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1.
PLoS One ; 19(5): e0302839, 2024.
Article in English | MEDLINE | ID: mdl-38696506

ABSTRACT

PURPOSES: Fractures of the inferior patellar pole, unlike other patellar fractures, present challenges for traditional surgical fixation methods. This article introduces the clinical technique and outcomes of using Kirschner wire tension band combined with anchor screw cross-stitch fixation for comminuted inferior patellar pole fractures. METHODS: This retrospective case series study included 14 patients with comminuted inferior patellar pole fractures treated at our institution from September 1, 2020, to April 30, 2022. All patients underwent surgery using the Kirschner wire tension band with anchor screw cross-stitch technique. Follow-up assessments involved postoperative X-rays to evaluate fracture healing, as well as clinical parameters such as healing time, Visual Analog Scale (VAS) scores, range of motion (ROM), and Bostman scores. RESULTS: All patients were followed for an average of over 12 months, with no cases of internal fixation failure. Knee joint stability and function were excellent. X-rays revealed an average healing time of approximately 10.79 ± 1.53 weeks, hospitalization lasted 5.64 ± 1.15 days, surgery took approximately 37.86 ± 5.32 minutes, and intraoperative blood loss was 33.29 ± 8.15 ml. One patient experienced irritation from the internal fixation material. At the final follow-up, the Bostman score averaged 28.29 ± 0.83, knee joint flexion reached 131.07° ± 4.88°, all patients achieved full knee extension, and the VAS score was 0.36 ± 0.63. CONCLUSION: Kirschner wire tension band with anchor screw cross-stitch fixation for comminuted inferior patellar pole fractures delivered satisfactory clinical outcomes. This surgical method, characterized by its simplicity and reliability, is a valuable addition to clinical practice.


Subject(s)
Bone Wires , Fracture Fixation, Internal , Fractures, Comminuted , Patella , Humans , Male , Female , Adult , Patella/surgery , Patella/injuries , Fractures, Comminuted/surgery , Fracture Fixation, Internal/methods , Fracture Fixation, Internal/instrumentation , Retrospective Studies , Middle Aged , Range of Motion, Articular , Treatment Outcome , Fractures, Bone/surgery , Fracture Healing , Knee Joint/surgery , Knee Joint/physiopathology , Young Adult , Bone Screws , Suture Anchors
2.
Front Surg ; 11: 1383401, 2024.
Article in English | MEDLINE | ID: mdl-38817945

ABSTRACT

Background: In recent years, 3D printing technology has made significant strides in the medical field. With the advancement of orthopedics, there is an increasing pursuit of high surgical quality and optimal functional recovery. 3D printing enables the creation of precise physical models of fractures, and customized personalized steel plates can better realign and more comprehensively and securely fix fractures. These technologies improve preoperative diagnosis, simulation, and planning for complex limb fractures, providing patients with better treatment options. Patients and methods: Five typical cases were selected from a pool of numerous patients treated with 3D printing technology combined with personalized custom steel plates at our hospital. These cases were chosen to demonstrate the entire process of printing 3D models and customizing individualized steel plates, including details of the patients' surgeries and treatment procedures. Literature reviews were conducted, with a focus on highlighting the application of 3D printing technology combined with personalized custom steel plates in the treatment of complex limb fractures. Results: 3D printing technology can produce accurate physical models of fractures, and personalized custom plates can achieve better fracture realignment and more comprehensive and robust fixation. These technologies provide patients with better treatment options. Conclusion: The use of 3D printing models and personalized custom steel plates can improve preoperative diagnosis, simulation, and planning for complex limb fractures, realizing personalized medicine. This approach helps reduce surgical time, minimize trauma, enhance treatment outcomes, and improve patient functional recovery.

