Two pairs of phloroglucinol enantiomers from Hypericum wightianum and their stereochemical structures / 中国中药杂志

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.

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 phloroglucinol from Dryopteris fragrans and its antibacterial activity in vitro / 中国中药杂志

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.

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.

A new phloroglucinol compound from Dryopteris fragrans / 中国中药杂志

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".

Secondary metabolites as a survival strategy in plants of high mountain habitats / Metabolitos secundarios como estrategia de supervivencia en plantas de hábitat de alta montaña

This review work focuses on how the secondary chemistry could help in the survival of plants in high mountain habitats under extreme environmental conditions. The elevated levels of stress in high areas of the tropic and subtropic change dramatically not only by following the annual cycles of winter and summer but they also change in a single day. Some species, however, are able to successfully grow at heights more than 3000 m in the tropical mountains due, in part, to highly specialized physiological processes that affect their physical and chemical responses. In this study, it describes some strategies of how the secondary metabolites could help the plants to stand the high levels of stress in the high mountain ecosystems.

Este trabajo de revisión se centra en cómo la química secundaria podría ayudar en la supervivencia de plantas en hábitats de alta montaña en condiciones ambientales extremas. Los altos niveles de estrés en las zonas altas del trópico y subtrópico cambian dramáticamente no solo al seguir los ciclos anuales de invierno y verano, sino que también cambian en un solo día. Sin embargo, algunas especies pueden crecer con éxito a alturas superiores a 3000 m en las montañas tropicales debido, en parte, a procesos fisiológicos altamente especializados que afectan sus respuestas físicas y químicas. En esta revisión, se describen algunas estrategias de cómo los metabolitos secundarios podrían ayudan a las plantas a soportar los altos niveles de estrés en los ecosistemas de alta montaña.

Cryopreservation of banana's cv Grand Naine in vitro rhizomes

ABSTRACT The preservation of banana genetic material is usually performed through seedlings. However, most banana cultivars do not produce seed and are propagated vegetatively. Therefore, cryopreservation is a feasible technique that allows the preservation of banana genotypes indefinitely. For the success of cryopreservation protocols, the selection of cryoprotectants and pre-freezing techniques are important factor. Therefore, the objective of this study was to verify the effects of different cryoprotectants with and without 1% phloroglucinol and pre-cooling periods on the development of a protocol for cryopreservation of in vitro rhizomes ofMusa accuminata(AAA) cv Grand Naine banana. The addition of 1% phloroglucinol to the cryoprotective solutions, such as PVS2 enhanced recovery of cryopreserved banana rhizomes. In addition, pre-cooling of explants in ice for 3 hours in PVS2 + 1% of phloroglucinol allowed efficient cryopreservation of banana rhizomes, followed by successful recovery and regeneration of in vitro shoots of banana cv Grand Naine.

Effect of antispasmodic agents for the treatment of irritable bowel syndrome

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.

Phloroglucinol combined with parecoxib for cystospasm after transurethral resection of the prostate / 中华男科学杂志

<p><b>Objective</b>To evaluate the effect and safety of phloroglucinol combined with parecoxib on cystospasm after transurethral resection of the prostate (TURP).</p><p><b>METHODS</b>We conducted a prospective randomized case-control study on 98 patients treated by TURP. After operation, the patients were randomly assigned to a treatment (n=50) and a control group (n=48), the former treated by intravenous injection of 80 mg phloroglucinol qd plus 40 mg parecoxib bid while the latter given 80 mg phloroglucinol only, both for 3 successive days. Then we recorded the frequency and duration of cystospasm, visual analogue scales (VAS), adverse reactions, post-operative bladder irrigation time, catheter-indwelling time, and hospital stay and compared them between the two groups of patients.</p><p><b>RESULTS</b>Compared with the controls, the patients in the treatment group showed a significantly lower frequency of cystospasm (［1.95±0.14］ vs ［0.70±0.65］ times, P<0.01), duration of cystospasm (［0.44±0.21］ vs ［0.12±0.14］ min, P<0.01), and VAS score (2.70±1.80 vs 1.90±1.30, P<0.01) at 48－72 hours after TURP, but no statistically significant differences were found between the control and treatment groups in the post-operative bladder irrigation time (［2.75±0.87］ vs ［2.64±0.83］ d, P>0.05), catheter-indwelling time (［3.52±0.32］ vs ［3.44±0.42］ d, P>0.05), and hospital stay (［5.23±0.81］ vs ［5.10±0.73］ d, P>0.05), and no obvious adverse reactions were observed in either of the two groups.</p><p><b>CONCLUSIONS</b>Phloroglucinol combined with parecoxib is more effective and safer than phloroglucinol alone in relieving postoperative cystospasm after TURP.</p>

Protective effect of phloroglucinol against gamma radiation-induced oxidative stress in hair follicles

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.

