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1.
Opt Lett ; 49(18): 5264-5267, 2024 Sep 15.
Article in English | MEDLINE | ID: mdl-39270281

ABSTRACT

Chaotic dynamics of semiconductor lasers under optical feedback are useful for random bit generation (RBG). By exploring on an ultra-long feedback loop, a single-mode laser in a route-to-chaos unveils an emission intensity with intermittent microwave bursts, for which a fast form of timing-based RBG is demonstrated. Each microwave burst corresponds to a packet of periodic intensity oscillations at the relaxation resonance. Numerous bursts are found intermittently within a round trip. Repetitions of these intermittent microwave bursts are observed across consecutive round trips. Randomness is extracted from the timing of the bursts as far as the feedback is reinitialized. With a 5-km fiber for feedback to the laser, over 104 intermittent bursts of microwave at 7 GHz are obtained per round trip, where the irregular timing in the envelope leads to RBG at 9.6 Gbps. Such experimental results feature the form of timing-based RBG that is very fast by comparison, carried by the microwave, and stored in the feedback nonlinear dynamics.

2.
Bioorg Chem ; 151: 107692, 2024 Oct.
Article in English | MEDLINE | ID: mdl-39102757

ABSTRACT

As one of a traditional Chinese medicine with dual applications in both medicinal treatment and dietary consumption, the mature seeds of D. lablab were reported to be rich in saponins and have a good effect on inflammatory related diseases. However, the substance basis for its anti-inflammatory activity remains unclear. Thus, a comprehensive phytochemical investigation on triterpenoid saponins from D. lablab seeds was carried out, resulting in the isolation and identification of twenty-one new triterpenoid saponins including dolilabsaponins A1-A4, B, C, D1-D3, E-M, N1, N2 and O (1-21) along with thirteen known analogs (22-34). Notably, the known saponins, 31, 32, and 34 were obtained from Leguminosae family for the first time. The 1H and 13C NMR data of saponins 24 and 28 were firstly reported here. Additionally, lipopolysaccharide (LPS)-stimulated RAW264.7 cells model was utilized to assess inhibitory activities of compounds 1-34 on nitric oxide (NO) production. The results revealed that compounds 1-3, 9, 10, 13-15, 18, 22, 23 and 28-34 significantly suppressed the elevation of NO levels in LPS-induced RAW264.7 cells at the concentration of 30 µM, exhibiting a concentration-dependent manner at 3, 10, and 30 µM. The results suggested that compounds 1-3, 9, 10, 13-15, 18, 22, 23, and 28-34 possessed potential anti-inflammatory activity. Further western blot assay demonstrated that 1, 9, 10, 13, 14, and 18 suppressed inflammatory response via down-regulated the expression levels of inflammatory factors, tumor necrosis factor-alpha and interleukin-6.


Subject(s)
Dolichos , Lipopolysaccharides , Nitric Oxide , Saponins , Seeds , Saponins/pharmacology , Saponins/chemistry , Saponins/isolation & purification , Mice , RAW 264.7 Cells , Animals , Seeds/chemistry , Nitric Oxide/antagonists & inhibitors , Nitric Oxide/biosynthesis , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Molecular Structure , Dolichos/chemistry , Structure-Activity Relationship , Dose-Response Relationship, Drug , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/isolation & purification
3.
Int J Mol Sci ; 25(8)2024 Apr 19.
Article in English | MEDLINE | ID: mdl-38674061

ABSTRACT

Chronic inflammation is a significant contributor to the development of cancer, cardiovascular disease, diabetes, obesity, autoimmune disease, inflammatory bowel disease, and other illnesses. In the academic field, there is a constant demand for effective methods to alleviate inflammation. Astragalin (AST), a type of flavonoid glycoside that is the primary component in several widely used traditional Chinese anti-inflammatory medications in clinical practice, has garnered attention from numerous experts and scholars. This article focuses on the anti-inflammatory effects of AST and conducts research on relevant literature from 2003 to 2023. The findings indicate that AST demonstrates promising anti-inflammatory potential in various models of inflammatory diseases. Specifically, AST is believed to possess inhibitory effects on inflammation-related factors and protein levels in various in vitro cell models, such as macrophages, microglia, and epithelial cells. In vivo studies have shown that AST effectively alleviates neuroinflammation and brain damage while also exhibiting potential for treating moderate diseases such as depression and stroke; it also demonstrates significant anti-inflammatory effects on both large and small intestinal epithelial cells. Animal experiments have further demonstrated that AST exerts therapeutic effects on colitis mice. Molecular biology studies have revealed that AST regulates complex signaling networks, including NF-κB, MAPK, JAK/STAT pathways, etc. In conclusion, this review will provide insights and references for the development of AST as an anti-inflammatory agent as well as for related drug development.


