Publications by authors named "Huiyuan Gao"

63 Publications

Anti-inflammatory Cassane-Type Diterpenoids from the Seed Kernels of .

J Nat Prod 2021 08 1;84(8):2175-2188. Epub 2021 Aug 1.

School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.

Eighteen cassane diterpenoids, including five new lactam-type (-), 12 new lactone-type (- and -), and one known compound (), were isolated from . To our knowledge, this is the first study on the seed kernels of , and cassane derivatives were discovered in this plant for the first time. Their structures including absolute configurations were established by extensive spectroscopic methods complemented with single-crystal X-ray diffraction analyses and ECD calculations. Compounds - were identified as a group of rare cassane diterpenoids possessing a lactam D-ring instead of a typical lactone moiety. Biological evaluation revealed that compounds - exhibited effective inhibitory effects on NO production in the LPS-induced RAW 264.7 macrophages, with IC values in the range 8.2-11.2 μM. Compound suppressed the excessive production of NO by down-regulating the expression of inducible nitric oxide synthase enzymes (iNOS) and reducing the enzymatic activity of iNOS. Moreover, the intermolecular interaction and binding mode between compound and iNOS were elaborated by conducting a molecular docking study.
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http://dx.doi.org/10.1021/acs.jnatprod.1c00233DOI Listing
August 2021

New cassane- and norcassane-type diterpenoids from the seed kernels of Caesalpinia sinensis and their anti-inflammatory activity in vitro.

Fitoterapia 2021 Sep 24;153:104978. Epub 2021 Jun 24.

School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, PR China; Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China. Electronic address:

The first investigation of phytochemistry on the seed kernels of Caesalpinia sinensis led to the isolation and characterization of six new compounds including three tricyclic-type cassane diterpenoids (1--3) and three norcassane-type diterpenoids (4-6), together with three know compounds (7-9). Compounds 1-9 represented the first discovery of cassane-type diterpenoids from C. sinensis. Their structures were elucidated by a combination of spectroscopic analysis, single-crystal X-ray diffraction experiment and ECD calculation. The characters for compounds 4 and 5 possessing the 15,16-degradative cassane skeleton were observed, which was extremely rare structural type in the genus Caesalpinia. The anti-inflammatory activities of all isolates were evaluated via examining their inhibitory effects against NO production in LPS-simulated RAW 264.7 cells. The results demonstrated that compound 1 exhibited the most significantly inhibitory efficacy with inhibition rate 67.3% at 10 μM. The iNOS enzyme activity assay further revealed that compound 1 showed potent NO inhibitory effect by reducing the enzymatic activity of iNOS.
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http://dx.doi.org/10.1016/j.fitote.2021.104978DOI Listing
September 2021

The severe toxicity of CuO nanoparticles to the photosynthesis of the prokaryotic algae Arthrospira sp.

Environ Sci Pollut Res Int 2021 Oct 27;28(38):54105-54116. Epub 2021 May 27.

State Key Laboratory of Crop Biology, Shandong Key Laboratory of Crop Biology, College of Life Sciences, Shandong Agricultural University, Tai'an, Shandong, 271018, People's Republic of China.

This research first verified that prokaryotic algae are more sensitive to toxicity of CuO nanoparticles (CuO NPs) than eukaryotic algae and that CuO NPs damaged photosynthesis of prokaryotic algae (Arthrospira sp.) but had no effect on respiration. The Cu released by CuO NPs caused a bending deformation of the thylakoid, which was an important cause of the decline in photosynthetic capacity. In addition, the D1 protein was the most susceptible site to CuO NPs. The degradation of D1 protein reduced photosynthetic electron transport, which enhanced the excess excitation energy to cause the accumulation of reactive oxygen species (ROS) to further result in oxidative stress on algae. Dissolved organic matter (DOM) increased the toxicity of CuO NPs to photosynthesis of Arthrospira sp. The damage of photosynthesis caused by CuO NPs is an important reason why CuO NPs have a serious toxicity to algae.
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http://dx.doi.org/10.1007/s11356-021-14341-3DOI Listing
October 2021

Four new cassane-type diterpenoids from the seed kernels of Roxb.

Nat Prod Res 2021 May 5:1-8. Epub 2021 May 5.

School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, People's Republic of China.

The first investigation of chemical composition in seed kernels of Roxb. resulted in the separation of four new cassane diterpenes, including three furanoditerpenes (, and ) and one tricyclic type (). It was the first found cassane diterpenoids from this plant. Their gross structures were elucidated by means of comprehensive spectroscopic analysis (UV, IR, NMR, HRESIMS) as well as electronic circular dichroism (ECD) calculation. The compound possess a rare isomerized dihydrofuran ring in structure framework. In bioassay, compounds - exhibited moderate anti-inflammatory activity by inhibiting production of NO in LPS-induced RAW 264.7 cells.
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http://dx.doi.org/10.1080/14786419.2021.1919107DOI Listing
May 2021

Two new cassane-type diterpenoids from the seed kernels of (Linn.) Roxb. and their anti-inflammatory activity.

Nat Prod Res 2021 Mar 4:1-8. Epub 2021 Mar 4.

School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, People's Republic of China.

In this study, phytochemical investigation on the chloroform soluble fraction of seed kernels of led to the isolation of two new cassane-type diterpenoids, norcaesalpinin Q () and caesalpinin MR (), together with seven known compounds (-). The structures of the new compounds were elucidated on the basis of extensive NMR spectroscopic and mass spectrometric analyses, and their absolute configurations were determined by electronic circular dichroism (ECD) calculations. All compounds were evaluated for inhibitory effects against NO production of RAW264.7 cells induced by LPS, and compounds , and could inhibited the production of NO at the concentration of 50 µM.
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http://dx.doi.org/10.1080/14786419.2021.1896511DOI Listing
March 2021

Quinetides: diverse posttranslational modified peptides of ribonuclease-like storage protein from as markers for differentiating ginseng species.

