Hyperforin is a representative polycyclic polyprenylated acylphloroglucinols (PPAPs) that exerts a variety of pharmacological activities. The complete biosynthesis pathway of hyperforin has not been elucidated due to its complex structure and unclear genetic background of its source plants. This mini-review focuses on the bioactivity and biosynthesis of hyperforin. These analyses can provide useful insights into the biosynthesis investigations of hyperforin and other PPAPs with complex structures.
Phloroglucinol/chemistry* ; Terpenes/chemistry* ; Hypericum/chemistry* ; Molecular Structure

OBJECTIVETo investigate the chemical constituents from the aerial parts of Hyperricum monogynum.

METHODCompounds were isolated by various column chromatography and identified by spectral analysis.

RESULTTen compounds were isolated and identified as quercetin, quercitrin, hyperoside, rutin, (-)-epicatechin, 3,5-dihydroxy-1-methoxy-xanthone, 3,4-O-isopropylidenyl shikimic acid, shikimic acid, daucosterol, and oleanoic acid.

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

Hypericum ; chemistry ; Plant Components, Aerial ; chemistry ; Plants, Medicinal ; chemistry ; Quercetin ; analogs & derivatives ; chemistry ; isolation & purification

OBJECTIVETo investigate the chemical constituents of Hypericum petiolulatum.

METHODThe chemical constituents were isolated and purified by column chromatography on silica gel, macroporous adsorbent resin, Sephadex LH-20, and preparative HPLC. Structures of the compounds were identified by NMR and MS spectroscopic methods.

RESULTNine lignans were obtained and their structures were elucidated as (-)-(2R, 3R)-1-O-feruloyl-8,8'-bisdihydrosiringenin (1), (-) -secoisolariciresinol 4-O-beta-D-glucopyrano-side (2), isolariciresinol-beta-4'-O-beta-D-glucopyranoside (3), 5-methoxy-9beta-xylopyra-nosyl-(+) -isolariciresinol (4), (+) -lyoniresinol 2alpha-O-beta-D-xylopyranoside (5), 5-methoxy-9-beta-xylopyranosyl-(-) -isolariciresinol (6), isolariciresinol 6a-O-beta-D-gluco-side (7), (+)-lyoniresinol 3alpha-O-beta-D-xylopyranoside (8) and 7-methoxy-5-benzofuranpropanol 4'-O-beta-D-glucopyranoside (9).

CONCLUSIONCoupound 1 was new and compounds 2-9 were obtained from the genus Hypericum for the first time.

Drugs, Chinese Herbal ; chemistry ; Hypericum ; chemistry ; Lignans ; chemistry ; Magnetic Resonance Spectroscopy ; Mass Spectrometry

The chemical constituents in the ethanol extract of Hypericum wightianum(Hypericaceae) were purified by column chromatography and identified via magnetic resonance imaging(NMR), high-resolution mass spectrum, and circular dichroism. A total of 22 compounds were identified, including eight polyprenylated phloroglucinols(1-8), three chromones(9-11), and three terpenoids(14-16) and so on. Among them, compounds 16 and 17 were first reported in the genus Hypericum, and compounds 1-11, 14, 15, and 19 were first isolated from H. wightianum. Compounds 1-4 were previously reported as two pairs of enantiomers. This study reported the chiral resolutions and absolute configurations of compounds 1-4 for the first time.
Phloroglucinol ; Hypericum/chemistry* ; Molecular Structure ; Magnetic Resonance Spectroscopy ; Drugs, Chinese Herbal/chemistry*

Repeated silica gel column chromatography, reversed-phase C_(18) column chromatography, Sephadex LH-20 column chromatography, high performance liquid chromatography and semi-preparative medium pressure liquid chromatography were performed to separate and purify the chemical constituents of Hypericum lagarocladum. Spectroscopic methods such as mass spectrometry(MS) and nuclear magnetic resonance(NMR) combined with physicochemical properties were adopted in identifying the structure of the isolated compounds. Ten compounds were isolated from the ethyl acetate fraction of H. lagarocladum and identified as lagarxanthone A(1), 1,7-dihydroxyxanthone(2), 3,4,5-trihydroxyxanthone(3), 2,7-dihydroxy-1-methoxyxanthone(4), 1,3-dihydroxy-7-methoxyxanthone(5), 1,5-dihydroxy-8-methoxyxanthone(6), 3,4-dihydroxy-2-methoxyxanthone(7), 3,4-dihydroxy-5-methoxyxanthone(8), 2,3-dimethoxyxanthone(9), and 2,3,4-trimethoxyxanthone(10). Among them, compound 1 was a new compound, and compounds 2-10 were isolated from this plant for the first time. These ten compounds were tested for glucose uptake in L6 cells, and the results showed that all the compounds had no significant effect on glucose uptake.
Hypericum/chemistry* ; Xanthones ; Chromatography, High Pressure Liquid ; Magnetic Resonance Spectroscopy ; Glucose

Five new polycyclic polyprenylated acylphloroglucinols (1-5), ascyrones A-E, and four known compounds (6-9) were isolated from the aerial parts of Hypericum ascyron. All of the isolates containing a bicyclo[3.3.1]nonane-2,4,9-trione core and a benzoyl group, belonged to type B bicyclic polyprenylated acylphloroglucinols (BPAPs). Their structures and absolute configurations were established based on spectroscopic analyses and calculated electronic circular dichroism (ECD) data. The anti-inflammatory, neuroprotective and cytotoxicity activities of compounds 1-4 and 6-9 were evaluated. Compound 6 exhibited obvious anti-inflammatory activity in lipopolysaccharide (LPS)-induced RAW264.7 cells. Compounds 1 and 9 exhibited slight cytotoxicity against Hep3B cells. Meanwhile, compound 1 showed mild neuroprotective activity against corticosterone (CORT)-induced PC12 cell damage at 10 μmol·L^-1.
Animals ; Anti-Inflammatory Agents/pharmacology* ; Hypericum/chemistry* ; Molecular Structure ; PC12 Cells ; Phloroglucinol/pharmacology* ; Rats

OBJECTIVETo establish a high performance capillary electrophoresis method with diode array detection (HPCE-DAD) for simultaneous determination of rutin, isoquercitrin, hyperoside, quercitrin, kaempferol and quercetin in Hyperici Japonici Herba.