Subject(s)
Anti-Inflammatory Agents , Kaempferols , Humans , Animals , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/therapeutic use , Kaempferols/pharmacology , Kaempferols/therapeutic use , Inflammation/drug therapy , Inflammation/metabolism , Inflammation/pathology , Signal Transduction/drug effects
4.
Molecules ; 29(5)2024 Mar 03.
Article in English | MEDLINE | ID: mdl-38474647

ABSTRACT

A chemical study of Aesculus wilsonii Rehd. (also called Suo Luo Zi) and the in vitro anti-inflammatory effects of the obtained compounds was conducted. Retrieving results through SciFinder showed that there were four unreported compounds, aeswilosides I-IV (1-4), along with fourteen known isolates (5-18). Their structures were elucidated by extensive spectroscopic methods such as UV, IR, NMR, [α]D, and MS spectra, as well as acid hydrolysis. Among the known ones, compounds 5, 6, 8-10, and 12-16 were obtained from the Aesculus genus for the first time; compounds 7, 11, 17, and 18 were first identified from this plant. The NMR data of 5 and 18 were reported first. The effects of 1-18 on the release of nitric oxide (NO) from lipopolysaccharide (LPS)-induced RAW264.7 cells were determined. The results showed that at concentrations of 10, 25, and 50 µM, the novel compounds, aeswilosides I (1) and IV (4), along with the known ones, 1-(2-methylbutyryl)phloroglucinyl-glucopyranoside (10) and pisuminic acid (15), displayed significant inhibitory effects on NO production in a concentration-dependent manner. It is worth mentioning that compound 10 showed the best NO inhibitory effect with a relative NO production of 88.1%, which was close to that of the positive drug dexamethasone. The Elisa experiment suggested that compounds 1, 4, 10, and 15 suppressed the release of TNF-α and IL-1ß as well. In conclusion, this study enriches the spectra of compounds with potential anti-inflammatory effects in A. wilsonii and provides new references for the discovery of anti-inflammatory lead compounds, but further mechanistic research is still needed.


Subject(s)
Aesculus , Mice , Animals , Aesculus/chemistry , Anti-Inflammatory Agents/pharmacology , RAW 264.7 Cells , Tumor Necrosis Factor-alpha , Seeds/chemistry , Lipopolysaccharides/pharmacology , Nitric Oxide/analysis
5.
Molecules ; 29(16)2024 Aug 07.
Article in English | MEDLINE | ID: mdl-39202831

ABSTRACT

The occurrence of inflammation is closely related to the activation of the NLRP3 inflammasome. IL-1ß produced during the activation of the NLRP3 inflammasome has strong pro-inflammatory activity and can also promote the release of inflammatory factors by other immune cells, exacerbating inflammatory damage to tissues. Utilizing IL-1ß as the detection index to find small-molecule inhibitors targeting NLRP3 from natural products will benefit the search for drugs for inflammation-related diseases. During the exploration of anti-inflammatory active components derived from the flowers of Dolichos lablab L., an ingredient in traditional Chinese medicine with dual applications in both medicinal treatment and dietary consumption, fourteen compounds (1-14), including seven previously unreported ones, named flosdolilabnitrogenousols A-D (1-4) and flosdolilabsaponins A-C (5-7), were found. Their structures were established through extensive NMR spectra determination, HR-ESI-MS analysis, ECD calculations, and chemical reactions. Flosdolilabsaponin A (5) stands out as an exceptionally rare tetracyclic lactone oleane-type saponin. Additionally, the inhibitory activity on IL-1ß release of all compounds, without cytotoxicity, was evaluated using BMDMs stimulated with LPS/Nigericin. An Elisa assay revealed that compounds 1, 8, 9, and 11-14 exhibited significant inhibition of IL-1ß release at a concentration of 30 µM. Structure-activity relationships were also discussed. This study indicates that D. lablab flowers possess anti-inflammatory activity, which might exert its effect by suppressing the activation of the NLRP3 inflammasome.