J Ginseng Res 2020 Sep 29;44(5):680-689. Epub 2019 May 29.

CAS Key Laboratory of Separation Sciences for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China.

Background: Peptides have diverse and important physiological roles in plants and are ideal markers for species identification. It is unclear whether there are specific peptides in L. (PQ). The aims of this study were to identify Quinetides, a series of diverse posttranslational modified native peptides of the ribonuclease-like storage protein (ginseng major protein), from PQ to explore novel peptide markers and develop a new method to distinguish PQ from

Methods: We used different fragmentation modes in the LTQ Orbitrap analysis to identify the enriched Quinetide targets of PQ, and we discovered Quinetide markers of PQ and using ultrahigh-performance liquid chromatography-quadrupole time-of-flight mass spectrometry analysis. These "peptide markers" were validated by simultaneously monitoring Rf and F11 as standard ginsenosides.

Results: We discovered 100 Quinetides of PQ with various post-translational modifications (PTMs), including a series of glycopeptides, all of which originated from the protein ginseng major protein. We effectively distinguished PQ from using new "peptide markers." Four unique peptides (Quinetides TP6 and TP7 as markers of PQ and Quinetides TP8 and TP9 as markers of ) and their associated glycosylation products were discovered in PQ and .

Conclusion: We provide specific information on PQ peptides and propose the clinical application of peptide markers to distinguish PQ from .
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http://dx.doi.org/10.1016/j.jgr.2019.05.010DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7471211PMC
September 2020

A natural BACE1 and GSK3β dual inhibitor Notopterol effectively ameliorates the cognitive deficits in APP/PS1 Alzheimer's mice by attenuating amyloid-β and tau pathology.

Clin Transl Med 2020 Jul 11;10(3):e50. Epub 2020 Jul 11.

Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, People's Republic of China.

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http://dx.doi.org/10.1002/ctm2.50DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7418795PMC
July 2020

Application of the Chinese Version of the BIS/BAS Scales in Participants With a Substance Use Disorder: An Analysis of Psychometric Properties and Comparison With Community Residents.

Front Psychol 2020 8;11:912. Epub 2020 May 8.

Medical Psychological Center, Second Xiangya Hospital, Central South University, Changsha, China.

Carver and White developed the Behavioral Inhibition/Behavioral Activation Scales (the BIS/BAS Scales) based on Reinforcement Sensitivity Theory proposed by Gray. Subsequent studies proposed that substance abuse was closely related to Behavioral Inhibition System (BIS) and Behavioral Activation System (BAS). However, researches on the psychometric properties of the BIS/BAS scales in clinical samples are scarce. The present study was conducted to analyze the applicability of the BIS/BAS scales in a sample suffering from a substance use disorder (SUD) and undergoing treatment in compulsory detoxification institutions ( = 1117). Meanwhile, 822 community residents were selected for comparison. Confirmatory factor analysis was carried out to examine the construct validity and the results showed that the five-factor model was the best fit for people with a substance use disorder' data. Besides, Cronbach's alpha coefficient for the total scale was 0.808, indicating the satisfactory internal consistency reliability. Analysis of the correlation coefficient of the questionnaire with the corresponding personality traits showed that BAS was more associated with the impulsive trait. Surprisingly, participants with a substance use disorder showed more insensitivity for the reward dimension compared with that of community residents and the result of comparison between two samples supported joint subsystems hypothesis. Generally, the BIS/BAS scales showed good reliability and validity. These findings provide more direct evidence on the personality traits of people with a substance use disorder and should form the basis for further research.
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http://dx.doi.org/10.3389/fpsyg.2020.00912DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7225352PMC
May 2020

Response to Comments on "The toxicological effects of oxybenzone, an active ingredient in suncream personal care products, on prokaryotic alga Arthrospira sp. and eukaryotic alga Chlorella sp."

Aquat Toxicol 2020 09 14;226:105500. Epub 2020 May 14.

State Key Laboratory of Crop Biology, Taian, China; College of Horticulture Science and Engineering, Shandong Agricultural University, Taian, China. Electronic address:

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http://dx.doi.org/10.1016/j.aquatox.2020.105500DOI Listing
September 2020

Insensitivity to Success and Failure: An Experimental Study of Performance-Based Feedback in Depression.

Front Psychol 2020 23;11:670. Epub 2020 Apr 23.

Medical Psychological Center, The Second Xiangya Hospital, Central South University, Changsha, China.

Objective: This experimental study set out to examine the effects of performance feedback (success or failure) on depressed emotions and self-serving attribution bias in inpatients suffering from major depressive disorder (MDD).

Methods: The study was based on a 2 × 2 experimental design in which 71 MDD patients and 59 healthy controls participated. Both groups (MDD and controls) were randomly assigned to two conditions: success or failure in the performance feedback. A section of Raven's Standard Progressive Matrices (SPM) was used as a bogus test of the participants' reasoning abilities, and the Core Depressive Factor of the Zung Self-Rating Depression Scale was used to measure changes in depressed emotion in the subjects following the performance feedback. Participants then rated the accuracy of the SPM as a measure of their reasoning capacity.

Results: The levels of depressed emotions in patients with MDD did not differ significantly under the two feedback conditions. In contrast, depressed emotion levels increased significantly in healthy individuals in response to failure feedback but did not change in response to success feedback. With regard to the ratings of SPM accuracy, there was no significant difference across the two feedback conditions for depressed patients; however, the accuracy ratings were higher in the success condition than in the failure condition for the controls.

