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A new flavonol glycoside from the flowers of Hosta plantaginea with cyclooxygenases-1/2 inhibitory and antioxidant activities
Abstract
Hosta plantaginea was a traditional Chinese medicinal plants used to treat inflammatory and painful diseases with partial scientific validation. Solvent extractions followed by repeated chromatographic purification of the H. plantaginea flowers led to the isolation of one new flavonoid glycoside, hostaflavone A (1), together with one related known compound, kaempferol-3-O-sophoroside-7-O-glucoside (2), and their structures were elucidated on the basis of chemical and spectral evidence, as well as by comparison with literature data. Compounds 1 and 2 were evaluated for the anti-inflammatory activites against cyclooxygenases (COX-1 and COX-2) and DPPH free radical-scavenging activities in vitro. The results revealed that 1 and 2 exhibited significant COX-1 inhibition and moderate COX-2 inhibition compared to the reference celecoxib. Additionally, 1 and 2 displayed insignificant antioxidant activities compared to the positive control L-ascorbic acid.
... Its crude extract exhibits anti-inflammatory, antitumor, anti-viral, antimicrobial and other effects [8][9][10]. In our previous study, 16 flavonoids (1-16) and 3 phenylethanoid glycosides (17)(18)(19) comprising kaempferol (1), astragalin (2), kaempferol-7-O-β-D-glucopyranoside (3), kaempferol-3,7-di-O-β-D-glucopyranoside (4), kaempferol-3-O-sophoroside (5), plantanone A (6), kaempferol- (11), plantanone B (12), plantanone D (13), naringenin (14), dihydrokaempferol (15), hostaflavanone A (16), phenethyl-O-β-D-glucopyranoside (17), phenethanol-β-gentiobioside (18) and phenethyl-O-rutinoside (19), were isolated from the ethanolic extract of H. plantaginea flowers [11][12][13][14][15]. Of these, all constituents except 13-15 exhibited potential inhibitory effect on cyclooxygenase 2 (COX-2) in vitro. ...
... Its crude extract exhibits anti-inflammatory, antitumor, anti-viral, antimicrobial and other effects [8][9][10]. In our previous study, 16 flavonoids (1-16) and 3 phenylethanoid glycosides (17)(18)(19) comprising kaempferol (1), astragalin (2), kaempferol-7-O-β-D-glucopyranoside (3), kaempferol-3,7-di-O-β-D-glucopyranoside (4), kaempferol-3-O-sophoroside (5), plantanone A (6), kaempferol- (11), plantanone B (12), plantanone D (13), naringenin (14), dihydrokaempferol (15), hostaflavanone A (16), phenethyl-O-β-D-glucopyranoside (17), phenethanol-β-gentiobioside (18) and phenethyl-O-rutinoside (19), were isolated from the ethanolic extract of H. plantaginea flowers [11][12][13][14][15]. Of these, all constituents except 13-15 exhibited potential inhibitory effect on cyclooxygenase 2 (COX-2) in vitro. ...
... Our previous studies reported the isolation and identification of 16 flavonoids and 3 phenylethanoid glycosidescomprising kaempferol (1), astragalin (11), plantanone B (12), plantanone D (13), naringenin (14), dihydrokaempferol (15), hostaflavanone A (16), phenethyl-O-β-D-glucopyranoside (17), phenethanol-β-gentiobioside (18) and phenethyl-O-rutinoside (19) from the ethanolic extract of H. plantaginea flowers, a plant (Voucher specimen number: YZH201409) which was identified by professor Guoyue Zhong (Jiangxi University of Chinese Medicine, Nanchang, China) [11][12][13][14][15]. Moreover, the purity of each compound was greater than 97% as determined by high performance liquid chromatography analysis. ...
Background
The flower of Hosta plantaginea (Lam.) Aschers has traditionally been used in China as an important Mongolian medicine for the treatment of inflammatory diseases with limited scientific evidence. In previous studies, 16 flavonoids and 3 phenylethanoid glycosides (1–19) were isolated from the ethanolic extract of H. plantaginea flowers. Nevertheless, the anti-inflammatory effects of these constituents remain unclear. In the present study, the anti-inflammatory effects of these 19 constituents and their underlying mechanisms were assessed in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages.
Methods
The viability of RAW 264.7 macrophages was detected by Cell Counting Kit-8 (CCK-8) assay. Meanwhile, nitric oxide (NO) production was measured by Griess assay, while the secretion of tumor necrosis factor α (TNF-α), prostaglandin E2 (PGE2), interleukin 1β (IL-1β) and IL-6 in LPS-induced macrophages was determined by enzyme-linked immunosorbent assay (ELISA). Furthermore, the protein expression of nuclear factor kappa B (NF-κB) p65 and phosphorylated NF-κB p65 was evaluated by Western blot analysis.
Results
All constituents effectively suppressed excessive NO production at a concentration of 40 μM with no toxicity to LPS-induced RAW 264.7 macrophages. Among them, five flavonoids (1, 4–6 and 15) and one phenylethanoid glycoside (17) remarkably prevented the overproduction of NO with median inhibitory concentration (IC50) values in the range of 12.20–19.91 μM. Moreover, compounds 1, 4–6, 15 and 17 potently inhibited the secretion of TNF-α, PGE2, IL-1β and IL-6, and had a prominent inhibitory effect on the down-regulation of the phosphorylated protein level of NF-κB p65.
Conclusion
Taken together, compounds 1, 4–6, 15 and 17 may be useful in managing inflammatory diseases by blocking the NF-κB signaling pathway and suppressing the overproduction of inflammatory mediators.
... Over the past few years, secondary metabolites from natural products play an important role in the development of new drugs [1]. Higher plants represent sources of abundant phytochemicals with a wide range of biological effects and have attracted more attention in the past decades [2][3][4][5][6]. Consequently, most medicinal plants belong to higher plants have been widely to treat many human diseases in traditional folk medicine [1,[7][8][9]. ...
... The anti-inflammatory effect of the sample against COX-2 inhibition was determined using colorimetric COX-2 inhibitor screening assay kit (no. S0168) and using celecoxib as the positive drug [2][3][4]. Briefly, 75 μL of assay buffer, 5 μL of cofactor working solution, and 5 μL of working solution were mixed with 5 μL of the sample at different concentrations and then incubated at 37°C. ...
... DPPH Radical Scavenging Activity. The DPPH radical scavenging activity of the sample was provided in our previously published articles [2][3][4]. Briefly, 150 μL of DPPH solution (dissolved 0.2 mM in methanol) was mixed with 50 μL of the sample at different concentrations. The mixture was stirred and incubated in the dark at 30°C for 30 min, and the absorbance was determined at 517 nm (A sample ). ...
Dendropanax dentiger root is a traditional medicinal plant in China and used to treat inflammatory diseases for centuries, but its phytochemical profiling and biological functions are still unknown. Thus, a rapid, efficient, and precise method based on ultra high-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (UHPLC-Q-TOF-MS/MS) was applied to rapidly analyse the phytochemical profiling of D. dentiger with anti-inflammatory and antioxidant activities in vitro. As a result, a total of 78 chemical compositions, including 15 phenylpropanoids, 15 alkaloids, 14 flavonoids, 14 fatty acids, 7 phenols, 4 steroids, 4 cyclic peptides, 3 terpenoids, and 2 others, were identified or tentatively characterized in the roots of D. dentiger. Moreover, alkaloid and cyclic peptide were reported from D. dentiger for the first time. In addition, the ethanol crude extract of D. dentiger roots exhibited remarkable anti-inflammatory activity against cyclooxygenase- (COX-) 2 inhibitory and antioxidant activities in vitro. This study is the first to explore the phytochemical analysis and COX-2 inhibitory activity of D. dentiger. This study can provide important phytochemical profiles and biological functions for the application of D. dentiger roots as a new source of natural COX-2 inhibitors and antioxidants in pharmaceutical industry.
... Natural medicine is considered a quite important resource for drug discovery and has increasingly attracted the attention of researchers [1][2][3][4]. In Chinese folk medicine, several traditional Chinese medicines (TCMs) are used as diuretic drugs, but most of them lack pharmacological studies to explain their material basis and its mechanisms [5]. ...