Subject(s)
Anti-Inflammatory Agents , Flowers , Interleukin-1beta , NLR Family, Pyrin Domain-Containing 3 Protein , Interleukin-1beta/metabolism , Interleukin-1beta/antagonists & inhibitors , Flowers/chemistry , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Animals , NLR Family, Pyrin Domain-Containing 3 Protein/metabolism , NLR Family, Pyrin Domain-Containing 3 Protein/antagonists & inhibitors , Mice , Plant Extracts/pharmacology , Plant Extracts/chemistry , Humans , Molecular Structure , Inflammasomes/metabolism , Inflammasomes/antagonists & inhibitors , Inflammasomes/drug effects
6.
Int J Mol Sci ; 24(24)2023 Dec 16.
Article in English | MEDLINE | ID: mdl-38139367

ABSTRACT

Ulcerative colitis, an immune-mediated inflammatory disease of the gastrointestinal tract, places a significant financial burden on patients and the healthcare system. Recently, reviews of the pomegranate and the abundant medicinal applications of its ellagitannins, as well as its pharmacological action, phytochemicals, metabolism, and pharmacokinetics, have been completed. However, summaries on their anti-ulcerative colitis effects are lacking. Numerous preclinical animal investigations and clinical human trial reports demonstrated the specific therapeutic effects of pomegranate and the effect of its ellagitannins against ulcerative colitis. According to the literature collected by Sci-finder and PubMed databases over the past 20 years, this is the first review that has compiled references regarding how the rich ellagitannins found in pomegranate have altered the ulcerative colitis. It was suggested that the various parts of pomegranates and their rich ellagitannins (especially their primary components, punicalagin, and ellagic acid) can inhibit oxidant and inflammatory processes, regulate the intestinal barrier and flora, and provide an anti-ulcerative colitis resource through dietary management.


Subject(s)
Colitis, Ulcerative , Lythraceae , Pomegranate , Animals , Humans , Colitis, Ulcerative/drug therapy , Hydrolyzable Tannins/pharmacology , Hydrolyzable Tannins/therapeutic use , Fruit/chemistry
7.
Int J Mol Sci ; 24(3)2023 Jan 23.
Article in English | MEDLINE | ID: mdl-36768602

ABSTRACT

Colorectal carcinoma (CRC) is a kind of malignant tumor closely related to ulcerative colitis. Xanthone derivatives are one of the most promising therapeutic drugs which have been used in phase I/II clinical trials for cancer therapy. Our previous study indicated that the aerial parts of Gentianella acuta Michx. Hulten (GA) was rich in xanthones and showed a good therapeutic effect on ulcerative colitis in mice, suggesting that GA xanthones might have some therapeutic or ameliorative effects on CRC. However, no relevant study has been reported. This study aims to find the effective substances of GA inhibiting CRC and clarify their mechanism. Solvent extraction, column chromatographic separation, and LC-MS analysis were used to characterize the 70% EtOH extract of GA and track xanthones abundant fraction XF. MTT assay was carried out to clarify the activity of GA fractions; the result showed XF to be the main active fraction. LC-MS analysis was executed to characterize XF, 38 xanthones were identified. Network pharmacology prediction, in vitro activity screening, and molecular docking assay were combined to predict the potential mechanism; the PI3K/Akt/mTOR signaling pathway was found to be most important. Western blot assay on the main active xanthones 1,3,5-trihydroxyxanthone (16), 1,3,5,8-tetrahydroxyxanthone (17), 1,5,8-trihydroxy-3-methoxyxanthone (18), and 1,7-dihydroxy-3,8-dimethoxyxanthone (19) was used to verify the above prediction; these xanthones were found to inhibit the PI3K/Akt/mTOR signaling pathway, and 17 played a significant role among them through Western blot assay using PI3K/AKT/mTOR agonist IGF-1. In conclusion, this study demonstrated that GA xanthones were effective compounds of GA inhibiting CRC by regulating PI3K/Akt/mTOR signaling pathway transduction, at least. Importantly, 1,3,5,8-tetrahydroxyxanthone (17), the most abundant active xanthone in GA, might be a candidate drug for CRC.


