ABSTRACT
This study investigates Symplocos cochinchinensis (Lour.) S. Moore leaves and stems, commonly known as Symplocos, a plant indigenous to Asia renowned for its traditional use in holistic medicine. A comprehensive phytochemical analysis of S. cochinchinensis led to the isolation of two new lignans, namely symplolignans A and B (1 and 2) along with eleven known lignan glucosides: nortrachelogenin 4-O-ß-D-glucopyranoside (3), nortracheloside (4), matairesinol 4-O-ß-D-glucopyranoside (5), lariciresinol 4'-O-ß-D-glucopyranoside (6), balanophonin 4-O-ß-D-glucopyranoside (7), dehydrodiconiferyl alcohol 4-O-ß-D-glucopyranoside (8), dehydrodiconiferyl alcohol γ'-O-ß-D-glucopyranoside (9), 3-(ß-D-glucopyranosyloxymethyl)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-(2R,3S)-dihydrobenzofura (10), and pinoresinol 4'-O-ß-D-glucopyranoside (11). Their chemical structures were elucidated using 1D- and 2D-NMR, mass spectrometry, and their spectroscopic data were compared with those reported in literatures. Furthermore, all compounds were evaluated for their hepatoprotective effects using the Resazurin reduction assay in HepG2 hepatocellular carcinoma cells. Compounds 1, 5, 7, and 8 exhibited notable hepatoprotective efficacy, with cell viability ranging from 105.0±2.6 to 109.2±3.3 at a concentration of 10â µM. This research highlights the therapeutic potential of these compounds and enhanced to the understanding of lignans and neolignans in liver cell proliferation.
ABSTRACT
Phytochemical studies on Aphanamixis plants have attracted considerable attention over the past few decades due to the structural diversities and significant biological activities of terpenoids produced by these plants. In the present study, five new acyclic diterpene lactone derivatives, aphanamixionolides A-E (1-5), and three known tirucallane-type triterpenes, namely, piscidinol A (6), hispidone (7), and bourjotinolone A (8), were isolated from the leaves of Aphanamixis polystachya. Their structures were elucidated by comprehensive analyses of HR-ESI-MS and NMR spectroscopic data and by comparison with those reported in the literature. Absolute configurations of the new compounds were determined by experimental and TD-DFT calculated ECD spectra. Compounds 1-8 inhibited NO production with IC50 values of 10.2-37.7 µM, which are comparable to positive control l-NMMA (IC50: 31.5 µM).
ABSTRACT
Four new acylated oleanane-type triterpene saponins, symplosaponins A-D (1-4) were successfully isolated from the leaves of Symplocos cochinchinensis (Lour.) S. Moore, alongside with five known compounds (5-9), 2-methoxy-4-prop-1-enylphenyl-1-O-ß-D-apiofuranosyl-(1 â 6)-ß-D-glucopyranoside (5), and 1-[O-ß-d-xylopyranosyl-(1 â 6)-O-ß-d-glucopyranosyl]-2,6-dimethoxy-4-propenyl-phenol (6), 6-O-p-coumaroylsucrose (7), arillatose B (8), and (-)-secoisolariciresinol-O-ß-D-glucopyranoside (9). The structures of these compounds were elucidated through spectroscopic methods, comparison with existing data, and chemical methods. Furthermore, all compounds were assessed for their impact on hepatocellular viability using the Resazurin reduction assay. These investigations aimed to explore the potential hepatoprotective properties of isolated compounds. As a result, 1-[O-ß-d-xylopyranosyl-(1 â 6)-O-ß-d-glucopyranosyl]-2,6-dimethoxy-4-propenyl-phenol (6) and (-)-secoisolariciresinol-O-ß-D-glucopyranoside (9) demonstrated statistically significant hepatoprotective activity in a concentration-dependent manner.