Phloroglucinol protects the urinary bladder via inhibition of oxidative stress and inflammation in a rat model of cyclophosphamide-induced interstitial cystitis / 中华医学杂志(英文版)

<p><b>BACKGROUND</b>Phloroglucinol plays an important role in oxidative stress and inflammatory responses. The effects of phloroglucinol have been proven in various disease models. The aim of the present study was to investigate the efficacy and possible mechanisms of phloroglucinol in the treatment of interstitial cystitis (IC).</p><p><b>METHODS</b>Thirty-two female Sprague-Dawley (SD) rats were used in this study. IC was induced by intraperitoneal injection of cyclophosphamide (CYP). Rats were randomly allocated to one of four groups (n = 8 per group): A control group, which was injected with saline (75 mg/kg; i.p.) instead of CYP on days 1, 4, and 7; a chronic IC group, which was injected with CYP (75 mg/kg; i.p.) on days 1, 4, and 7; a high-dose (30 mg/kg) phloroglucinol-treated group; and a low-dose (15 mg/kg) phloroglucinol-treated group. On day 8, the rats in each group underwent cystometrography (CMG), and the bladders were examined for evidence of oxidative stress and inflammation. Statistical analysis was performed by analysis of variance (ANOVA) followed by least square difference multiple comparison post-hoc test.</p><p><b>RESULTS</b>Histological evaluation showed that bladder inflammation in CYP-treated rats was suppressed by phloroglucinol. CMG revealed that the CYP treatment induced overactive bladder in rats that was reversed by phloroglucinol. Up-regulated tumor necrosis factor-α and interleukin-6 expression in the CYP-treated rats were also suppressed in the phloroglucinol treated rats. CYP treatment significantly increased myeloperoxidase activity as well as the decreased activities of catalase of the bladder, which was reversed by treatment with phloroglucinol.</p><p><b>CONCLUSIONS</b>The application of phloroglucinol suppressed oxidative stress, inflammation, and overactivity in the bladder. This may provide a new treatment strategy for IC.</p>

Phloroglucinol: safe and effective for the prevention of bladder spasm after TURP / 中华男科学杂志

<p><b>OBJECTIVE</b>To evaluate the efficacy of phloroglucinol in preventing bladder spasm after transurethral resection of the prostate (TURP).</p><p><b>METHODS</b>Using 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.</p><p><b>RESULTS</b>The 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.</p><p><b>CONCLUSION</b>Phloroglucinol is safe and effective for the prevention and treatment of bladder spasm following TURP.</p>

Comparison of efficacy of injection diclofenac sodium alone and with combination of phoroglucinol in the treatment of acute ureteric colic

To compare the efficacy of diclofenac sodium alone and with combination of phioroglucinol in the 4reatment of ureteric colic. This Quasi-experimental study was carried out in the Surgical Department, Combined Military Hospital, Kharian during the period from June 2006 to December 2006. A total of 60 cases of acute ureteric colic entered the study. Pain scores were measured both on 100 mm visual analogue scale and on categorical verbal scale as baseline and at 15, 30, 45, 60 and 120 minutes after administering the study drug, duration of analgesia was also noted. The efficacy of both the treatment groups was assessed by calculating the difference in mean pain scores, by noting the time when complete pain relief was achieved, by the duration of analgesia and by comparing the response of he drug. Mean pain score in patients treated with combination was significantly less than patients treated with diclofenac sodium alone [p<0.05]. Combination of diclofenac and phloroglucinol was better than diclofenac alone in achieving rapid and complete pain relief

Dereplication of bioactive constituents of the genus hypericum using LC-[+,-]-ESI-MS and LC-PDA techniques: Hypericum triquterifolium as case study

Utilizing liquid chromatography-electro spray ionization-mass spectrometry [LC-[+,-]-ESI-MS] and liquid chromatography-photodiode array detection [LC-PDA] techniques, a dereplication strategy for the analysis of the secondary metabolites constituents of the genus Hypericum has been developed. From the crude methanolic extract of the aerial parts of H. triquetrifolium [leaves, stems, and flowers] and on the basis of their UV- profiles, chromatographic retention times and [+,-]-ESI-MS [TIC and SIM] mass spectral data, seven known [1-7] compounds were dereplicated fairly rapidly. The compounds were classified into three structural classes: phloroglucinols: hyperfirin and adhyperfirin; naphthodianthrones: hypericin, pseudo-hypericin, proto-hypericin, and protopseudo-hypericin; and the flavonoid rutin

