ABSTRACT
Using various chromatographic separations, six glycoside derivatives (1-6), including one new ent-labdane glucoside named cayratioside (1), were isolated from the methanol extract of Cayratia geniculata stems and leaves. Their structures were elucidated by detailed analysis of the 1D, 2D NMR, and HRESIQTOF mass spectra. The inhibitory effect of 1-6 on LPS-induced NO production in RAW264.7 cells was also evaluated. Among isolated compounds, 1 exhibited moderate activity with an IC50 value of 59.65 ± 1.85 µM.
ABSTRACT
Phytochemical study on the aerial parts of Yua thomsonii resulted in the isolation of 11 secondary metabolites, including a new caffeoyl quinic acid derivative, 3-O-trans-caffeoyl-4-O-acetylquinic acid methyl ester (1), a new dihydrobenzofuran neolignan, 3,5-dimethoxy-4-(1â³,3â³-dihydroxy-2â³-propyloxyl)-4',7-epoxy-8,5'-neolignan-4,9,9'-triol (3) and nine known compounds, methyl 4-O-coumaroylquinate (2), (7S*,8S*)-3-methoxy-3',7-epoxy-8,4'-oxyneolignan-4,9,9'-triol (4), kompasinol A (5), lyoniresinol (6), schizandriside (7), (-)-isolariciresinol 3a-O-ß-D-xylopyranoside (8), lyoniside (9), vitexin (10) and luteolin 4'-O-ß-glucopyranoside (11). Their structures were elucidated using comprehensive spectroscopic methods, including 1D and 2D NMR and HRESI mass spectra. The absolute configurations of 1 and 3 were deduced by electronic circular dichroism spectroscopy. Compounds 1, 3, 5 and 6 exhibited nitric oxide (NO) inhibitory effects, with IC50 values ranging from 12.18 to 29.45 µM. However, compounds 1, 3, 6 and 8 were non-cytotoxic towards HepG2 and MCF-7 carcinoma cells.
ABSTRACT
Six new acylated flavonoid glycosides namely barringosides J - O (1-6) along with tephrokaempferoside and barringoside D were isolated from the branches and leaves of Barringtonia pendula. The structural elucidation was confirmed by extensive analysis of their spectroscopic data including HRQTOFMS, 1D and 2D NMR experiments. Moderate inhibitory effects on LPS-induced NO production in RAW264.7 cells were observed for barringosides M (4) and N (5) with IC50 values of 48.40 ± 3.01 and 56.61 ± 3.87 µM, whereas weak inhibition was found for compounds 1-3, 6, and 7 with IC50 values ranging from 64.91 ± 3.68 to 79.80 ± 3.90 µM.
Subject(s)
Barringtonia , Flavonoids , Animals , Mice , Flavonoids/pharmacology , Flavonoids/chemistry , Lipopolysaccharides/pharmacology , Nitric Oxide , Barringtonia/chemistry , Molecular Structure , Glycosides/pharmacology , Glycosides/chemistry , RAW 264.7 CellsABSTRACT
Chemical investigation of corn silk resulted in the isolation of nine secondary metabolites, including a new ent-kaurane diterpenoid, zeamaysditerpene A (1) and eight known compounds, stigmaydene A (2), stigmaydene J (3), stigmaydene L (4), stigmane D (5), demethyltorosaflavone D (6), chrysoeriol 6-C-ß-boivinopyranosyl-7-O-ß-D-glucopyranoside (7), deoxypodophyllotoxin (8), and α-peltatin glucoside (9). Their structures were elucidated using a combination of spectroscopic methods, including 1D and 2D NMR and HRESIQTOF mass spectra. The absolute configuration of 1 was deduced by applying electronic circular dichroism (ECD) calculation method. Among the isolates, only 6 displayed significant inhibition against PTP1B activity in a dose-dependent manner, with an IC50 value of 10.7 ± 0.1 µM. Furthermore, molecular docking simulation was carried out to explore the action perspective of 6 inside the enzyme PTP1B. This finding suggests that 6 might be a potential lead for the development of a new anti-diabetic agent.
