1.Isolation and quantification of a 17-epi-dammarane triterpenoid rhuslactone from roots of Rhus chinensis and its preventive effects on coronary heart disease and thrombosis in zebrafish.
Ling-Jie RUAN ; Li-Na HUANG ; Xin-Yi GAO ; Chang-Jie LAI ; Lin-Jing ZHANG ; Yu-Fan WU ; Mei SHA ; Miao YE
China Journal of Chinese Materia Medica 2023;48(6):1558-1567
Based on mass spectrometry(MS)-guided separation strategy, compound 1 was obtained from the roots of Rhus chinensis. By comprehensive analysis of high resolution-electrospray ionization-mass spectrometry(HR-ESI-MS), nuclear magnetic resonance(NMR) data, and quantum chemical calculation of NMR(qcc-NMR) parameters, compound 1 was elucidated as rhuslactone, a 17-epi-dammarane triterpenoid with a rare 17α-side chain. An HPLC-ELSD method for its quantification in R. chinensis was established and adopted for the quantification of rhuslactone in different batches of R. chinensis. Rhuslactone displayed a good linear relationship within the range of 0.021 3-1.07 μmol·mL~(-1 )(r=0.997 6), and the average recovery was 99.34% [relative standard deviation(RSD) 2.9%). Moreover, the results of the evaluation test of the preventive effects of rhusalctone on coronary heart disease(CHD) and thrombosis showed that rhuslactone(0.11 nmol·mL~(-1)) significantly alleviated heart enlargement and venous congestion and increased cardiac output(CO), blood flow velocity(BFV), and heart rate, thereby reducing thrombus formation in zebrafish with CHD. The effects of rhuslactone on CO and BFV were superior to that of digoxin(1.02 nmol·mL~(-1)), and its effect on improving heart rate was comparable to that of digoxin. This study provides experimental references for the isolation, identification, quality control, and application of rhuslactone from R. chinensis against CHD. It is worth mentioning that this study has discussed some omissions in the determination of the stereochemistry of C-17 in dammarane triterpenoids in the present coursebook Chemistry of Chinese Medicine and some research papers, that is, the compound may be 17-epi-dammarane triterpenoid. This paper has also proposed steps for the establishment of C-17 stereochemistry.
Animals
;
Zebrafish
;
Rhus/chemistry*
;
Triterpenes/analysis*
;
Coronary Disease
;
Thrombosis
2.Purification and component identification of total proanthocyanidins in Choerospondias axillaris pericarp.
Tong JIANG ; Tong ZHU ; Fei TENG ; Dan YANG ; Jing-Jing ZHU ; Zhi-Min WANG ; Zhi-Gao LIU ; Ji-Yan LIU
China Journal of Chinese Materia Medica 2021;46(12):2923-2930
The present study determined the quantitative markers of total proanthocyanidins in the purification of the industrial waste Choerospondias axillaris pericarp based on the comparison results of high-performance liquid chromatography(HPLC) and mass spectrometry(MS) and optimized the purification process with two stable procyanidins as markers. The adsorption and desorption of five different macroporous adsorption resins, the static adsorption kinetics curve of NKA-Ⅱ resin, the maximum sample load, and the gradient elution were investigated. The UPLC-Q-TOF-MS/MS was employed for qualitative analysis of the newly-prepared total proanthocyanidins of C. axillaris pericarp. As revealed by the results, NKA-Ⅱ resin displayed strong adsorption and desorption toward total proanthocyanidins. The sample solution(50 mg·mL~(-1)) was prepared from 70% ethanol crude extract of C. axillaris pericarp dissolved in water and 7-fold BV of the sample solution was loaded, followed by static adsorption for 12 h. After 8-fold BV of distilled water and 6-fold BV of 10% ethanol were employed to remove impurities, the solution was eluted with 8-fold BV of 50% ethanol, concentrated, and dried under reduced pressure, and purified total proanthocyanidin powder was therefore obtained. Measured by vanillin-hydrochloric acid method, the purity and transfer rate of total proanthocyanidins were 47.67% and 59.92%, respectively, indicating the feasibi-lity of the optimized process. UPLC-Q-TOF-MS/MS qualitative analysis identified 16 procyanidins in C. axillaris total proanthocyanidins. The optimized purification process is simple in operation and accurate in component identification, and it can be applied to the process investigation of a class of components that are difficult to be separated and purified. It can also provide technical support and research ideas for the comprehensive utilization of industrial waste.
