ABSTRACT
Two new polyisoprenylated benzophenones, planchoniones A (1) and B (2), together with two known benzophenones (3, 4) and six known xanthones (5-10), were isolated from an ethyl acetate extract of the pericarp of Garcinia planchonii Pierre. Their structures were established using spectroscopic methods, mainly 1D and 2D NMR. The four benzophenones were evaluated for their cytotoxicity against MCF-7 human breast cancer cells, and showed almost no activity. Meanwhile, compounds 5-10 were investigated for their inhibitory effects towards α-glucosidase, and γ-mangostin (5) exhibited the most remarkable effect with IC50 value of 15.3 ± 0.9 µM (compared with acarbose, IC50 = 224.9 ± 3.6 µM).
Subject(s)
Garcinia , Xanthones , Humans , Garcinia/chemistry , Benzophenones/pharmacology , Benzophenones/chemistry , Xanthones/pharmacology , Xanthones/chemistry , Magnetic Resonance Spectroscopy , alpha-Glucosidases/metabolism , Molecular StructureABSTRACT
Two new xanthones, oblongixanthones I (1) and J (2), and seven known compounds (3-9), were isolated from an EtOAc extract of the twigs of Garcinia oblongifolia. Their structures were elucidated using spectroscopic methods, mainly 1 D and 2 D NMR. The antidiabetic effects of the two new compounds were evaluated using α-glucosidase and PTP1B inhibition assays. Both compounds displayed strong inhibition towards α-glucosidase with IC50 values of 258.7 ± 49.3 and 187.1 ± 27.5 µM, respectively (compared with acarbose, IC50 = 900.0 ± 3.0 µM) and moderate effects against PTP1B with IC50 values of 93.9 ± 12.3 and 64.1 ± 5.8 µM, respectively (compared with RK682, IC50 = 4.4 ± 0.3 l µM).
Subject(s)
Garcinia , Xanthones , Xanthones/chemistry , Xanthones/pharmacology , Hypoglycemic Agents/chemistry , Hypoglycemic Agents/pharmacology , Molecular Structure , Garcinia/chemistry , alpha-Glucosidases/metabolismABSTRACT
Nine compounds including a new one, garcichaudiic acid (1), were isolated from the bark of G. gaudichaudii and their structures were characterized mainly by 1 D and 2 D NMR experiments. The antioxidant capacity of the isolated compounds was determined using DPPH radical scavenging assay and the anti-hyperglycemic activity was assessed by measuring the inhibitory effect against α-glucosidase. Among them, compound 4 showed higher antioxidant activity than the positive control, ascorbic acid, while both compounds 1 and 7 exhibited more significant α-glucosidase inhibitory activity than the reference drug acarbose. Molecular docking analysis of the bioactive compounds was also performed to examine the binding modes and key interactions with the catalytic site.
Subject(s)
Antioxidants , Garcinia , Antioxidants/chemistry , alpha-Glucosidases/metabolism , Glycoside Hydrolase Inhibitors/chemistry , Molecular Docking Simulation , Garcinia/chemistryABSTRACT
Two new triterpenoids, entanolide (1) and methyl 3,4-secotirucalla-23-oxo-4(28),7,24-trien-21-al-3-oate (2), together with nine known compounds (3-11), were isolated from the bark of Entandrophragma angolense. Their structures were elucidated based on spectroscopic analyses, mainly 1 D and 2 D NMR spectral data. Compounds 1-6 and 8 were evaluated for their cytotoxicity against HepG2 cells, and compounds 2-5 exhibited weak activities.
Subject(s)
Meliaceae , Triterpenes , Humans , Triterpenes/chemistry , Molecular Structure , Plant Bark/chemistry , Magnetic Resonance Spectroscopy , Hep G2 Cells , Meliaceae/chemistryABSTRACT
Two new rocaglamides, 8b-O-5-oxohexylrocaglaol (1) and elaeagnin (2), together with twelve known compounds, were isolated from the bark of Aglaia elaeagnoidea and the whole tree of A. odorata. Their structures were determined using spectroscopic methods, mainly 1D and 2D NMR. Cytotoxic activity against HepG2 human liver cancer cells of the isolated compounds was evaluated in vitro using the SRB assay. Three rocaglamide derivatives, dehydroaglaiastatin (13), 8b-O-5-oxohexylrocaglaol (1) and rocaglaol (5), exhibited significant effects with IC50 values of 0.69, 4.77 and 7.37 µM, respectively.