... e purpose of the present study was to evaluate the diuretic and antidiuretic activities of the ethanol extract (LS) and its four fractions (LSA, LSB, LSC, and LSD) of L. supina in normal rats within 24 h. For the efficacy evaluation, the urine output volume, urinary electrolyte concentrations (Na + and K + ), and pH values were measured at different time points (1,2,4,6, and 24 h) after administration, and the Na + -K + -ATPase, angiotensin II (Ang II), atriopeptin (ANP), antidiuretic hormone (ADH), aldosterone (ALD), and TNFα and IL-6 levels in urine and serum were detected within 24 h after administration. ...
... e diuretic activity was determined according to the method published previously [14,15]. All rats were randomly assigned into 13 groups (n � 8 per group): (1) control group (water-loaded rats), (2) 13.6 mg/kg BW of LSD. And each group was given the corresponding drug, and the control group received an equivalent amount of water with 0.3% CMC-Na. ...
Lagopsis supina is a well-known traditional Chinese medicine and used as an agent for diuresis in China for centuries. This is the first time to evaluate the diuretic activity of the ethanol extract of L. supina (LS) and its four fractions (LSA, LSB, LSC, and LSD) in normal rats. After the administration of LS-H, LS-M, LSB-H, and LSC-L, the urine output of the rats was significantly increased, while the urine excretion was significantly reduced after treatment with LSB-L. The urine Na ⁺ excretion was remarkably increased with LS-H, LS-M, LSA-H, LSA-L, LSB-H, LSC-L, and LSD-L, and the urine K ⁺ excretion was significantly increased after administration of LS-H and LSB-H. Moreover, the urine Na ⁺ and K ⁺ excretion was significantly reduced after treatment with LSC-H and LSD-H. However, the urine pH values and urine and serum Na ⁺ -K ⁺ -ATPase levels did not show remarkable change after administration of LS or its four fractions in comparison with the control group. On the contrary, LS and its four fractions can suppress the renin-angiotensin-aldosterone system (RAAS), including ADH arrest by LSB-H, LSB-L, LSC-L, LSD-L, and LSD-H and ALD arrest by LSD-L, as well as promote ANP release by LS-M, LSB-H, LSC-H, and LSD-H, while furosemide can suppress only arrest of ADH within 24 h compared with the control group. In addition, LS and its four fractions did not change the urine and serum TNF- α and IL-6 levels in normal rats within 24 h. This study will provide a quantitative basis for explaining the natural medicinal use of LS as a diuretic agent for edema and promoting the diuretic process.
... Ohwi originated in Japan and is cultivated as an ornamental plant in many regions of China [1]. The genus Hosta is a particularly rich source of polyphenolics and flavonoids, which have been linked to antioxidant and anti-inflammatory effects [2][3][4][5][6]. However, the total phenolic and flavonoid contents (TPC and TFC), as well as the antioxidant and α-glucosidase inhibitory activities, have not been reported from the genus Hosta, except that some flavonoids were moderate against the DPPH free radical scavenging activity in our previous articles [3][4][5][6]. ...
... The genus Hosta is a particularly rich source of polyphenolics and flavonoids, which have been linked to antioxidant and anti-inflammatory effects [2][3][4][5][6]. However, the total phenolic and flavonoid contents (TPC and TFC), as well as the antioxidant and α-glucosidase inhibitory activities, have not been reported from the genus Hosta, except that some flavonoids were moderate against the DPPH free radical scavenging activity in our previous articles [3][4][5][6]. ...
The total phenolic and flavonoid contents (TPC and TFC) from the genus Hosta with antioxidant and α-glucosidase inhibitory activities were reported for the first time. Sixteen extracts from the aboveground and underground parts of the four Hosta species, including H. plantaginea, H. ventricosa, H. ensata, and H. albofarinosa, using reflux extraction (RE) and ultrasound-assisted extraction (UAE) techniques have high TPC and TFC with good antioxidant and α-glucosidase inhibitory activities. Furthermore, no significant differences on extraction yields, TPC, and TFC were found between RE and UAE techniques. Additionally, extracts from the aboveground parts of the four Hosta species had higher TPC, TFC, antioxidant, and α-glucosidase inhibitory activities compared to the underground parts by means of RE or UAE techniques. Lastly, the extracts of H. albo-marginata displayed a very remarkable α-glucosidase inhibitory activity compared to the positive control acarbose. The relationships of sixteen extracts of the four Hosta species were analyzed by RE and UAE techniques between extraction yields, TPC, TFC, antioxidant activity, and α-glucosidase inhibitory activity. The present study demonstrated that H. plantaginea, H. ventricosa, H. ensata, and H. albofarinosa could be new sources of natural antioxidants and antidiabetes for pharmaceutical and industrial purposes.
... Therefore, a rapid and sensitive method to figure out the chemical components in the roots of S. cathayensis was urgently needed. Conventional separation and identification processes were time and plant material consuming [9][10][11][12][13], whereas the use of a rapid, efficient, and prescise method focused on identification chemical components was very important for TCMs. Over the past decade, UHPLC coupled with high-resolution mass spectrometry (HRMS) has become the prime tool for investigating the chemical profiling of TCMs, because of its advantages on the peak capacity, resolution, separation time, and detection sensitivity, all of which are suitable for addressing the complicated characteristics of the constituents in TCMs [14][15][16][17]. ...
... Conventional separation and identification processes were time and plant material consuming [9][10][11][12][13], whereas the use of a rapid, efficient, and prescise method focused on identification chemical components was very important for TCMs. Over the past decade, UHPLC coupled with highresolution mass spectrometry (HRMS) has become the prime tool for investigating the chemical profiling of TCMs, because of its advantages on the peak capacity, resolution, separation time, and detection sensitivity, all of which are suitable for addressing the complicated characteristics of the constituents in TCMs [14][15][16][17]. ...
Semiliquidambar cathayensis Chang was a traditional medicinal plant and used to treat rheumatism arthritis and rheumatic arthritis for centuries in China with no scientific validation, while only 15 components were reported. Thus, a rapid, efficient, and precise method based on ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (UHPLC-Q-TOF-MS/MS) was applied in both positive- and negative-ion modes to rapidly analysis the main chemical compositions in S. cathayensis for the first time. Finally, a total of 85 chemical compositions, including 35 alkaloids, 12 flavonoids, 7 terpenoids, 5 phenylpropanoids, 9 fatty acids, 7 cyclic peptides, and 10 others were identified or tentatively characterized in the roots of S. cathayensis based on the accurate mass within 5 ppm error. Moreover, alkaloid, flavonoid, phenylpropanoid, and cyclic peptide were reported from S. cathayensis for the first time. This rapid and sensitive method was highly useful to comprehend the chemical compositions and will provide scientific basis for further study on the material basis, mechanism and clinical application of S. cathayensis roots.
... Analytical grade quinine hydrochloride (Sigma Aldrich: 48457, USA) and chloroquine diphosphate (Sigma Aldrich: C6628, UK) served as positive controls in the evaluation of antiplasmodial activity [26] . As in previously study, chloroquine also served as a positive control when evaluating the inhibitory activity of hemozoin synthesis [27] and Lascorbic acid (Sigma Aldrich: A7506, China) a positive control in antioxidant activity assay as in the past [28] . It made it possible to prepare a standard curve with 5 successive dilutions of order 2 made from a solution of ascorbic acid at 40 μg / ml (y = 0.0298X +0.0071; r 2 = 0.9997). ...
... Compounds 128 and 129 were evaluated for anti-inflammatory activity against cyclooxygenases (COX-1 and COX-2) in vitro. The results revealed that 1 and 2 exhibited significant COX-1 and moderate COX-2 inhibition compared to the reference celecoxib (He et al. 2019). A new flavan-3-ol glycoside, hostaflavanol A (130), along with two related known ones, including dihydrokaempferol (131) and naringenin (132), was isolated by silica gel and ODS column chromatography from the 80% ethanol extract of Hosta plantaginea flowers. ...
Enzymes are biologically active complex protein molecules that catalyze most chemical reactions
in living organisms, and their inhibitors accelerate biological processes. This review emphasizes
medicinal food plants and their isolated chemicals inhibiting clinically important enzymes in
common diseases. A mechanistic overview was investigated to explain the mechanism of these
food bases enzyme inhibitors. The enzyme inhibition potential of medicinal food plants and their
isolated substances was searched in Ovid, PubMed, Science Direct, Scopus, and Google Scholar.
