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Molecular diversity analysis of Tetradium ruticarpum (WuZhuYu) in China based on inter-primer binding site (iPBS) markers and inter-simple sequence repeat (ISSR) markers.

Jing-Yuan XU ; Yan ZHU ; Ze YI ; Gang WU ; Guo-Yong XIE ; Min-Jian QIN

Chinese Journal of Natural Medicines (English Ed.).2018;16(1):1-9. doi:10.1016/S1875-5364(18)30024-4

"Wu zhu yu", which is obtained from the dried unripe fruits of Tetradium ruticarpum (A. Jussieu) T. G. Hartley, has been used as a traditional Chinese medicine for treatment of headaches, abdominal colic, and hypertension for thousands of years. The present study was designed to assess the molecular genetic diversity among 25 collected accessions of T. ruticarpum (Wu zhu yu in Chinese) from different areas of China, based on inter-primer binding site (iPBS) markers and inter-simple sequence repeat (ISSR) markers. Thirteen ISSR primers generated 151 amplification bands, of which 130 were polymorphic. Out of 165 bands that were amplified using 10 iPBS primers, 152 were polymorphic. The iPBS markers displayed a higher proportion of polymorphic loci (PPL = 92.5%) than the ISSR markers (PPL = 84.9%). The results showed that T. ruticarpum possessed high loci polymorphism and genetic differentiation occurred in this plant. The combined data of iPBS and ISSR markers scored on 25 accessions produced five clusters that approximately matched the geographic distribution of the species. The results indicated that both iPBS and ISSR markers were reliable and effective tools for analyzing the genetic diversity in T. ruticarpum.
Base Sequence ; Binding Sites ; DNA Fingerprinting ; DNA Primers ; metabolism ; DNA, Plant ; genetics ; isolation & purification ; Evodia ; classification ; genetics ; Genetic Markers ; genetics ; Genetic Variation ; Interspersed Repetitive Sequences ; genetics ; Phylogeny ; Polymorphism, Genetic ; Random Amplified Polymorphic DNA Technique ; Terminal Repeat Sequences ; genetics

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UHPLC-LTQ-Orbitrap-based metabolomics coupled with metabolomics pathway analysis method for exploring the protection mechanism of Kudiezi injection in a rat anti-ischemic cerebral reperfusion damage model.

Si-Yi LIU ; Wei CAI ; Fei WANG ; Ying LIU ; Zhan-Peng SHANG ; Xiu-Ping ZHANG ; Zi-Jian WANG ; Jian-Qiu LU ; Jia-Yu ZHANG

Chinese Journal of Natural Medicines (English Ed.).2017;15(12):955-960. doi:10.1016/S1875-5364(18)30013-X

Kudiezi injection has been used extensively in the treatment of cerebrovascular and cardiovascular diseases. However, its therapeutic effects and underlying mechanism of action are not fully understood. The aim of the present study was to clarify the protective mechanisms of Kudiezi injection on cerebral ischemic injury, using metabolomics methods. Middle cerebral artery occlusion (MCAO) was introduced in rats to build the cerebral ischemic damage. UHPLC-LTQ-Orbitrap-based analytical method was established for analysis of the metabolites. The raw mass data of all samples were normalized with Sieve 2.2 software and then introduced to orthogonal partial least squares discriminant analysis (OPLS-DA) model. Finally, 23 metabolites in plasma (15 were tentatively identified) were chosen as potential biomarkers, according to accurate mass measurements (< 5 ppm), MS/MS fragmentation patterns, and diagnostic product ions. Furthermore, on the basis of metabolic pathway analysis via metabolomics pathway analysis (MetPA), we first discovered that the protection mechanism in anti-ischemic cerebral reperfusion damage of Kudiezi injection was possibly related to the biosynthesis of phenylalanine, tyrosine, and tryptophan. The present study provided a useful approach for exploring the mechanism of ischemic stroke and evaluating the efficacy of Kudiezi injection or other traditional medicines.
Animals ; Asteraceae ; chemistry ; Biomarkers ; blood ; Brain Ischemia ; blood ; complications ; drug therapy ; Disease Models, Animal ; Drugs, Chinese Herbal ; pharmacology ; therapeutic use ; Injections ; Male ; Metabolic Networks and Pathways ; drug effects ; Metabolomics ; Plant Extracts ; pharmacology ; therapeutic use ; Rats ; Rats, Sprague-Dawley ; Reperfusion Injury ; blood ; drug therapy

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Cycloartane triterpenoid and its glucoside isolated from Cassia occidentalis.

