Two new xanthones from the pericarp of Garcinia mangostana

Two new xanthones, designated garcimangosxanthone F (1) and garcimangosxanthone G (2), were isolated from the EtOAc-soluble fraction of ethanolic extract from the pericarp of Garcinia mangostana. Their structures were established as 1,6,7-trihydroxy-5-(3-methylbut-2-enyl)-8-(3-hydroxy-3-methylbutyl)-6′,6′-dimethylpyrano[2′,3′:3,2]xanthone and 1,6,7-trihydroxy-5-(3-methylbut-2-enyl)-8-(3-hydroxy-3-methylbutyl)-6′,6′-dimethyl-4′,5′-dihydropyrano[2′,3′:3,2]xanthone, respectively, on the basis of their 1D, 2D NMR and MS data interpretation.     

Mangostanaxanthone VIII,a new xanthone from Garcinia mangostana and its cytotoxic activity

A new prenylated xanthone, mangostanaxanthone VIII (7) and six known metabolites: gartanin (1), 1,3,8-trihydroxy-2-(3-methyl-2-butenyl)-4-(3-hydroxy-3-methylbutanoyl)-xanthone (2), rubraxanthone (3), 1,3,6,7-tetrahydroxy-8-prenylxanthone (4), garcinone C (5), and xanthone I (9-hydroxycalabaxanthone) (6) were separated from the EtOAc-soluble fraction of the air-dried pericarps of Garcinia mangostana (Clusiaceae). Their structures have been verified on the basis of spectroscopic data analysis as well as comparison with the literature. The cytotoxic activity of 7 was assessed against MCF7, A549, and HCT116 cell lines using sulforhodamine B (SRB) assay. Compound 7 showed significant cytotoxic potential against MCF7 and A549 cell lines with IC₅₀s 3.01 and 1.96 μM, respectively compared to doxorubicin (0.06 and 0.44 μM, respectively). However, it exhibited moderate activity towards HCT116 cell line.     

A novel xanthone dimer derivative with antibacterial activity isolated from the bark of Garcinia mangostana

A novel xanthone dimer derivative, garmoxanthone (1), together with 10 known compounds (2–11), were isolated from bark of Garcinia mangostana. Their structures were established through spectroscopic methods. Garmoxanthone exhibited strong inhibitory activities against MRSA ATCC 43300 and MRSA CGMCC 1.12409 (with MIC values of both 3.9 μg/mL) and moderate activities against tested strains of Vibrio (with MIC values ranging from 15.6 to 31.2 μg/mL). Garmoxanthone is a unique xanthone dimer with linkage of a fused 5/6 ring system and its absolute configuration was elucidated on the basis of experimental and calculated electronic circular dichroism. Garmoxanthone exhibited strong antibacterial activity which partially validated the ethnobotanical use of G. mangostana in the treatment of infections.     

Two New Prenylated Xanthones from the Pericarp of Garcinia mangostana (Mangosteen)

Two new prenylated xanthones (=9H‐xanthen‐9‐ones), garcimangosxanthones D ( 1 ) and E ( 2 ), together with the six known xanthones 3 – 8 , were isolated from the pericarp of Garcinia mangostana. Their structures were determined by analysis of their spectroscopic data. All of the isolated compounds were biologically evaluated for their in vitro cytotoxic activity against A549, Hep‐G2, and MCF‐7 human‐cancer cell lines and antioxidant activity. Compound 1 exhibited moderate cytotoxicity against Hep‐G2 (IC₅₀=19.2 μM ) and weak cytotoxicity against MCF‐7 (IC₅₀=62.8 μM ) cell lines, and compound 2 showed moderate cytotoxicity against A549, Hep‐G2, and MCF‐7 cell lines with IC₅₀ values of 12.5–20.0 μM (Table 2). Both compounds 1 and 2 demonstrated a weak antioxidant activity with ferric reducing antioxidant power (FRAP) values of 41±7 and 130±4 μmol/g, respectively (Table 3).     