Cholinesterase, amylase, glucosidase, xanthine oxidase, tyrosinase, urease, lipoxygenase, and others
were inhibited by crude extracts, solvent fractions, or isolated pure chemicals from medicinal food
plants. Several natural compounds have shown tyrosinase inhibition potential, including quercetin,
glabridin, phloretin-4-O-β-D-glucopyranoside, lupinalbin, and others. Some of these compounds’
inhibitory kinetics and molecular mechanisms are also discussed. Phenolics and flavonoids inhibit
enzyme activity best among the secondary metabolites investigated. Several studies showed
flavonoids’ significant antioxidant and anti-inflammatory activities, highlighting their medicinal
potential. Overall, many medicinal food plants, their crude extracts/fractions, and isolated compounds
have been studied, and some promising compounds depending on the enzyme have been found.
Still, more studies are recommended to derive potential pharmacologically active functional foods.
... Both compounds showed significant COX-1 and moderate COX-2 inhibitory effects, as well as insignificant antioxidant activity. The results of this study provided a scientific support for the use of H. plantaginea flowers for the treatment of inflammatory diseases in traditional Mongolian medicine(He et al., 2018). ...
Liver problems are a worldwide concern, and conventional medicinal therapies are ineffective. Hence, safeguarding the healthy liver is vital for good health and well-being. Infections due to virus, immune problems, cancer, alcohol abuse, and an overdose of drugs are some of the causes of liver diseases. Antioxidants derived from medicinal plants and conventional dietary sources can protect the liver from damages caused by oxidative stress system and various chemicals. Plants and plant-derived phytochemicals are appealing hepatoprotective agents since they have less side effects and still there is a lot of interest shown in using herbal tonics for treating liver disorders. This review therefore primarily focuses on newly discovered medicinal plants and compounds produced from plants that fall under the classifications of flavonoids, alkaloids, terpenoids, polyphenolics, sterols, anthocyanins, and saponin glycosides, all of which have the potential to be hepatoprotective. Hosta plantaginea, Ligusticum chuanxiong, Daniella oliveri, Garcinia mangostana, Solanum melongena, Vaccinium myrtillus, Picrorhiza kurroa, and Citrus medica are some potential plants having hepatoprotective effects. We conclude that these phytochemicals and the plant extracts listed above are used in the future to treat a variety of liver diseases, additional research is still needed to develop safer and more potent phytochemical drugs.
... Analytical grade quinine hydrochloride (Sigma Aldrich: 48457, USA) and chloroquine diphosphate (Sigma Aldrich: C6628, UK) served as positive controls in the evaluation of antiplasmodial activity [26] . As in previously study, chloroquine also served as a positive control when evaluating the inhibitory activity of hemozoin synthesis [27] and Lascorbic acid (Sigma Aldrich: A7506, China) a positive control in antioxidant activity assay as in the past [28] . It made it possible to prepare a standard curve with 5 successive dilutions of order 2 made from a solution of ascorbic acid at 40 μg / ml (y = 0.0298X +0.0071; r 2 = 0.9997). ...
... The magnificent structural diversity of natural compounds has enormous medicinal significance which resulted in discovery of a wide spectrum of therapeutic compounds such as morphine, atropine, vincristine, colchicine and so on (Azam, 2017;Khazir et al., 2013). COX-2 inhibitory potential of several natural products based on glycoside moiety are frequently documented (Ghareeb et al., 2018;He et al., 2019). A carboxylic acid aliphatic moiety and a glucoside moiety make up the molecular structure of CI-01, which makes it particularly beneficial in terms of its capacity to interact with the COX-2 enzyme. ...
Carya illinoinensis (Family Juglandaceae) is frequently used in traditional medicine for its antimicrobial, antioxidant, anti-rheumatic, anti-diabetic, and diuretic activities. Column chromatography was used to separate phytoconstituents from an ethanolic extract of powered bark. The terpenoid glycosidic compound, CI-01, was isolated as light-yellow crystalline powder in 0.33% (w/w) yield having melting point 94–96 °C, RF value 0.57 (in MeOH:CHCl3;20:80), UV absorption maxima 242 nm in methanol and molecular ion [M + H]⁺ peak at 420.4 m/z. Based on high-performance thin-layer chromatography and spectral data, the isolated compound CI-01, was identified as Farnesoic acid -l-glucoside. The ethanolic extract of Carya illinoinensis (CIE) at doses of 100 and 200 mg/kg and isolated compound CI-01 at 10 mg/kg dose were used for studying anti-inflammatory and antinociceptive effects. After 5 h of treatment with CI-01, the mean increase in paw volume was 0.459 ± 0.054 ml, which is corresponding to the standard drug indomethacin's 0.443 ± 0.041 ml. However, CIE groups receiving 100 and 200 mg/kg exhibited 0.518 ± 0.068 and 0.486 ± 0.048 ml, respectively. Compared to the control group of mice, animals treated with CIE and CI-01 dramatically reduced the number of writhes caused by acetic acid. AutoDock Vina program was used for molecular docking of the compound CI-01 with various targets, including COX-1, COX-2, inducible nitric oxide synthase, tumor necrosis factor-α, and opioid receptors exhibiting mean binding energies of -5.36, -7.37, -7.24, -4.27, and -7.04 kcal/mol, respectively. In conclusion, CI-01, isolated from Carya illinoinensis extract, demonstrated anti-inflammatory and antinociceptive activities at a dose of 10 mg/kg and displayed promising interaction with COX-2 in molecular docking study.
Ethnopharmacological relevance:
Hosta plantaginea (Lam.) Aschers flowers (HPF) are well-known for their high flavonoid content, which contribute to their widely as traditional Chinese medicine for alleviating inflammation. Despite their recognized potential, information regarding the total flavonoid (TF) in HPF and its therapeutic application in treating chronic prostatitis (CP) remains unknown.
Aim of the study:
We aimed to investigate the extraction optimization, constituent analysis, and alleviating effect of TF on CP as well asits potential mechanism.
Materials and methods:
The optimized extraction of TF from HPF was explored using response surface methodology with a Box-Behnken design model. The major flavonoids in TF were identified based on UHPLC-MS approach. Efficacy of TF (25 and 100 mg/kg, p.o.) on CP was evaluated in prostate antigen emulsion-induced autoimmune CP rat model by measuring prostatic index, the levels of leukocytes and elevated lecithin body, as well as histopathological examination. The protein expression contents were detected by western blotting. Additionally, the antioxidant (DPPH and ABTS) and anti-inflammatory (cyclooxygenase 2, COX-2 inhibitory) effects of TF were also evaluated in vitro.
Results:
The optimized conditions for TF extraction were determined as 60% ethanol concentration, 30 mL/g liquid-to-solid ratio, 30 min extraction time, and 90 °C extraction temperature, and the extraction ratio is 65.98 ± 2.14%. A total of 15 major flavonoids in TF were characterized by comparison with reference standards. TF ameliorated the efficacy of CP in rats in a dose-independent manner, including reduced prostatic index and leukocytes levels, elevated lecithin body levels, ameliorated histopathological damage to prostate, and suppressed phosphorylated protein expressions of nuclear factor kappa-B (NF-κB) p65, inhibitor of NF-κB alpha (IκBα), c-Jun N-terminal kinase (JNK), p38 mitogen-activated protein kinase (MAPK), extracellular signal-regulated kinase (Erk), just another kinase 1 (JAK1), signal transducer and activator of transcription 3 (STAT3), phosphoinositide 3-kinase (PI3K) and protein kinase B (Akt). Simultaneously, the IC50 of TF to DPPH, ABTS radicals, and COX-2 were 2.02, 1.79, and 0.0838 mg/mL, respectively.
Conclusions:
We first demonstrated that TF from HPF represents a promising candidate to alleviate CP through suppression of NF-κB, MAPKs, JAK-STAT, and PI3K-Akt signaling pathways.
Background:
Hosta plantaginea (Lam.) Aschers flower is a famous Mongolian folk medicine in China and has a therapeutic effect on acute pharyngitis (AP). However, the effect and potential mechanism of H. plantaginea flower on AP have not been fully elucidated.
Aim of the study:
The present work aimed to evaluate the effects and mechanisms of the crude extract of H. plantaginea flowers (HP) and its four fractions of petroleum ether fraction (HPA), ethyl acetate fraction (HPB), n-butanol fraction (HPC), and water residue (HPD) against AP in rats.