3.
Chem Biodivers ; 21(5): e202400030, 2024 May.
Article in English | MEDLINE | ID: mdl-38511964

ABSTRACT

A traditional Chinese medicine ingredient, dendrobine, has been demonstrated to have anti-inflammatory properties. However, due to its poor anti-inflammatory properties, its clinical use is limited. Consequently, we have designed and synthesized 32 new amide/sulfonamide dendrobine derivatives and screened their anti-inflammatory activities in vitro. Experiments showed that nitric oxide (NO) generation in lipopolysaccharide (LPS)-induced RAW264.7 cells was strongly reduced by derivative 14, with an IC50 of 2.96 µM. Western blot research revealed that 14 decreased the concentration-dependent expression of cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (INOS). Molecular docking was used to predict the binding of the inflammation-associated proteins COX-2 and INOS to compound 14.


Subject(s)
Amides , Cyclooxygenase 2 , Lipopolysaccharides , Molecular Docking Simulation , Nitric Oxide Synthase Type II , Nitric Oxide , Sulfonamides , Animals , Mice , RAW 264.7 Cells , Sulfonamides/chemistry , Sulfonamides/pharmacology , Sulfonamides/chemical synthesis , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Nitric Oxide Synthase Type II/metabolism , Nitric Oxide Synthase Type II/antagonists & inhibitors , Nitric Oxide/antagonists & inhibitors , Nitric Oxide/biosynthesis , Nitric Oxide/metabolism , Cyclooxygenase 2/metabolism , Amides/chemistry , Amides/pharmacology , Amides/chemical synthesis , Structure-Activity Relationship , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/chemical synthesis , Molecular Structure , Dose-Response Relationship, Drug , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Anti-Inflammatory Agents, Non-Steroidal/chemical synthesis , Anti-Inflammatory Agents, Non-Steroidal/chemistry
4.
Fitoterapia ; 174: 105878, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38417683

ABSTRACT

Six previously undescribed clerodane diterpenes, cardorubellas A-F (1-6), along with seven known ones (7-13), were isolated from the aerial parts of Callicarpa pseudorubella. Their chemical structures were established by analysis of 1D and 2D NMR, HR-ESI-MS, X-ray diffraction, and electronic circular dichroism (ECD) data. Notably, cardorubella B (2) represented the first examples of naturally occurring succinic anhydride-containing clerodane diterpenes derivatives. The anti-proliferative activities of these compounds were assessed. Remarkably, compound 2 exhibited comparable inhibitory activity against HEL cell lines, surpassing the positive control with an IC50 value of 14.01 ± 0.77 µM, compared to 17.02 ± 4.70 µM for 5-fluorouracil.


Subject(s)
Callicarpa , Diterpenes, Clerodane , Diterpenes , Diterpenes, Clerodane/pharmacology , Diterpenes, Clerodane/chemistry , Callicarpa/chemistry , Molecular Structure , Cell Line , Magnetic Resonance Spectroscopy , Diterpenes/pharmacology
5.
Chem Biodivers ; 21(3): e202400184, 2024 Mar.
Article in English | MEDLINE | ID: mdl-38372676

ABSTRACT

The phytochemical study of Peucedanum praeruptorum led to the isolation of twenty-five coumarins (1-25). Of which, (±) praeruptol A (±1), one pair of previous undescribed seco-coumarin enantiomers were obtained. Their structures were established according to HR-ESI-MS, NMR, X-ray single crystal diffraction analysis, as well as ECD calculation. All compounds were tested for anti-inflammatory activity in the RAW264.7 macrophage model, and eight compounds (7-10, and 13-16) exhibited significant inhibitory effects with IC50 values ranging from 9.48 to 34.66 µM. Among them, compound 7 showed the strongest inhibitory effect, which significantly suppressed the production of IL-6, IL-1ß, and TNF-α, as well as iNOS and COX-2 in a concentration-dependent manner. Further investigated results showed that compound 7 exerted an anti-inflammatory effect via the NF-κB signaling pathway.