ABSTRACT
Five asterosaponins (1-5), including one new compound named protonodososide (1), were isolated from the methanol extract of the starfish Protoreaster nodosus, after subjecting to various chromatographic separations. The structural elucidation was confirmed by careful analysis of the 1D, 2D NMR, and HR ESI QTOF mass spectra. The cytotoxicity of isolated compounds was evaluated on five human cancer cell lines including HepG2, KB, MCF7, LNCaP, and SK-Mel2.
Subject(s)
Antineoplastic Agents , Starfish , Animals , Humans , Starfish/chemistry , Magnetic Resonance Spectroscopy , Cell Line, Tumor , Spectrometry, Mass, Electrospray Ionization , Antineoplastic Agents/chemistry , Molecular StructureABSTRACT
From the MeOH residue of Barringtonia macrocarpa branches and leaves, one new isoryanodane diterpene, barringisol (1), and two new isoryanodane diterpene glucosides, barringisosides A and B (2 and 3), were obtained using various chromatographic isolations. The structural characterization was confirmed by spectroscopic methods including 1D, 2D NMR and HR-ESI-QTOF-MS. This is the first isolation of isoryanodane diterpene derivatives from Barringtonia species. Moreover, the in vitro cytotoxicity of 1-3 on three human cancer cell lines (HepG2, LNCaP and MCF7) was also accessed using SRB assays.
ABSTRACT
Using combined chromatographic methods, two new sesquiterpene glucosides, vulgarosides A (1) and B (2), and two known analogs ainsliaside E (3) and pumilaside A (4) were isolated from the aerial parts of Artemisia vulgaris. Their chemical structures were established by spectroscopic methods, including one and two-dimensional nuclear magnetic resonance (1 D and 2 D-NMR) spectroscopy and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). In addition, their cytotoxicity on five human cancer cell lines, including KB (epidermoid carcinoma), HepG2 (hepatocarcinoma), MCF7 (breast carcinoma), SK-Mel-2 (melanoma), and LNCaP (prostate cancer) was also evaluated by the SRB assay. However, none of the tested eudesmane sesquiterpene glycosides showed significant cytotoxicity (IC50>100 µM).
Subject(s)
Artemisia , Neoplasms , Sesquiterpenes, Eudesmane , Sesquiterpenes , Humans , Artemisia/chemistry , Glucosides/chemistry , Sesquiterpenes, Eudesmane/pharmacology , Sesquiterpenes, Eudesmane/analysis , Sesquiterpenes/pharmacology , Sesquiterpenes/analysis , Plant Components, Aerial/chemistry , Molecular StructureABSTRACT
Three new glucosides, ziberthinosides A-C (1-3), and six known compounds, cleomiscosins A-D (4-7), sporogen AO-2 (8) and sapinofuranone A (9), were isolated from a methanol extract of Durio zibethinus fruit peels. Their chemical structures were elucidated by analyses of their 1 D/2D NMR and HR-ESI-MS data as well as by comparison with the literature values. The absolute configuration of sporogen AO-2 (8) was confirmed by ECD calculation. Of the isolates, compounds 8 and 9 were cytotoxic toward all MCF7, HepG2 and SK-LU-1 cell lines, with IC50 values ranging from 10.7 to 34.9 µM. Our results contribute to better understanding of the chemical constituents of the high valued durian fruit and their pharmacological effect, such as cytotoxicity.
ABSTRACT
Three new sulfated naphthopyrone derivatives namely delicapyrons F-H (1-3) and two new sulfated anthraquinone derivatives namely delicaquinons A (4) and B (5), together with 6-methoxycomaparvin-5-methylether-8-O-sodium sulfate (6), 6-methoxycomaparvin-8-O-sodium sulfate (7), comaparvin-8-O-sodium sulfate (8), and 3-propyl-1,6,8-trihydroxy-9,10-anthraquinone-6-O-sodium sulfate (9) were isolated from the Vietnamese crinoid Comanthus delicata. Their chemical structures were elucidated by extensive analysis of the one dimensional (1D) and 2D-NMR, high resolution electrospray ionization quadrupole time-of-flight (HR-ESI-QTOF) mass spectra as well as calculation of optical rotation. In addition, significant cytotoxicity was observed for 6 against LNCaP (prostate cancer) cell line with IC50 value of 20.29 ± 2.43 µM, whereas moderate or weak cytotoxic effects were observed for 1-3 and 5-8 on SK-Mel-2 (melanoma) cell line and 7 and 8 against LNCaP cell line, with IC50 values ranging from 49.96 ± 1.74 to 76.92 ± 5.85 µM.