Subject(s)
Colitis, Ulcerative , Colorectal Neoplasms , Gentianella , Xanthones , Mice , Animals , Proto-Oncogene Proteins c-akt/metabolism , Gentianella/chemistry , Phosphatidylinositol 3-Kinases/metabolism , Molecular Docking Simulation , Signal Transduction , TOR Serine-Threonine Kinases/metabolism , Xanthones/pharmacology , Xanthones/chemistry , Colorectal Neoplasms/drug therapy , Cell Proliferation
8.
Opt Lett ; 47(4): 858-861, 2022 Feb 15.
Article in English | MEDLINE | ID: mdl-35167543

ABSTRACT

Optical injection into a chaotic laser under feedback is investigated for dimension enhancement. Although injecting a solitary laser is known to be low-dimensional, injecting the laser under feedback is found to enhance the correlation dimension D2 in experiments. Using an exceptionally large data size with a very large reconstruction embedding dimension, efficient computation is enabled by averaging over many short segments to carefully estimate D2. The dimension enhancement can be achieved together with time-delay signature suppression. The enhancement of D2 as a fundamental geometric quantifier of attractors is useful in applications of chaos.

9.
Molecules ; 27(14)2022 Jul 20.
Article in English | MEDLINE | ID: mdl-35889496

ABSTRACT

Punica granatum L. (Punicaceae) is a popular fruit all over the world. Owning to its enriched polyphenols, P. granatum has been widely used in treating inflammation-related diseases, such as cardiovascular diseases and cancer. Twenty polyphenols, containing nine unreported ones, named punicagranins A-I (1-9), along with eleven known isolates (10-20), were obtained from the peels. Their detailed structures were elucidated based on UV, IR, NMR, MS, optical rotation, ECD analyses and chemical evidence. The potential anti-inflammatory activities of all polyphenols were examined on a lipopolysaccharide (LPS)-induced inflammatory macrophages model, which indicated that enhancing nitric oxide (NO) production in response to inflammation stimulated in RAW 264.7 cells was controlled by compounds 1, 3, 5-8, 10, 11, 14 and 16-20 in a concentration-dependent manner. The investigation of structure-activity relationships for tannins 6-8 and 12-20 suggested that HHDP, flavogallonyl and/or gallagyl were key groups for NO production inhibitory activity. Western blotting indicated that compounds 6-8 could down-regulate the phosphorylation levels of proteins p38 MAPK, IKKα/ß, IκBα and NF-κB p65 as well as inhibit the levels of inflammation-related cytokines and mediators, such as IL-6, TNF-α, iNOS and COX-2, at the concentration of 30 µM. In conclusion, polyphenols are proposed to be the potential anti-inflammatory active ingredients in P. granatum peels, and their molecular mechanism is likely related to the regulation of the p38 MAPK and NF-κB signaling pathways.


Subject(s)
Lythraceae , Pomegranate , Animals , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/therapeutic use , Cytokines/metabolism , Inflammation/drug therapy , Inflammation/metabolism , Lipopolysaccharides/pharmacology , Mice , NF-kappa B/metabolism , Nitric Oxide/metabolism , Polyphenols/pharmacology , Polyphenols/therapeutic use , RAW 264.7 Cells , Signal Transduction , p38 Mitogen-Activated Protein Kinases/metabolism
10.
Molecules ; 25(3)2020 Jan 29.
Article in English | MEDLINE | ID: mdl-32013151