Subject(s)
Coumarins , NF-kappa B , NF-kappa B/metabolism , Coumarins/pharmacology , Coumarins/metabolism , Anti-Inflammatory Agents/pharmacology , Plant Extracts/chemistry , Signal Transduction , Lipopolysaccharides/pharmacology
6.
Biochem Pharmacol ; 219: 115960, 2024 01.
Article in English | MEDLINE | ID: mdl-38049008

ABSTRACT

Prostate cancer is the most common malignant tumor among men worldwide. Currently, the main treatments are radical prostatectomy, radiotherapy, chemotherapy, and endocrine therapy. However, most of them are poorly effective and induce side effects. Polo-like kinase 1 (PLK1) regulates cell cycle and mitosis. Its inhibitor BI2536 promotes the therapeutic effect of nilotinib in chronic myeloid leukemia, enhances the sensitivity of neural tube cell tumors to radiation therapy and PLK1 silencing enhances the sensitivity of squamous cell carcinoma to cisplatin. Therefore, the aim of this study was to evaluate the effect of the PLK1 inhibitor L-shaped ortho-quinone analog TE6 on prostate cancer. In vitro on prostate cancer cells showed that TE6 inhibited PLK1 protein expression and consequently cell proliferation by blocking the cell cycle at G2 phase. In vivo on a subcutaneous tumor model in nude mice confirmed that TE6 effectively inhibited tumor growth in nude mice, inhibited PLK1 expression and regulated the expression of cell cycle proteins such as p21, p53, CDK1, Cdc25C, and cyclinB1. Thus, PLK1 was identified as the target protein of TE6, these results reveal the critical role of PLK1 in the growth and survival of prostate cancer and point out the ability of TE6 on targeting PLK1, being a potential drug for prostate cancer therapy.


Subject(s)
G2 Phase , Polo-Like Kinase 1 , Prostatic Neoplasms , Quinones , Polo-Like Kinase 1/antagonists & inhibitors , Quinones/chemistry , Quinones/pharmacology , Prostatic Neoplasms/drug therapy , G2 Phase/drug effects , Cell Proliferation/drug effects , Heterografts , Humans , Animals , Mice , Male , Protein Kinase Inhibitors/chemistry , Protein Kinase Inhibitors/pharmacology , Protein Kinase Inhibitors/therapeutic use , Cell Line, Tumor , Molecular Structure
7.
Chem Biodivers ; 21(2): e202301703, 2024 Feb.
Article in English | MEDLINE | ID: mdl-38055204

ABSTRACT

Three undescribed limonoids (1-3), named aglaians G-I, and one new natural product azedaralide (4), together with nine known analogues (5-13) were isolated from the branches and leaves of Aglaia lawii by RP C18 column, silica gel column, Sephadex LH-20 column chromatography and preparative HPLC. The structures of the new compounds were elucidated by IR, HRESIMS, 1D, 2D NMR, electronic circular dichroism (ECD) calculations and X-ray crystallography diffraction analysis. The results of bioassay showed that the compound 12 exhibited potential inhibitory activity against six human tumor cell lines (MDA-MB-231, MCF-7, Ln-cap, A549, HeLa and HepG-2) with IC50 values as 8.0-18.6 µM.


Subject(s)
Aglaia , Antineoplastic Agents , Limonins , Humans , Aglaia/chemistry , Limonins/pharmacology , Limonins/chemistry , Molecular Structure , Cell Line, Tumor
8.
Fitoterapia ; 171: 105708, 2023 Dec.
Article in English | MEDLINE | ID: mdl-37866424

