Hypericum species are distributed widely in China, especially in the southwest. This genus is rich in species types in China, including 55 species and 8 subspecies. The main chemical constituents of Hypericum species are flavonoids, xanthones and polycyclic polyprenylated acylphloroglucinols(PPAPs). PPAPs are characterized by polycyclic and branched-chain substitutions in their structures, which make their structure types diverse. Moreover, they have been found to have antitumor, antiviral, antibacterial, anti-inflammatory and other biological activities. This research classified and summarized 344 polycyclic polyprenylated acylphloroglucinols from Hypericum plants in order to provide a scientific basis for further development and utilization of PPAPs from the genus.
Flavonoids ; Hypericum ; Molecular Structure ; Phloroglucinol/pharmacology* ; Xanthones

OBJECTIVETo isolate and identify the active xanthone glycosides in Halenia elliptica.

METHODThe compounds were isolated by column chromatography, semi-preparative high performance liquid chromatography and related techniques. Their structures were elucidated through spectroscopic analysis (NMR and MS).

RESULTSix xanthone glycosides were isolated and identified as: 2,3,5-trimethoxy-1-O-primeverosyloxyxanthone (1), 2, 3, 4, 5-tetramethoxy-1-O-primeverosyloxyxanthone (2), 2, 3, 5, 7-tetramethoxy-1-O-primeverosyloxyxanthone (3), 2, 3, 7-trimethoxy-1-O-primeverosyloxyxanthone (4), 2, 3, 4, 7-tetramethoxy-1-O-primeverosyloxyxanthone (5), and 2, 3, 4, 5, 7-pentamethoxy-1-O-primeverosyloxyxanthone (6).

CONCLUSIONCompounds 4-6 were isolated from this plant for the first time.

Drugs, Chinese Herbal ; chemistry ; Gentianaceae ; chemistry ; Glycosides ; chemistry ; Xanthones ; chemistry

OBJECTIVETo study the chemical constituents from the whole plants of Polygala telephioides.

METHODCompounds were isolated by repeated silica gel and Sephadex LH -20 column chromatography, and their structures were determined by spectral analysis and physicochemical properties.

RESULTSix xanthones were isolated from P. telephioides, and their structures were identified as 1, 3, 7-trihydroxyxanthone (1), 1, 7-dihydroxy-3-methoxyxanthone (2), 1, 3-dihydroxyxanthone (3), 1, 7-dihydroxyxanthone (4), 1-methoxy-2, 3-methylenedioxyxanthone (5) and 1, 7-dimethoxyxanthone (6).

CONCLUSIONAll the compounds were obtained from this plant for the first time.

Plants, Medicinal ; chemistry ; Polygala ; chemistry ; Xanthones ; chemistry ; isolation & purification

To investigate the inhibitory effects of two xanthone compounds, 1-hydroxy-2,3,4,8-4 methoxy xanthone(here in after referred to as Fr15) and 1-hydroxy-2,3,4,6-4 methoxy xanthone(here in after referred to as Fr17), on the proliferation of hepatocellular carcinoma cells HepG2, and to further investigate their mechanism in combination with transcriptomics. Cell counting was used to detect the effects of two kinds of xanthone compounds Fr15 and Fr17(0, 0.03, 0.15, 0.3 mmoL·L~(-1)) on the proliferation of HepG2 cells; the effects of the two compounds Fr15 and Fr17 on HepG2 cell cycle were detected by flow cytometry; the changes of autophagosomes count in cells were observed under fluorescence microscope; the expression of autophagy marker proteins autophagy marker proteins SQSTM 1(p62) and microtubule associated protein 1 light chain 3 Ⅰ/Ⅱ(LC3 Ⅰ/Ⅱ) in the cells was detected by Western blot; the differentially expressed genes between the control group and the experimental group were analyzed by RNA-seq transcriptome sequencing; qRT-PCR was used to verify the differentially expressed genes in sequencing. The results showed that compounds Fr15 and Fr17 inhibited the proliferation of HepG2 cells with the increase of drug concentration and time. Flow cytometry showed that compounds Fr15 and Fr17 had little effect on HepG2 cell cycle. Fluorescence microscopy results showed that the number of autophagosomes in cells increased with the increase of drug concentration. Western blot showed that the expression of p62 protein was decreased and the expression of LC3-Ⅱ protein was significantly increased after drug addition. The results of RNA sequencing showed that 26 102 and 52 351 differentially expressed genes were obtained in Fr15 and Fr17 respectively. Analysis of KEGG showed that drug treatment had a great effect on autophagy pathway. qRT-PCR verified that 6 up-regulated genes were related to autophagy, and their trend was consis-tent with sequencing results, where all 6 genes showed an up-regulated trend. Two xanthone compounds Fr15 and Fr17 may inhibit proliferation of HepG2 cells by inducing autophagy.
Apoptosis ; Autophagy ; Cell Cycle ; Hep G2 Cells ; Xanthones

OBJECTIVETo identify the endophyte strain E8 with high activity from Curcuma wenyujin and study its secondary metabolites.

METHODThe strain E8 was identified by morphological observation and ITS sequence analysis. Manifold chromatographic methods were used to separate and purify the chemical constituents of fermentation broth from strain E8, and their structures were identified by physiochemical properties and spectral data.