Adsorption
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Anacardiaceae
;
Chromatography, High Pressure Liquid
;
Plant Extracts
;
Proanthocyanidins/analysis*
;
Resins, Synthetic
;
Tandem Mass Spectrometry
3.Effect of total phenolic part of Rhus chinensis against myocardial ischemia in mice.
Fu-Xing GE ; Xiao-Jing MA ; Jun-Jun LI ; Xiao-Chun ZHOU ; Mei-Wen HUANG ; Miao YE ; Wei XU ; Peng-Fei TU ; Xing-Yun CHAI
China Journal of Chinese Materia Medica 2021;46(9):2254-2259
Rhus chinensis is an important resource plant. The aqueous extract of R. chinensis roots or stems was to produce Shuguantong Syrup, which is mainly used for the treatment of coronary heart disease and angina pectoris with definite curative effect. On this basis, the crude phenolic part of R. chinensis prepared by macroporous resin was evaluated for the cardio protective effect against myocardial ischemia in mice. The results showed that the phenolic part group with oral administration at the dosages of 190.8-381.6 mg·kg~(-1), compared with the model group, reduced the values of left ventricular end systolic diameter(LVEDs) and the left ventricular end diastolic diameter(LVEDd), and increased the cardiac ejection fraction(EF) and left ventricular fractional shortening(FS) rate, which could effectively improve cardiac function and exert its anti-myocardial ischemia effect, and reduce the rising levels of creatine kinase isoenzyme(CK-MB) and lactate dehydrogenase(LDH) in serum. HE staining showed that the phenolic part group reduced the infiltration of myocardial inflammatory cells and alleviated the degree of myocardial fibrosis and collagen deposition. TUNEL staining showed that the blue-green fluorescence of the phenolic part group decreased successively, and the degree of myocardial cell apoptosis was reduced. Immunohistochemical staining suggested that it could reduce the number of positive cells for p53 protein expression and significantly improve myocardial cell damage. All above data suggested that the phenolic part group had an anti-mycardial ischemis effect. Related mechanism studies revealed that the crude phenolic part could regulate the expressions of the p53 gene(p53), Bcl-2-associated X protein(Bax), B lymphoma-2 gene(Bcl-2), and caspase-3 protein(caspase-3) in myocardial tissue, suggesting that it could reduce cardiac remodeling and myocardial ischemic damage, and improve cardiac function by inhibiting myocardial apoptosis.This research laid a foundation for the elucidation of the pharmacological ingredients R. chinensis.
Animals
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Apoptosis
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Mice
;
Myocardial Ischemia/drug therapy*
;
Myocardium
;
Myocytes, Cardiac
;
Plant Extracts/pharmacology*
;
Rhus
;
bcl-2-Associated X Protein
4.Analysis of the chloroplast genome characteristics of Rhus chinensis by de novo sequencing.
Ruihua ZUO ; Ping JIANG ; Chuanbo SUN ; Cunwu CHEN ; Xinjian LOU
Chinese Journal of Biotechnology 2020;36(4):772-781
Rhus chinensis is an important economic species, which could provide raw materials for pharmaceutical and industrial dyes. Rhus chinensis is famous for its resistance to drought, cold, and salt. It grows in temperate, warm temperate, and subtropical regions. We report here Rhus chinensis chloroplast genomes by de novo sequencing. The results show that the length of Rhus chinensis was 159 082 bp, exhibiting a typical four-part structure with two single-copy regions (long single copy [LSC] and short single copy [SSC] sections) separated by a pair of inverted repeats (IRs). The length of LSC and SSC was 85 394 bp and 18 663 bp, respectively. The genomes contained 126 genes, including 88 protein encoding genes, 8 rRNA and 30 tRNA genes. In the chloroplast genome, 61.97% of the sequence were gene coding region. In the sequence of gene encoding region, the vast majority of sequences were protein encoding region, accounting for 86.65%, followed by rRNA (10 620 bp, 10.77%) and tRNA (2 540 bp, 2.58%). In Rhus chinensis chloroplast genome, only 8 genes contain introns, all containing 1 intron except ycf3 gene (2 introns). The Rhus chinensis chloroplast genome contains 755 SSR locies. SSR mainly consists of dinucleotide and mononucleotide, accounting for 60% (453) and 28.74% (217) respectively. The clustering results show that Anacardiaceae were closest to Rhus chinensis, followed by Aceraceae and Sapindaceae. This study provides a molecular basis for the classification of Rhus chinensis.