Subject(s)
Oleanolic Acid , Phytochemicals , Plant Leaves , Saponins , Saponins/pharmacology , Saponins/isolation & purification , Saponins/chemistry , Molecular Structure , Humans , Plant Leaves/chemistry , Oleanolic Acid/pharmacology , Oleanolic Acid/analogs & derivatives , Oleanolic Acid/isolation & purification , Oleanolic Acid/chemistry , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Animals , Hep G2 Cells , Rats , Protective Agents/pharmacology , Protective Agents/isolation & purification , Triterpenes/pharmacology , Triterpenes/isolation & purification , Triterpenes/chemistryABSTRACT
Four undescribed spirostan glycosides, (25S)-5α-spirostan- 12-one-2α,3ß-diol-3-O-ß-D-glucopyranosyl-(1â4)-ß-D-galactopyranoside (1), (25S)-5α-spirostan-12-one-2α,3ß-diol-3-O-ß-D-galatopyranosyl-(1â2)-ß-D-glucopyranosyl- (1â4)-ß-D-galactopyranoside (2), (25S)-5α-spirostan-12-one-2α,3ß-diol-3-O-ß-D-glucopyranosyl-(1â2)-[ß-D-glucopyranosyl-(1â3)]-ß-D-glucopyranosyl-(1â4)-ß-D-galactopyranoside (3), and hecogenin 3-O-ß-D-glucopyranosyl-(1â3)-[ß-D-xylopyranosyl-(1â2)]-ß-D-glucopyranosyl-(1â4)-[α-L-rhamnopyranosyl-(1â2)]-ß-D-galactopyranoside (4), together with eleven known compounds (5-15) were isolated from the branches and leaves of Tribulus terrestris. Their chemical structures were established through spectroscopic methods, including HR-ESI-MS, 1D-, and 2D-NMR spectra. Preliminary biological evaluation on NO production inhibitory activity in LPS activated RAW 264.7â cells showed that compoundsâ 1-3, 5, and 6 had significant inhibitory effects with IC50 values ranging from 2.4 to 18.3â µM, compared to that of the positive control compound, dexamethazone (IC50 13.6â µM).
ABSTRACT
Phytochemical study on the methanol extract of the stem barks of Aphanamixis polystachya led to the isolation of four previously undescribed (1-4) and ten known compounds (5-14). Their chemical structures were elucidated to be 11-methoxysawaranospiroride C (1), 6α,9S,10,13-tetrahydroxymegastigmane-3-one (2), 11-hydroxyaphanamixin B (3), (2Z,6E,13E)-2,6,13-triene-11,15-dihydroxyphytanic acid (4), cinnacasside D (5), cinnacasside E (6), vilsonol F (7), (3S,5R,6S,7E,9R)-3,5,6,9-tetrahydroxy-7-en-megastigmane (8), (3S,5R,6R,7E,9R)-3,6,9,10-tetrahydroxy-7-en-megastigmane (9), citroside A (10), threo-1-(3,4,5-trimethoxyphenyl)-1,2,3-propanetriol (11), 3,4,5-trimethoxyphenyl-1-O-ß-D-glucopyranoside (12), p-coumaric acid (13), ferulic acid (14) by HR-ESI-MS, ECD, 1D-, and 2D-NMR spectra. Compounds 1, 3, 4, and 9 showed NO production inhibitory activity in LPS activated RAW 264.7 cells with IC50 values of 42.0, 67.9, 20.5, and 78.6â µM, respectively, while the remaining compounds were inactive with IC50 values over 100â µM.
ABSTRACT
In this study, four undescribed bibenzyl derivatives (1-4), together with seven known compounds (5-11) were isolated from the aerial parts of Dendrobium officinale. Their chemical structures were determined to be (7'S,8'S) -9''-acetyldendrocandin U (1), (7'S,8'S) -4'-methoxydendrocandin T (2), (7'R,8'S) -dendrocandin B (3), (1S,2R) -5'''-methoxydendrofindlaphenol C (4) by analyzing of the spectroscopic data including HR-ESI-MS, 1D-, and 2D-NMR spectra. The absolute configurations of compounds 1-4 were determined by the electronic circular dichroism (ECD) spectra. Compounds 1-3, 5, 10 and 11 inhibited α-glucosidase with the IC50 values ranging from 56.3 to 165.3â µM, compounds 1-3, 5, 7-10 inhibited α-amylase with the IC50 values ranging from 65.2 to 177.6â µM.