ABSTRACT

Five undescribed triterpenoids and steroids (1-5), as well as ten known compounds, were purified from the branches and leaves of Cipadessa baccifera. Notably, 1 and 2 are rare cipadesin-type limonoids with an unusual 8,30-epoxide ring and 1,8-ether linkage, respectively. Compound 5 possessed pregnane steroid skeleton with an uncommon 5/6/6/6/5-fused ring system. Their structures were constructed by extensive spectroscopic analysis (NMR, IR, UV, and HRESIMS), and their absolute configurations were confirmed by ECD calculations and quantum chemical calculations. All the isolates were in vitro assayed for their antimicrobial potentials against 6 pathogenic microorganisms and antiproliferation activities against five human cancer cell lines. As a result, compounds 5, 12, 13, and 14 exhibited moderate antibacterial activities (MIC: 25-50 µg/mL). Moreover, 5 showed cytotoxicity against five cancer cell lines with IC50 values ranging from 8.0 to 19.9 µM.


Subject(s)
Limonins , Meliaceae , Triterpenes , Humans , Molecular Structure , Steroids , Cell Line, Tumor , Meliaceae/chemistry
9.
Bioorg Med Chem Lett ; 96: 129527, 2023 11 15.
Article in English | MEDLINE | ID: mdl-37852423

ABSTRACT

Most clinical drugs used to treat inflammation have serious gastrointestinal, renal, and cardiovascular side effects during long-term treatment. The development of new anti-inflammatory agents from natural products and their derivatives is a powerful approach to overcome these adverse effects. Batatasin III, a bibenzyl natural product, has been found to have anti-inflammatory activity. Compared with other anti-inflammatory agents, batatasin III has a simple and unique structure. Therefore, batatasin III and its analogs might have the potential to treat inflammation with only mild adverse effects as a new type of anti-inflammatory agent. Herein, we synthesized 26 batatasin III analogs and evaluated the anti-inflammatory activity in vitro. Analog 21 significantly inhibited (p < 0.01) nitric oxide production with an IC50 value of 12.95 µM. Western blot analysis further revealed that 21 reduced iNOS, phosphorylated p65, and ß-catenin expression in a concentration-dependent manner. These results indicated that 21 could be a potential lead compound for developing a drug candidate for ulcerative colitis. Molecular docking analysis showed that p65 might be a potential target of 21 for the treatment of inflammatory disease. In addition, we analyzed the structure-activity relationship of the analogs, which provides a basis for future structural modifications.


Subject(s)
Anti-Inflammatory Agents , Colitis, Ulcerative , Humans , Molecular Docking Simulation , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/therapeutic use , Inflammation/drug therapy , Inflammation/metabolism , Structure-Activity Relationship , Colitis, Ulcerative/drug therapy , Nitric Oxide/metabolism , Lipopolysaccharides/pharmacology , Nitric Oxide Synthase Type II/metabolism
10.
Cell Death Discov ; 9(1): 143, 2023 May 01.
Article in English | MEDLINE | ID: mdl-37127677

ABSTRACT

Vascular endothelial is considered to be a key factor in the pathogenesis of erectile dysfunction (ED). The purpose is to reveal the research trend of the field of ED and vascular endothelium. In addition, the goal is to discover the role and mechanism of vascular endothelium in ED. Bibliometrics and visualization methods based on CiteSpace were selected. We conducted the co-authorship analysis of countries, institutions and authors, co-occurrence analysis of keywords, and co-citation analysis of literature and authors through CiteSpace 6.1.R3. 1431 articles from Web of Science Core Collection (WOSCC) were included in the analysis from 1991 to 2022. We found some influential and cutting-edge nodes in each map, including countries, institutions, authors, articles, etc. Stem cell, therapy, oxidative stress, cavernous nerve injury, radical prostatectomy, fibrosis, erectile function, mesenchymal stem cell, and apoptosis may be hot keywords. In conclusion, the efficacy and mechanisms of stem cells and their derivatives in the treatment of diabetes (DM) ED and cavernous nerve injury (CNI) ED are the future research trends. Stem cells therapy for ED is a hot spot in this field, which side notes that stem cells may work mainly through improving endothelial function. Vascular endothelial cells and VEGF may repair nerve and cavernous smooth muscle directly or indirectly, and finally polish up erectile function.