Materials and methods:
A 15% ammonia-induced AP rat model in rats was established. Therapeutic effects of HP and HPÃ D in model rats were evaluated based on body weight, histopathological analysis, and inflammatory parameters, including tumor necrosis factor α (TNF-α), prostaglandin E2 (PGE2), interleukin 1β (IL-1β), and IL-6. The protein expression of nuclear factor kappa-B p65 (NF-κB p65), inhibitor of NF-κB alpha (IκBα), c-Jun N-terminal kinases (JNK), mitogen-activated protein kinase (MAPK) p38, extracellular signal-regulated kinase (Erk), just another kinase 1 (JAK1), signal transducer and activator of transcription 3 (STAT3), phosphoinositide 3-kinase (PI3K), and protein kinase B (Akt) were detected by a Western blotting assay.
Results:
HP, HPB, and HPC treatments markedly alleviated AP in rats by increasing body weight and improving pathological damages in pharyngeal tissues. In addition, HP, HPB and HPC treatments significantly inhibited inflammation, including decreasing the levels of TNF-α, PGE2, IL-1β, and IL-6, and suppressing phosphorylated protein expression of p65, IκBα, JNK, p38, Erk, JAK1, STAT3, PI3K, and Akt in pharyngeal tissues of rats.
Conclusion:
Collectively, HP, HPB, and HPC can attenuate pharynx injury in rats by suppressing inflammation via inhibition of NF-κB, MAPKs, JAK-STAT, and PI3K-Akt pathways, which supports the traditional use of H. plantaginea flowers.
A new phenol derivative, hostaphenol A (1), along with 16 known ones (2-17) were isolated from an ethanolic extract of the whole plants of Hosta ensata F. Maek. Their structures were elucidated by HRMS and NMR data as well as comparison with those reported in literature. The report of the first cyclopeptide and compounds 5, 6, 8, 10, 12-15, and 17 in the Asparagaceae family. Compound 2, as well as compounds 3, 4, 7, 9, 11, and 16 were reported for the first time from the Hosta genus and this plant, respectively. All compounds significantly reduced nitric oxide (NO) production at a concentration of 40 μM with no toxicity in RAW 264.7 cells stimulated by lipopolysaccharide. Among them, compounds 2-5 (40 μM) exerted obvious NO inhibitory activities, and their inhibition rate was exceeded 50%.
Traditional Chinese medicine is the main source of natural products due to its remarkable clinical efficacy. Syringa oblata Lindl (S. oblata) was widely used because of its extensive biological activities. However, to explore the antioxidant components of S. oblata against tyrosinase, the experiments of antioxidation in vitro were employed. At the same time, the determination of TPC was also use to assess the antioxidant ability of CE, MC, EA and WA fractions and the liver protective activity of the EA fraction was evaluated by mice in vivo. Next, UF-LC-MS technology was performed to screen and identify the efficient tyrosinase inhibitors in S. oblata. The results showed that alashinol (G), dihydrocubebin, syripinin E and secoisolariciresinol were characterized as potential tyrosinase ligands and their RBA values were 2.35, 1.97, 1.91 and 1.61, respectively. Moreover, these four ligands can effectively dock with tyrosinase molecules, with binding energies (BEs) ranging from 0.74 to -0.73 kcal/mol. In addition, tyrosinase inhibition experiment was employed to evaluate the tyrosinase inhibition activities of four potential ligands, the result showed that compound 12 (alashinol G, IC50 = 0.91 ± 0.20 mM) showed the strongest activity to tyrosinase, followed by secoisolariciresinol (IC50 = 0.99 ± 0.07 mM), dihydrocubebin (IC50 = 1.04 ± 0.30 mM) and syripinin E (IC50 = 1.28 ± 0.23 mM), respectively. The results demonstrate that S. oblata might have excellent antioxidant activity, and UF-LC-MS technique is a effective means to filter out tyrosinase inhibitors from natural products.
Hosta plantaginea (Lam.) Aschers flower is traditionally used in China as an important herbal medicine for the treatment of inflammatory disease. The present study isolated one new compound, namely (3R)-dihydrobonducellin (1), and five known ones, p-hydroxycinnamic acid (2), paprazine (3), thymidine (4), bis(2-ethylhexyl) phthalate (5), and dibutyl phthalate (6) from H. plantaginea flowers. These structures were elucidated from spectroscopic data. Among them, compounds 1-4 remarkably suppressed nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW 264.7 cells with half maximal inhibitory concentration (IC50) values of 19.88 ± 1.81, 39.80 ± 0.85, 19.03 ± 2.35, and 34.63 ± 2.38 μM, respectively. Furthermore, compounds 1 and 3 (20 μM) significantly decreased levels of tumor necrosis factor α (TNF-α), prostaglandin E2 (PGE2), interleukin 1β (IL-1β), and IL-6. Additionally, compounds 1 and 3 (20 μM) prominently reduced the phosphorylation protein level of nuclear factor kappa-B (NF-κB) p65. The present findings indicated that compounds 1 and 3 may be new candidates against inflammation via blocking the NF-κB signaling pathway.
Ethnopharmacological relevance:
Hosta plantaginea (Lam.) Aschers flower is an important Mongolian medicine beneficial in the treatment of chronic prostatitis (CP) in the absence of scientific evidence.
Aim of the study:
The aim of this study was to reveal the therapeutical effects and potential mechanisms of H. plantaginea flowers extract (HP) and its different polarity fractions (HPA∼D) on autoimmune CP (ACP) model rats.
Materials and methods:
Sprague-Dawley male rats were randomly assigned to 13 groups (n = 6/group). Except the sham group, all rats were injected with a mixture of prostate antigen and complete Freund's adjuvant on days 0, 7, and 21 to establish ACP model rats. Afterwards, ACP model rats were orally gavaged with HP or HPA∼D (1 and 4 g/kg of raw herbal material) or positive drug (prostate, 200 mg/kg) daily from day 21 to day 50 for 30 days, while the sham and model groups were treated simultaneously with isopyknic of 0.3% sodium carboxymethyl cellulose. Histopathological analysis, biochemical parameters, and protein expression of prostate tissues were investigated.
Results:
In comparison with the model group, all fraction groups experienced improved CP effects, including restored body weight, reduced prostate gland edema and prostate index, decreased prostatic leukocytes, increased prostatic lecithin bodies, and alleviated histopathological damage to prostate tissue. Furthermore, all fraction groups markedly inhibited the phosphorylated protein of nuclear factor kappa-B p65 (NF-κB p65), NF-κB inhibitor alpha (IκBα), c-Jun N-terminal kinase (JNK), p38 mitogen-activated protein kinase (MAPK), extracellular signal-regulated kinase (Erk), just another kinase 1 (JAK1), signal transducer and activator of transcription 3 (STAT3), phosphoinositide 3-kinase (PI3K), and protein kinase B (Akt) than the model group.
Conclusion:
All fractions of HP exerted significant anti-CP effects by inhibiting NF-κB, MAPKs, JAK-STAT and PI3K-Akt pathways in ACP model rats. These findings provide scientific evidence that H. plantaginea flowers can be used as a pivotal Mongolian medicine in clinical applications for the treatment of CP.
Flower plants are popular all over the world and important sources of ornamental plants, bioactive molecules and nutrients. Flowers have a wide range of biological activities and beneficial pharmacological effects. Flowers and their active ingredients are becoming more and more popular in the preparation of food, drugs and industrial products. This paper summarizes the active ingredients, pharmacological activities and applications in the pharmaceutical and food industries of flower plants in recent years. In addition, the possible molecular mechanism of pharmacological effects of flower plants were also discussed. 302 active constituents from 55 species of flower plants were summarized, including flavonoids (115), terpenoids (90), phenylpropanoids (20), alkaloids (13), organic acids (27) and others (37). The pharmacological effects of flower plants are very extensive, mainly including antioxidant, anti-inflammatory, anti-tumor, anti-virus, and hypoglycemic. The mechanisms of anti-inflammatory, anti-tumor and hypoglycemic activities present the characteristics of multi-way and multi-target. Because of its rich nutrients, bioactive ingredients and plant essential oils, and its wide sources, flower plants are widely used in food, beverage, cosmetics and drug research. Flower plants also play an important role in pharmaceutical industry, food industry and other fields.