Subject(s)
Dendrobium , Glycoside Hydrolase Inhibitors , Plant Components, Aerial , alpha-Amylases , alpha-Glucosidases , Dendrobium/chemistry , alpha-Amylases/antagonists & inhibitors , alpha-Amylases/metabolism , alpha-Glucosidases/metabolism , Glycoside Hydrolase Inhibitors/pharmacology , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/isolation & purification , Plant Components, Aerial/chemistry , Stilbenes/chemistry , Stilbenes/pharmacology , Stilbenes/isolation & purification , Structure-Activity Relationship , Molecular Structure , Molecular ConformationABSTRACT
In this study, nine triterpene glycosides including seven previously undescribed compounds (1-7), were isolated from leaves of Cryptolepis buchananii R.Br. ex Roem. and Schult. using various chromatographic methods. The chemical structures of the compounds were elucidated to be 3-O-ß-D-glucopyranosyl-(1 â 6)-ß-D-glucopyranosyluncargenin C 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (1), 3-O-ß-D-glucopyranosyl-(1 â 2)-ß-D-glucopyranosyluncargenin C 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (2), 3-O-ß-D-glucopyranosyl-(1 â 2)-ß-D-glucopyranosyluncargenin C 28-O-ß-D-glucopyranosyl-(1 â 4)-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (3), 3-O-ß-D-glucopyranosyl-(1 â 2)-ß-D-glucopyranosylhederagenin 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (4), 3-O-ß-D-glucopyranosylarjunolic acid 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (5), 3-O-ß-D-glucopyranosyl-(1 â 2)-ß- D-glucopyranosyl-6ß,23-dihydroxyursolic acid 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (6), 3-O-ß-D-glucopyranosyl-6ß,23-dihydroxyursolic acid 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (7), asiatic acid 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (8), and 3-O-ß-D-glucopyranosylasiatic acid 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (9), through infrared, high-resolution electrospray ionization mass spectrometry, one- and two-dimensional nuclear magnetic resonance spectral analyses. The isolates inhibited nitric oxide production in lipopolysaccharide-activated RAW 264.7 cells, with half-maximal inhibitory concentration (IC50) values of 18.8-58.5 µM, compared to the positive control compound, dexamethasone, which exhibited an IC50 of 14.1 µM.
Subject(s)
Glycosides , Nitric Oxide , Plant Leaves , Triterpenes , Triterpenes/chemistry , Triterpenes/pharmacology , Triterpenes/isolation & purification , Nitric Oxide/metabolism , Glycosides/chemistry , Glycosides/pharmacology , Glycosides/isolation & purification , Mice , Animals , Molecular Structure , Plant Leaves/chemistry , RAW 264.7 Cells , Plant Extracts/chemistry , Plant Extracts/pharmacologyABSTRACT
In this study, seven new pentacyclic triterpene glycosides, named dendrocinaosides A-G (1-7), and six known ones (8-13) were isolated from the whole plants of Dendrobium officinale. Their structures were determined by analyses of HR-ESI-MS, 1D and 2D NMR spectra. Compounds 1-4, 8, and 9 potentially inhibited α-glucosidase and α-amylase activities with the IC50 values ranging from 31.3 ± 2.2 to 42.4 ± 2.5 µM for anti α-glucosidase and from 36.5 ± 1.8 to 56.4 ± 2.0 µM for anti α-amylase activities, respectively, which were lower than that of the positive control, acarbose, showing IC50 values of 47.1 ± 1.4 µM for anti α-glucosidase and 145.7 ± 2.2 µM for anti α-amylase.
