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

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.
Biological Products ; Hypericum ; Molecular Structure ; Phloroglucinol

Two phloroglucinol compounds(1-2) were isolated and purified from 95% ethanol extract of Dryopteris fragrans through various column chromatographies on silica gel, Sephadex LH-20, medium pressure column chromatography, and preparative HPLC. Their structures were elucidated as 2',4',6'-trihydroxy-5'-methyl acetate-3'-methyl-1'-butyrophenone(1) and aspidinol B(2) based on their chemical and physicochemical methods and spectroscopic data. Compound 1 is a new phloroglucinol compound named "dryofraginol".
Chromatography, High Pressure Liquid ; Dryopteris ; Ethanol ; Phloroglucinol ; Plant Extracts

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

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

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*

Antispasmodics are effective in reducing abdominal pain and controlling spasm. Irritable bowel syndrome (IBS) patients have characteristic key factors such as intestinal motility disorder and visceral hypersensitivity. So antispasmodics have been used in the treatment of IBS for decades. Mebeverine blocks intestinal peristalsis but are not significantly better than placebo. Alverine citrate combined with simethicone is effective treatment option in IBS. Otilonium and pinaverium bromide are poorly absorbed agents, so they have mostly local effect with minimal systemic adverse events. Phloroglucinol controls acute exacerbation of abdominal pain effectively. Tiropramide reduce abdominal discomfort without serious adverse events. Fenoverine control spasm in spastic colon but does not affect normal contraction. Trimebutine have dual actions that it inhibits hyperactive colon and activates hypomotile colon. Each drug has advantages and disadvantages. Antispasmodics are considered as the first treatment option of pain-dominant IBS.
Abdominal Pain ; Citric Acid ; Colon ; Gastrointestinal Motility ; Humans ; Hypersensitivity ; Irritable Bowel Syndrome ; Muscle Spasticity ; Parasympatholytics ; Peristalsis ; Phloroglucinol ; Simethicone ; Spasm ; Trimebutine

A new phloroglucinol was isolated from 50% ethanol extract of Dryopteris fragrans by silica gel column chromatography, Sephadex LH-20 gel column chromatography, thin-layer chromatography(TLC), and preparative liquid column chromatography. On the basis of MS, ~1H-NMR, ~(13)C-NMR, and reference materials, compound 1 was identified as 2,5-cyclohexadien-1-one, 2-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(1-isobutyl)phenyl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(1-oxobutyl)(1), and named disaspidin BB. Compound 1 was evaluated for its antibacterial activity. The experimental results showed that compared with the commonly used topical antibiotics erythromycin or mupirocin, disaspidin BB exhibited significant antibacterial activities against Staphylococcus epidermidis(SEP), S. haemolyticus(SHA), and methicillin-resistant S. aureus(MRSA)(P<0.05). Additionally, disaspidin BB was sensitive to ceftazidime-resistant SEP1-SEP4, SHA5-SHA7, MRSA8, and MRSA9. The MIC values of disaspidin BB against SEP and SHA were 1.67-2.71 μg·mL~(-1) and 10.00-33.33 μg·mL~(-1) respectively. Disaspidin BB has good antibacterial activities and deserves development as a new anti-infective drug for external use.
Anti-Bacterial Agents/pharmacology* ; Dryopteris ; Methicillin-Resistant Staphylococcus aureus ; Microbial Sensitivity Tests ; Phloroglucinol/pharmacology* ; Plant Extracts/pharmacology*

When exposed to gamma-rays, hair follicular cells immediately go through apoptosis, which hampers their rapid differentiation essential for the regeneration of hair. Phloroglucinol (PG) is a phenolic compound of Ecklonia cava, brown algae abundant in Jeju island, Korea. Containing plentiful polyphenols, PG is known for its instructive effects by inhibiting apoptosis, scavenging oxygen radicals, and protecting cells against oxidative stress. In this study, we demonstrate that PG rescues radiosensitive hair follicular cells from gamma radiation-induced apoptosis and DNA damage. To identify protective capacity of PG on hair follicles, we irradiated with 8.5 Gy (1.5 Gy/min) of gamma-rays to the whole body of C57BL/6 mice at day 6 after depilation with or without PG. In mice exposed to radiation, the expression of proapoptotic molecule p53 was downregulated in the skin of PG treated group. On immunohistochemical observation of the skin, PG inhibited the immunoreactivity of p53 and cleaved caspase-3. PG treatment protected hair follicular cells from cell death due to gamma-radiation. Our results suggest that PG presents radioprotective effects by inhibiting apoptosis of radiosensitive hair follicular cells and can protect hair follicular cells from gamma-ray induced damage.
Animals ; Apoptosis ; Caspase 3 ; Cell Death ; DNA Damage ; Hair Follicle* ; Hair Removal ; Hair* ; Korea ; Mice ; Oxidative Stress* ; Phaeophyta ; Phenol ; Phloroglucinol* ; Polyphenols ; Reactive Oxygen Species ; Regeneration ; Skin

OBJECTIVETo evaluate the efficacy of phloroglucinol in preventing bladder spasm after transurethral resection of the prostate (TURP).

METHODSUsing the random sampling method, we assigned 74 cases of TURP into a treatment group (n = 39), given 80 mg phloroglucinol every day for 3 days, and a control group (n = 35), left untreated. Then we observed the frequency, duration and pain of bladder spasm within the 3 days and compared them between the two groups.

RESULTSThe mean frequency, duration and pain visual analogue score of bladder spasm were (4.3 +/- 1.2) times, (7.2 +/- 2.1) min and 3.2 +/- 1.6 respectively in the treatment group, as compared with (7.5 +/- 2.4) times, (15.6 +/- 6.8) min and 4.7 +/- 2.3 in the control, with statistically significant differences between the two groups (P < 0.05). And no obvious adverse reactions were found in the treatment group.

CONCLUSIONPhloroglucinol is safe and effective for the prevention and treatment of bladder spasm following TURP.

Aged ; Aged, 80 and over ; Humans ; Male ; Middle Aged ; Phloroglucinol ; therapeutic use ; Postoperative Complications ; prevention & control ; Transurethral Resection of Prostate ; adverse effects ; Urinary Bladder Neck Obstruction ; etiology ; prevention & control