11.
Plant Dis ; 2023 Feb 12.
Article in English | MEDLINE | ID: mdl-36774563

ABSTRACT

Tobacco (Nicotiana tabacum L.) is one of the most widely cultivated economic crops in approximately 120 countries (Peedin 2011). In July 2020 and 2021, typical symptoms of tobacco anthracnose were widely found in the flue-cured tobacco-planted areas of Wufeng, Xuan'en, and Xianfeng, Hubei Province, China. The disease incidence reached up to 60% in some fields at that time, with estimated 10,000 ha of the cultivated area affected. On tobacco leaves, lesions were initially water soaked and yellow green, and these enlarged to produce dark-brown necrosis which became cracked after drying, extending until the leaves withered. After surface-sterilization with 75% ethanol for 45 s and 5% sodium hypochlorite for 60 s, diseased leaf tissues were washed with sterilized water for 60 s three times and then cultured on potato dextrose agar (PDA) plates for seven days at 25°C in the dark. Isolates of Colletotrichum sp. were consistently recovered with isolation rate of 71%, and the five isolates BB005ES1, BB005ES2, BB005ES3, BB005ES4 and BB005ES5 were used to further evaluate characteristics of the pathogen. On PDA medium for seven days, the aerial hyphae of cultures were dense and blanket-like. The aerial surface of the colony was dark gray to white, and the center of the basal surface of the colony was orange-red. Conidia were transparent, aseptate, smooth-walled, straight, cylindrical with one end obtuse and the other end funnel-shaped, and the size was 11.8-12.0 µm×2.7-2.9 µm (n=100). Appressoria were single, smooth, black, oval or irregular shapes with size of 4.6-4.9 µm×8.5-8.7 µm (n=100). The most typical feature of Colletotrichum acutatum species complex is the shape of conidia which have at least one acute end (Damm et al., 2012). Thus, the five strains were identified as part of the Acutatum complex. The sequences of ACT, TUB2, CHS-1, GAPDH and ITS were then amplified from the five strains (Damm et al., 2012), and all the five strains had the similar sequence for each gene (Accession numbers in GeneBank: ON637946, ON637947, ON637945, ON637948 and ON394623). The combined sequences ACT-TUB2-CHS-1-GAPDH-ITS of the five strains were used for constructing multigene phylogenetic tree using Maximum Parsimony method (Prihastuti et al. 2009), and C. gloeosporioides (IMI356878) was selected as an outgroup. The five strains were found to be closely related to the type strains of C. nymphaeae. Hence, the five isolated strains were identified as C. nymphaeae. Pathogenicity of the five strains was determined by placing seven-day-old fungal plugs on attached leaves of 20-day-old tobacco plants in lab. After inoculation, plants were incubated in a 28°C and 95% RH incubator in the dark for five days. The five strains caused the typical dark brown lesions on all inoculated tobacco leaves, whereas no disease symptoms were found on the healthy tobacco leaves for agar-plug inoculation controls. Koch's postulates were fulfilled by re-isolating C. nymphaeae from diseased leaves. Previously, only C. fructicola, C. nicotiance, C. orbiculare and C. cliviicola were documented as causal agents of tobacco anthracnose (Wang et al. 2016;Wang et al. 2022). To our knowledge, this is the first report of C. nymphaeae causing tobacco anthracnose worldwide.

12.
Molecules ; 29(1)2023 Dec 20.
Article in English | MEDLINE | ID: mdl-38202622

ABSTRACT

Five undescribed steroids and one sesquiterpene, named Aglaians A-F, along with sixteen known analogs, have been isolated from the branches and leaves of Aglaia lawii. Its structure was elucidated by IR, HRESIMS, 1D and 2D NMR, quantum-chemical calculations, electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. The cytotoxic and antibacterial activities of six human tumor cell lines were evaluated (MDA-MB-231, MCF-7, Ln-cap, A549, HeLa, and HepG-2), and four strains of bacteria (Bacterium subtilis, Phytophthora cinnamomic, Acrogenic bacterium, and Ralstonia solanacearum). The bioassay results indicated that compounds 3 and 5 exhibited moderate antitumor activity with IC50 values ranging from 16.72 to 36.14 µM. Furthermore, compounds 3-5 possess antibacterial activities against four bacteria with MIC values of 25-100 µM.