ABSTRACT
A phytochemical study of the aerial parts of Piper mutabile C. DC. revealed seven undescribed compounds [two (2-7')-neolignans and five polyoxygenated cyclohexene glycosides] and six known propenylcatechol derivatives. The chemical structures of the isolated compounds were elucidated by extensive HR-ESI-MS and NMR analyses, as well as comparison with the literature. The absolute configurations of the (2-7')-neolignans were confirmed by GIAO 13C NMR calculations with a sorted training set strategy and TD-DFT calculation ECD spectra. The (2-7')-neolignans and polyoxygenated cyclohexene glycosides are unusual in natural sources. Undescribed neolignans 1 and 2 inhibited NO production in RAW 264.7 cells, with respective IC50 values of 14.4 and 9.5 µM.
Subject(s)
Cyclohexenes , Glycosides , Lignans , Nitric Oxide , Phytochemicals , Piper , Plant Components, Aerial , Nitric Oxide/biosynthesis , Nitric Oxide/metabolism , Nitric Oxide/antagonists & inhibitors , RAW 264.7 Cells , Mice , Piper/chemistry , Molecular Structure , Plant Components, Aerial/chemistry , Animals , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Lignans/pharmacology , Lignans/isolation & purification , Lignans/chemistry , Glycosides/pharmacology , Glycosides/isolation & purification , Glycosides/chemistry , Cyclohexenes/pharmacology , Cyclohexenes/isolation & purification , ChinaABSTRACT
Chemical study on marine sponge-derivated fungus Aspergillus nidulans resulted in the isolation of seven depsidones (1-7) and two macrocyclic peptides (8 and 9). Their chemical structures were elucidated by extensive analyses of HRESIMS and NMR spectral data, as well as comparison with the literature. Compoundâ 1 was an undescribed depsidone. All compounds exhibited significant antimicrobial activity (MICs: 2-128â µg/mL) towards at least one of seven microbial strains, including Bacillus cereus, Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica, and Candida albicans. Of these, chlorinated depsidones (1-3, and 5) displayed potential antimicrobial activity. Nidulin (2) possessed good activity against tested strains except for S. enterica with MIC values in range of 2-16â µg/mL. Interestingly, undescribed depsidone 1 was selectively bioactive on the Gram-positive bacteria (MICs: 2-4â µg/mL) and yeast (MIC: 8â µg/mL) but inactivity on the Gram-negative bacteria (MICs: >256â µg/mL). Macrocyclic peptides, 8 and 9, displayed modest activity against E. faecalis strain with MIC values of 32 and 128â µg/mL, respectively.
Subject(s)
Anti-Infective Agents , Aspergillus nidulans , Porifera , Animals , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Infective Agents/chemistry , Microbial Sensitivity Tests , Peptides/pharmacologyABSTRACT
From the methanol extract of the Cryptolepis buchananii fruits, four undescribed pentacyclic triterpenene glycosides (1-4) and five known pentacyclic triterpenenes (5-9) were isolated. Their structures were determined to be uncargenin C 28-O-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranosyl ester (1), 3-O-ß-D-glucopyranosyluncargenin C 28-O-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranosyl ester (2), 3-O-ß-D-glucopyranosyl-(1â6)-ß-D-glucopyranosyl-6ß,23-dihydroxyursolic acid 28-O-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranosyl ester (3), 3-O-ß-D-glucopyranosyl-(1â2)-ß-D-glucopyranosylasiatic acid 28-O-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranosyl ester (4), asiatic acid (5), 2α,3ß,23-trihydroxyoleana-11,13(18)-dien-28-oic acid (6), arjunolic acid (7), 6ß-hydroxyarjunolic acid (8), and actinidic acid (9) based on analyses of their HR-ESI-MS, 1D and 2D NMR spectra. All the isolates showed significantly NO production inhibition in LPS-activated RAW264.7 cells with the IC50 values ranging from 18.79 to 37.57â µM, compared to that of the positive control compound, dexamethasone, which showed IC50 value of 14.05â µM.