Genome, Chloroplast
;
genetics
;
Open Reading Frames
;
Phylogeny
;
Rhus
;
classification
;
genetics
;
Sequence Analysis, DNA
5.Study on chemical constituents from Mastic (Pistacia lentiscus).
Wei LIU ; Lin CHEN ; Zhao-Guang WANG ; Hao CUI ; Tao YUAN
China Journal of Chinese Materia Medica 2020;45(13):3169-3174
Phytochemical investigation on the methanolic extract of Mastic by using various chromatographic techniques led to the isolation of 9 compounds. Based on the analysis of spectroscopic data(NMR and MS) and/or comparisons with the data reported in the literature, their structures were elucidated as 3β,8α,13-trihydroxypolypoda-14-methoxy-14-methyl-17,21-diene(1), 4-hydroxymyrtenal(2),3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1, 2-diol(3), 2-oxo-Δ~3-4,5,5-trimethylcyclopentynyl acidic acid(4),(1S,2R,3R,5R)-6,6-dimethyl-4-methylidenebicyclo[3.1.1]-heptane-2,3-diol(5),(4R)-1-methyl-4-(1-hydroxyisopropyl)cyclohexene-6-one(6), 6,6-dimethyl-4-hydroxy[3.1.1]hept-2-ene-2-carboxylic acid(7), 6,6-dimethyl[3.1.1]hept-2-ene-2-carboxylic acid(8), 6,6-dimethyl-4-oxobicyclo[3.1.1]hept-2-ene-2-carboxylic acid(9). Compound 1 is a new compound and 2-9 were isolated from this species for the first time. In vitro cytotoxicity assay results indicated that compounds 1, 6 and 7 showed significant inhibitory effects against human lung cancer cell line A549 with IC_(50) values of 20.4, 25.1 and 22.5 μmoL·L~(-1).
Humans
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Magnetic Resonance Spectroscopy
;
Phytochemicals
;
Pistacia
6.A 5-year retrospective review of children with peanut allergy in the largest paediatric hospital in Singapore
May Ping LEE ; Seyed Ehsan SAFFARI ; Wenyin LOH ; Si Hui GOH ; Anne GOH ; Wen Chin CHIANG ; Kok Wee CHONG
Asia Pacific Allergy 2020;10(1):6-
BACKGROUND: The prevalence of peanut allergy (PA) among children has increased significantly over the past decade. Even though the prevalence of PA in Singapore is considered low, peanut is the top trigger for food-induced anaphylaxis in Singaporean children.OBJECTIVE: To describe the demographic characteristics and clinical features of children with PA.METHODS: This is a 5-year retrospective review of children diagnosed with PA based on clinical history coupled with a positive skin prick test to peanut or positive oral food challenge results.RESULTS: There were 269 patients (53.9% males) with a clinical diagnosis of PA. The median age at first allergic presentation for the PA group was 24 months old, with interquartile range of 13–39 months. The most common form of peanut introduced was roasted peanut. The rate of peanut anaphylaxis was 7.1%. Concomitant tree nut sensitization was found in 32.3% of this cohort, predominantly to cashew nut. Majority of them have a personal history of atopy – 75.8% with eczema, 63.6% with allergic rhinitis, and 19.7% with asthma.CONCLUSION: This is the first large review of peanut-allergic children in Singapore. Prospective population-based studies are needed to establish the true prevalence and risk factors associated with the development of this potentially life-threatening condition.