METHODBased on the mode of capillary zone electrophoresis, 40 mmol x L(-1) borax was used as buffer solution (pH 8.62), uncoated fused silica capillary (56 cm x 64.5 cm x 75 microm) was used, separation voltage was 25 kV, detection wavelength was at 206 nm, column temperature was maintained at 25 degrees C, and sample was injected at 50 mbar, 8 s.

RESULTSix flavonoids showed good linearity (r > 0.9953) in the range of the tested concentration, the average recoveries of the method were between 98.8%-102.9%.

CONCLUSIONThe method is simple, accurate and reproducible, and can be used for quality control of Hyperici Japonici Herba.

Electrophoresis, Capillary ; methods ; Flavonoids ; analysis ; Hydrogen-Ion Concentration ; Hypericum ; chemistry ; Temperature

This study employed the α-glucosidase inhibitory activity model as an anti-diabetic assay and implemented a bioactivity-guided isolation strategy to identify novel natural compounds with potential therapeutic properties. Hypericum sampsoniiwas investigated, leading to the isolation of two highly modified seco-polycyclic polyprenylated acylphloroglucinols (PPAPs) (1 and 2), eight phenolic derivatives (3-10), and four terpene derivatives (11-14). The structures of compounds 1 and 2, featuring an unprecedented octahydro-2H-chromen-2-one ring system, were fully characterized using extensive spectroscopic data and quantum chemistry calculations. Six compounds (1, 5-7, 9, and 14) exhibited potential inhibitory effects against α-glucosidase, with IC₅₀ values ranging from 0.050 ± 0.0016 to 366.70 ± 11.08 μg·mL^-1. Notably, compound 5 (0.050 ± 0.0016 μg·mL^-1) was identified as the most potential α-glucosidase inhibitor, with an inhibitory effect about 6900 times stronger than the positive control, acarbose (IC₅₀ = 346.63 ± 15.65 μg·mL^-1). A docking study was conducted to predict molecular interactions between two compounds (1 and 5) and α-glucosidase, and the hypothetical biosynthetic pathways of the two unprecedented seco-PPAPs were proposed.
Molecular Structure ; Hypericum/chemistry* ; alpha-Glucosidases ; Magnetic Resonance Spectroscopy ; Glycoside Hydrolase Inhibitors/pharmacology*

OBJECTIVETo study the constituents of Hypericum attenatum.

METHODThe compounds were isolated by chromatography on silica gel, the structures were identified by their physical, chemical properties and IR, NMR and MS spectral data respectively.

RESULTNine compounds were isolated and identified as p-hydroxybenzoic acid (1), 6, 9-dihydroxy-4, 7-megastigmadien-3-one (2), butyl alcohol-O-alpha-D-fructoside (3), 24-ethyl-cholest-7-ene-3 beta, 5 alpha, 6 beta-thtroil (4), hexanol (5), 1 beta, 6 alpha-dihydroxyeudesmane-4(14)-ene (6), beta-sitosterol (7), 5, 5-dimethyl-4-hydroxy-tetrahydrofuran-2-one (8), beta-daucosterol (9).

CONCLUSIONAll of the compounds were isolated from H. attenuatum for the first time.

Hexanols ; chemistry ; isolation & purification ; Hypericum ; chemistry ; Norisoprenoids ; chemistry ; isolation & purification ; Parabens ; chemistry ; isolation & purification ; Plant Components, Aerial ; chemistry ; Plants, Medicinal ; chemistry

OBJECTIVETo study the chemical constituents from Hypericum perforatum.

METHODCompouds were isolated by chromatographic techniques. Their structures were identified by spectral methods. The inhibitory activity of recombinant human PTP1B was evaluated.

RESULTNine compounds were elucidated as D-Mannitol (1), 1,2-benzenedicarboxylic acid bis(1-methylpropyl) ester (2), (7E, 6R,9S)-9-hydroxy-4,7-megastigmadien-3-one (3), (6S,9R)-roseoside (4) , 2,6-dimethoxy-4-hydroquinone-l-O-beta-D-glucopyranoside (5), 2,6-di-methoxy-4-hydroxybenzyl alcohol 1 -O-beta-D-glucopyranoside (6), syringate 4-O-beta-glucopyranoside (7), hypericin (8), skyrin-6-0-beta-D-glucopyranoside (9) , (R)-2,3-dihydroxypropyl 3,4-dihydroxy-benzoate (10). At a concentration of 2 micromol x L(-1), compound 8 inhibited recombinant human PTP1B with inhibitory rate of 96.4% and IC50 of 2.5 micromol x L(-1).

CONCLUSIONcompound 10 was new, compounds 2-4, 7 were obtained from Hypericum for the first time and compounds 5-6 was isolated from this plant for the first time. Compound 8 showed remarkable PTP1B inhibitory activity.

Anthraquinones ; chemistry ; isolation & purification ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Glucosides ; chemistry ; isolation & purification ; Hypericum ; chemistry ; Molecular Structure ; Norisoprenoids ; chemistry ; isolation & purification