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

The recent progresses on chemical components and pharmacological activities of the genus Gentiana were summarized. The main chemical constituents of this genus are iridoids, xanthone and flavone. There were more than ninety iridoid compounds, one hundred xanthone compounds, and thirty four flavone compounds isolated up till now. And flavone compounds were obtained mainly from aerial part. The plants of this genus had broad bioactivities such as antifungal activity, anti-inflammatory activity and liver protective effect. These mentioned above would be helpful for further studies on the plants of the genus Gentiana.
Animals ; Drugs, Chinese Herbal ; chemistry ; pharmacology ; Flavones ; Flavonoids ; chemistry ; pharmacology ; Gentiana ; chemistry ; Humans ; Xanthones ; chemistry ; pharmacology

The xanthones in the ethyl acetate extract of Comastoma pedunlulatum were investigated. The chromatographic and spectroscopic techniques were used to isolate and identify the constituents. Nine xanthones were isolated from the active parts of the ethyl acetate portion of the 70% ethanolic extract of C. Pedunlulatum, which possess the protective activity against hepatocyte damage caused by DL-GalN, and identified as 1,8-dihydroxy-2,6-dimethoxyxanthone (1), 8-hydroxy-1,2,6-trimethoxyxanthone (2), 1,6,8-trihydroxy-2-methoxyxanthone (3), 1,8-dihydroxy-3,5-dimethoxyxanthone (4), 1-hydroxy-3,5,8-trimethoxyxanthone (5), 1 -hydroxy-3,7-dimethoxyxanthone (6), 1,2,6,8-tetrahydroxyxanthone (7), 1,3,7-trihydroxy4- methoxyxanthone (8), 6,8-dihydroxy-1, 2-dimethoxyxanthone (9). Among them, compounds 6-9 were isolated from the genus Comastoma for the fist time.
Gentianaceae ; chemistry ; Plant Extracts ; analysis ; isolation & purification ; Xanthones ; analysis ; 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

OBJECTIVETo study the chemical constituents from the herb of Gentianopsis paludosa.

METHODColumn chromatogrophy and spectral analysis were used to isolate and identify the constituents.

RESULTSix compounds were isolated and identified as 1,7-dihydroxy-3,8-dimethoxyxanthone (I), 1-hydroxy-3, 7, 8-trimethoxyxanthone (II), 1, 8-dihydroxy-3, 7-dimethoxyxanthone (III), 1-hydroxy-3, 7-dimethoxyxanthone (IV), beta-sitosterol (V), daucosterol (VI).

CONCLUSIONCompounds III-VI were isolated from the plant for the first time.

Gentianaceae ; chemistry ; Plants, Medicinal ; chemistry ; Sitosterols ; chemistry ; isolation & purification ; Xanthones ; chemistry ; isolation & purification

An HPLC method for simultaneous determination of chlorogenic acid and mangiferin in original medicinal materials and decoction pieces of Pyrrosiae Folium was developed. The assay was performed on a Diamonsil C18 (4.6 mm x 250 mm, 5 microm) column eluted with a mobile phase consisted of acetonitrile and 0.5% phosphoric acid solution in gradient elution at a flow rate of 1.0 mL x min(-1). The column temperature was set at 25 degrees C. The detection wavelength was 320 nm. The results showed that The linear ranges of chlorogenic acid and mangiferin were 5.2-130 mg x L(-1) (r = 0.9999) and 1.2-18 microg x mL(-1) (r = 0.9999), and the average recoveries (n=6) were 97.9% (RSD 1.9%) and 99.6% (RSD 2.9%), respectively. The method was simple, reproducible and valid. It can be used for quality evaluation and control of original medicinal materials and decoction pieces of Pyrrosiae Folium.
Chlorogenic Acid ; analysis ; Chromatography, High Pressure Liquid ; Plants, Medicinal ; chemistry ; Reproducibility of Results ; Xanthones ; analysis

AIMTo study the active constituents of Swertia davidi Franch..

METHODSChromatography was used to isolate and purify the chemical components, their structures were identified by spectral analysis.

RESULTSThree compounds were identified as 1,7-dihydroxy-3,8-dimethoxyxanthone (gentiacaulein) (V), 1,8-dihydroxy-3,7-dimethoxyxanthone (methylswertianin) (VI) and 1,8-dihydroxy-3,4,7-trimethoxyxanthone (VII).

CONCLUSIONCompound VII is a novel xanthone, named daviditin A, the others were isolated from Swertia davidi Franch. for the first time.

Molecular Structure ; Plants, Medicinal ; chemistry ; Swertia ; chemistry ; Xanthones ; chemistry ; isolation & purification