Kaempferol 3-O-(2G-glucosylrutinoside)-7-O-glucoside (KGG) has isolated from Hosta plantaginea flowers and possessed an inhibitory effect on cyclooxygenase 2 (COX-2), could be effective in inhibiting inflammation. However, the anti-inflammatory activity and mechanism of KGG remain unknown. In this study, for the first time, the anti-inflammatory effect of KGG and its potential molecular mechanisms were explored in cells. KGG had no cytotoxicity at concentrations of 1.25, 2.5, 5, 10, 20, and 40 μM by Cell Counting kit-8 assay in RAW 264.7 cells. Besides, KGG concentration-dependently (1.25, 2.5, and 5 μM) inhibited secretions of nitric oxide (NO), prostaglandin E2 (PGE2), tumor necrosis factor α (TNF-α), interleukin 1β (IL-1β), and IL-6 in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Western blot showed that the phosphorylation of nuclear factor kappa-B (NF-κB) p65, inhibitor of NF-κB (IκB), p38 MAPK, c-Jun N-terminal kinases (JNK), extracellular signal-regulated kinase (Erk), and protein kinase B (Akt), together with inducible nitric oxide synthase (iNOS) and COX-2 were significantly attenuated by KGG (1.25, 2.5, and 5 μM) in a concentration-dependent relationship. Meanwhile, KGG remarkably enhanced the protein expression of IκB. Taken together, KGG may be one of bioactive phytochemicals from H. plantaginea flowers, and be an anti-inflammatory agent via inhibiting NF-κB, mitogen-activated protein kinases (MAPKs), and Akt signaling pathways.
Background
Equisetum ramosissimum is a pteridophyte plant used in Moroccan traditional medicine for its diuretic and antidiabetic properties. The species is known to reduce blood cholesterol levels and is given in cases of gonorrhea.
Objective
The present work aims to explore the potential use of the crude butanolic (BE) and methanolic (ME) extracts of E. ramosissimum in the management of pain, inflammation and oxidative stress, and their chemical characterization.
Methods
The phytochemical investigation of E. ramosissimum was initially done by colorimetric methods, followed by High Performance Liquid Chromatography coupled with Mass Spectroscopy (HPLC-MS). Its antioxidant activity was evaluated using radical scavenging activity in 2,2- diphenyl-1-picrylhydrazyl radical (DPPH), reducing power and β-carotene/linoleic acid bleaching assays. The analgesic activity was evaluated by acetic acid in mice and hot-plate-test in rat models. Rate paw edema and ear edema were used as anti-inflammatory models.
Results
The chemical quantification revealed appreciable levels of phenolic compounds. The results of HPLC-UV and HPLC-MS highlighted the presence of kaempferol3-O-sophoroside7-Oglucoside, kaempferol3,7-O-diglucoside, vanillin, ferulic acid and tannic acid. The maximum IC50 was obtained for BE by DPPH test (0.064±0.0004mg/mL). BE exhibited an interesting antinociceptive effect; inhibition of writhes, 3.83±0.48 at 600mg/kg, increased the latency period on the hotplate- test, i.e., 14.98S±0.57S at 400mg/kg after 120min. Furthermore, the results reported a significant inhibition of rate-paw edema and ear edema for both extracts at a dose of 400mg/kg.
Conclusion
BE and ME of E. ramosissimum were found to contain a significant amount of flavonoids, especially derivatives of kaempferol, which can explain the interesting effectiveness properties. Possible applications in the food and pharmaceutical industries are suggested.
Hosta ventricosa is a plant that can be used for medicine and diet. It has been proven to have anti-inflammatory, antibacterial and antitumor activities, and one of its main constituents is polysaccharides. However, studies on polysaccharides of Hosta ventricosa are limited, and their physiological activities have not been clarified. Therefore, isolation, purification and characterization of Hosta ventricosa root polysaccharides (HVRPp-1) were performed in this research. Furthermore, the effect of HVRPp-1 on tert-butyl hydroperoxide (t-BHP)-induced oxidative damage in HepG2 cells was investigated in vitro. The results showed that HVRPp-1 is a nonhomogeneous polysaccharide that could protect HepG2 cells from oxidative damage through the C-Jun N-terminal kinase (JNK)/nuclear factor erythroid 2-related factor 2 (Nrf2) signaling pathway. In conclusion, this research proved the antioxidant mechanism of HVRPp-1 for the first time, providing a reliable theoretical basis for basic research on Hosta ventricosa polysaccharides and the possibility of their application in functional foods.
Only the dried stigma of the saffron, a flower deemed as the most valuable spice globally, is utilized for industrial production. Hence, there exists a growing interest in utilizing saffron floral bio-residues. The anti-hyperuricemic activity of a flavonoid extract from saffron floral bio-residues was assessed in potassium oxonate-induced hyperuricemia mice. In addition, an ultra-high performance liquid chromatography-triple quadrupole mass spectrometry method was established and validated to determine the pharmacokinetics of five main flavonoids and three phase-II metabolites in rat plasma after oral administration of the flavonoid extract for the first time. Compared with pharmacokinetic parameters of kaempferol-3-O-sophoroside, the most abundant flavonoid in the extract, and its aglycone kaempferol, we observed that coexisting compounds significantly reduced the absorption, accelerated the excretion of kaempferol-3-O-sophoroside, while significantly increasing the absorption and prolonging the residence time of kaempferol in the flavonoid extract. These results suggest the promising potential of the flavonoid extract from saffron floral bio-residues as an anti-hyperuricemic agent. Kaempferol was absorbed in plasma at high concentrations owing to the biotransformation of kaempferol glycosides in vivo.
Ethnopharmacological relevance
Hostaflavone A (HA) is a new flavonoid component isolated from the flower of Hosta plantaginea (Lam.) Asch., which is commonly used as a folk herbal to treat inflammatory diseases in China. Nevertheless, the anti-inflammatory effect of HA remains unknown.
Aim of the study
This work aimed to evaluate the HA with anti-inflammatory activity and mechanism in RAW 264.7 macrophages activated by lipopolysaccharide (LPS).
Materials and methods
Anti-inflammatory effect of HA was evaluated by measuring of cell viability, nitric oxide (NO), prostaglandin E2 (PGE2), tumor necrosis factor α (TNF-α), interleukin 1β (IL-1β) and IL-6 levels in RAW 264.7 cells. In parallel, the HA action mechanism of nuclear factor kappa B (NF-κB) p65, inhibitor of NF-κB (IκB), inducible nitric oxide synthase (iNOS), cyclooxygenase 2 (COX-2), c-Jun N-terminal kinases (JNK), extracellular signal-regulated kinase (Erk), p38, and protein kinase B (Akt) were detected by Western blot analysis.
Results
HA has no cytotoxicity at concentrations as high as 40 μM. Besides, HA concentration-dependently clearly suppressed the overproduction of NO, PGE2, TNF-α, IL-1β and IL-6 in RAW 264.7 cells induced by LPS. In addition, HA remarkably reduced the upregulation of phosphorylated NF-κB p65, phosphorylated IκB, phosphorylated JNK, phosphorylated Erk and phosphorylated p38, together with iNOS and COX-2 protein expressions in a concentration-dependent manner.
Conclusion
HA blocked the LPS activated inflammation via suppressing NF-κB, iNOS, COX-2, mitogen-activated protein kinases (MAPKs) and Akt pathways in RAW 264.7 cells, and might be a new anti-inflammatory agent.
The flowers of Hosta plantaginea (Lam.) Aschers are commonly used for the treatment of inflammatory diseases in traditional Chinese medicine with limited scientific evidence. Plantanone C (PC) is a new phytochemical isolated from H. plantaginea flowers; nevertheless, the anti-inflammatory effect remains unknown. Herein, we aimed to study the anti-inflammatory effects of PC and its underlying molecular mechanisms in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages. The cell viability of PC-treated RAW 264.7 macrophage was measured by the Cell Counting kit-8 (CCK-8) assay. The anti-inflammatory effect of PC was investigated by measuring the levels of inflammatory mediators and pro-inflammatory cytokines using the Griess reaction and enzyme-linked immunosorbent assay (ELISA). Furthermore, the mechanism of action of PC was evaluated by Western blot analysis. The results showed that PC was not cytotoxic at concentrations as high as 40 μM. Furthermore, PC potently suppressed LPS-stimulated overproduction of nitric oxide (NO), prostaglandin E2 (PGE2), tumor necrosis factor α (TNF-α), interleukin 1β (IL-1β) and IL-6 in RAW 264.7 macrophages. Western blot demonstrated that PC remarkably suppressed the phosphorylation of nuclear factor kappa-B (NF-κB) p65, inhibitor of NF-κB (IκB), c-Jun N-terminal kinases (JNK), extracellular signal-regulated kinase (Erk), p38, and protein kinase B (Akt), as well as inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX-2) in a concentration-dependent manner. Taken together, these findings suggest that PC exhibits anti-inflammatory effects by inhibiting NF-κB, iNOS, COX-2, mitogen-activated protein kinases (MAPKs), and Akt signaling pathways in RAW 264.7 macrophages.