ABSTRACT

To clarify whether flavonoids and phenols in Allium mongolicum Regel have the effect of improving gastrointestinal function and analyze its quality, this study was designed to isolate and identify them from the aerial parts of A. mongolicum by using various chromatographic and spectrophotometric methods, a bioassay on motility of mouse isolated intestine tissue, as well as qualitative analysis using liquid chromatography/mass spectrometry (LC-MS) analysis. As a result, 31 flavonoids and phenolic acids were obtained and identified, including six new flavonoid glycosides, mongoflavonosides A1 (1), A2 (2), A3 (3), A4 (4), B1 (5), B2 (6), and four new phenolic acid glycosides, mongophenosides A1 (7), A2 (8), A3 (9), B (10). Among them, eleven flavonoids and three phenolic acids showed significant increase in the height of mouse small intestinal muscle. It was a first systematic bioactive constituents' study for A. mongolicum on gastrointestinal tract. Furthermore, according to the retention time (tR) and the exact mass-to-charge ratio (m/z), thirty-one compounds were unambiguously identified by comparing to the standard references by using LC-MS. Then, on the basis of generalized rules of MS/MS fragmentation pattern, chromatographic behaviors, as well as biosynthetic laws of the 31 isolates, five flavonoid glycosides and one phenolic acid glycoside were tentatively speculated. On the basis of the study, a fast analysis method for flavonoids and phenolic acids in A. mongolicum was established.


Subject(s)
Allium/chemistry , Flavonoids/chemistry , Hydroxybenzoates/chemistry , Phytochemicals/chemistry , Plant Components, Aerial/chemistry , Plant Extracts/chemistry , Animals , Flavonoids/pharmacology , Gastrointestinal Motility/drug effects , Hydroxybenzoates/pharmacology , Mice , Molecular Structure , Phytochemicals/pharmacology , Plant Extracts/pharmacology , Spectrum Analysis
11.
Molecules ; 25(17)2020 Aug 20.
Article in English | MEDLINE | ID: mdl-32825257

ABSTRACT

Two new 12,23-epoxydammarane-type saponins, notoginsenosides NL-I (1) and NL-J (2), were isolated and identified from Panax notoginseng leaves through the combination of various chromatographies and extensive spectroscopic methods, as well as chemical reactions. Among them, notoginsenoside NL-J (2) had a new skeleton. Furthermore, the lipopolysaccharide (LPS)-induced RAW 264.7 macrophage model was used to identify the in vitro anti-inflammatory activity and mechanisms of compounds 1 and 2. Both of them exerted strong inhibition on nitric oxide (NO) productions in a concentration-dependent manner at 1, 10, and 25 µM. Moreover, these two compounds significantly decreased the secretion of tumor necrosis factor-alpha (TNF-α), interleukin 6 (IL-6), cyclooxygenase-2 (COX-2), nuclear factor kappa-B (NF-κB/p65), and nitric-oxide synthase (iNOS) in LPS-activated RAW 264.7 cells.


Subject(s)
Anti-Inflammatory Agents , Panax notoginseng/chemistry , Plant Leaves/chemistry , Saponins , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/pharmacology , Cyclooxygenase 2/biosynthesis , Cytokines/biosynthesis , Lipopolysaccharides/toxicity , Mice , Nitric Oxide Synthase Type II/biosynthesis , RAW 264.7 Cells , Saponins/chemistry , Saponins/isolation & purification , Saponins/pharmacology , Transcription Factor RelA/metabolism
12.
Molecules ; 25(17)2020 Aug 24.
Article in English | MEDLINE | ID: mdl-32847104

ABSTRACT

Yucca schidigera Roezl (Mojave), a kind of ornamental plant belonging to the Yucca genus (Agavaceae), whose extract exhibits important roles in food, beverage, cosmetic and feed additives owing to its rich spirostanol saponins. To provide a comprehensive chemical profiling of the spirostanol saponins in it, this study was performed by using a multi-phase liquid chromatography method combining a reversed phase chromatography T3 column with a normal phase chromatography silica column for the separation and an ESI-Q-Exactive-Orbitrap MS in positive ion mode as the detector. By comparing the retention time and ion fragments with standards, thirty-one spirostanol saponins were identified. In addition, according to the summary of the chromatographic retention behaviors and the MS/MS cleavage patterns and biosynthetic pathway, another seventy-nine spirostanol saponins were speculatively identified, forty ones of which were potentially new ones. Moreover, ten novel spirostanol saponins (three pairs of (25R/S)-spirostanol saponin isomer mixtures) were targeted for isolation to verify the speculation. Then, the comprehensive chemical profiling of spirostanol saponins from Y. schidigera was reported here firstly.