Subject(s)
Aglaia , Sesquiterpenes , Humans , Steroids/pharmacology , Anti-Bacterial Agents/pharmacology , Cell Line, Tumor , Sesquiterpenes/pharmacology
13.
Chem Biodivers ; 19(10): e202200676, 2022 Oct.
Article in English | MEDLINE | ID: mdl-36069263

ABSTRACT

Three new flavonoids, 4'-O-ß-D-glucopyranosyl-2S,3R-3,7-dihydroxy-3'-methoxyflavan (1), (3R)-7,4'-dihydroxy-5,3'-methoxychalcone (2), (3S)-7,2',3'-trihydroxy-6,4'-dimethoxylisoflavan (3), and one new natural occurring product, (3S)-6,2',3'-trihydroxy-7,4'-dimethoxylisoflavan (4), together with eleven known ones (5-15), were isolated from the roots of Indigofera stachyodes. The structures of these compounds were confirmed by UV, IR, MS, and NMR spectroscopic analysis. The absolute configurations of new compounds were elucidated by ECD spectra and chemical method. All the isolated flavonoids were screened for their antioxidant abilities to scavenge DPPH and ABTS+ . As results, compounds 2-4, 10, and 15 exhibited remarkable scavenging activity against both ABTS+ and DPPH, with the IC50 values less than 20 µM. In addition, compounds 1, 6-9, and 13 exhibited potential antioxidant scavenging activities, IC50 values were in the range of 17.96∼85.91 µM.


Subject(s)
Flavonoids , Indigofera , Flavonoids/pharmacology , Flavonoids/chemistry , Antioxidants/pharmacology , Antioxidants/chemistry , Molecular Structure
14.
Front Chem ; 10: 911201, 2022.
Article in English | MEDLINE | ID: mdl-35755263

ABSTRACT

Six new bibenzyls (three pairs of enantiomers), bletstrins D-F (1-3), were isolated from the ethyl acetate-soluble (EtOAc) extract of tubers of Bletilla striata (Thunb.) Rchb f. Their structures, including absolute configurations, were determined by 1D/2D NMR spectroscopy, optical rotation value, and experimental electronic circular dichroism (ECD) data analyses, respectively. Compounds 1-3 possess a hydroxyl-substituted chiral center on the aliphatic bibenzyl bridge, which represented the first examples of natural bibenzyl enantiomers from the genus of Bletilla. The antibacterial, antitumor necrosis factor (anti-TNF-α), and neuroprotective effects of the isolates have been evaluated. Compounds 3a and 3b were effective against three Gram-positive bacteria with minimum inhibitory concentrations (MICs) of 52-105 µg/ml. Compounds 2a and 2b exhibited significant inhibitory effects on TNF-α-mediated cytotoxicity in L929 cells with IC50 values of 25.7 ± 2.3 µM and 21.7 ± 1.7 µM, respectively. Subsequently, the possible anti-TNF-α mechanism of 2 was investigated by molecular docking simulation. Furthermore, the neuroprotective activities were tested on the H2O2-induced PC12 cell injury model, and compounds 2b, 3a, and 3b (10 µM) could obviously protect the cells with the cell viabilities of 57.86 ± 2.08%, 64.82 ± 2.84%, and 64.11 ± 2.52%, respectively.