Shi-Fei LI ; Shun-Lin LI

Chinese Journal of Natural Medicines (English Ed.).2017;15(12):950-954. doi:10.1016/S1875-5364(18)30012-8

In the present study, one new cycloartane triterpenoid, named cycloccidentalic acid C (1) and its glucoside, cycloccidentaliside VI (2) were isolated from the whole plant of Cassia occidentalis. Their structures were elucidated by a combinational analyses of 1D and 2D NMR data and HRMS. Compound 2 showed modest anti-HIV-1 activity with EC value of 1.44 μmol·L and TI (Therapeutic Index) value of 15.59.
Anti-HIV Agents ; isolation & purification ; pharmacology ; Cell Line, Tumor ; Cell Survival ; drug effects ; Glucosides ; chemistry ; pharmacology ; toxicity ; Humans ; Inhibitory Concentration 50 ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Plant Extracts ; chemistry ; isolation & purification ; pharmacology ; toxicity ; Senna Plant ; chemistry ; Triterpenes ; chemistry ; isolation & purification ; pharmacology ; toxicity

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Three new anthraquinone derivatives isolated from Symplocos racemosa and their antibiofilm activity.

Umar FAROOQ ; Sara KHAN ; Sadia NAZ ; Ajmal KHAN ; Afsar KHAN ; Ayaz AHMED ; Abdur RAUF ; Syed Majid BUKHARI ; Shujaat Ali KHAN ; Arfa KAMIL ; Nadia RIAZ ; Abdur Rahman KHAN

Chinese Journal of Natural Medicines (English Ed.).2017;15(12):944-949. doi:10.1016/S1875-5364(18)30011-6

Three new alkyl substituted anthraquinone derivatives, trivially named as symploquinones A-C (Compounds 1-3) were isolated from Symplocos racemosa. The structures of these compounds were determined on the basis of extensive spectroscopic analyses (UV, IR, Mass, H- and C-NMR, and two-dimensional (2D) NMR techniques). The resulting data were also compared with the reported literature. These compounds were then subjected to antibacterial or antibiofilm testing. Compounds 1 and 3 exhibited good antibacterial activity in the concentration range of 160-83 μg·mL against Streptococcus mutans, methicillin resistant Staphylococcus aureus and Proteus mirabilis. Both compounds were further screened for anti-biofilm activity, which revealed promising activities at sub-MIC concentrations. None of the compounds were found to be active against Klebsiella pneumoniae.
Anthraquinones ; chemistry ; isolation & purification ; pharmacology ; Anti-Bacterial Agents ; chemistry ; isolation & purification ; pharmacology ; Biofilms ; drug effects ; growth & development ; Ericales ; chemistry ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Methicillin-Resistant Staphylococcus aureus ; drug effects ; physiology ; Microbial Sensitivity Tests ; Proteus mirabilis ; drug effects ; physiology ; Spectrophotometry, Infrared ; Streptococcus mutans ; drug effects ; physiology

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Lignans and diterpenes isolated from Tirpitzia ovoidea and their biological activities.

Xue-Yan YANG ; Yi-Fan ZHANG ; Li-Jia LIU ; Yi WANG ; Ming-Ying SHANG ; Feng XU ; Guang-Xue LIU ; Shao-Qing CAI

Chinese Journal of Natural Medicines (English Ed.).2017;15(12):938-943. doi:10.1016/S1875-5364(18)30010-4