Antioxidant Properties of Garcinia Mangostana L (Mangosteen) Rind

Many diseases correlate with antioxidant deficiencies. Garcinia mangostana L rind (GMR) belong to waste product, contains xanthones which are antioxidant compounds. The aim of this study was to determine antioxidant properties of its ethanolic extract, hexane, ethylacetate, butanol, and water fractions in DPPH scavengingactivity, level of SOD and total antioxidant (TAS) compared against α-mangostin. Extract and all of these fractions had high DPPH trapping activity while α-mangostin had low activity. Level of SOD was highest in GMR water fraction while TAS level was highest in GMR ethylacetate fraction. It was concluded that GMR products had potential antioxidant properties     

Multitarget Action of Xanthones from Garcinia mangostana against α-Amylase, α-Glucosidase and Pancreatic Lipase

Digestive enzymes such α-amylase (AA), α-glucosidase (AG) and pancreatic lipase (PL), play an important role in the metabolism of carbohydrates and lipids, being attractive therapeutic targets for the treatment of type 2 diabetes and obesity. Garcinia mangostana is an interesting species because there have been identified xanthones with the potential to inhibit these enzymes. In this study, the multitarget inhibitory potential of xanthones from G. mangostana against AA, AG and PL was assessed. The methodology included the isolation and identification of bioactive xanthones, the synthesis of some derivatives and a molecular docking study. The chemical study allowed the isolation of five xanthones (1–5). Six derivatives (6–11) were synthesized from the major compound, highlighting the proposal of a new solvent-free methodology with microwave irradiation for obtaining aromatic compounds with tetrahydropyran cycle. Compounds with multitarget activity correspond to 2, 4, 5, 6 and 9, highlighting 6 with IC₅₀ values of 33.3 µM on AA, 69.2 µM on AG and 164.4 µM on PL. Enzymatic kinetics and molecular docking studies showed that the bioactive xanthones are mainly competitive inhibitors on AA, mixed inhibitors on AG and non-competitive inhibitors on PL. The molecular coupling study established that the presence of methoxy, hydroxyl and carbonyl groups are important in the activity and interaction of polyfunctional xanthones, highlighting their importance depending on the mode of inhibition.     

A Novel Xanthone from Garcinia oligantha

One novel xanthone, oliganthone A ( 1 ), was isolated from the stems of the plant Garcinia oligantha. It features the O‐bearing C(3)‐atom and absence of C(4) compared with the structures of related known xanthones, which have never been reported before. The structure of this compound was elucidated by spectroscopic analysis. Compound 1 showed strong HeLa cell growth‐inhibiting effects with IC₅₀ values below 10 μM .     

A new prenylated biflavonoid from the leaves of Garcinia dulcis

A new prenylated biflavonoid, named dulcisbiflavonoid A, together with five biflavonoids were isolated from the leaves of Garcinia dulcis. Their structures were elucidated by analysing their spectroscopic data, especially 1D and 2D NMR.     

Application of Phytochemical and Elemental Profiling,Chemometric Multivariate Analyses,and Biological Activities for Characterization and Discrimination of Fruits of Four Garcinia Species

Abstract

Species of Garcinia (Guttiferae) are used for flavoring curries, as a supplement, and to treat various diseases. This study describes the comparison and discrimination of Garcinia cambogia, Garcinia indica, Garcinia mangostana and Garcinia atroviridis fruits by analyzing their major phytochemicals, elemental content, antioxidant, antidiabetic, and anticholinesterase enzymes activities. For phytochemical and elemental profiling, ultraviolet (UV), near infrared/infrared (NIR/IR), inductively coupled plasma-optical emission spectroscopy (ICP-OES) and ICP-mass spectrometric (ICP-MS) techniques were used. The chemometric multivariate tests of linear discriminant and principal component analyses (LDA, PCA) were used to discriminate the subject fruit samples. Spectroscopic data showed resonances of phenolics and flavonoidal constituents present in the fruits. G. mangostana exhibited the highest phenolics (721.6 to 2815.3?µM GAE/g), whereas G. cambogia was rich in flavonoids (51.9 to 2709.2?µM QE/g). Anthocyanin (cyanidin-3-O-glucoside) evaluated by high performance liquid chromatographic was 9.01?mg/kg in G. mangostana fruit. In the analyzed fruits, Ca, K and Na were high, trace essential elements were at appreciable contents, whereas the toxic elements As, Cd, Tl, and Pb were within the safe limits. G. mangostana contained potent free radicals and cholinesterase enzyme inhibitors, whereas G. cambogia inhibited α-amylase enzyme more significantly. PCA and LDA discriminated the fruit samples with distinct classification and variability indices. The analyzed fruits were shown to be good sources of free radicals, cholinesterase, and α-amylase enzymes inhibition, mineral and essential elements, and safe for human consumption.     