Ethnopharmacological relevance
The root of Dendropanax dentiger (Harms) Merr. is a pivotal folk Chinese medicine against rheumatoid arthritis (RA) with no scientific validation.
Aim of the study
This study was conducted to explore the anti-RA effect of the D. dentiger extract on complete Freund's adjuvant-induced arthritis (AIA) in rats and identified its major bio-constituents.
Materials and methods
Dendropanax dentiger roots extracts (127.5, 255.0 and 510.0 mg/kg, once daily) were orally at day 7 post-administration adjuvant and lasting for 22 days. The therapeutic effects of D. dentiger roots extract on AIA rats were investigated by body weight growth, arthritis score, thymus and spleen indices, and histopathological analysis. Moreover, the levels of rheumatoid factor (RF), C-reactive protein (CRP), tumor necrosis factor alpha (TNF-α), interleukin-1β (IL-1β), IL-4, IL-6, IL-10, IL-17, cyclooxygenase-2 (COX-2), 5-lipoxygenase (5-LOX) and matrix metalloproteinase-2 (MMP-2) were also evaluated. Finally, the major constituents were isolated and identified from D. dentiger roots extract with COX-2 inhibitory and antioxidant activities.
Results
Dendropanax dentiger roots extract remarkably alleviated the histological lesions of knee joint, increased body weight growth, decreased arthritis score, and reduced thymus and spleen indices in model rats. In parallel, the levels of RF, CRP, TNF-α, IL-1β, IL-6, IL-17, COX-2, 5-LOX and MMP-2 were observably downregulated, while the levels of IL-4 and IL-10 were prominently upregulated in D. dentiger roots extract-treated rats. Meanwhile, 14 compounds were isolated and identified from D. dentiger roots extract, and four phenol derivatives (1, 4, 6 and 7) exhibited remarkable COX-2 inhibitory and antioxidant activities.
Conclusions
Dendropanax dentiger roots extract possessed persuasive anti-RA effect may be partly responsible for phenol derivatives via modulation of inflammatory biomarkers, and supports the traditional folk use of D. dentiger in China.
Ethnopharmacological relevance
Malvaviscus arboreus is traditionally used in Mexico and Central America for culinary and medicinal purposes. Leaves and flowers of this species are commonly used for preparation of salads, herbal teas and herbal dyes. Panamanian, Guatemalan and Mexican healers use this medicinal plant for the management of fever, respiratory complications, dysentery, liver and gallbladder problems, stomachache and gastritis between other health troubles.
Aim of the study
Considering the traditional use of M. arboreous as well as its content in flavonoids and other polyphenols, the objective of this work was to evaluate the gastroprotective effect of an aqueous extract and identify the potential bio-active principles from flowers of this species.
Material and methods
Fresh flowers of Malvaviscus arboreus were collected, dried, and macerated with water. The aqueous extract (ExAq) was partitioned using an immiscible mixture of water and ethyl acetate, giving an aqueous (MaAq) and organic (MaEA) fractions. The gastroprotective effect was carried out using an ethanol-induced gastric ulcer experimental test in male rats. While tween 20 was used as a negative control, famotidine (10 mg/kg) and L-arginine (300 mg/kg) were used as positive controls. Compounds 1 and 2 were isolated by several chromatographic techniques and the chemical characterization was carried out by means of the analysis of the NMR spectra in one and two dimensions.
Results
The integrate extract (ExAq) to 250, 500 and 750 mg/kg showed gastroprotective effect with high levels of 97.8%, 79.5% and 91.1% respectively. The organic fraction (MaEA) displayed a protection of 91.2%, 96.0% and 99.4% when it was evaluated at 125, 250 and 500 mg/kg respectively. Comparison of these results with famotidine at 10 mg/kg (83% of gastroprotection) indicated that ethyl acetate fraction showed a better gastroprotection. The bio-guided separation of this organic mixture, allowed obtaining the most active fraction (C1F4, 60 mg/kg) which was finally purified to obtain two glycosylated flavonols: kaempferol 3-O-D-sophoroside (1) and kaempferol 3-O-D-sambubioside (2). This mixture of flavonoids (40 y 60 mg/kg) showed 93.7 and 92% of gastroprotective activity respectively.
Conclusion
This study allowed demonstrating that an aqueous extract and its organic fraction (MaEA) from M. arboreous contain glycosylated flavonoids (1 and 2) which are responsible of the gastroprotective properties of M. arboreous. These results will be used in the future development of a standardized treatment useful in the therapeutic management of gastric ulcers.
The root of Dendropanax dentiger (Harms) Merr. is a traditional Chinese medicine that has been used to treat inflammation-related diseases with little scientific validation. In this study, a bioassay-guided phytochemical investigation of D. dentiger led to the isolation of 19 phenylpropanoid derivatives including one new compound (1) and 18 known ones (2-19). Their structures were elucidated by NMR and HRMS as well as comparison with literature data. The ability of cyclooxygenase-2 (COX-2) inhibition and antioxidant of all isolated compounds were measured in vitro. Chlorogenic acid derivatives (14-19) exhibited outstanding COX-2 inhibitory (IC50 = 5.1-93.4 μM) and antioxidant (IC50 = 13.2-31.9 μM) activities. Moreover, the tight structure-activities relationships were proposed. This is the first report on the COX-2 inhibitory activity of phenylpropanoids and D. dentiger.
Ethnopharmacological relevance
The genus Hosta (Liliaceae family) represents an interesting source of natural bio-constituents, and the 50 species of this genus are widespread in the world. Five species have been used as traditional East Asian medicines for treating inflammation and pain-related diseases. However, the available data for this genus have not been comprehensively reviewed regarding their extracts and secondary metabolites.
Aim of the study
The present review aims to provide a deeper insight, better awareness and detailed knowledge of traditional uses, phytochemistry, pharmacology along with toxicological aspects of the genus Hosta in the past decades (February 1964 to August 2020). In addition, the relevance among traditional uses, pharmacology and phytochemistry in folk medicines were extensively discussed.
Materials and methods
The relevant information of Hosta species was obtained from several databases. Moreover, the medical books, PhD and MSc dissertations in Chinese were also used to perform this work.
Results
Comprehensive analysis of the afore-mentioned databases, medical books and dissertations confirmed that ethnomedical uses of Hosta genus plants had been recorded in China, Japan, Korea and other countries. To date, only eight species have been studied for chemical constituents, and a total of 200 secondary metabolites (not include essential oil constituents), including steroids, flavonoids, alkaloids, furan derivatives, phenylpropanoids, phenethyl derivatives, terpenoids, aliphatics, and others. The crude extracts and isolated chemical constituents exhibited anti-inflammatory and analgesic, antioxidant, anti-tumor, anti-viral, acetylcholinesterase inhibitory, antimicrobial, anti-chronic prostatitis, and other effects. Moreover, only the n-butanol fraction of H. ventricosa (Salisb.) Stearn roots showed moderate acute toxicity in mice. In addition, the relevance among traditional uses, pharmacology and phytochemistry in folk medicines were extensively discussed.
Conclusions
Hosta spp. are plants rich in steroids and flavonoids with valuable medicinal properties; though, there are several gaps in understanding the traditional uses in the current available data. More high scientific quality preclinical studies with new methodology are necessary to assess the safety, efficacy and mechanism of these plants.
Ethnopharmacological relevance:
The flower of Hosta plantaginea (Lam.) Aschers (Liliaceae) is a traditional medicinal material in Mongolian medicine for treating sore throat, hoarseness, pulmonary fever, and toxic fever in folk. The present work investigated anti-prostate cancer and hepatoprotective activities of flavonoid derivatives from H. plantaginea (Lam.) Aschers.
Aim of the study:
To isolate and identify the chemicals of H. plantaginea (Lam.) Aschers for anti-prostate cancer and hepatoprotective activities.
Materials and methods:
Active chemicals were isolated and purified from H. plantaginea (Lam.) Aschers by chromatographic methods, and their structures were established on spectroscopic analysis and references. These compounds were evaluated for their anti-prostate cancer activities using the LNCaP prostate cancer cells, and assayed for their hepatoprotective activities on CCl4-induced injury of human L-O2 cells, respectively.