Subject(s)
Saponins , Triterpenes , Cryptolepis , Esters , Fruit , Glycosides/pharmacology , Glycosides/chemistry , Lipopolysaccharides/pharmacology , Pentacyclic Triterpenes/pharmacology , Saponins/chemistry , Triterpenes/pharmacology , Triterpenes/chemistryABSTRACT
Four undescribed phenolic glycosides including three stilbene derivatives (1 and 3) and sodium salt of 3 (2), and a chalcone glycoside (4), together with thirteen known compounds (5-17) were isolated from the leaves of Syzygium attopeuense (Gagnep.) Merr. & L.M.Perry. Their chemical structures were elucidated to be (Z)-gaylussacin (1), 6''-O-galloylgaylussacin sodium salt (2), 6''-O-galloylgaylussacin (3), 4'-O-[ß-D-glucopyranosyl-(1â6)-glucopyranosyl]oxy-2'-hydroxy-6'-methoxydihydrochalcone (4), gaylussacin (5), pinosilvin 3-O-ß-D-glucopyranoside (6), myricetin-3-O-(2''-O-galloyl)-α-L-rhamnopyranoside (7), myricetin-3-O-(3''-O-galloyl)-α-L-rhamnopyranoside (8), myricetin-3-O-α-L-rhamnopyranoside (9), quercitrin (10), myricetin-3-O-ß-D-glucopyranoside (11), myricetin-3-O-ß-D-galactopyranoside (12), quercetin 3-O-α-L-arabinopyranoside (13), myricetin-3-O-2''-O-galloyl)-α-L-arabinopyranoside (14), (+)-gallocatechin (15), (-)-epigallocatechin (16), and 3,3',4'-trimethoxyellagic acid 4-O-ß-D-glucopyranoside (17) by the analysis of HR-ESI-MS, 1D and 2D NMR spectra in comparison with the previously reported data. Compounds 1-3, 5, and 6 significant inhibition of NO production in LPS-activated RAW264.7 cells, with IC50 values ranging from 18.37±1.38 to 35.12±2.53â µM, compared to a positive control (dexamethasone) with an IC50 value of 15.37±1.42â µM.
Subject(s)
Glycosides , Syzygium , Glycosides/pharmacology , Glycosides/chemistry , Nitric Oxide , Phenols/pharmacology , Sodium , Molecular StructureABSTRACT
Five new flavonoid C-glycosides named desmodinosides A-E (1-5) and one known compound, apigenin 6-C-ß-d-xylopyranosyl-2''-O-ß-D-glucopyranoside (6) have been isolated from the methanol extract of the aerial parts of Desmodium heterocarpon var. stigosum. These compounds were determined by 1D and 2D-NMR and HR-MS spectroscopies. The methanol extract of this plant, in particular, demonstrated hepatoprotection and antifungal inhibition. This extract has a remarkable hepatoprotection and activity-dose response with an EC50 of 43.07 µg/mL. The hepatoprotective effect on human liver hepatoma cells (HepG2) of the isolated flavonoid C-glycosides 1-6 was observed. Desmodinosides A-C (1-3) were found to exhibit moderate hepatoprotective activity on HepG2 cells. Of these, compound 2 showed the best hepatoprotective activity with an EC50 value of 74.12 µg/mL. While compounds 1 and 3 displayed EC50 values of 271.21 and 211.99 µg/mL, respectively. Quercetin, a positive control, also caused an EC50 value of 36.42 µg/mL. In addition to having hepatoprotective effect, the methanol extract had an inhibitory effect on the growth of oomycete; it inhibited Phytophthora infestans with IC50 of 13.3 µg/mL and IC90 of 78.7 µg/mL. The oomycete inhibition was directly attributed to compounds 5 and 6, which significantly inhibited P. infestans with IC50 values of 27.4 and 24.7 µg/mL, respectively. Both 5 and 6 and methanol extract were active against P. infestanse in a dose-dependent manner. Our study demonstrated for the first time the new flavonoid C-glycosides from D. heterocarpon var. stigosum and their novel pharmacological properties. The study findings also suggest the plant extract and its metabolites could be used as a new botanical source of bioactive compounds.