Subject(s)
Aglaia , Aglaia/chemistry , Hep G2 Cells , Humans , Magnetic Resonance Spectroscopy , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/pharmacologyABSTRACT
Three new limonoids, walsucochinones A-C (1-3), along with eight known compounds, were isolated from an ethyl acetate extract of the bark of Walsura cochinchinensis. Their structures were determined using spectroscopic techniques, mainly 1-D and 2-D NMR. The ethyl acetate extract showed cytotoxic activity against MCF-7 human breast cancer cells and cytotoxicity of the isolated compounds were evaluated in vitro using the SRB assay. Walsucochinone C (3) exhibited the most active effect with IC50 value of 16.4⯱â¯0.2⯵M.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Limonins/pharmacology , Meliaceae/chemistry , Plant Bark/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Humans , Inhibitory Concentration 50 , Limonins/isolation & purification , MCF-7 Cells , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , VietnamABSTRACT
Two new compounds, fuscaxanthones J (1) and K (2), together with eight known xanthones (3 - 10) were isolated from an ethyl acetate extract of the roots of Garcinia fusca. Their structures were determined using spectroscopic methods, mainly 1D- and 2D-NMR. α-Glucosidase inhibitory activity of the isolated compounds was evaluated and fuscaxanthone J (1) showed the most significant effect with an IC50 value of 8.3 ± 1.8 µm (compared with acarbose, IC50 = 214.5 ± 2.3 µm).
Subject(s)
Garcinia/chemistry , Glycoside Hydrolase Inhibitors/pharmacology , Plant Roots/chemistry , Xanthones/pharmacology , Dose-Response Relationship, Drug , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/isolation & purification , Humans , Molecular Structure , Structure-Activity Relationship , Xanthones/chemistry , Xanthones/isolation & purification , alpha-Glucosidases/metabolismABSTRACT
An ethyl acetate extract the bark of Garcinia xanthochymus exhibited strong inhibition towards α-glucosidase and PTP1B with IC50 values of 0.3±0.1µg/mL and 2.3±0.4µg/mL, respectively. Chemical constituents of the extract were therefore examined, and two new compounds, xanthochymusxanthones A (1) and B (2), along with ten known xanthones (3-12), were isolated. Their structures were determined using spectroscopic methods, mainly 1D and 2D NMR. Inhibitory activity of the isolated compounds was then tested, and subelliptenone F (12) showed significant effect towards α-glucosidase with IC50 value of 4.1±0.3µM (compared with acarbose, IC50=900.0±3.0µM) whilst xanthochymusxanthone B (2) exhibited remarkable activity towards PTP1B with IC50 value of 8.0±0.6µM (compared with RK682, IC50=4.4±0.3µM).
Subject(s)
Garcinia/chemistry , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/pharmacology , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , Xanthones/chemistry , Xanthones/pharmacology , Diabetes Mellitus/drug therapy , Diabetes Mellitus/metabolism , Glycoside Hydrolase Inhibitors/isolation & purification , Humans , Hypoglycemic Agents/chemistry , Hypoglycemic Agents/isolation & purification , Hypoglycemic Agents/pharmacology , Models, Molecular , Plant Bark/chemistry , Protein Tyrosine Phosphatase, Non-Receptor Type 1/metabolism , Xanthones/isolation & purification , alpha-Glucosidases/metabolismABSTRACT
Three new xanthones, oblongixanthone F-H (1-3), along with eight known xanthones (4-11), were isolated from an EtOAc extract of the twigs of Garcinia oblongifolia. Their structures were elucidated by spectroscopic analysis including 1D- and 2D-NMR spectroscopy and mass spectrometry. The antidiabetic effects of all isolated compounds were evaluated by in vitro α-glucosidase and PTP1B inhibition assays. Compound 11 was the most active compound, and inhibited α-glucosidase and PTP1B with IC50 values of 1.7±0.5 and 14.1±3.5µM, respectively.
Subject(s)
Garcinia/chemistry , Hypoglycemic Agents/chemistry , Xanthones/chemistry , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/isolation & purification , Humans , Hypoglycemic Agents/isolation & purification , Molecular Structure , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , Xanthones/isolation & purification , alpha-Glucosidases/metabolismABSTRACT
Four new prenylated depsidones, oliveridepsidones A-D, were isolated from the bark of Garcinia oliveri collected in Vietnam. Their structures were elucidated using mainly NMR techniques ((1)H and (13)C NMR, HMQC, HMBC and NOE experiments).