15.
Mitochondrial DNA B Resour ; 7(5): 867-869, 2022.
Article in English | MEDLINE | ID: mdl-35602328

ABSTRACT

Uncaria macrophylla Wall. 1824 is one of the five original plants of Uncariae Ramulus cum Uncis, and its molecular genetic relationship with other four remains unclear. Here, we reported the complete chloroplast genome of U. macrophylla. The chloroplast genome is 155,145 bp in length, which includes paired inverted repeat regions of 25,665 bp, a large single-copy region of 85,758 bp and a small single-copy region of 18,057 bp. In total, 127 genes were predicted, including 81 protein-coding genes, 38 tRNA genes, and 8 rRNA genes. The phylogenetic analysis based on whole chloroplast genome sequences showed that U. macrophylla is closely related to U. rhynchophylla.

16.
Fitoterapia ; 160: 105217, 2022 Jul.
Article in English | MEDLINE | ID: mdl-35561838

ABSTRACT

Two pairs of new enantiomeric flavonolignans, ±stachyols A and B (±1 and ± 2), along with two novel isoflavanelignans, stachyols C and D (3 and 4) were isolated from the roots of Indigofera stachyodes. Their chemical structures and absolute configurations were determined using nuclear magnetic resonance and comparison of experimental and theoretical electronic circular dichroism (ECD) spectra, as well as quantum chemical calculations. Of those compounds, 1 and 2 represented the first examples of flavonolignans with 5-deoxyflavonoids adduct phenylpropanoids. Moreover, 3 and 4 possess an unprecedented skeleton with isoflavanes adduct phenylpropanoids. The antioxidant activity was evaluated for all compounds in terms of ABTS+ and DPPH bioassays. Compounds 3 and 4 exhibited significant radical-scavenging activity in the ABTS+ assay, with IC50 values of 15.15 and 5.83 µM, respectively.


Subject(s)
Flavonolignans , Indigofera , Antioxidants/chemistry , Antioxidants/pharmacology , Circular Dichroism , Molecular Structure , Plant Roots
17.
Phytochemistry ; 200: 113186, 2022 Aug.
Article in English | MEDLINE | ID: mdl-35500784

ABSTRACT

Eleven undescribed limonoids, cipacinerasins A-K, involving of four diverse carbon skeletal types, along with fifteen known analogues, were isolated from the branches and leaves of Cipadessa baccifera. Within them, cipacinerasins A and B feature a rearranged tetrahydropyranyl ring B formed between C-8 and C-30, are unusual miscellaneous-type limonoids. Cipacinerasins E and F are rare trijugin-type limonoids, of which the D-ring δ-lactone is cleaved. Their structures were elucidated on the basis of extensive spectroscopic data (HRESIMS, NMR, UV and IR), electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. All compounds were evaluated in vitro cytotoxicity against five human tumor cell lines (K562, HeLa, PC3, LN-Cap and Hell), and cipacinerasin E showed moderate antitumor activity with IC50 values ranging from 8.0 to 24.8 µM.


Subject(s)
Limonins , Meliaceae , Cell Line, Tumor , Limonins/chemistry , Limonins/pharmacology , Meliaceae/chemistry , Molecular Structure , Plant Leaves/chemistry
18.
Front Chem ; 10: 1107824, 2022.
Article in English | MEDLINE | ID: mdl-36704617

ABSTRACT

Hepatocellular carcinoma (HCC), the most common malignancy of the liver, exhibits high recurrence and metastasis. Structural modifications of natural products are crucial resources of antitumor drugs. This study aimed to synthesize C-14 derivatives of tetrandrine and evaluate their effects on HCC. Forty C-14 sulfonate tetrandrine derivatives were synthesized and their in vitro antiproliferative was evaluated against four hepatoma (HepG-2, SMMC-7721, QGY-7701, and SK-Hep-1) cell lines. For all tested cells, most of the modified compounds were more active than the lead compound, tetrandrine. In particular, 14-O-(5-chlorothiophene-2-sulfonyl)-tetrandrine (33) exhibited the strongest antiproliferative effect, with half-maximal inhibitory concentration values of 1.65, 2.89, 1.77, and 2.41 µM for the four hepatoma cell lines, respectively. Moreover, 33 was found to induce apoptosis via a mitochondria-mediated intrinsic pathway via flow cytometry and western blotting analysis. In addition, colony formation, wound healing, and transwell assays demonstrated that 33 significantly inhibited HepG-2 and SMMC-7721 cell proliferation, migration, and invasion, indicating that it might potentially be a candidate for an anti-HCC therapy in the future.

