well as analyses of coupling constants and optical rotation data. The isolated lignans and allylbenzene derivatives were evaluated for their anti-HBV activities in vitro using the HBV transfected Hep G2.2.15 cell line. The most active compounds, magnolol and 9-ß-xylopyranosyl-isolariciresinol, exhibited significant anti-HBV activities with IC(50) values of 2.03 and 6.58µM for secretion of HBsAg, with no cytotoxicity, and of 3.76 and 24.86µM for secretion of HBeAg, with no cytotoxicity.
Subject(s)
Antiviral Agents/isolation & purification , Antiviral Agents/pharmacology , Hepatitis B virus/drug effects , Moraceae/chemistry , Plant Bark/chemistry , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Hep G2 Cells , Hepatitis B Surface Antigens/metabolism , Hepatitis B e Antigens/metabolism , Humans , Inhibitory Concentration 50 , Methanol/chemistryABSTRACT
A new lignan, (7'R,8'R)-threo-strebluslignanol-2-O-beta-D-glucopyranoside, along with 8 known compounds (2-9) were isolated from the water-soluble part of the MeOH extract of the heartwood of Streblus asper. Their structures were elucidated through various spectroscopic methods, including 1D NMR (1H NMR, 13C NMR), 2D NMR (HMQC, HMBC, and NOESY), and HRMS. The stereochemistry at the chiral centers was determined using the CD spectrum, as well as analyses of coupling constants and optical rotation data. In the preliminary bioassay, the isolated compounds did not show anti-HBV activities in vitro using the HBV transfected HepG2.2.15 cell line.
Subject(s)
Moraceae/chemistry , Plant Extracts/analysis , Hepatitis B virus/drug effects , Lignans/analysis , Lignans/chemistry , Lignans/pharmacology , Magnetic Resonance Spectroscopy , Solubility , Water/chemistryABSTRACT
The extracts from leaves, heartwood, barks and roots of the Streblus asper were investigated for anti-HBV activities, separately. The results suggested that the MeOH extracts of the heartwood, barks, and roots exhibited good anti-HBV activities. Further investigations displayed that ethyl acetate and n-butanol soluble parts of their MeOH extracts showed more significant anti-HBV activities. Moreover, a new lignan, together with 11 known compounds, was isolated from n-butanol-soluble part of MeOH extract of the roots of S. asper. The structures were elucidated by spectroscopic methods, including 1D NMR ((1)H NMR, (13)C NMR), 2D NMR (HMQC, HMBC) and HR-EI-MS experiments. Compounds 1-3 were evaluated for their anti-HBV activities. Honokiol showed significant anti-HBV activity with IC(50) values of 3.14µM and 4.74µM for HBsAg and HBeAg with no cytotoxicity respectively, while lamivudine (3TC, positive control) exhibited weak anti-HBV activity with IC(50) values of 11.81µM and 25.80µM for HBsAg and HBeAg respectively.
Subject(s)
Antiviral Agents/therapeutic use , Biphenyl Compounds/therapeutic use , Hepatitis B virus/drug effects , Hepatitis B/drug therapy , Lignans/therapeutic use , Moraceae/chemistry , Phytotherapy , Plant Extracts/therapeutic use , Antiviral Agents/isolation & purification , Antiviral Agents/pharmacology , Biphenyl Compounds/isolation & purification , Biphenyl Compounds/pharmacology , Hep G2 Cells , Hepatitis B/virology , Humans , Inhibitory Concentration 50 , Lamivudine/isolation & purification , Lamivudine/pharmacology , Lignans/isolation & purification , Lignans/pharmacology , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Roots/chemistry , Plant StructuresABSTRACT
Three new lignans, erythro-strebluslignanol (1), threo-7'-methoxyl strebluslignanol (2) and erythro-7'-methoxyl strebluslignanol (3), together with twelve known compounds were isolated from the n-butanol and chloroform fractions of the heartwood of Streblus asper. Their structures were elucidated through extensive spectroscopic methods, including MS and 2D NMR experiments (HMQC and HMBC). The stereochemistry at the chiral center was determined using CD spectra, as well as analysis of coupling constants and optical rotation data, respectively. Primary bioassays showed that 6-hydroxyl-7-methoxyl-coumarin (5) and ursolic acid (10) showed anti-HBV activities, with IC(50) values of 29.60 µM and 89.91 µM for HBsAg at no cytotoxicity, and IC(50) values of 46.41 µM and 97.61 µM for HBeAg at no cytotoxicity, respectively.
Subject(s)
Antiviral Agents/pharmacology , Hepatitis B virus/drug effects , Lignans/pharmacology , Moraceae/chemistry , Plant Extracts/pharmacology , Antiviral Agents/chemistry , Antiviral Agents/isolation & purification , Biological Assay , Biphenyl Compounds/chemistry , Biphenyl Compounds/isolation & purification , Biphenyl Compounds/pharmacology , Cell Line , Cell Survival , Coumarins/chemistry , Coumarins/isolation & purification , Coumarins/pharmacology , Hepatitis B Surface Antigens/drug effects , Hepatitis B e Antigens/drug effects , Humans , Inhibitory Concentration 50 , Lignans/chemistry , Lignans/isolation & purification , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Triterpenes/chemistry , Triterpenes/isolation & purification , Triterpenes/pharmacology , Wood/chemistry , Ursolic AcidABSTRACT
OBJECTIVE: To study the chemical constituents of Rubus parvifoliu. METHODS: The constituents were isolated by column chromatography and their structures were elucidated through spectroscopic analysis such as 1H-NMR, 13C-NMR, FT-IR, et al. RESULTS: Seven compounds were isolated from the roots of Rubus parvifolius L., they were identified as p-sitosterol (I), lauric acid (II), O-nitrophenol (III), beta-daucosterol (IV), euscaphic acid (V), camelliagenin A (VI) and(+) -catech in (VII). CONCLUSION: Compounds III and VII are isolated from the plant for the first time.