Studies on chemical constituents in fruits of Eucalyptus globulus / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents in the fruits of Eucalyptus globulus Labill.</p><p><b>METHOD</b>The chemical constituents were isolated by various column chromatographic methods and structurally elucidated by IR, NMR and MS evidences.</p><p><b>RESULT</b>Fifteen compounds were obtained and identified as beta-sitosterol (1), betulinic acid (2), stigmasterol (3), euscaphic acid (4), 2a-Hydroxybetulinic acid (5), macrocarpal B (6), macrocarpal A (7), oleanolic acid (8), 3,4,3'-O-trimethylellagic acid (9), 3-O-methylellagic acid 4'-O-(2"-O-acetyl )-alpha-L-rhamnopyranoside (10), camaldulenside (cypellocarpin C, 11), 3-O-methylellagic acid 4'-O-alpha-L-rhamnopyranoside (12), 3-O-methylellagic acid (13), ellagic acid (14), and gallic acid (15).</p><p><b>CONCLUSION</b>Compounds 4 and 5 from genera Eucalyptus, 1, 3 and 11 from plant E. globulus, and 6, 7, 9 and 15 from the fruits of E. globulus were isolated for the first time.</p>

Phloroglucinol in irritable bowel syndrome

To determine the efficacy and tolerability of phloroglucinol, an antispasmodic agent in the treatment of Irritable Bowel Syndrome [IBS]. It was an open label [quasi interventional] study. One hundred patients coming to the gastroenterology clinics of Aga Khan University Hospital with IBS as defined by the Rome II criteria were enrolled between February 2004 and September 2004 to participate in the trial and were treated as outpatients. Phloroglucinol [Himont] 50mg orally three times daily was given for two months. Symptoms were assessed before and during treatment using a questionnaire. One hundred patients were enrolled in the study. Of them 61% [61/100] were males and 39% [39/100] were females. Their mean age was 41'14 years. Sixty-eight patients completed the study and 28 dropped out. On Phloroglucinol treatment there was an overall statistically significant improvement in abdominal pain [p<0.001], frequency of stools per day [p<0.001], urgency [p<0.001], passage of mucus per rectum [p<0.001], sense of incomplete defecation [p=0.001] and bloating [p=0.001]. However, no response was seen in the feature of straining in both genders [p=0.676]. The difference in response to treatment according to gender separately showed statistically significant improvement in the sense of incomplete defecation in females alone [p=0.003]

Phloroglucinol for acceleration of labor: Double blind, randomized controlled trial

To determine the effects of Phloroglucinol in acceleration of labour and its adverse effects on mother and foetus. A double blind randomized, placebo controlled trial was conducted on 100 patients in active phase of uncomplicated labour selected by convenient sampling. Patients were given Phloroglucinol or Placebo [distilled water] intravenously. Progress of labour was plotted on Partogram. Any adverse effects of the drug on mother and fetus were noted. Student's t-test was applied for statistical analysis. In patients receiving Phloroglucinol there was a mean 34% reduction in duration of 1st stage of labour and a mean 23% reduction in 2nd stage as compared to Placebo group respectively. Blood loss >500ml was observed in 2% patients. Otherwise there were no adverse effects on mother or foetus. Phloroglucinol shortens the duration of labour, is non toxic to both mother and fetus and does not cause primary post partum haemorrhage

Efficient clonal propagation method for Decalepis hamiltonii, an endangered shrub, under the influence of phloroglucinol.

A highly efficient two stage protocol was developed for induction of multiple shoots from single node in vitro shoot tip explants of Decalepis hamiltonii. It was found that phloroglucinol (PG) had synergistic effect on shoot multiplication when added with N6-benzyladenine and gibberellic acid. This protocol uses PG for both multiple shoot induction from nodal explants, elongation of primary shoots and initiation of adventitious shoot formation from primary shoots, which was more in presence of triacontanol (TRIA). Maximum number of shoots per culture was observed on the medium containing N6-benzyladenine (1.1 microM; BA), GA3 (5.8 microM) and PG (800 microM). Sub-culturing of the shoots onto MS medium containing optimum concentration of BA (5.6 microM), PG (200 microM) and TRIA (0.011 microM) produced elongated shoots along with secondary shoot formation. The long shoots were rooted on alpha-naphthalene acetic acid (5.38 microM; NAA) and PG (400 microM) containing medium. The rooted plantlets were hardened and their field survival rate was 80-90%.