RESULTThe strain E8 belongs to P. oxalicum. Four compounds were isolated from the fermentation broth of this strain and elucidated as chrysophanol, emodin, secalonic acid A and beta-sitosterol.

CONCLUSIONThe endophyte P. oxalicum was isolated from medicinal plant Curcuma wenyujin for the first time. Four compounds were first isolated from endophytic fungus in C. wenyujin. Thus, microbial fermentation is a new access for these compounds production.

Anthraquinones ; analysis ; Curcuma ; microbiology ; Emodin ; analysis ; Fermentation ; Penicillium ; genetics ; isolation & purification ; metabolism ; Sitosterols ; analysis ; Xanthones ; analysis

OBJECTIVETo study the metabolism of mangiferin by human intestinal bacteria in vitro.

METHODHuman intestinal bacteria and mangiferin were incubated under anaerobic conditions in vitro. The metabolite was separated and purified by D101 macroporous resin column and preparation high performance liquid chromatography, and its structure was identified by MS and NMR.

RESULTAfter 12 h incubation with human intestinal bacteria, the content of mangiferin metabolite reached the maximum, and it was determined as 1, 3, 6, 7-tetrahydroxyxanthen by MS and NMR.

CONCLUSIONMangiferin can be metabolized in vitro by human intestinal bacteria into its aglycone (1, 3, 6, 7-tetrahydroxyxanthen).

Bacteria ; metabolism ; Chromatography, High Pressure Liquid ; Humans ; Intestines ; microbiology ; Xanthones ; metabolism

To study the xanthones from the leaves of Calophyllum inophyllum Linn., several chromatography methods were employed to isolate the constituents. Investigation on the CHCl3 extract led to the isolation of a new xanthone named inophyxanthone A (1) and four known compounds, which were pancixanthone A (2), gerontoxanthone B (3), jacareubin (4) and pyranojacareubin (5). Among them, compound 2 was obtained from this plant firstly, and compound 3 was obtained for the first time from this genus. The structure of inophyxanthone A (1) was identified as 1, 3, 5-trihydroxy-2-(1, 1-dimethylallyl)xanthone by spectral analysis.
Calophyllum ; chemistry ; Molecular Structure ; Plant Leaves ; chemistry ; Plants, Medicinal ; chemistry ; Xanthones ; chemistry ; isolation & purification

To study xanthones from the barks of Garcinia xanthochymus, the constituents were isolated by normal-phase and reverse-phase silica gel column chromatography from the EtOAc extract. Their structures were elucidated by spectral analysis. Three new xanthones were purified and identified as 1,2,5-trihydroxy-6-methoxyxanthone (1), 1,4,6-trihydroxy-5-methoxyxanthone (2), 1,2,7-trihydroxy-4-(1,1-dimethylallyl) xanthone (3).
Garcinia ; chemistry ; Molecular Structure ; Plant Bark ; chemistry ; Plants, Medicinal ; chemistry ; Xanthones ; chemistry ; isolation & purification

AIMTo investigate the bioactive constituents from the mycelium of Penicillium thomii. Which isolated from Anemone collected in Qingdao beach.

METHODSThe constituents were separated by using various chromatography and the structures were identified on the basis of extensive spectral analysis.

RESULTSFive compounds, namely penicillixanthone A (I), p-methylbenzolic acid (II), 1-O-hexadecanoyl-2-O-(9-octadecenoyl)-3-O-(9, 12-octadecadienoyl) glycerol (III), 5 alpha, 8 alpha-epidioxy-24 zeta-methylcholesta-6, 22-dien-3 beta-ol (IV) and 1, 6, 8-trihydroxyl-3-methyl-9, 10-anthracenedione (V), were isolated from the mycelium of Penicillium thomii.

CONCLUSIONPenicillixanthone A is a new compound, while the others are isolated from Penicillium thomii for the first time.

Animals ; Molecular Conformation ; Molecular Structure ; Penicillium ; chemistry ; isolation & purification ; Sea Anemones ; microbiology ; Xanthones ; chemistry ; isolation & purification

OBJECTIVETo investigate the chemical constituents of the aerial parts of Polygala sibirica systematically.

METHODSThe chemical constituents were isolated by various column chromatographic methods. The structures were identified by spectral data.

RESULTTen compounds were isolated and identified as 6-hydroxy-1, 2, 3, 7-tetramethoxy xanthone (1); 1, 2, 3, 6, 7-heptamethoxy xanthone (2); 1, 7-didydroxy-2, 3-methylenedioxy xanthone (3); 1, 7-dihydroxy-2, 3-dimethoxy xanthone (4); 1, 3, 7-trihydroxy-2-methoxy xanthone (5); 1, 6, 7-trihydroxy-2, 3-dimethoxy xanthone (6); alpha-spinasterol (7); alpha-spinasterolic-3-O-beta-D-glucoside (8); squalene (9) and polygital (10).

CONCLUSIONCompounds 1-10 were isolated from this species for the first time.

Plant Components, Aerial ; chemistry ; Plant Extracts ; chemistry ; Polygala ; chemistry ; Xanthones ; chemistry