Conclusion: Individuals with MDD exhibit blunted emotional reactivity when experiencing new positive or negative social stimuli, supporting the theory of Emotion Context Insensitivity. In addition, self-serving attribution bias does not occur in MDD, which is consistent with the theory of learned helplessness in depression.
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http://dx.doi.org/10.3389/fpsyg.2020.00670DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7191081PMC
April 2020

Application of the Chinese version of the addiction profile index (API) in drug users: an analysis of validity and measurement invariance across genders.

Subst Abuse Treat Prev Policy 2020 04 9;15(1):28. Epub 2020 Apr 9.

Medical Psychological Center, The Second Xiangya Hospital, Central South University, Changsha, Hunan, 410011, China.

Background: In China, substance use disorders represent a significant burden on public health and the economy. However, while the range of drugs and drug markets expands and diversifies, the instruments available to evaluate users' dependence statuses from multiple dimensions have become insufficient. Accordingly, the present study presents the Chinese version of the Addiction Profile Index (API), explores its reliability and validity, and investigates the measurement invariance between males and females with substance use disorders.

Methods: The API, a self-report questionnaire, was administered to 2252 people with substance use disorders who were undergoing treatment in compulsory detoxification institutions located in five provinces in China (943 females; mean age = 33.5 years old, SD = 8.6). Additionally, to ensure the authenticity of the collected data, the study's volunteers completed the Drug Use Disorders Identification Test (DUDIT), DUDIT-Extended (DUDIT-E), and the Health Scale for Drug Abusers (HSDA).

Results: The revised API, with its updated substance list, featured 34 items. The new four-factor model, incorporating behavioral symptoms of dependence, impact on social life, cravings, and motivations for detoxification, explained 55.30% of the total variance, indicating a good fit. Moreover, Cronbach's α and mean item coefficient values showed good internal consistency reliability. Regarding criterion validity, the revised factors were moderately to highly correlated with their corresponding subscales in the DUDIT, DUDIT-E, and HSDA. In addition, the multigroup confirmatory factor analysis demonstrated that a measurement invariance of the revised four-factor model across genders was supported, fully assuming different degrees of invariance. The three factors of symptoms, social life, and motivation exhibited significant differences between male and female participants in the t test results (p < 0.01).

Conclusions: The Chinese version of the API shows good psychometric properties in terms of reliability and validity, and exhibits measurement equivalence across the genders. Therefore, it could be used to comprehensively assess the severity of drug dependence in people with substance use disorders.
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http://dx.doi.org/10.1186/s13011-020-00263-9DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7146950PMC
April 2020

The bifunctional enzyme, GenB4, catalyzes the last step of gentamicin 3',4'-di-deoxygenation via reduction and transamination activities.

Microb Cell Fact 2020 Mar 10;19(1):62. Epub 2020 Mar 10.

School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University, No.103 Wenhua Road, Shenyang, Liaoning, China.

Background: New semi-synthetic aminoglycoside antibiotics generally use chemical modifications to avoid inactivity from pathogens. One of the most used modifications is 3',4'-di-deoxygenation, which imitates the structure of gentamicin. However, the mechanism of di-deoxygenation has not been clearly elucidated.

Results: Here, we report that the bifunctional enzyme, GenB4, catalyzes the last step of gentamicin 3',4'-di-deoxygenation via reduction and transamination activities. Following disruption of genB4 in wild-type M. echinospora, its products accumulated in 6'-deamino-6'-oxoverdamicin (1), verdamicin C2a (2), and its epimer, verdamicin C2 (3). Following disruption of genB4 in M. echinospora ΔgenK, its products accumulated in sisomicin (4) and 6'-N-methylsisomicin (5, G-52). Following in vitro catalytic reactions, GenB4 transformed sisomicin (4) to gentamicin C1a (9) and transformed verdamicin C2a (2) and its epimer, verdamicin C2 (3), to gentamicin C2a (11) and gentamicin C2 (12), respectively.

Conclusion: This finding indicated that in addition to its transamination activity, GenB4 exhibits specific 4',5' double-bond reducing activity and is responsible for the last step of gentamicin 3',4'-di-deoxygenation. Taken together, we propose three new intermediates that may refine and supplement the specific biosynthetic pathway of gentamicin C components and lay the foundation for the complete elucidation of di-deoxygenation mechanisms.
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http://dx.doi.org/10.1186/s12934-020-01317-0DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7063804PMC
March 2020

Comparison of toxicological effects of oxybenzone, avobenzone, octocrylene, and octinoxate sunscreen ingredients on cucumber plants (Cucumis sativus L.).

Sci Total Environ 2020 Apr 22;714:136879. Epub 2020 Jan 22.

State Key Laboratory of Crop Biology, Shandong Agricultural University, Taian, China; College of Horticulture Science and Engineering, Shandong Agricultural University, Taian, China. Electronic address:

Oxybenzone (OBZ), avobenzone (AVB), octocrylene (OCR) and octinoxate (OMC) are ultraviolet (UV) filters commonly added to chemical sunscreens. These UV filters are known to widely contaminate the environment through a variety of anthropogenic sources, including sewage discharge. However, systematic studies of the damage caused by these four UV filters and their toxicopathological differences in a variety of plant species are lacking. In this study, we demonstrated that irrigation with water containing these four UV filters could significantly inhibit the aboveground growth of cucumber plant. All of the UV filters decreased photosynthesis through nonstomatal factors but via different inhibitory mechanisms. Only OBZ inhibited photosynthesis by directly inhibiting photosynthetic electron transport, while the other three (AVB, OCR, and OMC) inhibited photosynthesis by inhibiting the Calvin-Benson cycle. Additionally, these four UV filters also decreased plant respiration under long-term treatment. Photosynthesis and respiration inhibition led to the over production of reactive oxygen species (ROS) and the formation of lipid peroxidation damage products, which further damaged the structure and function of plant cells, causing secondary pathologies and potentially leading to reduced crop yields. The study also demonstrated that these four UV filters caused different degrees of phototoxic damage to cucumber plants. On the basis of comprehensive evaluation, we speculated that the order of the four UV filters in terms of plant damage was OBZ > AVB > OMC > OCR. Because of the severe damaging effects of these UV filters on plant growth, the application of contaminated biosolids/reclaimed water in agriculture reduces agricultural production and may damage ecosystems. The results of this study can advance recognition of the hazards associated with environmental and agricultural pollution via UV filters and encourage consumers and the industry to limit or reduce the application of cosmetics and over-the-counter drugs containing these substances.
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http://dx.doi.org/10.1016/j.scitotenv.2020.136879DOI Listing
April 2020

New cassane-type diterpenoids from kernels of Caesalpinia bonduc (Linn.) Roxb. and their inhibitory activities on phosphodiesterase (PDE) and nuclear factor-kappa B (NF-κB) expression.

Bioorg Chem 2020 03 9;96:103573. Epub 2020 Jan 9.

School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China; Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China. Electronic address:

In this paper, chemical investigation on the chloroform soluble fraction of seed kernels of Caesalpinia bonduc resulted in the isolation of five new cassane diterpenoids: norcaesalpinin O (1), norcaesalpinin P (2), caesalpinin MQ (3), caesall O/P (4/5) and seven known compounds (6-12). Compounds structures were elucidated by H NMR, C NMR, 2D NMR, HR-MS and ECD (electronic circular dichroism) spectral analysis. The characters for new compounds with the presence of an aromatized C ring or demethyl group at C-17 position in the structures were found. By means of bioactive screenings, the inhibitory effect on type-4 phosphodiesterase (PDE4, the target protein of asthma disease) and nuclear factor-kappa B (NF-κB) expression were valued. Compound 1 was found to exhibit moderate inhibitory activity on PDE4 and much better binding affinity than other structures by docking studies for interaction analyzing. Compounds 6, 10 and 11 displayed considerable inhibitory strength against NF-κB expression with inhibitory ratio 48.6%, 42.9% and 37.1% at 10 µM, respectively. The isolation of cassane-type diterpenoids with anti-inflammation activity from C. bonduc implied that this plant might be a good source for anti-inflammation agents finding.
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http://dx.doi.org/10.1016/j.bioorg.2020.103573DOI Listing
March 2020

The toxicological effects of oxybenzone, an active ingredient in suncream personal care products, on prokaryotic alga Arthrospira sp. and eukaryotic alga Chlorella sp.

Aquat Toxicol 2019 Nov 6;216:105295. Epub 2019 Sep 6.

State Key Laboratory of Crop Biology, China; College of Life Sciences, Shandong Agricultural University, China.

Oxybenzone (OBZ; benzophenone-3, CAS# 131-57-7) is a known pollutant of aquatic and marine ecosystems, and is an ingredient in over 3000 personal care products, as well as many types of plastics. The aim of this study is to explore the different toxicities of OBZ on an eukaryotic (Chlorella sp.) and a prokaryotic algae (Arthrospira sp.). OBZ is a photo-toxicant, with all observed toxicities more sever in the light than in the dark. Cell growth and chlorophyll inhibition were positively correlated with increasing OBZ concentrations over time. Twenty days treatment with OBZ, as low as 22.8 ng L, significantly inhibited the growth and chlorophyll synthesis of both algae. Both algae were noticeably photo-bleached after 7 days of exposure to OBZ concentrations higher than 2.28 mg L. Relatively low OBZ concentrations (0.228 mg L) statistically constrained photosynthetic and respiratory rates via directly inhibiting photosynthetic electron transport (PET) and respiration electron transport (RET) mechanisms, resulting in over production of reactive oxygen species (ROS). Transmission and scanning electron microscopy showed that the photosynthetic and respiratory membrane structures were damaged by OBZ exposure in both algae. Additionally, PET inhibition suppressed ATP production for CO assimilation via the Calvin-Benson cycle, further limiting synthesis of other biomacromolecules. RET restriction limited ATP generation, restricting the energy supply used for various life activities in the cell. These processes further impacted on photosynthesis, respiration and algal growth, representing secondary OBZ-induced algal damages. The data contained herein, as well as other studies, supports the argument that global pelagic and aquatic phytoplankton could be negatively influenced by OBZ pollution.
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http://dx.doi.org/10.1016/j.aquatox.2019.105295DOI Listing
November 2019

The dietary freeze-dried fruit powder of Actinidia arguta ameliorates dextran sulphate sodium-induced ulcerative colitis in mice by inhibiting the activation of MAPKs.

Food Funct 2019 Sep 27;10(9):5768-5778. Epub 2019 Aug 27.

School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.

In this study, we aimed at investigating the antiinflammatory activity of the freeze-dried fruit powder of Actinidia arguta (FAA) on dextran sulphate sodium (DSS)-induced ulcerative colitis (UC) in mice and the effect of its extract on lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. For pharmacodynamic studies, the oral administration of FAA (300 or 600 mg kg) could decrease the disease activity index (DAI), reduce the incidence of colon and spleen edemas (caused by inflammation), and alleviate the pathological changes in UC. For research involving biochemical indicators, FAA could decrease the expression of inflammatory markers (such as myeloperoxidase (MPO)) and attenuate the oxidative stress levels. ELISA results revealed that the expressions of proinflammatory cytokines (IL-1β, IL-6, and TNF-α) were downregulated by FAA. Furthermore, the expression levels of the inflammation-induced activation of p38, JNK, and ERK were decreased by FAA. Hence, it was concluded that FAA could alleviate the UC symptoms in mice and the inflammatory response of macrophages via the MAPK signal pathway. Overall, FAA might have the potential to treat UC when used as a dietary supplement.
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http://dx.doi.org/10.1039/c9fo00664hDOI Listing
September 2019

Pharmacokinetic and tissue distribution studies of cassane diterpenoids, in rats through an ultra-high-performance liquid chromatography-Q exactive hybrid quadrupole-Orbitrap high-resolution accurate mass spectrometry.