A new lignan, tirpitzin A (17) together with 20 known compounds (1-16, and 18-21) were isolated from the ethyl acetate soluble fraction of ethanol extract of the aerial parts of Tirpitzia ovoidea. The structure of new compound was elucidated by means of spectroscopic analysis. Of the known compounds, 7-21 were isolated from Linaceae family for the first time. The pharmacological activity of the crude extracts was tested using a mouse inflammation model induced by dimethyl benzene. The results demonstrated that the ethyl acetate soluble fraction had anti-inflammatory activity. Moreover, the cytotoxic and anti-inflammatory activities of some compounds were studied. The new compound 17 showed moderate cytotoxic effect against BxPC-3 cell line (IC = 19.51μmol·L) and Compound 10 showed significant cytotoxicity against HepG2, HL-60, U87 and BxPC-3 cell lines with IC values in the range 4.2-8.3μmol·L. Additionally, Compounds 2, 10, 11, and 13 exhibited potent inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages at the concentration of 50μmol·L.
Animals ; Anti-Inflammatory Agents ; chemistry ; pharmacology ; Cell Line, Tumor ; Cell Survival ; drug effects ; Disease Models, Animal ; Diterpenes ; chemistry ; pharmacology ; toxicity ; HL-60 Cells ; Hep G2 Cells ; Humans ; Inhibitory Concentration 50 ; Lignans ; chemistry ; pharmacology ; toxicity ; Linaceae ; chemistry ; Macrophages ; drug effects ; Mice ; Nitric Oxide ; metabolism ; Plant Components, Aerial ; chemistry ; Plant Extracts ; chemistry ; pharmacology ; toxicity ; RAW 264.7 Cells

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Synthesis and anti-hepatocellular carcinoma activity of novel O-vinyl diazeniumdiolate-based nitric oxide-releasing derivatives of oleanolic acid.

Yu ZOU ; Chang YAN ; Jing-Chao LIU ; Zhang-Jian HUANG ; Jin-Yi XU ; Jin-Pei ZHOU ; Hui-Bin ZHANG ; Yi-Hua ZHANG

Chinese Journal of Natural Medicines (English Ed.).2017;15(12):928-937. doi:10.1016/S1875-5364(18)30009-8

Considering that high levels of nitric oxide (NO) exert anti-cancer effect and the derivatives of oleanolic acid (OA) have shown potent anti-cancer activity, new O-vinyl diazeniumdiolate-based NO releasing derivatives (5a-l, 11a-l) of OA were designed, synthesized, and biologically evaluated in the present study. These derivatives could release different amounts of NO in liver cells. Among them, 5d, 5i, 5j, 11g, 11h, and 11j released more NO in SMMC-7721 cells and displayed stronger proliferative inhibition against SMMC-7721 and HepG2 cells than OA and other tested compounds. The most active compound 5j showed almost 20-fold better solubility than OA in aqueous solution, released larger amounts of NO in liver cancer cells than that in normal ones, and exhibited potent anti-hepatocellular carcinoma activity but little effect on the normal liver cells. The inhibitory activity against the cancer cells was significantly diminished upon addition of an NO scavenger, suggesting that NO may contribute, at least in part, to the activity of 5j.
Antineoplastic Agents ; chemical synthesis ; chemistry ; pharmacology ; Apoptosis ; drug effects ; Azo Compounds ; chemistry ; Carcinoma, Hepatocellular ; drug therapy ; pathology ; Cell Proliferation ; drug effects ; Cells, Cultured ; Drug Screening Assays, Antitumor ; Hep G2 Cells ; Hepatocytes ; drug effects ; metabolism ; pathology ; Humans ; Liver Neoplasms ; drug therapy ; pathology ; Nitric Oxide ; chemistry ; Nitric Oxide Donors ; chemical synthesis ; chemistry ; pharmacology ; Oleanolic Acid ; analogs & derivatives ; chemistry ; pharmacology

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HPPR encodes the hydroxyphenylpyruvate reductase required for the biosynthesis of hydrophilic phenolic acids in Salvia miltiorrhiza.