Anacardium
;
Anaphylaxis
;
Arachis
;
Asia
;
Asthma
;
Child
;
Cohort Studies
;
Diagnosis
;
Eczema
;
Humans
;
Nuts
;
Peanut Hypersensitivity
;
Prevalence
;
Prospective Studies
;
Retrospective Studies
;
Rhinitis, Allergic
;
Risk Factors
;
Singapore
;
Skin
;
Trees
7.Comparative of functional components, antioxidant and α-glucosidase inhibition activities between Choerospondias axillaris fruit peel vinegar and apple vinegar.
Tong JIANG ; Xin-Lin LYU ; Xiang-Wei LI ; Zi-Yang LI ; Dan YANG ; Zi-Long ZHANG ; Jing-Jing ZHU ; Zhi-Min WANG ; Zhi-Gao LIU ; Ji-Yan LIU
China Journal of Chinese Materia Medica 2020;45(5):1180-1187
Based on the idea of plant metabolomics, ultra performance liquid chromatography-quadrupole time-of-flight mass spectrometry(UPLC-Q-TOF-MS/MS) was used to compare the chemical composition between 6 batches of fruit vinegar brewed from Choerospondias axillaris fruit peel and 6 batches of apple vinegar purchased from 3 companies. Antioxidant and α-glucosidase inhibition activities were also tested in vitro. A total of 43 compounds were identified by reference substance, liquid chromatography-mass spectrometry(LC-MS/MS) fragmentation information or literature data. A total of 40 compounds were identified in the C. axillaris fruit peel vinegar. A total of 16 compounds were identified in apple vinegar. There were 13 common ingredients including organic acids and esters such as citric acid, 2-isopropyl malic acid, and triethyl citrate. The results of partial leastsquares-discriminant analysis(PLS-DA) indicated that they had 33 significantly different compounds such as proanthocyanidin oligomer, quercetin-3-O-rhamnoside and heptadecanoic acid. The proanthocyanidins and flavonoid glycosides in C. axillaris peel vinegar were more abundant than apple vinegar, so it had better health function than ordinary fruit vinegar. The results showed that C. axillaris fruit peel vinegar had stronger antioxidant and α-glucosidase inhibition activities in vitro. The vinegar brewed from waste C. axillaris fruit peel had more chemical ingredients than the apple vinegar. C. axillaris fruit peel vinegar had better biological activity and health function, so it had good development prospect. This study provided the scientific evidence for exploiting the C. axillaris fruit peel into high value-added products. It also provided ideas for the comprehensive development and utilization of similar Chinese medicine waste.
Acetic Acid/pharmacology*
;
Anacardiaceae/chemistry*
;
Antioxidants
;
Chromatography, High Pressure Liquid
;
Fruit/chemistry*
;
Glycoside Hydrolase Inhibitors/pharmacology*
;
Malus/chemistry*
;
Plant Extracts
;
Tandem Mass Spectrometry
;
alpha-Glucosidases
8.The current status and issue of food allergen labeling in Korea
You Hoon JEON ; Hyun Hee KIM ; Yong Mean PARK ; Gwang Cheon JANG ; Hye Young KIM ; Hye Yung YUM ; Jihyun KIM ; Kangmo AHN ; Taek Ki MIN ; Bok Yang PYUN ; Sooyoung LEE ; Kyung Won KIM ; Yoon Hee KIM ; Jeongmin LEE ; So Yeon LEE ; Woo Kyung KIM ; Tae Won SONG ; Jeong Hee KIM ; Yong Ju LEE ;
Allergy, Asthma & Respiratory Disease 2019;7(2):67-72
With increasing need to prevent serious food allergy reactions, Korean food allergen labeling regulation has been revised repeatedly. This paper aims to summarize current statuses of food allergen labeling in Korea and foreign countries and to analyze the issue of food allergen labeling regulation. Korean food labeling regulation currently requires 19 items and 22 foods to be reported on labels (eggs, milk, buckwheat, peanut, soybean, wheat, mackerel, crab, shrimp, pork, peach, tomato, sulfite, walnut, chicken, beef, squid, shellfish, and pine nut). However, some common food triggers (for example, almond, cashew nut, and kiwi fruit) are not included in the current labeling regulation. Another issue is that the Korean labeling regulation has not yet been fully implemented for nonprepacked foods; thus, consumers still have difficulty in correctly identifying allergenic ingredients in food. It should be assessed whether warning statements for cross-contamination are reasonable. To prevent the occurrence of serious reactions from accidental ingestion, efforts must be made to solve recently raised issues including the items required to be listed on food labels, the system of standards for labeling and display methods.