Biomed Chromatogr 2019 Oct 11;33(10):e4610. Epub 2019 Jul 11.

Department of Pharmacology, Mudanjiang Medical College, Mudanjiang, People's Republic of China.

Cassane diterpenoids (CA) are considered as the main active constituents of medicinal plants belonging to the Caesalpinia genus. Three cassane derivatives, bonducellpin G (BG), 7-O-acetyl-bonducellpin C (7-O-AC) and caesalmin E (CE), isolated from Caesalpinia minax Hance seeds, showed strong anti-inflammatory activity. In this paper, pharmacokinetics (BG, 7-O-AC, CE) and tissue distribution (7-O-AC, CE) properties were studied for the first time using a reliable, sensitive and rapid UHPLC-Q-Orbitrap HR-MS to develop new anti-inflammatory agents. A novel quantitative method with full scan in positive ion mode was used to determine the contents of compounds. They were separated using acetonitrile-water (0.1% formic acid) as gradient mobile phase. The calibration curve displayed good linearity and the lower limit of quantitation was 0.005-0.02 μg/mL for all analytes. Meanwhile, the absorption, distribution, metabolism, excretion (ADME) property was predicted using PreADMET web. The pharmacokinetic parameters indicated that they were absorbed quickly, eliminated rapidly together with high blood concentration. The results of tissue distribution demonstrated that CE was distributed rapidly and widely among tissues, and stomach was the main tissue site of CE and 7-O-AC, followed by small intestine/liver. This study indicates that the structures and dosages of active CA should be modified to help improve the absorption rate and residence time, and the findings are helpful for the pharmaceutical design of CA derivatives.
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http://dx.doi.org/10.1002/bmc.4610DOI Listing
October 2019

Measurement of ultra-trace level of intact oxytocin in plasma using SALLE combined with nano-LC-MS.

J Pharm Biomed Anal 2019 Sep 13;173:62-67. Epub 2019 Apr 13.

CAS Key Laboratory of Separation Sciences for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, China. Electronic address:

Measurement of peptides such as oxytocin in plasma is a critical challenge in clinical research because of their extreme low concentrations as well as the tremendous interferencing substances co-presented in plasma. In this study, we developed an efficient salt-out assisted liquid-liquid extraction (SALLE) to treat plasma, and then analyzed the samples using nano-LC-MS to quantify intact oxytocin (OT) in human and rat plasmas. Our results showed that the use of SALLE (Isopropanol/KHPO (4 M)) allows efficient removal of various disrupters, including proteins, inorganic salts, and lipids, which helps avoid the risk of blocked capillary columns and matrix effects. Moreover, instant SALLE can reduce the possible binding between OT and proteins, thus allowing high repeatability of OT extraction from the original plasma. This combination of SALLE and nano-LC-MS method provided in the end a 1 pg/m L of detection limit. Comparative analysis showed that the concentration of OT in the plasma taken from 12 volunteers ranged from 3 to 214 pg/m L, about one order less than those in the plasma of rats. Compared to the previously reported LC-MS and immunoassay methods, the combination of SALLE and nano-LC-MS permits reliable measurement of intact OT even in human plasma. Our approach may be an alternative method for quantitative determination of other ultra-trace peptides in plasma, which would help the investigators understand the role of peptides in behaviours and diseases.
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http://dx.doi.org/10.1016/j.jpba.2019.04.023DOI Listing
September 2019

Computational investigations of gram-negative bacteria phosphopantetheine adenylyltransferase inhibitors using 3D-QSAR, molecular docking and molecular dynamic simulations.

J Biomol Struct Dyn 2020 Mar 30;38(5):1435-1447. Epub 2019 Apr 30.

Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, People's Republic of China.

Phosphopantetheine adenylyltransferase (PPAT) has been recognized as a promising target to develop novel antimicrobial agents, which is a hexameric enzyme that catalyzes the penultimate step in coenzyme A biosynthesis. In this work, molecular modeling study was performed with a series of PPAT inhibitors using molecular docking, three-dimensional qualitative structure-activity relationship (3D-QSAR) and molecular dynamic (MD) simulations to reveal the structural determinants for their bioactivities. Molecular docking study was applied to understand the binding mode of PPAT with its inhibitors. Subsequently, 3D-QSAR model was constructed to find the features required for different substituents on the scaffolds. For the best comparative molecular field analysis (CoMFA) model, the and values of which were calculated as 0.702 and 0.989, while they were calculated as 0.767 and 0.983 for the best comparative molecular similarity index analysis model. The statistical data verified the significance and accuracy of our 3D-QSAR models. Furthermore, MD simulations were carried out to evaluate the stability of the receptor-ligand contacts in physiological conditions, and the results were consistent with molecular docking studies and 3D-QSAR contour map analysis. Binding free energy was calculated with molecular mechanics generalized born surface area approach, the result of which coincided well with bioactivities and demonstrated that van der Waals accounted for the largest portion. Overall, our study provided a valuable insight for further research work on the recognition of potent PPAT inhibitors.Communicated by Ramaswamy H. Sarma.
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http://dx.doi.org/10.1080/07391102.2019.1608305DOI Listing
March 2020

Three-Dimensional Structure of PANI/CdS NRs-SiO₂ Hydrogel for Photocatalytic Hydrogen Evolution with High Activity and Stability.