Guo-Quan WANG ; Jun-Feng CHEN ; Bo YI ; He-Xin TAN ; Lei ZHANG ; Wan-Sheng CHEN

Chinese Journal of Natural Medicines (English Ed.).2017;15(12):917-927. doi:10.1016/S1875-5364(18)30008-6

Salvia miltiorrhiza is a medicinal plant widely used in the treatment of cardiovascular and cerebrovascular diseases. Hydrophilic phenolic acids, including rosmarinic acid (RA) and lithospermic acid B (LAB), are its primary medicinal ingredients. However, the biosynthetic pathway of RA and LAB in S. miltiorrhiza is still poorly understood. In the present study, we accomplished the isolation and characterization of a novel S. miltiorrhiza Hydroxyphenylpyruvate reductase (HPPR) gene, SmHPPR, which plays an important role in the biosynthesis of RA. SmHPPR contained a putative catalytic domain and a NAD(P)H-binding motif. The recombinant SmHPPR enzyme exhibited high HPPR activity, converting 4-hydroxyphenylpyruvic acid (pHPP) to 4-hydroxyphenyllactic acid (pHPL), and exhibited the highest affinity for substrate 4-hydroxyphenylpyruvate. SmHPPR expression could be induced by various treatments, including SA, GA, MeJA and Ag, and the changes in SmHPPR activity were correlated well with hydrophilic phenolic acid accumulation. SmHPPR was localized in cytoplasm, most likely close to the cytosolic NADPH-dependent hydroxypyruvate reductase active in photorespiration. In addition, the transgenic S. miltiorrhiza hairy roots overexpressing SmHPPR exhibited up to 10-fold increases in the products of hydrophilic phenolic acid pathway. In conclusion, our findings provide a new insight into the synthesis of active pharmaceutical compounds at molecular level.
Amino Acid Sequence ; Benzofurans ; Biosynthetic Pathways ; genetics ; Cinnamates ; Depsides ; Gene Expression Regulation, Plant ; genetics ; Oxidoreductases ; genetics ; Phenylpropionates ; metabolism ; Phenylpyruvic Acids ; metabolism ; Phylogeny ; Plant Proteins ; genetics ; metabolism ; Plant Roots ; chemistry ; enzymology ; genetics ; metabolism ; Plants, Genetically Modified ; Recombinant Proteins ; analysis ; biosynthesis ; Salvia miltiorrhiza ; chemistry ; enzymology ; genetics ; metabolism ; Sequence Alignment

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Preparation and physicochemical characterization of T-OA PLGA microspheres.

Jing FU ; Xiao-Xu DONG ; Zu-Ping ZENG ; Xing-Bin YIN ; Fa-Wei LI ; Jian NI

Chinese Journal of Natural Medicines (English Ed.).2017;15(12):912-916. doi:10.1016/S1875-5364(18)30007-4

As the carrier of water-insoluble drugs, microspheres can play a role in increasing solubility and delaying releasing essence. The objective of this study was to improve the solubility and to delay the release of a newly discovered antitumor compound 3β-hydroxyolea-12-en-28-oic acid-3, 5, 6-trimethylpyrazin-2-methyl ester (T-OA). Early-stage preparation discovery concept (EPDC) was employed in the present study. The preparation, physicochemical characterization, and drug release properties of PLGA microspheres were evaluated. T-OA-loaded PLGA microspheres were prepared by an oil-in-water (O/W) emulsification solvent evaporation method. Characterization and release behaviors of the T-OA PLGA microspheres were evaluated by X-ray diffract (XRD), differential scanning calorimetry (DSC), Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), and high performance liquid chromatography (HPLC). The results demonstrated that T-OA-loaded PLGA microspheres could be successfully obtained through solvent evaporation method with appropriate morphologic characteristics and high encapsulation efficiency. The XRD analysis showed that T-OA would be either molecularly dispersed in the polymer or distributed in an amorphous form. The DSC and FTIR analysis proved that there were interactions between T-OA and PLGA polymer. SEM observations displayed the morphology of the microspheres was homogeneous and the majority of the spheres ranged between 50 and 150 μm. The drug release behavior of the microspheres in the phosphate buffered saline medium exhibited a sustained release and the duration of the release lasted for more than 23 days, which was fit with zero-order release pattern with r = 0.9947. In conclusion, TOA-loaded PLGA microspheres might hold great promise for using as a drug-delivery system in biomedical applications.
Antineoplastic Agents ; chemistry ; Calorimetry, Differential Scanning ; Chemistry, Pharmaceutical ; Delayed-Action Preparations ; chemistry ; Drug Carriers ; chemical synthesis ; chemistry ; Lactic Acid ; chemical synthesis ; chemistry ; Microscopy, Electron, Scanning ; Microspheres ; Oleanolic Acid ; chemistry ; Polyglycolic Acid ; chemical synthesis ; chemistry ; Polylactic Acid-Polyglycolic Acid Copolymer ; Pyrazines ; chemistry ; Solubility ; Spectroscopy, Fourier Transform Infrared ; X-Ray Diffraction

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Atractylodes lancea rhizome water extract reduces triptolide-induced toxicity and enhances anti-inflammatory effects.