Subject(s)
Antineoplastic Agents , Neoplasms , Animals , Anthraquinones/chemistry , Anthraquinones/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Asian People , Echinodermata/chemistry , HumansABSTRACT
Using combined chromatographic separation techniques, three new triterpenoids named lycomclavatols A-C (1-3), a new natural product, methyl lycernuate-A (4), as well as seven known compounds (5-11), were isolated from the methanol extract of the whole plants of Lycopodium clavatum. Their chemical structures were established based on 1 D/2D NMR and HR-ESI-MS spectroscopic analyses. Among the isolates, compound 1 exhibited inhibitory activity on NO production in LPS-stimulated BV2 cells (IC50 = 36.0 µM). In addition, 1 was cytotoxic against both HepG2 and A549 cancer cell lines, with IC50 values of 40.7 and 87.0 µM, respectively. Compounds 10 and 11 showed cytotoxicity on only HepG2 and A549 cells, with IC50 values of 91.2 and 57.6 µM, respectively. Our results contribute to understanding more the secondary metabolites produced by L. clavatum and provide a scientific rationale for further investigations of anti-inflammatory and anticancer effects for this valuable medicinal plant.
Subject(s)
Lycopodium , Plants, Medicinal , Triterpenes , Lycopodium/chemistry , Triterpenes/pharmacology , Triterpenes/chemistry , Nitric Oxide/metabolism , Plants, Medicinal/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Inhibitory Concentration 50ABSTRACT
Phytochemical investigation of the branches and leaves of Alchornea annamica led to isolation of ten secondary metabolites, including two new megastigmane glucosides alnamicosides A (1) and B (2). The structure elucidation was confirmed by 1 D and 2 D NMR, ECD as well as HR-QTOF-MS experiments. The megastigmane derivatives 1 - 3 exhibited inhibitory effects on LPS-induced NO production in RAW264.7 cells with IC50 values of 78.72 ± 1.90, 77.40 ± 9.40 and 82.16 ± 4.56 µM, respectively. This is the first report on chemical constituents and biological activity of the plant A. annamica.
Subject(s)
Euphorbiaceae , Animals , Euphorbiaceae/chemistry , Mice , Phytochemicals/analysis , Plant Extracts/chemistry , Plant Leaves/chemistry , RAW 264.7 CellsABSTRACT
A new polyhydroxysteroid glycoside, regulusoside D (1), and a new polyhydroxylated steroid, (24S)-cholestane-3ß,5,6ß,8,15α,24-hexol (2), together with seven known compounds were purified from the starfish Pentaceraster regulus collected near Con Co Islands, Vietnam. The structure elucidation was confirmed by extensive analysis of their NMR and HR-QTOF mass experiments. Among isolated compounds, regulusoside D (1), (24S)-cholestane-3ß,5,6ß,8,15α,24-hexol (2), granulatoside A (4), 5α-cholestane-3ß,6ß,7α,15α,16ß,26-hexol (6), 5α-cholestane-3ß,6ß,7α,8ß,15α,16ß,26-heptol (7) and 5α-cholestane-3ß,6α,8,15α,16ß,26-hexol (8) exhibited strong inhibitory effects on LPS-induced NO production in RAW264.7 cells with IC50 values of 9.13 ± 1.17, 9.19 ± 0.77, 8.63 ± 3.31, 12.61 ± 0.51, 14.83 ± 3.02 and 10.98 ± 1.22 µM, respectively.
