ABSTRACT
Four xanthones, α-mangostin (1), ß-mangostin (2), mangostenol (3), mangaxanthone B (4), three benzophenones, mangaphenone (5), benthamianone (6), congestiflorone (7) and one sterol, stigmasterol (8) were isolated from the stem barks of Garcinia mangostana L. and G. benthamiana (Planch. & Triana) Pipoly. Compounds 1, 2, 4 and 5 exhibited significant cytotoxicity through MTT assay towards MCF-7 and MDA-MB-231 cells with the IC50 values range from 4.4 to 12.0 µM. Remarkably, mangaphenone (5) showed non-cytotoxicity against normal Vero cells, revealing its potential as lead compound for anti-breast cancer drug. Structure-activity relationship postulated that the prenyl and hydroxyl groups present in xanthones are important in promoting anti-proliferative effects. Molecular docking simulation study of 1, 2, 4 and 5 with 2OCF and 4PIV implied that the induction of apoptosis for both cancer cells involve ER and FAS signaling pathways. Future study on the lead optimization of 5 is highly recommended.
Subject(s)
Breast Neoplasms , Garcinia mangostana , Garcinia , Xanthones , Animals , Breast Neoplasms/drug therapy , Chlorocebus aethiops , Female , Humans , Molecular Docking Simulation , Molecular Structure , Phytochemicals/pharmacology , Vero Cells , Xanthones/pharmacologyABSTRACT
A detailed chemical study on the ethyl acetate and methanol extracts of the stem bark of Garcinia mangostana resulted in the successful isolation of one new prenylated xanthone, mangaxanthone B (1), one new benzophenone, mangaphenone (2), and two known xanthones, mangostanin (3) and mangostenol (4). The structures of these compounds were elucidated through analysis of their spectroscopic data obtained using 1D and 2D NMR and MS techniques.
Subject(s)
Garcinia mangostana/chemistry , Plant Bark/chemistry , Plant Stems/chemistry , Benzophenones/chemistry , Clusiaceae/chemistry , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Structure , Xanthenes/chemistry , Xanthones/chemistryABSTRACT
A new coumarin, hoseimarin (1), together with four other xanthones, trapezifolizanthone (2), osajaxanthone (3), ß-mangostin (4) and caloxanthone A (5), were isolated from the stem bark of Calophyllum hosei. The structures of these compounds were established by using spectroscopic analysis which included (1)H NMR, (13)C NMR, COSY, DEPT, HMQC and HMBC experiments.
Subject(s)
Anti-Inflammatory Agents/isolation & purification , Calophyllum/chemistry , Coumarins/isolation & purification , Plants, Medicinal/chemistry , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Coumarins/chemistry , Coumarins/pharmacology , Isoflavones/chemistry , Isoflavones/isolation & purification , Lipopolysaccharides/pharmacology , Macrophages/drug effects , Mice , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Bark/chemistry , Xanthones/chemistry , Xanthones/isolation & purificationABSTRACT
Our phytochemical study on the stem bark of Garcinia mangostana has led to the discovery of a new furanoxanthone, mangaxanthone A (1), together with five known analogs. The five known analogs that were isolated are α-mangostin (2), ß-mangostin (3), cowagarcinone B (4), and dulcisxanthone F (5). The structural elucidations of these compounds were carried out by interpreting their spectroscopic data, mainly 1D and 2D NMR spectra and MS.