Yuan WEI ; Dan-Juan SUI ; Hai-Miao XU ; Zhen OUYANG ; Na WU ; Du-Jun WANG ; Xiao-Yan ZHANG ; Da-Wei QIAN

Chinese Journal of Natural Medicines (English Ed.).2017;15(12):905-911. doi:10.1016/S1875-5364(18)30006-2

The present study was designed to explore the influence of water extracts of Atractylodes lancea rhizomes on the toxicity and anti-inflammatory effects of triptolide (TP). A water extract was prepared from A. lancea rhizomes and co-administered with TP in C57BL/6 mice. The toxicity was assayed by determining serum biochemical parameters and visceral indexes and by liver histopathological analysis. The hepatic CYP3A expression levels were detected using Western blotting and RT-PCR methods. The data showed that the water extract of A. lancea rhizomes reduced triptolide-induced toxicity, probably by inducing the hepatic expression of CYP3A. The anti-inflammatory effects of TP were evaluated in mice using a xylene-induced ear edema test. By comparing ear edema inhibition rates, we found that the water extract could also increase the anti-inflammatory effects of TP. In conclusion, our results suggested that the water extract of A. lancea rhizomes, used in combination with TP, has a potential in reducing TP-induced toxicity and enhancing its anti-inflammatory effects.
Animals ; Anti-Inflammatory Agents ; isolation & purification ; pharmacology ; Atractylodes ; chemistry ; Cytochrome P-450 Enzyme System ; genetics ; Diterpenes ; toxicity ; Edema ; chemically induced ; pathology ; Enzyme Induction ; drug effects ; Epoxy Compounds ; toxicity ; Gene Expression Regulation ; drug effects ; Herb-Drug Interactions ; Liver ; drug effects ; pathology ; Male ; Mice ; Mice, Inbred C57BL ; Phenanthrenes ; toxicity ; Plant Extracts ; isolation & purification ; pharmacology ; Plants, Medicinal ; chemistry ; Rhizome ; chemistry ; Water ; chemistry

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Effects of Gardenia jasminoides extracts on cognition and innate immune response in an adult Drosophila model of Alzheimer's disease.

Wei-Wei MA ; Ye TAO ; Yan-Ying WANG ; I-Feng PENG

Chinese Journal of Natural Medicines (English Ed.).2017;15(12):899-904. doi:10.1016/S1875-5364(18)30005-0

Herbal extracts have been extensively used worldwide for their application on memory improvement, especially among aged and memory-deficit populations. In the present study, the memory loss induced by human Abeta protein over-expression in fruitfly Alzheimer's disease (AD) model was rescued by multiple extracts from Gardenia jasminoides. Three extracts that rich with gardenia yellow, geniposide, and gardenoside components showed distinct rescue effect on memory loss. Further investigation on adding gardenoside into a formula of Ganoderma lucidum, Panax notoginseng and Panax ginseng (GPP) also support its therapeutic effects on memory improvement. Interestingly, the application of GPP and gardenoside did not alter the accumulation of Abeta proteins but suppressed the expression of immune-related genes in the brain. These results revealed the importance and relevancy of anti-inflammation process and the underlying mechanisms on rescuing memory deficits, suggesting the potential therapeutic use of the improved GPP formulation in improving cognition in defined population in the future.
Alzheimer Disease ; drug therapy ; Animals ; Antimicrobial Cationic Peptides ; genetics ; Brain ; drug effects ; immunology ; Cognition ; drug effects ; Disease Models, Animal ; Drosophila ; Drosophila Proteins ; genetics ; Gardenia ; chemistry ; Gene Expression Regulation ; drug effects ; Immunity, Innate ; drug effects ; Iridoids ; chemistry ; isolation & purification ; pharmacology ; Plant Extracts ; chemistry ; isolation & purification ; pharmacology ; Polymerase Chain Reaction

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