Subject(s)
Starfish , Steroids , Animals , Glycosides/chemistry , Glycosides/pharmacology , Magnetic Resonance Spectroscopy , Mice , RAW 264.7 Cells , Starfish/chemistry , Steroids/chemistry , Steroids/pharmacologyABSTRACT
Chemical investigation of a peanut-associated fungal strain Aspergillus niger IMBC-NMTP01 resulted in isolation and identification of 14 secondary metabolites, including two new, epi-aspergillusol (1) and aspernigin (3), and 12 known compounds: pyrophen (2), 2-(hydroxyimino)-3-(4-hydroxyphenyl)propanoic acid (4), aspergillusol A (5), rubrofusarin B (6), nigerasperone A (7), fonsecin (8), TMC-256C1 (9), pyranonigrin A (10), orlandin (11), nigerasperone C (12), asperpyrone A (13), and 5-(hydroxymethyl)-2-furancarboxylic acid (14). Compounds 9, 12-14 showed cytotoxicity toward all six human cancer cell lines, including HepG2, KB, HL-60, MCF-7, SK-Mel2, and LNCaP, with IC50 values ranging from 8.4 to 84.5 µM, compounds 3-5 were cytotoxic against five cancer cell lines except HepG2, whereas 1 exhibited cytotoxicity toward HepG2, KB, and MCF-7 cells. All of the compounds, except 2 and 13, inhibited NO overproduction in LPS-induced RAW264.7 cells. In addition, all of the compounds displayed antimicrobial effects against Enterococcus faecalis, whereas 13 compounds, except 10, significantly inhibited the growth of the yeast Candida albicans.
Subject(s)
Anti-Infective Agents , Aspergillus niger , Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Arachis , Cell Line, Tumor , Humans , MCF-7 Cells , Molecular StructureABSTRACT
Chemical investigation of the roots of Codonopsis javanica resulted in isolation of 12 compounds, including one new polyacetylene, codojavanyol (1), one new phenolic glycoside, codobenzyloside (7), and 10 known compounds, (2E,8E)-9-(tetrahydro-2H-pyran-2-yl)nona-2,8-diene-4,6-diyl-1-ol (2), lobetyol (3), lobetyolin (4), lobetyolinin (5), cordifolioidyne B (6), benzyl-α-L-arabinopyranosyl (1-6)-ß-D-glucopyranoside (8), (Z)-8-ß-D-glucopyranosyloxycinnamic acid (9), syringin (10), syringaresinol (11), and tryptophan (12). Their structures were elucidated by 1 D and 2 D NMR and MS spectroscopic analyses in comparison with the data reported in the literature. The stereochemistry of the C-2' position of 1 was identified based on time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculation. Among the isolates, compounds 3-5 were shown to have weak cytotoxicity toward three human carcinoma cell lines, including lung (A549), liver (HepG2), and breast (MCF7), with the induction of 41.4 to 55.6% cell death at the concentration of 100 µM.
Subject(s)
Codonopsis , Codonopsis/chemistry , Glycosides/chemistry , Humans , Molecular Structure , Phenols/analysis , Plant Roots/chemistry , Polyacetylene PolymerABSTRACT
Phytochemical investigation of a methanol extract of Panax pseudoginseng flower buds resulted in the isolation of 22 dammarane-type triterpenoid saponins, including three new compounds, pseudoginsenosides A-C (1-3), and 19 known analogs. Their chemical structures were identified by the comprehensive spectroscopic methods, including 1 D and 2 D NMR and mass spectra. In addition, their cytotoxic effects toward three human carcinoma cell lines, including liver (HepG2), breast (MCF7), and lung (A549) were also evaluated.
Subject(s)
Antineoplastic Agents , Panax , Saponins , Triterpenes , Antineoplastic Agents/analysis , Flowers/chemistry , Humans , Molecular Structure , Panax/chemistry , Saponins/chemistry , Triterpenes/chemistry , DammaranesABSTRACT
Fourteen polyhydroxylated steroids including six new compounds, ehrensteroids A - F (1-6), were isolated from the Vietnamese soft coral Sarcophyton ehrenbergi after applying various chromatographic separations. The structure elucidation was done by detailed analysis of 1D, 2D NMR and HR QTOF mass spectra. In addition, significant cytotoxicity (IC50 values ranging from 8.45 ± 0.56 to 38.27 ± 2.39 µM) against all five tested cancer cell lines as LU-1 (lung cancer), HepG2 (hepatoma cancer), MCF-7 (breast cancer), HL-60 (acute leukemia), and SW480 (colon adenocarcinoma) was observed for compounds 1, 2, 6-10, and 12-14, whereas this activity on LU-1 (IC50 = 21.91 ± 2.72 µM) and HepG2 (IC50 = 20.32 ± 0.03 µM) cell lines was also observed for 4.