Nanomaterials (Basel) 2019 Mar 13;9(3). Epub 2019 Mar 13.

College of Chemical Engineering, Hebei Key Laboratory for Environment Photocatalytic and Electrocatalytic Materials, North China University of Science and Technology, Tangshan 063210, Hebei, China.

Three-dimensional PANI/CdSNRs-SiO₂ hydrogel (CdS NRs-PANI-SiO₂) was synthesized by loading polyaniline (PANI) onto the semiconductor CdS nanorods (NRs) surface and loading the binary complex on SiO₂ gel. The structure, optical properties, and electrochemical properties of the composite were studied in detail. The hydrogen production amount of CdS NRs-PANI (3%)-SiO₂ (20%) increased in comparison with CdS NRs and reached 43.25 mmol/g in 3 h under visible light. The three-dimensional structure of SiO₂ hydrogel increased the specific surface area of the catalyst, which was conducive to exposing more active sites of the catalyst. In addition, the conductive polymer PANI coated on CdS NRs played the role of conductive charge and effectively inhibited the photo-corrosion of CdS NRs. In addition, the recovery experiment showed that the recovery rate of the composite catalyst reached 90% and hydrogen production efficiency remained unchanged after five cycles, indicating that the composite catalyst had excellent stability.
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http://dx.doi.org/10.3390/nano9030427DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6474035PMC
March 2019

Naturally occurring cassane diterpenoids (CAs) of Caesalpinia: A systematic review of its biosynthesis, chemistry and pharmacology.

Fitoterapia 2019 Apr 27;134:226-249. Epub 2019 Feb 27.

Key Laboratory of Structure-Based Drug Design, Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China. Electronic address:

Natural products, especially diterpenoids, are enriched with numerous compounds with a broad spectrum of therapeutic indications, suggesting that functional moieties serve as a core pharmacophore. Cassane diterpenoids (CAs), as the main and characteristic constituents of medical plants in the Caesalpinia genus, have been widely studied due to their bioactivities, and >450 compounds have been reported since the 1960s, including 283 compounds that have been reported in the past decade. There are five main types of structures for these compounds: tricyclic cassane diterpenoids with a fused furan ring (I) or butanolide lactone (II), tricyclic cassane diterpenoids (III), norcassane diterpenoids (IV), and other types (V). CAs derivatives have a wide range of biological properties, including anti-inflammatory, antimalarial, antitumour, antiviral, antimicrobial, antinociceptive, and antioxidant effects. This review highlights the role of the biosynthetic pathway, including those with abnormal skeletons, as well as advances in structure, pharmacological activities and primarily mechanisms of CAs obtained from the Caesalpinia genus. The findings herein provide new insights into the development of this kind of natural diterpenoids.
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http://dx.doi.org/10.1016/j.fitote.2019.02.023DOI Listing
April 2019

Natural barrigenol-like triterpenoids: A comprehensive review of their contributions to medicinal chemistry.

Phytochemistry 2019 May 26;161:41-74. Epub 2019 Feb 26.

Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China. Electronic address:

Barrigenol-like triterpenoids (BATs), which contain an unusual oleanane substituted by many hydroxyl groups as the skeleton, are subdivided into five subtypes: barrigenol A, barrigenol A, barrigenol R, barringtogenol C, and 16-deoxybarringtogenol C. The variations in acyl derivatives, hydroxyl groups, and carbohydrate chains in their structures have enhanced the diversity of BATs. Moreover, the stable polyhydroxy-replaced pentacyclic skeleton provides an ideal platform for structural modifications. To date, more than 500 BAT derivatives have been isolated from plants. Synchronously, BATs possess anti-tumour, anti-Alzheimer's disease, anti-inflammatory, anti-microbial, anti-obesity and anti-allergic activities by regulating numerous cellular molecules. Some BAT derivatives, such as escin obtained from Aesculus hippocastanum L. and xanthoceraside isolated from Xanthoceras sorbifolia Bunge, have been used to treat encephaloedema or inflammatory diseases. This review aims to provide comprehensive information about the chemistry, sources, bioavailability, and anti-tumour effects of BATs, with a particular emphasis on the molecular mechanisms of action. The pharmacokinetics and clinical progress are also concerned. More than 300 structures identified over past 25 years are summarized here (249 compounds) and in the supplementary information (114 compounds). Accordingly, the pharmaceutical activity of barrigenol triterpenoids suggests that some compounds should be developed as promising anti-tumour or anti- Alzheimer's disease agents in future.
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http://dx.doi.org/10.1016/j.phytochem.2019.01.017DOI Listing
May 2019

In Silico Exploration of the Molecular Mechanism of Cassane Diterpenoids on Anti-inflammatory and Immunomodulatory Activity.

J Chem Inf Model 2019 05 14;59(5):2309-2323. Epub 2019 Mar 14.

Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education , Shenyang Pharmaceutical University , Shenyang 110016 , People's Republic of China.

Cassane diterpenoids (CAs), recognized as main constituents of many medical plants of the genus Caesalpinia, exhibit diverse bioactivities, including anti-inflammatory and immunomodulatory activity, and also showed a therapeutic effect on rheumatoid arthritis (RA) according to previous work, including ours. In this study, 102 CA compounds were selected to explore the possible molecular mechanism of this class of natural products on anti-inflammatory and immunomodulatory activity using RA as a disease model through a series of in silico methods: chemical-similarity-based target prediction, molecular docking, and molecular dynamics (MD) simulation. As a consequence, four signaling pathways (TCR signaling pathway, TLR signaling pathway, VEGF signaling pathway, and osteoclast differentiation pathway) by which CAs exert their effect on inflammation and immunomodulation were identified. Furthermore, the binding modes of CAs complexing with several crucial targets, which were picked out by credible docking results and took part in these signaling pathways, were explored by MD simulations. This is the first time that the molecular mechanism of the anti-RA activity of natural CAs has been investigated with in silico methods, and these findings might explain the activity of CAs on anti-inflammation and immunomodulation, which could supply a valuable reference for drug design research on CAs.
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http://dx.doi.org/10.1021/acs.jcim.8b00862DOI Listing
May 2019

A new sesquiterpenoid glycoside from .