Subject(s)
Plant Extracts/chemistry , Saponins , Spirostans , Yucca/chemistry , Chromatography, High Pressure Liquid , Saponins/chemistry , Saponins/isolation & purification , Silica Gel , Spirostans/chemistry , Spirostans/isolation & purification , Tandem Mass Spectrometry
13.
Chem Pharm Bull (Tokyo) ; 67(7): 634-639, 2019.
Article in English | MEDLINE | ID: mdl-31257318

ABSTRACT

The mango tree (Mangifera indica L.) is a tropical, perennial, woody evergreen plant belonging to the Anacardiaceae. In traditional medicine, dried mango tree leaves were considered useful in treating diabetes and respiratory infections. In this paper, we review the phytochemical research on mango leaves and the mechanisms of benzophenones in lipid metabolism regulation. Thirty-six benzophenones have been isolated from mango leaves; among them, mangiferin is the major compound. Structure-activity relationships of benzophenones in lipid accumulation and the mechanisms of action of mangiferin in lipid metabolism are summarized. After oral administration, mangiferin is partly converted to its active metabolite, northyariol, which contributes to the activation of sirtuin-1 and liver kinase B1 and increases the intracellular AMP level and AMP/adenosine triphosphate ratio, followed by AMP-activated protein kinase phosphorylation, leading to increased phosphorylation of sterol regulatory element-binding protein-1c. Current evidence supports ethnopharmacological uses of mango leaves in diabetes and points toward potential future applications.


Subject(s)
Benzophenones/chemistry , Mangifera/chemistry , AMP-Activated Protein Kinases/metabolism , Animals , Benzophenones/isolation & purification , Benzophenones/pharmacology , Lipid Metabolism/drug effects , Mangifera/metabolism , Plant Leaves/chemistry , Plant Leaves/metabolism , Structure-Activity Relationship , Xanthones/administration & dosage , Xanthones/chemistry , Xanthones/metabolism , Xanthones/pharmacology
14.
Chem Pharm Bull (Tokyo) ; 67(7): 654-665, 2019.
Article in English | MEDLINE | ID: mdl-31257321

ABSTRACT

Quassinoids, one kind of triterpenoids with multiple bioactivities such as anti-cancer, anti-malarial, anti-oxidative, anti-microbial, anti-diabetic, anti-viral, and anti-inflammatory effects, have drawn much attention in recent years. Between 2004 and 2018, the structural characteristics and plant sources of 190 quassinoids were reported. Herein, the structure-activity relationships (SARs) of quassinoids along with the anti-cancer mechanisms of four representative quassinoids, eurycomanone, bruceine D, dehydrobruceine B, and brusatol are discussed. This review might be useful for further research and development of quassinoids.


Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Quassins/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Antiprotozoal Agents/chemistry , Antiprotozoal Agents/isolation & purification , Antiprotozoal Agents/pharmacology , Antiviral Agents/chemistry , Antiviral Agents/isolation & purification , Antiviral Agents/pharmacology , Cell Survival/drug effects , Humans , Plants/chemistry , Plants/metabolism , Plasmodium falciparum/drug effects , Quassins/isolation & purification , Quassins/pharmacology , Structure-Activity Relationship , Tobacco Mosaic Virus/drug effects
15.
Molecules ; 24(15)2019 Jul 31.
Article in English | MEDLINE | ID: mdl-31370202

ABSTRACT

Pluchea indica Less. is a medicine and food dual-use plant, which belongs to the Pluchea genus, Asteraceae family. Its main constituents are quinic acids, flavonoids, thiophenes, phenolic acids, as well as sesquiterpenes. In order to provide a comprehensive chemical profiling of P. indica, an orthogonal chromatography combining reverse-phase chromatography BEHC18 column with a normal-phase chromatography silica column as the separation system and a ESI-Q-Orbitrap MS as the detector in both positive and negative ion modes were used. According to the retention time (tR) and the exact mass-to-charge ratio (m/z), 67 compounds were unambiguously identified by comparing to the standard references. Moreover, 47 compounds were tentatively speculated on the basis of the rules of MS/MS fragmentation pattern and chromatographic elution order generalized from the above-mentioned reference standards. Among them, 10 of them were potentially novel.