Results:
Four new flavonol-lignan heterodimers (1-4), together with nine known flavonoid derivatives (5-13) were isolated from this plant for the first time. Among them, some compounds exhibited moderate anti-prostate cancer and hepatoprotective activities.
Conclusion:
Compounds 1, 2, 5, and 6 showed anti-prostate cancer activities using the LNCaP prostate cancer cells with IC50 values of 17.84, 33.26, 54.13, and 81.55 μg/mL, and compounds 3, 4, 8, and 9 exhibited moderate hepatoprotective activities, respectively. A preliminary structure-activity relation was summarized in this paper.
Flowers of Hosta plantaginea have been used for the treatment of inflammation-related diseases in traditional Chinese medicine with limited scientific validation. In the present work, we reported one new rare methyl-flavonoid, plantanone D (1) and one known compound 4-hydroxybenzoic acid (2) from the flowers of H. plantaginea. Their structures were elucidated on the basis of chemical and spectral evidence, as well as by comparison with literature data. To the best of our knowledge, the methyl-flavonoid skeleton have not been reported from any species in Liliaceae family, compound 2 was isolated from the genus Hosta for the first time. The anti-inflammatory activities against cyclooxygenases (COX-1 and COX-2) and antioxidant activities in vitro results revealed that 1 exhibited significant COX-1 inhibition and moderate COX-2 inhibition compared to the reference celecoxib. Additionally, 1 displayed significant antioxidant activity compared to the positive control L-ascorbic acid.
A new flavan-3-ol glycoside, hostaflavanol A (1) along with two related known ones, including dihydrokaempferol (2) and naringnin (3) were isolated from the 80% ethanol extract of Hosta plantaginea flowers. Their structures were elucidated on the basis of chemical and spectral evidence, as well as by comparison with literature data. To the best our knowledge, compounds 2 and 3 were characterized for the first time from the Liliaceae family and genus Hosta, respectively. The anti-inflammatory activity against cyclooxygenases (COX-1 and COX-2) in vitro results revealed that compounds 1‒3 exhibited significant or moderate COX-1 and moderate COX-2 inhibitory effects with IC50 values of 23.7 ± 1.8, 31.6 ± 1.6, and 61.3 ± 3.1 μM for COX-1, as well as 46.7 ± 3.1, 71.2 ± 3.5, and 115.7 ± 6.5 μM for COX-2, respectively. Furthermore, the antioxidant activity of compounds 1‒3 was also measured by the DPPH method, 1‒3 exhibited significant or moderate antioxidant activities with IC50 values of 112.7 ± 3.8, 46.6 ± 1.3, and 82.4 ± 2.4 μM, respectively.
Hosta plantaginea (Lam.) Aschers, as a traditional folk medicine, has been widely used both as a single herb and in prescriptions in Asia mainly due to its anti-inflammatory and analgesic effects. A total of 101 compounds including steroids, flavonoids, alkaloids and others have been isolated from H. plantaginea. Modern pharmacology has revealed that H. plantaginea possesses various therapeutic effects such as anti-inflammatory, analgesic and antibacterial effects both in vitro and in vivo. Although a number of reports on the chemical constituents and pharmacological activities of this plant are available, there is limited research on the bioactive constituents and the mechanism of the biological activities of H. plantaginea. Thus, it is essential to strengthen the research on bioactive constituents and their mechanisms as well as their structure–function relationships in H. plantaginea. Up to now, only three compounds have been established for the quality control of H. plantaginea. However, a comprehensive review on the botany, traditional use, phytochemistry, quality control and pharmacology information about this plant has not been reported so far; thus, a systematic and comprehensive review is very necessary. Therefore, this paper provided a comprehensive overview on the botany, traditional use, phytochemistry, quality control and pharmacology of H. plantaginea and also provided evidence for its further research and clinical applications.
Two new pregnane glycosides, 2α, 3β-dihydroxy-5α-pregn-16-en-20-one-3-O-{α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside} (1) and 2α, 3β-dihydroxy-5α-pregn-16-en-20-one-3-O-{β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside}(2), have been isolated along with two known spirostanol saponins from the underground parts of Hosta ventricosa. Their structures were elucidated on the basis of chemical and spectral evidence. The anti-inflammatory activities of these steroidal glycosides were evaluated using a xylene-induced ear edema model. Our results indicated that the compounds exhibited promising anti-inflammatory activities.
Ethnopharmacological relevance
Lagopsis supina has been used as a traditional medicinal herb for centuries in China. In folk medicine, it is used for promoting blood circulation and removing blood stasis (PBCRBS), anti-inflammatory and diuretic activities. Modern pharmacological investigation have shown that L. supina have an improvement in blood and lymphatic microcirculation, myocardioprotective, and antioxidative activities. Although the pharmacological research of L. supina was more, there was no report on the diuretic activity.
Aim of the study
This study was to evaluate the diuretic activity and the underlying mechanism of an ethanol extract of L. supina (LS) in a rat model of traumatic blood stasis (TBS).
Materials and methods
There were 30 male Sprague-Dawley rats that were randomly assigned to the control group, TBS group, and LS group (10 animals in each group). LS was administered orally (460 mg/kg) once daily for 7 successive days. The control group and TBS group were given an equal amount of 0.3% sodium carboxymethyl cellulose (CMC-Na). For the efficacy evaluation, the urine output volume, the urinary electrolyte concentrations (Na⁺, K⁺, Cl⁻ and Ca²⁺) and pH value, the levels of angiotensin II (Ang II), atriopeptin (ANP), anti-diuretic hormone (ADH) and aldosterone (ALD), as well as aquaporin (AQP)-1, 2 and 3 protein expressions were detected in a rat model of TBS. The protein expressions of AQP-1, 2 and 3 were detected by quantitative immunohistochemistry (IHC) and Western blot analysis.
Results
In the efficacy evaluation, rat models treated with LS showed a significant increase in the total urine output (p < 0.01). The urinary electrolyte and the acid-base disturbances, including the decrease of Na⁺ and Ca²⁺ levels and the Na⁺/K⁺ value together with the increase in the Cl⁻ level and the pH value, in the urine of the LS group were compared with the TBS group. Moreover, the levels of Ang II, ADH and ALD of rat model were decreased after being treated with LS (p < 0.05 or p < 0.01), while the ANP level was increased (p < 0.05). In addition, the results of the quantitative IHC and the Western blot analysis showed that the expression levels of AQP-1, 2 and 3 proteins decreased significantly compared with those of the TBS group.
Conclusions
This is the first reported notable diuretic effect by LS, which probably was through the suppression of the renin-angiotensin-aldosterone system (RAAS) and the regulation of the signaling pathways of AQP-1, 2 and 3 protein expressions. Based on our results, we conclude that L. supina carries out its diuretic effect mainly by down-regulating the levels of AQP-1, 2 and 3 expressions in TBS rat model. These data also embody the traditional Chinese medicine (TCM) application principle of Huo xue li shui. These findings suggest that LS may warrant further evaluation as a possible agent for the diuretic drug in clinical applications. Further research is underway to elucidate the active compounds responsible for the diuretic activity of LS.
Two new phenolic glucosides, hostaflavanone A (1) and anti-1-phenylpropane-1,2-diol-2-O-β-d-glucopyranoside (2), together with six known compounds, anti-1-phenylpropane-1,2-diol (3), phenethyl-O-β-d-glucopyranoside (4), phenethanol-β-d-gentiobioside (5), phenethyl-O-rutinoside (6), (1S, 3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (7), and (1R, 3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (8), were isolated from the flower of Hosta plantaginea, and their structures were elucidated by nuclear magnetic resonance (NMR), high resolution electrospray ionization mass spectroscopy (HRESIMS), and circular dichroism (CD) analyses. The cyclooxygenases (COX-1 and COX-2) inhibition and antioxidant activities of compounds 1 and 4–6 were investigated, and they showed moderate cyclooxygenases inhibition activities. Moreover, only compound 1 exhibited moderate antioxidant activity, with an IC50 value of 83.2 μM, while 4–6 showed insignificant activity with IC50 values of 282, 257, and 275 μM, respectively. This is the first report of compounds 3 and 5–8 from the Liliaceae family. The chemotaxonomic significance of the isolated compounds was also summarized.