A new depsidone derivative from the leaves of Garcinia polyantha

One new depsidone, polyanthadepsidone A (1), together with four known compounds were isolated from the dichloromethane extract of the leaves of Garcinia polyantha. The structures of all compounds were determined by comprehensive analyses of their 1D and 2D NMR and EI mass spectral data. All the isolates exhibited suppressive effect on phagocytosis response upon activation with serum opsonised zymosan in the IC₅₀ range of 4.5–23.80 μM, tested in vitro for oxidative burst studies of whole blood.     

A new antioxidant xanthone from the pericarp of Garcinia mangostana Linn

The air-dried fruit hulls of Garcinia mangostana Linn. were extracted with 85% ethanol. Furthermore, a new xanthone, 1,3,6-trihydroxy-2,5-bis(3-methylbut-2-enyl)-6',6'-dimethyl-4',5'-dihydropyrano[2',3':7,8]xanthone, along with five known xanthones related to their antioxidant activity was purified by silica gel column chromatography and then identified using spectroscopic methods (1D and 2D NMR, MS). The antioxidant activities were evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging capability. An activity-guided isolation and purification process were used to identify the components, showing the strong DPPH radical-scavenging activity of G. mangostana.     

Polyprenylated Xanthones and Benzophenones from the Bark of Garcinia oblongifolia

A new polyprenylated xanthone (=9H‐xanthen‐9‐one) and a new polyprenylated benzophenone, namely oblongifolixanthone A ( 1 ) and garciniagifolone A ( 2 ), were isolated from the bark of Garcinia oblongifolia, together with five known compounds including the four xanthones 3 – 5 and 7 and a benzophenone 6 . The structures of 1 and 2 were established by detailed analysis of their spectroscopic data, especially 1D‐ and 2D‐NMR spectra and HR‐ESI‐MS data. All these compounds were assayed for their cytotoxic activities against three human tumor cell lines (HeLa, SGC7901, and HepG2). The 1,3,6,7‐tetrahydroxy‐9H‐xanthen‐9‐one ( 3 ) was inactive, and the other compounds showed weak to moderate activity.     

Novel and anti-inflammatory constituents of Garcinia subelliptica

Four novel phloroglucinol derivatives, garcinielliptones A (1), B (2), C (3), D (4), a novel triterpenoid, garcinielliptone E (5), and three known compounds were isolated from the seeds of Garcinia subelliptica. The structures, including relative configurations, were elucidated by means of spectroscopic data. Known compounds garsubellin A (6) and garcinielliptin oxide (7) showed potent inhibitory effects on the release of beta-glucuronidase, and beta-glucuronidase and histamine, respectively, from peritoneal mast cells stimulated with compound 48/80 in a concentration-dependent manner with IC(50) values of 15.6+/-2.5, and 18.2+/-3.6 and 20.0+/-2.7 microM, respectively. Compound 7 showed potent inhibitory effects on the release of beta-glucuronidase and lysozyme from neutrophils stimulated with formyl-Met-Leu-Phe(fMLP)/cytochalasin B (CB) in a concentration-dependent manner with IC(50) values of 15.7+/-3.0 and 23.9+/-3.2 microM, respectively. Compound 7 also showed potent inhibitory effect on superoxide formation from neutrophils stimulated with fMLP/CB also in a concentration-dependent manner with an IC(50) value of 17.9+/-1.5 microM.     

A Highly Rearranged Pentaprenylxanthonoid from the Resin of Garcinia hanburyi

Gamboketanol ( 1 ), a highly rearranged pentaprenylated xanthonoid, two new caged pentaprenylated xanthonoids, gambogefic acid A ( 2 ) and gambogellic acid A ( 3 ), together with two known compounds, were isolated from the acetone extract of the resin of Garcinia hanburyi. Their structures were established on the basis of extensive spectroscopic and mass‐spectrometric analyses. The cytotoxicity of compounds 1 – 3 against HeLa tumor cell line was evaluated, with all of them being modestly active.     

A new cytotoxic caged polyprenylated xanthone from the resin of Garcinia hanburyi

A new caged polyprenylated xanthone, gambogic aldehyde （1）, was isolated from the resin of Garcinia hanburyi. Its structure was elucidated on the basis of spectral data including 1D and 2D NMR data. In addition, the antiproliferative ability of compound 1 was determined in mouse leukemia P388 and P388/ADR cells.     

