A new polycyclic polyprenylated acylphloroglucinol from Hypericum pseudohenryi / 药学学报

Eight polycyclic polyprenylated acylphloroglucinols (PPAPs) were isolated from the 95% ethanol extract of Hypericum pseudohenryi by MCI column, silica gel column and preparative HPLC. These compounds were defined as hypseudohenrin L (1), hyperbeanin P (2), furohyperforin (3), furoadhyperforin (4), ascyronone F (5), attenuatumione E (6), hyphenrone T (7) and hyperforatone N (8), compound 1 is a new compound. Compounds 1, 3, 5, 7 showed an inhibitory effect on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in macrophage cells.

Ascyrones A-E, type B bicyclic ployprenylated acylphloroglucinol derivatives from Hypericum ascyron / 中国天然药物

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.

A new polycyclic polyprenylated acylphloroglucinols from Hypericum lagarocladum N. Robson / 药学学报

Silica gel column chromatography, reversed phase C18 column chromatography, Sephadex LH-20 gel column chromatography, high performance liquid chromatography and medium performance semi preparative liquid chromatography were performed to separate and purify the chemical constituents of Hypericum lagarocladum N. Robson. Spectroscopic methods such as MS and NMR combined with physicochemical properties were applied in identifying the structures of the isolated compounds. A total of 11 compounds were isolated and identified as hyperlagarone A (1), hyperpatulone E (2), hyperbeanol G (3), uralione D (4), tomoeone F (5), pyramidatone A (6), tomoeone A (7), tomoeone B (8), hyperbeanol C (9), hyperbeanol A (10), and hypercohone G (11), respectively. Compound 1 is a new polycyclic polyprenylated acylphloroglucinol derivative, and compounds 2-11 are isolated from this plant for the first time. 11 compounds were tested for glucose uptake in L6 cells, and the results showed that compounds 7 and 8 had significant effect on glucose uptake.

Polycyclic polyprenylated acylphloroglucinols from Hypericum species and their biological activities / 中国中药杂志

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.

Research progress of polycyclic polyprenylated acylphloroglucinols natural products / 中国中药杂志

Due to their fascinating chemical structures and extensive pharmacological activities, polycyclic polyprenylated acylphloroglucinols(PPAPs) have become one of the current research hotspots of natural products. In particular, some of the PPAPs not only have novel non-traditional skeleton types, but also contain more unknown possible activities, which are of great significance for the development of lead compounds. The structure, source, biosynthetic pathway and pharmacological activities of PPAPs with non-traditio-nal skeleton types isolated and identified in recent years are reviewed, in order to provide references for further research on such compounds.

Type B polycyclic polyprenylated acylphloroglucinols from the roots of Hypericum beanii / 中国天然药物

Two new type B polycyclic polyprenylated acylphloroglucinols (PPAPs) (1 and 2) and a known biogenetic precursor hyperbeanol Q (3) were isolated from the root extract of Hypericum beanii, a medicinal plant widespread in southwest China. Their chemical structures were elucidated by 1D/2D NMR and HRESIMS data analysis, and absolute configurations were determined through detailed electric circular dichroism (ECD) analysis including ECD exciton chirality, Mo

Chemical Constituents from Hypericum beanii / 中草药·英文版

Objective: To study the chemical constituents from the aerial parts of Hypericum beanii. Methods: Various chromatographic techniques were used to separate the constituents and their structures were elucidated on the basis of extensive spectroscopic interpretation. Results: Fifteen compounds were isolated from the aerial parts of H. beanii. Their structures were identified as hyperbeanol E (. 1), (E)-linalool-1-oic acid (. 2), (4S,5R)-5-(4'-methyl-3'-pentenyl)-4-hydroxy-5-methyl-dihydrofuran-2-one (. 3), benzoic acid (. 4), 4-(3-O-3')-3'-methylbutenyl-6-phenyl-pyran-2-one (. 5), 4-hydroxy-4a,7-dimethoxy-4,4a-dihydrodibenzo-p-dioxin-2(3H)-one (. 6), isoimperatorin (. 7), 2,3-dimethoxyxanthone (. 8), 3,4-dihydroxy-2-methoxyxanthone (. 9), osajaxanthone (. 10), nigrolineaxanthone F (. 11), hypercohone G (. 12), betulinic acid (. 13), oleanolic acid 3β-caffeate (. 14), and isoastilbin (. 15). Conclusion: Compound 1 is a new menthane monoterpene derivative which owns an extra lactone ring. Compounds 2-7 and 10-15 are isolated from genus Hypericum Linn. for the first time and the other compounds are first obtained from the plants in H. beanii.