Subject(s)
Antifungal Agents , Flavonoids , Humans , Antifungal Agents/pharmacology , Methanol , Molecular Structure , Glycosides , Plant Extracts/chemistryABSTRACT
A chemical study of the methanol extract of the aerial parts of Achyranthes aspera led to the isolation of four new flavonoid C-glycosides (1-4) along with eight known analogs (5-12). Their structures were elucidated by a combination of spectroscopic data analysis, HR-ESI-MS, 1D and 2D NMR spectra. All the isolates were evaluated their NO production inhibitory activity in LPS-activated RAW264.7 cells. Compounds 2, 4, and 8-11 showed significant inhibition with IC50 values ranging from 25.06 to 45.25â µM, compared to that of the positive control compound, L-NMMA, IC50 value of 32.24â µM, whereas the remaining compounds were weak inhibitory activity with IC50 values over 100â µM. This is the first report of 7 from Amaranthaceae family, and 11 from the genus Achyranthes.
Subject(s)
Achyranthes , Flavonoids , Flavonoids/pharmacology , Flavonoids/chemistry , Achyranthes/chemistry , Nitric Oxide , Plant Extracts/pharmacology , Plant Extracts/chemistry , Glycosides/pharmacology , Glycosides/chemistry , Molecular StructureABSTRACT
Three undescribed triterpene glycosides syzybullosides A-C (1-3) along with fourteen known compounds were isolated from the leaves of Syzygium bullockii (Hance) Merr.& L.M. Perry, including six triterpene glycosides (1-6), four phenolics (7-9, 17), four megastigmanes (10-13), and three flavonoids (14-16). The structures of 1-17 were elucidated by extensive spectroscopic analysis, including IR, HR-ESI-MS, 1D and 2D NMR spectra. Compounds 1-10 and 12-17 inhibited nitric oxide (NO) production in lipopolysaccharide activated RAW264.7 cells with IC50 values ranging from 1.30 to 13.70 µM, lower than that of the positive control compound, L-NMMA (IC50 = 33.8 µM).
Subject(s)
Syzygium , Triterpenes , Molecular Structure , Nitric Oxide , Glycosides/pharmacology , Glycosides/chemistry , Triterpenes/pharmacology , Triterpenes/chemistryABSTRACT
Four undescribed compounds (1-4) named pelliolatifolias A-D together with seven known compounds trans-clovamide (5), N-trans-caffeoyl-4-hydroxyphenylalanine methyl ester (6), N-trans-caffeoyl-3,4-dihydroxyphenylalanine methyl ester (7), luteolin 4'-O-ß-D-glucopyrannoside (8), cis-syringin (9), trans-syringin (10), and citroside A (11) have been isolated from the methanol extract of the Pellionia latifolia leaves. Their chemical structures were elucidated based on extensive analyses of HR-ESI-MS, 1D and 2D NMR, and CD spectra. Compounds 1-7, 9 and 10 showed moderate inhibition of NO production in LPS-activated RAW264.7 cells with their IC50 values ranging from 39.27 to 75.42â µM, compared to that of the positive control compound, dexamethasone, IC50 value of 14.20â µM.