Subject(s)
Anthozoa/chemistry , Antineoplastic Agents/pharmacology , Steroids/pharmacology , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Cell Proliferation/drug effects , Cell Survival/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Humans , Molecular Conformation , Stereoisomerism , Steroids/chemistry , Steroids/isolation & purification , Structure-Activity RelationshipABSTRACT
The MeOH extract of the Vietnamese octocoral Dendronephthya mucronata afforded four bicyclic lactones (1-4), including three new compounds namely dendronephthyones A-C (1-3), after subjecting it on various chromatographic separations. The structures of the isolated compounds were established by spectroscopic experiments including 1D, 2D NMR, CD and HR-QTOF-MS. In addition, compounds 1-4 were found to exhibit selective cytotoxicity against the HeLa human cancer cell line with IC50 values of 32.48 ± 2.15, 30.12 ± 1.86, 35.14 ± 1.57 and 14.45 ± 1.34 µM, respectively.
Subject(s)
Anthozoa/chemistry , Lactones/isolation & purification , Animals , Carbon-13 Magnetic Resonance Spectroscopy , Cell Death/drug effects , Cell Line, Tumor , Humans , Lactones/chemistry , Lactones/pharmacology , Proton Magnetic Resonance SpectroscopyABSTRACT
Sixteen sesquiterpenoids (1 - 16), including two new compounds namely saussucostusosides A and B (1 and 2), were isolated from the roots of Saussurea costus by various chromatographic separations. Their structures were elucidated by 1 D and 2 D NMR and HR-QTOF-MS experiments. Among isolated compounds, costunlide (6), 3ß-[4-hydroxymethacryloyloxy]-8α-hydroxycostunolide (10) and 11ß,13-dihydrozaluzanin C (16) exhibited potent inhibitory effects on LPS-induced NO production in RAW264.7 cells with IC50 values of 7.08 ± 0.34, 2.40 ± 0.06 and 5.55 ± 0.24 µM, respectively.
Subject(s)
Saussurea/chemistry , Sesquiterpenes/isolation & purification , Animals , Carbon-13 Magnetic Resonance Spectroscopy , Inhibitory Concentration 50 , Lipopolysaccharides/pharmacology , Mice , Nitric Oxide/biosynthesis , Plant Extracts/chemistry , Plant Roots/chemistry , Proton Magnetic Resonance Spectroscopy , RAW 264.7 Cells , Sesquiterpenes/chemistryABSTRACT
In our search for anti-inflammatory constituents from Vietnamese plants, the methanolic extract of Helicteres viscida was found to exhibit inhibitory effect on LPS-induced NO production in RAW264.7 cells. Phytochemical investigation of this plant led to isolation of four sulphated flavones (1-4), including one new compound 5,3',4'-trihydroxy-7-methoxy-8-O-sulphate flavone (1), and two pregnane-type steroids (5 and 6), including one new compound 7-epi-heligenin B (5). Their structures were elucidated by 1D and 2D NMR as well as HR-QTOF-MS experiments. Among isolated compounds, heligenin B (6) exhibited potent inhibitory effect on LPS-induced NO production in RAW264.7 cells with IC50 of 1.23 ± 0.05 µM. The activity of 6 was comparable to that of the positive control cardamonin.
Subject(s)
Flavones , Malvaceae , Flavones/pharmacology , Molecular Structure , Phytochemicals , Pregnanes , SulfatesABSTRACT
Two new megastigmane glucosides namely trewiosides A (1) and B (2), along with 20α-hydroxypregn-4-en-3-one ß-D-glucopyranoside (3), sugeroside (4), and schizandriside (5) were isolated from the branches and leaves of Alchornea trewioides. The structure elucidation was confirmed by extensive analysis of the one and two dimensional (1 and 2D) NMR, electronic circular dichroism (ECD) as well as high resolution electrospray ionization quadrupole time-of-flight (HR-ESI-QTOF) mass spectra. Noteworthily, the isolation of compounds 1 and 2 represents the second finding of megastigmane derivatives with a methoxycarbonyl group at C-5 to date. In addition, compound 3 showed weak cytotoxicity against three human cancer cell lines as A549 (lung carcinoma), HepG2 (hepatocarcinoma), and MCF7 (breast carcinoma). Besides, compounds 2 and 3 exhibited moderate inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells. Whereas, the remaining compounds 1, 4 and 5 showed weak inhibitory activity.