Nat Prod Res 2020 Apr 13;34(7):943-949. Epub 2019 Feb 13.

School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, People's Republic of China.

, known for the abundant bioactive components, is a precious traditional Chinese medicine. In this study, a novel guaiane sesquiterpenoid glycoside named (1, 5, 6, 7, 8, 11)-11, 13-dihydrodehydrocostuslactone-8--6'-2''()-butenoyl--D-glucopyranoside (), together with seven known compounds (-) were isolated from the dried aerial part of . Their structures were elucidated by spectroscopic and physico-chemical analyses. The antioxidant and anti-inflammatory activities of compound were investigated. And compound showed weak radical scavenging activity and low inhibitory activity on nitric oxide (NO) production.
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http://dx.doi.org/10.1080/14786419.2018.1543683DOI Listing
April 2020

Slower development of PSI activity limits photosynthesis during Euonymus japonicus leaf development.

Plant Physiol Biochem 2019 Mar 4;136:13-21. Epub 2019 Jan 4.

State Key Laboratory of Crop Biology, Shandong Agricultural University, Tai'an, Shandong, 271018, China; College of Life Sciences, Shandong Agricultural University, Tai'an, Shandong, 271018, China. Electronic address:

This study primarily explored the limiting factor for photosynthesis during the development of Euonymus japonicus leaves. The analysis of the chlorophyll fluorescence transient, pulse-modulated fluorescence, 820-nm reflection, and expression of core proteins for photosystems demonstrated that photosystem II (PSII) activity developed more rapidly than did photosystem I (PSI) activity. The slower development of the PSI activity restricted linear and cyclic electron transport and thus inhibited the production of ATP and NADPH, which inhibits the activation of Rubisco, resulting in low activity of carboxylation efficiency. The application of exogenous NADPH (50 μM) and ATP (100 μM) to leaves remarkably increased the P and CE in the youngest leaf but not in the fully expanded leaf, which indicated that an inadequate supply of the assimilatory power significantly inhibited CE and P. We concluded that the slower development of the PSI activity was one of the most important limiting factors for photosynthesis during the development of E. japonicus leaves.
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http://dx.doi.org/10.1016/j.plaphy.2019.01.004DOI Listing
March 2019

New sesquiterpenoid glycoside from the rhizomes of .

Nat Prod Res 2020 Apr 8;34(8):1138-1145. Epub 2019 Jan 8.

School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, People's Republic of China.

Six sesquiterpenoids and four lignans (-) were isolated from the -BuOH extract of the rhizomes of . Among them, the new sesquiterpenoid glycoside named (4 , 5, 7)-hinesolone-11---ᴅ-glucopyranoside (), along with three known compounds (-) were first obtained from this genus. All the isolates were elucidated by spectroscopic analyses and chemical methods, and the absolute configurations were assigned by electronic circular dichroism spectroscopy technique. In addition, the cytotoxic bioassay of compound was evaluated and results showed it had no significant antitumor activity against human cancer cell lines MCF-7, HepG-2 and Hela.
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http://dx.doi.org/10.1080/14786419.2018.1553170DOI Listing
April 2020

Significant inhibition of photosynthesis and respiration in leaves of Cucumis sativus L. by oxybenzone, an active ingredient in sunscreen.

Chemosphere 2019 Mar 3;219:456-462. Epub 2018 Dec 3.

State Key Laboratory of Crop Biology, China; College of Life Sciences, Shandong Agricultural University, China. Electronic address:

Oxybenzone (OBZ), an active ingredient in most sunscreens, was recently shown to be toxic to humans, corals and other animals. This study is the first to demonstrate that OBZ can significantly inhibit photosynthesis and respiration in the leaves of a higher plant, cucumber. An OBZ suspension content as low as 0.228 mg/L obviously inhibited the photosynthesis and respiration of cucumber. OBZ instantly inhibits the electron transport of chloroplasts and mitochondria in cucumber leaves. Probit analysis demonstrated that the effective content for 20% inhibition of photosynthetic electron transport was 11.7 mg/L (95% confidence level). The inhibition of photosynthesis and respiration restricts carbohydrate synthesis and ATP regeneration, respectively, limiting the energy available for metabolic processes including the synthesis of vital organic macromolecules such as proteins and nucleic acids in plant cells. The inhibition of photosynthesis also enhanced the excess excitation energy in chloroplasts, resulting in overproduction of reactive oxygen species (ROS), and the inhibition of respiration aggravated this process. ROS accumulation adversely affects the structure and function of proteins, DNA and membrane lipids in plant cells, interfering with normal metabolism and even leading to plant death. Therefore, reducing the use of OBZ is important for protecting global ecological security.
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http://dx.doi.org/10.1016/j.chemosphere.2018.12.019DOI Listing
March 2019

Rapid discrimination between red and white ginseng based on unique mass-spectrometric features.

J Pharm Biomed Anal 2019 Feb 3;164:202-210. Epub 2018 Oct 3.