Subject(s)
Catechin/isolation & purification , Nitrophenols/isolation & purification , Organophosphorus Compounds/isolation & purification , Plants, Medicinal/chemistry , Rosaceae/chemistry , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Catechin/chemistry , Molecular Structure , Nitrophenols/chemistry , Organophosphorus Compounds/chemistry , Plant Roots/chemistry , Plant Stems/chemistry , Sitosterols/chemistry , Sitosterols/isolation & purification , Triterpenes/chemistry , Triterpenes/isolation & purificationABSTRACT
Gaultheriadiolide (1), a new compound, together with the known dauosterol (2), ginkgetin (3), myricetin (4), 6-ethyl-5-hydroxy-2,7-dimethoxy-1,4-naphthoquinone (5), ursolic acid (6), methyl salicylate 2-O-beta-D-xylosyl(1-->6)beta-D-glucopyranoside (7), and methyl salicylate 2-O-beta-D-glucopyranoside (8) were isolated from Gaultheria yunnanensis. The structure was elucidated on the basic of spectral analysis, especially 1D and 2D NMR. Primary bioassays showed that compound 1 had medium cytotoxic activity against HEp-2 and HepG2 Cells, with IC(50) of 23.337 microM and 29.4497 microM, respectively.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Gaultheria/chemistry , Heterocyclic Compounds, 4 or More Rings/isolation & purification , Lactones/isolation & purification , Cell Line, Tumor , Drug Evaluation, Preclinical , Drugs, Chinese Herbal/chemistry , Heterocyclic Compounds, 4 or More Rings/chemistry , Humans , Lactones/chemistry , Molecular Structure , Seeds/chemistryABSTRACT
OBJECTIVE: To study the chemical constituents from the petroleum ether fraction of Buxus microphylla. METHODS: The petroleum ether fraction of Buxus microphylla was isolated and identified by silica gel column chromatography. And the anticancer activity of different chemical constituents was measured by MTT reduction test. RESULTS: Eight compounds were isolated and identified as lupeol (1), butulin (3), beta-sitosterol (4), stigmasterol (5), dibutyl phthalate (6), 3beta, 30-dihydroxy-lup-20 (29) ene (7), daucosterol (8). Compound 7 inhibited KB cells' proliferation in a dose-dependent manner. CONCLUSION: Compounds 2 - 5, 7, 8 are isolated from this genus for the first time. Compound 7 has certainly anticancer effects.
Subject(s)
Buxus/chemistry , Pentacyclic Triterpenes/isolation & purification , Plants, Medicinal/chemistry , Sitosterols/isolation & purification , Stigmasterol/isolation & purification , Chromatography, Thin Layer , Dibutyl Phthalate/chemistry , Dibutyl Phthalate/isolation & purification , Ethers , Magnetic Resonance Spectroscopy , Molecular Structure , Pentacyclic Triterpenes/chemistry , Sitosterols/chemistry , Stigmasterol/chemistryABSTRACT
In our ongoing investigation of the bioactive constituents from plants, two new lignans, magnolignan A-2-O-beta-D-glucopyranoside and strebluslignanol were isolated from heartwood of Streblus asper, along with three known lignans, magnolignan A, magnolol, and magnaldehyde D. 1D and 2D NMR experiments, including COSY, HMQC, and HMBC, and other spectroscopic methods, including UV, IR, and MS were used for the determination of the structures and NMR assignments. Primary bioassays showed that magnolignan A-2-O-beta-D-glucopyranoside and strebluslignanol have medium cytotoxic activity against HEp-2 and HepG2 cells, with IC(50) of 13.3 microM, 46.4 microM and 10.1 microM, 21.7 microM, respectively.
Subject(s)
Apoptosis/drug effects , Carcinoma, Hepatocellular/pathology , Lignans/administration & dosage , Lignans/chemistry , Magnetic Resonance Spectroscopy/methods , Moraceae/metabolism , Wood/chemistry , Cell Line, Tumor , Dose-Response Relationship, Drug , Humans , ProtonsABSTRACT
Phytochemical investigation of chemical constituents of the CHCl3 fraction of 75% alcohol extract from the leaves of Cyclocarya paliurus has resulted in the isolation of five compounds, alpha-boswellic (I), beta-boswellic (II), Oleanolic acid (III), 4-hydroxyl-3-methoxyl-benzoic acid (IV) and 3,6,3',5'-tetramenthox-5,7,4'-trihydroxy-flavonol (V). Their structures were elucidated on the basis of spectroscopic analyses, especially NMR. Compunds I, II, IV and V were obtained from this plant for the first time.