Subject(s)
Asteraceae/chemistry , Flavonoids/chemistry , Plant Components, Aerial/chemistry , Plant Extracts/chemistry , Chromatography, Liquid , Ethanol/chemistry , Flavonoids/isolation & purification , Humans , Silica Gel/chemistry , Spectrometry, Mass, Electrospray Ionization
16.
Molecules ; 25(1)2019 Dec 29.
Article in English | MEDLINE | ID: mdl-31905770

ABSTRACT

Inflammation is a very common and important pathological process that can cause many diseases. The discovery of anti-inflammatory drugs and the treatment of inflammation are particularly essential. Dammarane-type triterpenoid saponins (PNS) were demonstrated to show anti-inflammatory effects in the leaves of Panax notoginseng. Chromatographies and spectral analysis methods were combined to isolate and identify PNS. Moreover, the nitric oxide (NO) inhibitory activities of all compounds were examined in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. As a result, eleven new dammarane-type triterpenoid saponins, notoginsenosides NL-A1-NL-A4 (1-4), NL-B1-NL-B3 (5-7), NL-C1-NL-C3 (8-10), and NL-D (11) were isolated, and their structures were identified by using various spectrometric techniques and chemical reactions. Among them, compounds 4 and 11 were characterized by the malonyl substitution at 3-position. The 3-malonyl substituted dammarane-type terpennoids were first obtained from natural products. In addition, compounds 1, 2, 5, 6, and 8-10 were found to play an important role in suppressing NO levels at 50 µM, without cytotoxicity. All inhibitory activities were found to be dose-dependent.


Subject(s)
Antioxidants/pharmacology , Nitric Oxide/antagonists & inhibitors , Panax notoginseng/chemistry , Plant Leaves/chemistry , Saponins/pharmacology , Triterpenes/pharmacology , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Antioxidants/chemistry , Magnetic Resonance Spectroscopy , Mice , Molecular Structure , Nitric Oxide/metabolism , RAW 264.7 Cells , Saponins/chemistry , Triterpenes/chemistry , Dammaranes
17.
Molecules ; 24(17)2019 Aug 30.
Article in English | MEDLINE | ID: mdl-31480226

ABSTRACT

Four new phenolic components, eurylophenolosides A (1) and B (2), eurylolignanosides A (3) and B (4), along with twelve known compounds were isolated from the roots of Eurycoma longifolia Jack. The structure of these components was elucidated by using various spectral techniques and chemical reactions. Among the known isolates, syringaldehyde (12), 3-chloro-4-hydroxybenzoic acid (13), 3-chloro-4-hydroxyl benzoic acid-4-O-ß-d-glucopyranoside (14), and isotachioside (15) were isolated from the Eurycoma genus for the first time. Further, the NMR data of 14 was reported here firstly. Meanwhile, the nitric oxide (NO) inhibitory activities of all compounds were examined in lipopolysaccharide (LPS)-stimulated RAW264.7 cells at 40 µM. As results, piscidinol A (6), 24-epi-piscidinol A (7), bourjotinolone A (10), and scopoletin (16) were found to play important role in suppressing NO levels without cytotoxicity. Furthermore, the Western blot method was used to investigate the mechanism of compounds 6, 7, 10, and 16 by analysing the level of inflammation related proteins, such as inducible nitric oxide synthase (iNOS), interleukin-6 (IL-6), and nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) in LPS-stimulated RAW264.7 cells. Consequently, compounds 6, 7, 10, and 16 were found to significantly inhibit LPS-induced protein expression of IL-6, NF-κB and iNOS in NF-κB signaling pathway. Moreover, it was found that the protein expression inhibitory effects of 6, 7, and 16 exhibited in a dose-dependent manner. The mechanism may be related to the inhibition of the iNOS expressions through suppressing the IL-6-induced NF-κB pathway.