The medicinal parts of Hosta plantaginea includes the whole plant, roots, stems, and flowers with a long history used as traditional folk herbal medicine. It has been commonly used for hundreds of years in Mongolia solely or in complex preparation for the treatment of sore throat and other diseases. However, there are few non-systemic studies on anti-inflammatory material basis, mechanisms, and quality control of H. plantaginea so far as well. The crude extracts or pure compounds from H. plantaginea showed anti-inflammatory, analgesic, cytotoxic, anti-microbial, anti-viral, anti-AchE activities, etc. In addition, previous phytochemical studies on H. plantaginea have indicated that steroids, alkaloids, and flavonoids are the major constituents in this plant. In this paper, we have systematically summarized and analyzed the chemical constituents, pharmacological activities, clinical application, and quality control of folk medicine H. plantaginea, which provides the foundation for the rational use and comprehensive development of H. plantaginea. © 2016, Editorial Office of Chinese Traditional and Herbal Drugs. All right reserved.
Gymnosporia heterophylla (Celastraceae) is an African medicinal plants used to treat painful and inflammatory diseases with partial scientific validation. Solvent extractions followed by repeated chromatographic purification of the G. heterophylla aerial parts led to the isolation of one new β-dihydroagarofuran sesquiterpene alkaloid (1), and two triterpenes (2–3). In addition, eight known compounds including one β-dihydroagarofuran sesquiterpene alkaloid (4), and six triterpenes (5–10) were isolated. All structures were determined through extensive analysis of the NMR an MS data as well as by comparison with literature data. These compounds were evaluated for the anti-inflammatory activities against COX-1 and -2 inhibitory potentials. Most of the compound isolated showed non selective COX inhibitions except for 3-Acetoxy-1β-hydroxyLupe-20(29)-ene (5), Lup-20(29)-ene-1β,3β-diol (6) which showed COX-2 selective inhibition at 0.54 (1.85), and 0.45 (2.22) IC50, in mM (Selective Index), respectively. The results confirmed the presence of anti-inflammatory compounds in G. heterophylla which are important indicators for development of complementary medicine for inflammatory reactions; however, few could be useful as selective COX-2 inhibitor.
In this paper, we carried out a systematic chemical study on the ethyl acetate (EtOAc) extract from the flowers of Hosta plantaginea (Lam.) Aschers (H. plantaginea), which resulted in the isolation of a new compound (1) together with one known compound (2). The structure elucidations of new compound were carried out by 1D [¹H and ¹³C nuclear magnetic resonance (NMR)] and 2D‐NMR spectral analysis. Studies on the antibacterial activity established that compound 1 showed statistically higher inhibition against Staphylococcus aureus (S. aureus) compared to streptomycin and compound 2. Among the tested bacteria, Bacillus cereus (B. cereus) was the most sensitive and Yersinia enterocolitica (Y. enterocolitica) was found to be the most resistant. The antibacterial activities exhibited by compound 1 demonstrate their potential for use as nutraceuticals and in food preservation.
Practical applications
The flowers of H. plantaginea are used as a clinical medicine to treat many diseases, such as swelling, mastadenitis, otitismedia, anabrosis, lung heat, and terrific heat. Various pharmacological properties have been observed in some steroidal glycosides and alkaloids from H. plantaginea including cytotoxic and anti‐inflammatory. In the article, the antibacterial activities of two monoterpene glycosides from the flowers of H. plantaginea have been evaluated for the first time. Therefore, the results may have some useful practical implications at both the food and medicine technology.
OBJECTIVE: To investigate the chemical constituents of Hosta plantaginea (Lam.) Aschers. METHODS: The chemical constituents were isolated by Sephadex LH-20 and silica gel column chromatography. The structures of these compounds were identified by physiochemical properties and spectral analysis. RESULTS: Six compounds were isolated from the 95% ethanol extract of the flowers of Hosta plantaginea (Lam.) Aschers and elucidated as eicosan acid(I), hexadecanoic acid 2,3-dihydroxypropyl ester(II), kaempferol(III), quercertin(IV), kaempferol-3-O-rufinoside(V), kaempferol-7-O-β-D-glucoside(VI). CONCLUSION: Six compounds were isolated from Hosta plantaginea(Lam.) Aschers for the first time. Compound I, II, III, IV and V were isolated from the genus for the first time.
Seven new flavonoid glycosides (1-7), matteflavosides A-G, together with 12 known flavonoids (8-19) were isolated from the rhizomes of Matteuccia struthiopteris (L.) Todar. Their structures were established via the analyses of extensive spectroscopic data. All compounds were evaluated for their anti-influenza virus (H1N1) activity using the neuraminidase inhibition assay. The results showed that compound 7 exhibited significant inhibitory activity against the H1N1 influenza virus neuraminidase with an EC50 value of 6.8 ± 1.1 μM and an SI value of 34.4, and compounds 8 and 17 showed moderate inhibitory activity.
In this study, pollen morphology of 11 taxa of Hosta in China, three Chinese species, five introduced species, and three cultivars, was observed by scanning electron microscopy (SEM) and
compared with that of related genera (Hemerocallis, Agave, and Yucca). Pollen grains of Hosta were long-ellipsoidal or ellipsoidal, 20–65×52.5–142.5μm in size, bilaterally symmetrical, and monosulcate on the distal
face. Reticulate and rugulate exine ornamentation was observed in different taxa, and the rugulate type can be further divided
into rugulate, rugulate–baculate, and rugulate–granulate subtypes. The exine ornamentation may have evolved in the order:
reticulate→rugulate→rugulate–baculate→rugulate–granulate. Furthermore, the rugulate exine ornamentation was the predominant
ornamental type in Hosta except for one species with the reticulate type; this is markedly different from that of Hemerocallis, Agave and Yucca. Thus, our data support the proposal by Dahlgren and Clifford (The Monocotyledons: a comparative study. Academic Press, London,
1982) that these Hosta species constitute an independent family–Hostaceae.
KeywordsPollen morphology–
Hosta Tratt.–Exine ornamentation–Taxonomic significance
Leaves of Hosta ventricosa yielded eight kaempferol glycosides, of which six: the 3-(2G-glucosylrutinoside)-7-glucoside, 3-sophoroside-7-glucoside, 3-rutinoside-7-glucoside, 3-(2G-glucosylrutinoside), 3-sophoroside, 3-rutinoside were fully characterized and two: the 3-xylosylrutinoside-7-glucoside and 3-xylosylrutinoside were tentatively identified. Investigations included 1H-1H COSY and 1H-1H 2D J NMR analysis.
A new C22-steroid glycoside was isolated from the underground parts of Hosta plantaginea var. japonica, together with a known furostanol saponin and three known spirostanol saponins. The structure of the new steroid glycoside was characterized by spectroscopic analysis and acid-catalysed hydrolysis as 2 alpha, 3 beta, 16 beta-trihydroxy-5 alpha-pregn-20(21)-ene-carboxylic acid gamma-lactone 3-O-¿O-beta-D-glucopyranosyl-(1-->2)-O-beta-D-glucopyranosyl-(1--> 4)-beta-D-galactopyranoside¿. The isolated compounds were assayed for their cytostatic activity on leukaemia HL-60 cells. The spirostanol saponins showed cytostatic activity in a dose-dependent manner with the IC50 values ranging between 1 and 3 micrograms ml-1.
Five new benzylphenethylamine alkaloids, hostasine (1), 8-demethoxyhostasine, 8-demethoxy-10-O-methylhostasine, 10-O-methylhostasine, and 9-O-demethyl-7-O-methyllycorenine, along with 12 known compounds, were isolated from Hosta plantaginea by bioassay-guided fractionation. The structures of the new alkaloids were established by means of extensive spectroscopic methods, and the relative configuration of 1 was further confirmed by single-crystal X-ray diffraction. 7-Deoxy-trans-dihydronarciclasine (IC(50) = 1.80 microM), a known alkaloid, showed strong activity against tobacco mosaic virus by the half-leaf method. Some of these alkaloids were also evaluated for their inhibitory activity against acetylcholinesterase. 8-Demethoxy-10-O-methylhostasine was found to possess significant activity, with an IC(50) of 2.32 microM.
Comparison of anti-inflammatory effects and HPLC detection on different extracts from the flower of Hosta plantaginea in mice
- J W He
- L Yang
- J X Zhu
- X M Wang
- Z R Zhou
- W W He
- G Y Zhong