Topic
Xanthone
About: Xanthone is a research topic. Over the lifetime, 1639 publications have been published within this topic receiving 25870 citations. The topic is also known as: 9-oxo-xanthene & Diphenyline ketone oxide.
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TL;DR: A new caged-tetraprenylated xanthone, hanburinone (1), was isolated from the fresh fruits of Garcinia hanburyi together with four known Caged-Tetramerylated Xanthones; isomoreollin B (2), morellin (3), moreollic acid (4), and morellic acid(5), which showed moderately antibacterial activity against methicillin-resistant Staphylococcus aureus as discussed by the authors.
Abstract: A new caged-tetraprenylated xanthone, hanburinone (1), was isolated from the fresh fruits of Garcinia hanburyi together with four known caged-tetraprenylated xanthones; isomoreollin B (2), morellin (3), moreollic acid (4) and morellic acid (5). Their structures were elucidated by analysis of spectroscopic data and comparison of the NMR data with those reported previously. Compounds 4 and 5 showed moderately antibacterial activity against methicillin-resistant Staphylococcus aureus with a MIC value of 25 microg/ml.
12 citations
TL;DR: A new xanthone glycoside, sporormielloside, was isolated from an EtOAc extract of an endolichenic fungal strain Sporormiella irregularis and their plausible biosynthetic pathway was deduced.
Abstract: A new xanthone glycoside, sporormielloside (1), was isolated from an EtOAc extract of an endolichenic fungal strain Sporormiella irregularis (No. 71-11-4-1), along with two known xanthones (2, 3). Their structures were determined by detailed spectroscopic analysis (IR, MS, and 1D- and 2D-NMR), a chemical method, and a comparison of NMR data with closely related compounds previously reported. According to the structures of isolated compounds, their plausible biosynthetic pathway was deduced.
12 citations
TL;DR: The results indicate that synthesis of aminoalkanol derivatives of xanthone may lead to successful establishment of new potential anticancer chemicals, and the highest activity to inhibit motility and migration of cancer cells was demonstrated by 7, 12, 15, and by α-mangostin.
Abstract: A series of 15 derivatives of xanthone were synthesized and evaluated for the anticancer activity. The structure of the tested compounds was diversified to establish structureactivity relationships. The following evaluations were carried out: cytotoxicity-proliferation tests, apoptosis detection, expression of apoptosis and proliferation-related genes, expression and activity of gelatinases A and B, wound migration assays, and cell adhesion to MatrigelTMcoated plates. Four compounds (7, 12, 13 and 15) displayed direct cytotoxicity at micromolar concentrations toward the studied cell lines. They also significantly affected the expression of proliferationapoptosis markers, and 13 demonstrated as strong influence as α-mangostin, that served as a natural standard in our study. These four compounds also decreased the expression and activity of gelatinases, and inhibited the migration-motility potential of cancer cells. The influence of compounds 7 and 12 on MMPs mRNA levels even exceeded the activity of α-mangostin and shRNA-mediated silencing; zymography revealed that 7, 13 and 15 were as equally active as α-mangostin, despite their higher IC50 values. The highest activity to inhibit motility and migration of cancer cells was demonstrated by 7, 12, 15, and by α-mangostin; and this was almost equal to shRNA-mediated silencing. Structural features predetermining compound activity were: substitution at position C4 instead of C2, and presence of a chlorine atom and allyl moiety. These results indicate that synthesis of aminoalkanol derivatives of xanthone may lead to successful establishment of new potential anticancer chemicals.
12 citations
TL;DR: Two xanthones, 1,6-dihydroxy-4,5-dimethoxyxanthone (1) and 1,5,6trihydroxy-7,8-di(3-methyl-2-butenyl)-6′,6′-dimethylpyrano(2′,3′:3,4) xanthone as discussed by the authors, were isolated from the bark of Garcinia xanthochymus by normal phase and reverse phase silica gel column chromatography.
12 citations
TL;DR: In this article, the structures of (13a) and (17) were cosnfirmed using the long-range selective proton decoupling (LSPD) method.
Abstract: 2-[3-(1-Oxo-3-aminobut-2-enyl)-7-methoxy-5-methyl-4-oxo-4H-benzopyran-2-ylmethyl]dioxolans, (7a and b), with an ethoxycarbonylmethyl or methyl substituent on the 2-position, have been synthesised starting with three precursors corresponding to β-tetra-, β-tri-, and β-di-carbonyl compounds. Acid treatment of the 2-ethoxycarbonylmethyl compound (7a) afforded ethyl 3-(1-hydroxy-6-methoxy-3,8-dimethyl-9-oxoxanthen-2-yl)-3-oxopropanoate (13a) as the major product together with three minor products, including ethyl 2-acetyl-1-hydroxy-6-methoxy-8-methyl-9-oxoxanthen-3-ylacetate (11); whereas the 2-methyl compound (7b) yielded 2-acetyl1-hydroxy-6-methoxy-3,8-dimethylxanthen-9-one (13b), exclusively. The structures of (13a) and (17) were cosnfirmed by 13C n.m.r. Spectroscopy using the long-range selective proton-decoupling (LSPD) method. Formation of (13a) from (7a) is explained in terms of a Wessely–Moser rearrangement of the intermediary benzopyranone (9a) or the xanthone (10a) under mild acidic conditions. Base-catalysed cyclisation of the xanthone3-acetate (11) gave 8,10,11-trihydroxy-3-methoxy-1-methyl-12H-benzo[b]xanthen-12-one (20) in excellent yield.
12 citations