Subject(s)
Eurycoma/chemistry , Phytochemicals/analysis , Plant Roots/chemistry , Animals , Carbon-13 Magnetic Resonance Spectroscopy , Interleukin-6/metabolism , Mice , NF-kappa B/metabolism , Nitric Oxide/biosynthesis , Nitric Oxide Synthase Type II/metabolism , Phytochemicals/chemistry , Proton Magnetic Resonance Spectroscopy , RAW 264.7 Cells
18.
Int J Mol Sci ; 19(10)2018 Oct 07.
Article in English | MEDLINE | ID: mdl-30301267

ABSTRACT

Inflammatory bowel disease (IBD) is a serious digestive system disease, for which the clinical therapeutic choices remain limited. Dried fruits of Citrus aurantium L. (CAL) are a traditional medicine used for regulation of the digestive system. The aim of this study was to identify the regulatory effects of CAL on IBD and to clarify the mechanism of the active compounds. In trinitrobenzene sulfonic acid-induced IBD rats, 125 to 500 mg/kg of oral CAL significantly alleviated weight loss and diarrhea, decreased colitis inflammatory cell infiltration, and inhibited pro-inflammatory cytokine production. The mechanisms of characteristic flavonoids in CAL were evaluated involving inflammation and intestine contraction aspects. Naringenin, nobiletin, and hesperetin showed anti-inflammatory effects on lipopolysaccharide-induced RAW cells. The mechanism may be related to the inhibition of the tumor necrosis factor-α (TNF-α)-induced nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) pathway to suppress cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) expressions. Naringenin and nobiletin showed inhibitory effects on isolated jejunum contraction. The mechanism of naringenin is partly related to COX, NOS, inositol triphosphate (IP3), and finally, to decreased jejunum motility. This study demonstrated that CAL, and its flavonoids' regulatory effects on IBD through anti-inflammation and inhibition of intestine muscle contraction, can provide basic information on developing new drugs or supplements against IBD based on CAL.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Citrus/chemistry , Colitis, Ulcerative/drug therapy , Flavonoids/pharmacology , Jejunum/drug effects , Muscle Contraction , Animals , Anti-Inflammatory Agents/therapeutic use , Cell Line , Colitis, Ulcerative/etiology , Colitis, Ulcerative/metabolism , Cyclooxygenase 2/metabolism , Flavonoids/therapeutic use , Gastrointestinal Motility , Jejunum/metabolism , Male , Mice , NF-kappa B/metabolism , Nitric Oxide Synthase Type II/metabolism , Rats , Rats, Sprague-Dawley , Trinitrobenzenesulfonic Acid/toxicity , Tumor Necrosis Factor-alpha/metabolism
19.
Molecules ; 23(3)2018 Mar 13.
Article in English | MEDLINE | ID: mdl-29533968

ABSTRACT

Eudesmane-type sesquiterpenes have been reported to exhibit varieties of biological activities. During the process of investigating this kind of natural product from the root bark of Dictamnus dasycarpus Turcz., 13 eudesmane-type sesquiterpene glycosides including six new isolates, named as dictameudesmnosides A1 (1), A2 (2), B (3), C (4), D (5), and E (6), together with seven known ones (7-13), were obtained. Herein, their structures were determined by the analysis of physical data, spectroscopic analysis, and chemical methods. The existence of α-configuration glucose units in their structures (1-5, 8) is not very common in natural glycosidic components. Meanwhile, compounds 3-5, 7, and 9-13 displayed TG accumulation inhibitory effects on HepG2 cells.


Subject(s)
Dictamnus/chemistry , Glycosides/isolation & purification , Sesquiterpenes, Eudesmane/isolation & purification , Cell Proliferation/drug effects , Glycosides/chemistry , Glycosides/pharmacology , Hep G2 Cells , Humans , Molecular Structure , Plant Bark/chemistry , Sesquiterpenes, Eudesmane/chemistry , Sesquiterpenes, Eudesmane/pharmacology
20.
Molecules ; 23(1)2018 Jan 14.
Article in English | MEDLINE | ID: mdl-29342909

ABSTRACT

It is well known that spirostane-type saponins show various bioactivities. In our on-going program of screening these kinds of constituents from natural products, Yucca schidigera was found to be rich in them, and nine new spirostanol saponins, Yucca spirostanosides A1 (1), A2 (2), B1 (3), B2 (4), B3 (5), C1 (6), C2 (7), C3 (8), and D1 (9), together with five known ones (10-14) were isolated from the plant. Their structures were elucidated by extensive spectroscopic methods, including 1D and 2D NMR and MS spectra, and comparing with published data.


Subject(s)
Plant Extracts/chemistry , Saponins/chemistry , Yucca/chemistry , Magnetic Resonance Spectroscopy , Molecular Structure
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