CAS Key Laboratory of Separation Sciences for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, PR China. Electronic address:

Red ginseng (RG) and white ginseng (WG), two processed products of Panax ginseng C. A. Meyer, are in high demand due to their unique features. In this study, some of these unique features were identified and confirmed as biomarkers of RG by using ultra-high-performance liquid chromatography-mass spectrometry, data mining, support vector machine, and artificial neural network. Principal component analysis showed clear separation between the RG and WG extracts, indicating the presence of potential discriminators. In addition, 20 features that are dominant in RG were found by data mining. Samples of Panax quinquefolium (PQ) and Panax notoginseng (PN), close relatives of Panax ginseng C.A.Meyer, were investigated and it was found that 17 features which were absent in PQ and PN samples, were present in RG and WG. Five of these markers were identified as nitrogen-containing compounds that have not been previously reported. Finally, we found that RG can be identified among different ginseng medicinal herbs including RG, WG, PQ, and PN samples, by loading four feature markers corresponding to nitrogen-containing compounds into a discriminating model, based on a support vector machine or an artificial neural network. Thus, this study provides an efficient tool to identify RG during pharmacological research.
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http://dx.doi.org/10.1016/j.jpba.2018.10.007DOI Listing
February 2019

Mechanism of long-term toxicity of CuO NPs to microalgae.

Nanotoxicology 2018 10 5;12(8):923-939. Epub 2018 Sep 5.

a State Key Laboratory of Crop Biology, Shandong Key Laboratory of Crop Biology, College of Life Sciences , Shandong Agricultural University , Tai'an , Shandong , People's Republic of China.

Little is known regarding the detailed mechanism of CuO NPs' toxicity to microalgal primary metabolism pathway. Photosynthesis and respiration are the most important primary metabolism and the main sources of production of reactive oxygen species (ROS), but the effect of CuO NPs on both of them has not been systematically studied to date. Our research demonstrated that long-term treatment with CuO NPs significantly inhibited activities of photosynthesis and respiration in microalgae, and the photosynthesis was more sensitive to the toxicity of CuO NPs than respiration. CuO NPs could be absorbed by microalgae and be converted into CuO NPs concentrated in chloroplast. The internalized Cu, regardless of whether the exposure was Cu or CuO NPs had the same capacity to damage chloroplast structure. The result also shows that the oxygen-evolving complex (OEC) in the photosynthetic electron transport chain was the most sensitive site to CuO NPs and Cu-treated microalgae had the same damage site as that of CuO NPs, which may be related to the Mn cluster that is dissociated by Cu ions released from CuO NPs. The damage of OEC inhibited photosynthetic electron transport to increase excess excited energy, which caused the accumulation of ROS in chloroplast. The accumulation of ROS damaged the structure of cell membrane and aggravated the PSII photoinhibition, further decreasing the efficiency of light energy utilization. In conclusion, the Cu ionic toxicity of photosynthetic apparatus by CuO NPs resulted in the carbon starvation and the accumulation of ROS to inhibit the growth of microalgae.
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http://dx.doi.org/10.1080/17435390.2018.1498928DOI Listing
October 2018

Therapeutic effects of Caesalpinia minax Hance on complete Freund's adjuvant (CFA)-induced arthritis and the anti-inflammatory activity of cassane diterpenes as main active components.

J Ethnopharmacol 2018 Nov 13;226:90-96. Epub 2018 Aug 13.

Department of Pharmacology, Mudanjiang Medical College, Mudanjiang 157001, People's Republic of China. Electronic address:

Ethnopharmacological Relevance: Seeds of Caesalpinia minax Hance called 'Ku-Shi-Lian' (KSL) in China have been used as Zhuang or Dai folk medicines for treatment of common cold, fever, rheumatoid arthritis and dysentery for hundred years.

Aim Of The Study: This study aimed to investigate therapeutic efficacy of KSL extract using complete Freund's adjuvant (CFA) induced arthritis in a rat model and the anti-inflammatory activity of cassane diterpenes as the main active material basis of this herb.

Materials And Methods: Arthritis was induced in male Wistar rats (200-220 g) by immunization with CFA. Dexamethasone (DXMS) and Tripterygium glycosides (TG) were chosen as the positive drugs. Water soluble fraction (CMW, 1000 and 2000 mg/kg) and chloroform soluble fraction (CMC, 400 and 800 mg/kg) of KSL were orally administered from day 1 and continued for 21 days. Change of paw swelling perimeter, arthritics score, body weight growth, were observed, and the production of TNF-α, IL-1β and IL-6 in serum were measured by enzyme-linked immunosorbent assay (ELISA). The histological changes in the ankle joint were analyzed in adjuvant induced arthritis rats. Moreover, the inhibitory effect on mRNA expression of proinflammatory cytokine IL-1β, IL-6 and TNF-α of fourteen cassane diterpenes obtained from CMC extract were valued using the RAW 264.7 macrophages cell stimulated by lipopolysaccharide (LPS) assay.

Results: The chloroform soluble fraction (CMC) showed the significantly suppressed change of paw swelling perimeter, arthritics score and increased body weight loss. The overproduction of TNF-α, IL-1β and IL-6 were remarkably suppressed in the serum. Fourteen cassane derivatives as the main constituents of CMC extract showed the promising activity on the expression mRNA of cytokine IL-1β, IL-6 and TNF-α produced by macrophages cells.

Conclusions: In this study, the chloroform soluble fraction of 'KSL' (seeds of C. minax) was found to exert an anti-RA activity significantly in vivo for the first time, which indicted this fraction might be used as a powerful therapeutic agent for arthritis treatments. Cassane diterpenes, as the main constituents in this fraction, showed the anti-inflammation activity through the regulation of cytokine expression, which might be developed as target-agents for this national herb further developing.
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http://dx.doi.org/10.1016/j.jep.2018.08.011DOI Listing
November 2018
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