A new dihydrofurocoumarin from the fruits of Pandanus tectorius Parkinson ex Du Roi

From the fruit of Pandanus tectorius Parkinson ex Du Roi, one new dihydrofurocoumarin, named pandanusin A (1) and 15 known compounds, including one furanocoumarin (2), two coumarins (3, 4), four lignans (5–8), one neolignan (9), two flavonoids (10, 11), three phenolics (12–14), one monoglyceride (15) and one monosaccharide (16) were isolated by various chromatography methods. Among them, compounds (3–5) were obtained from the Pandanus genus for the first time and compounds (9–14, 16) were reported from this species for the first time. Their structures were elucidated by HR–ESI–MS, NMR 1D and 2D experiments and comparison with previous reported data. The α-glucosidase inhibitory activity of all compounds was measured. The isolated compounds (1–12, 14) showed better α-glucosidase inhibitory activity (IC₅₀ = 42.2, 36.5, 84.7, 73.2, 40.8, 26.7, 76.5, 33.8, 68.1, 14.4, 22.1, 81.5, 43.8 μM, respectively) than the standard drug acarbose (IC₅₀ = 214.5 μM).     

A new cytotoxic polycyclic polyprenylated acylphloroglucinol from Garcinia nujiangensis screened by the LC-PDA and LC-MS

Abstract

A new polycyclic polyprenylated acylphloroglucinol (1), nujiangefolin D, together with five known analogues (2–6), were isolated from the fruits of Garcinia nujiangensis. Compound 1 was screened by the LC-MS and LC-PDA. The structure of 1 was elucidated on the basis of extensive spectroscopic techniques including 1?D and 2?D NMR and MS analyses. The compounds isolated were evaluated for their cytotoxic activities against three cancer cell lines, 1 showed moderate cytotoxic activity against Hela, PANC-1, and MDA-MB-231 cell lines with IC₅₀ values of 5.6?±?0.1, 9.1?±?0.2, and 8.3?±?0.2?μM, respectively. The antitumor mechanism was explained via virtual docking of 1 to the main sites in the human serine/threonine-protein kinase mTOR (mTOR) crystal structure (PDB code: 4DRI). Furthermore, 1 may inhibit Hela cell proliferation through mTOR by the western blotting analysis. Taken together, 1 may be a potential mTOR inhibitor used for the treatment of cervical cancer.     

Structure elucidation and NMR spectral assignment of five new xanthones from the bark of Garcinia xanthochymus

Five new xanthones, namely Garcinexanthones A-E (1-5), were isolated from the barks of Garcinia xanthochymus. Their structures were elucidated by spectral analysis, primarily NMR, MS, and UV. The complete assignments of the (1)H NMR and (13)C NMR chemical shifts for the compounds were achieved by using 1D and 2D NMR techniques, including DEPT, HSQC, and HMBC NMR experiments.     

A new triterpenoid glucoside from Leucas zeylanica

Abstract

A new triterpenoid glucoside, leuctriterpencoside (1), along with two known compounds (2–3) were isolated from Leucas zeylanica. The structure of the new compound was elucidated using comprehensive spectroscopic methods. Compound 1 showed significant inhibitory activity against α-glucosidase (IC₅₀ value of 0.85?±?0.12?μM).     

Molecular docking studies and in vitro cholinesterase enzyme inhibitory activities of chemical constituents of Garcinia hombroniana

Garcinia species are reported to possess antimicrobial, anti-inflammatory, anticancer, anti-HIV and anti-Alzheimer's activities. This study aimed to investigate the in vitro cholinesterase enzyme inhibitory activities of garcihombronane C (1), garcihombronane F (2), garcihombronane I (3), garcihombronane N (4), friedelin (5), clerosterol (6), spinasterol glucoside (7) and 3β-hydroxy lup-12,20(29)-diene (8) isolated from Garcinia hombroniana, and to perform molecular docking simulation to get insight into the binding interactions of the ligands and enzymes. The cholinesterase inhibitory activities were evaluated using acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. In this study, compound 4 displayed the highest concentration-dependent inhibition of both AChE and BChE. Docking studies exhibited that compound 4 binds through hydrogen bonds to amino acid residues of AChE and BChE. The calculated docking and binding energies also supported the in vitro inhibitory profiles of IC₅₀. In conclusion, garcihombronanes C, F, I and N (1–4) exhibited dual and moderate inhibitory activities against AChE and BChE.