Subject(s)
Antioxidants/isolation & purification , Depsides/isolation & purification , Garcinia/chemistry , Lactones/isolation & purification , Plant Bark/chemistry , Antioxidants/chemistry , Depsides/chemistry , Lactones/chemistry , Magnetic Resonance Spectroscopy/standards , Molecular Conformation , Reference StandardsABSTRACT
Friedolanostanes, (22Z,24E)-3ß-acetoxy-9α-hydroxy-17,14-friedolanosta-14,22,24-trien-26-oic acid, (22Z,24E)-3ß,9α-dihydroxy-17,14-friedolanosta-14,22,24-trien-26-oic acid, (22Z,24E)-9α-hydroxy-3-oxo-17,14-friedolanosta-14,22,24-trien-26-oic acid, a friedocycloartane, (22Z,24E)-3α-hydroxy-17,13-friedocycloarta-12,22,24-trien-26-oic acid, and a benzophenone, benthaphenone, together with known compounds (22Z,24E)-3α,9α-dihydroxy-17,13-friedolanosta-12,22,24-trien-26-oic acid, methyl (24E)-3α,23-dihydroxy-17,14-friedolanosta-8,14,24-trien-26-oate, glutinol, lupeol, and stigmasterol, were isolated from leaves and bark of Garcinia benthami. Their structures were elucidated using spectroscopic techniques, mainly 1-D and 2-D NMR spectroscopy, and chemical correlations.
Subject(s)
Benzophenones/isolation & purification , Garcinia/chemistry , Lanosterol/analogs & derivatives , Lanosterol/isolation & purification , Triterpenes/isolation & purification , Benzophenones/chemistry , Lanosterol/chemistry , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Bark/chemistry , Plant Leaves/chemistry , Stereoisomerism , Triterpenes/chemistry , Triterpenes/pharmacology , VietnamSubject(s)
Bridged Bicyclo Compounds/chemistry , Phloroglucinol/analogs & derivatives , Sirtuins/antagonists & inhibitors , Terpenes/chemistry , Bridged Bicyclo Compounds/toxicity , Cell Proliferation/drug effects , Cells, Cultured , Humans , Magnetic Resonance Spectroscopy , Molecular Structure , Phloroglucinol/chemistry , Phloroglucinol/toxicity , Sirtuin 1 , Sirtuin 2 , Sirtuins/metabolism , Terpenes/toxicityABSTRACT
A new polyisoprenylated benzophenone, guttiferone I, together with the known compounds cambogin, 1,7-dihydroxyxanthone, 1,3,6,7-tetrahydroxyxanthone and 1,3,5,6-tetrahydroxyxanthone were isolated from the stem bark of Garcinia griffithii. The acetone extract of the heartwood of Garcinia mangostana contained one new diprenylated xanthone (mangoxanthone) and a new benzophenone (3',6-dihydroxy-2,4,4'-trimethoxybenzophenone) as well as the known xanthones dulxanthone D, 1,3,7-trihydroxy-2-methoxyxanthone, 1,3,5-trihydroxy-13,13-dimethyl-2H-pyran[7,6-b]xanthen-9-one. Their structures were established on the basis of spectroscopic studies and chemical correlation.
Subject(s)
Benzophenones/chemistry , Garcinia mangostana/chemistry , Garcinia/chemistry , Xanthones/chemistry , Benzophenones/isolation & purification , Molecular Structure , Plant Bark/chemistry , Plant Stems/chemistry , Xanthones/isolation & purificationABSTRACT
The bark of Garcinia merguensis yielded 10 xanthones, merguenone, 1,5-dihydroxy-6'-methyl-6'-(4-methyl-3-pentenyl)-pyrano(2',3':3,2)-xanthone, subelliptenone H, 8-deoxygartanin, rheediaxanthone A, morusignin G, 6-deoxyjacareubin, 1,3,5-trihydroxy-4,8-di(3-methylbut-2-enyl)-xanthone, rheediachromenoxanthone and 6-deoxyisojacareubin. The structure of merguenone was determined using spectroscopic techniques, mainly 1D and 2D NMR spectroscopy.