19.
Environ Sci Pollut Res Int ; 28(48): 68244-68250, 2021 Dec.
Article in English | MEDLINE | ID: mdl-34268694

ABSTRACT

Hexachlorocyclohexane (HCH), a typical organochloride pesticide, is one of the persistent organic pollutants. Despite the ban on technical grade HCH, it has been continuously observed at a steady level in the environment. The photochemical degradation of ß-HCH in snow and ice under ultraviolet (UV) irradiation was investigated in this study. The effects of pH as well as common chemical components in snow on the degradation kinetics were investigated. In addition, the photodegradation products were determined and the reaction mechanism was hypothesized. The results showed that under UV irradiation, ß-HCH can be photolyzed in snow and ice, with the photochemical degradation process conforming to the first-order kinetic equation. Changing the pH and adding Fe2+ had minimal effect on the photochemical degradation kinetics, while the presence of acetone, NO2-, NO3- and Fe3+ significantly inhibited the process. The addition of hydrogen peroxide slightly inhibited the photochemical degradation of ß-HCH. Finally, the reaction rate, products and degradation mechanism of ß-HCH in snow were compared with those in the ice phase. The photochemical degradation rate of ß-HCH in snow was approximately 24 times faster than that in the ice phase. The photolysis product of ß-HCH in snow was α-HCH, produced by the isomerization of ß-HCH. However, in ice, in addition to α-HCH, pentachlorocyclohexene was produced by dechlorination. The results of this study are helpful in understanding the transformation of organochlorine pesticides in snow and ice, as well as in providing a theoretical basis for snow and ice pollution prevention and control.


Subject(s)
Hexachlorocyclohexane , Hydrocarbons, Chlorinated , Hexachlorocyclohexane/analysis , Hydrocarbons, Chlorinated/analysis , Ice , Snow
20.
J Hazard Mater ; 261: 500-11, 2013 Oct 15.
Article in English | MEDLINE | ID: mdl-23988575

ABSTRACT

The photoconversion of 4-chlorophenol (4-CP) in a simulated sunlight-Fenton system was investigated in ice and aqueous solution. It was found that the hydroxyl radical (OH) had an important effect on the photoconversion of 4-CP in both phases, but the effects of Cl(-), SO4(2-), NO3(-), and HCO3(-) were different. In aqueous solution, the photoconversion efficiency of 4-CP was proportional to the OH concentration, and hence, Cl(-) and HCO3(-) as OH scavengers prohibited the photoconversion; SO4(2-) had little effect; NO3(-) promoted the process under certain conditions owing to OH being generated by the photolysis of NO3(-). In ice, however, the photoconversion efficiency of 4-CP was not proportional to the concentration of OH. The photoconversion efficiency of 4-CP increased with increasing concentrations of all ions, although the OH remained almost constant, only increasing or decreasing slightly. This provides new evidence for the presence of a quasi-liquid layer (QLL). Hydroxylation products were detected in both phases. All photoproducts in aqueous solution contained only a single benzene ring, whereas in ice, dimers were also detected.


Subject(s)
Chlorophenols/chemistry , Chlorophenols/radiation effects , Environmental Pollutants/chemistry , Environmental Pollutants/radiation effects , Hydrogen Peroxide/chemistry , Hydroxyl Radical/chemistry , Ice , Iron/chemistry , Photolysis , Sunlight
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