Subject(s)
Nitric Oxide , Phenylpropionates , Esters , Glucosides , Molecular StructureABSTRACT
Phytochemical investigation on the aerial parts of Elsholtzia blanda Benth. afforded four new oleuropeic acid derivatives (1-4), named as elsholblanosides A-D, respectively, together with 11 known compounds (5-15). Their structures were determined based on extensive analyses of HR-ESI-MS, 1D and 2D NMR, and ECD spectra. Compounds 1-4 and 14 showed moderate NO production inhibition in LPS-activated RAW264.7 cells with their IC50 values ranging from 23.2 to 86.33â µM, compared to that of the positive control compound, dexamethasone, IC50 value of 16.9â µM.
Subject(s)
Cyclohexanecarboxylic Acids , Lamiaceae , Animals , Mice , Lipopolysaccharides/pharmacology , Lamiaceae/chemistry , RAW 264.7 Cells , Molecular StructureABSTRACT
Plants of the Schisandra genus are commonly used in folk medicinal remedies. Some Schisandra species and their lignans have been reported to improve muscle strength. In the present study, four new lignans, named schisacaulins A-D, together with three previously described compounds ananonin B, alismoxide, and pregomisin were isolated from the leaves of S. cauliflora. Their chemical structures were determined by extensive analyses of HR-ESI-MS, NMR, and ECD spectra. Schisacaulin D and alismoxide significantly stimulated skeletal muscle cell proliferation by increasing the number of fused myotubes and expression of myosin heavy chain (MyHC) which may be good candidates for the treatment of sarcopenia.
Subject(s)
Lignans , Schisandra , Schisandra/chemistry , Lignans/chemistry , Plant Leaves/chemistry , Cell Proliferation , Muscle, SkeletalABSTRACT
Phytochemical study on the leaves of Amentotaxus yunnanensis led to the isolation of seventeen phenolic compounds including sixteen neolignans and lignans, and one flavone glycoside. Three among the isolates were previously unreported neolignans and named as amenyunnaosides A-C, respectively. Their structures were elucidated by extensive analyses of HR-ESI-MS, 1D and 2D NMR, and ECD spectra. The isolated neolignans potentially inhibited NO production in LPS-activated RAW264.7 cells with their IC50 values ranging from 11.05 to 44.07â µM, compared to that of the positive control compound, dexamethasone, IC50 value of 16.93â µM. Additionally, amenyunnaoside A dose-dependently reduced production of IL-6 and COX-2 but did not effect to that of TNF-α at concentrations of 0.8, 4, and 20â µM.
Subject(s)
Lignans , Lignans/chemistry , Anti-Inflammatory Agents/chemistry , Glycosides/chemistry , Magnetic Resonance Spectroscopy , Plant Leaves/chemistry , Molecular Structure , Nitric OxideABSTRACT
A new isopropyl chromone (1) and a new flavanone glucoside (2) together with eleven known compounds (3-13) were isolated from the leaves of Syzygium cerasiforme (Blume) Merr. & L.M.Perry. Their structures were elucidated as 5,7-dihydroxy-2-isopropyl-6,8-dimethyl-4H-chromen-4-one (1), 5,7-dihydroxyflavanone 7-O-ß-D-(6''-O-galloylglucopyranoside) (2), strobopinin (3), demethoxymatteucinol (4), pinocembrin-7-O-ß-D-glucopyranoside (5), (2S)-hydroxynaringenin-7-O-ß-D-glucopyranoside (6), afzelin (7), quercetin (8), kaplanin (9), endoperoxide G3 (10), grasshopper (11), vomifoliol (12), litseagermacrane (13) by the analysis of HR-ESI-MS, NMR, and CD spectral data. Compounds 1, 2, 5, 6 and 10 inhibited NO production on LPS-activated RAW264.7 cells with IC50 values of 12.28±1.15, 8.52±1.62, 7.68±0.87, 9.67±0.57, and 6.69±0.34â µM, respectively, while the IC50 values of the other compounds ranging from 33.38±0.78 to 86.51±2.98â µM, compared to that of the positive control, NG -monomethyl-L-arginine acetate (L-NMMA) with an IC50 value of 32.50±1.00â µM.