Anacardium
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Arachis
;
Chickens
;
Decapodiformes
;
Eating
;
Fagopyrum
;
Food Hypersensitivity
;
Food Labeling
;
Hypersensitivity
;
Juglans
;
Korea
;
Lycopersicon esculentum
;
Milk
;
Nuts
;
Perciformes
;
Prunus dulcis
;
Prunus persica
;
Red Meat
;
Shellfish
;
Soybeans
;
Triticum
9.Cross-reactivity of pink peppercorn in cashew and pistachio allergic individuals
Joan Jue Ying TOO ; Lynette Pei Chi SHEK ; Mohana RAJAKULENDRAN
Asia Pacific Allergy 2019;9(3):e25-
BACKGROUND: The Pink peppercorn belongs to the same Anacardiaceae family as cashew and pistachio. However, the cross-reactivity of pink peppercorn with cashew and pistachio has yet to be studied. To date, there has been a single case report of anaphylaxis to pink peppercorn in a cashew and pistachio allergic individual. OBJECTIVE: We aim to demonstrate cross-sensitization to pink peppercorn in cashew and/or pistachio allergic children. METHODS: A small descriptive cohort study looking at cross-sensitization of pink peppercorn in cashew and/or pistachio allergic children was conducted. Children with a history of reaction to pistachio and/or cashew nut underwent skin prick tests to the pink peppercorn species Schinus terebinthifolius to determine cross-sensitization. RESULTS: Out of the 21 cashew and/or pistachio allergic subjects, 16 (76.2%) demonstrated cross-sensitization to pink peppercorn. None of the subjects had any knowledge of previous exposure or allergic reactions to pink peppercorn. DISCUSSION: This study demonstrates potential cross-reactivity between pink peppercorn and cashew and pistachio. While an oral food challenge to pink peppercorn would have been important in demonstrating clinical cross-reactivity, this was not performed due to ethical constraints. We hope to increase the awareness of pink peppercorn as a potential and hidden source of allergen and encourage further studies to demonstrate the clinical cross-reactivity and to better delineate the major allergen involved.
Anacardiaceae
;
Anacardium
;
Anaphylaxis
;
Child
;
Cohort Studies
;
Cross Reactions
;
Food Hypersensitivity
;
Hope
;
Humans
;
Hypersensitivity
;
Nuts
;
Pistacia
;
Skin
10.Intestinal absorption of phenolic acids in Rhus chinensis extracts by in situ single-pass perfusion model in rats.
Xiao-Ying WANG ; Hong LIAN ; Xiao-Yi LU ; Zhang-Wen XU ; Wen XU ; Miao YE ; Wei XU ; Hai-Yin ZHENG
China Journal of Chinese Materia Medica 2019;44(11):2373-2378
The intestinal absorption properties of four main effective components(gallic acid, ocinolglucoside, ethyl gallate and penta-O-galloyl-β-D-glucose) in Rhus chinensis extracts were investigated by in situ single-pass intestinal perfusion model in rats. The liquid accumulation of perfusion was corrected by gravimetry. The HPLC method was established to determine the concentration of the four effective components in the intestinal perfusion. It showed significant differences(P<0.05) in absorption rate constant(K_a) and effective permeability(P_(eff)) among the three concentrations of components, and the absorption of the four effective components in different intestinal segments was saturated at high concentrations. At the same concentration, there were significant differences in K_a and P_(eff) of the four components in each intestinal segment(P<0.05). The order of K_a and P_(eff) of the four components in the intestine was penta-O-galloyl-β-D-glucose>ethyl gallate>gallic acid>ocinolglucoside, with significant differences between them(P<0.05). In conclusion, gallic acid, orpheolglucoside, ethyl gallate and pentacyl-glucose could be absorbed in the whole intestine. Their absorption rate and permeation ability were related to the intestinal section and the perfusate concentration. These results indicated potential active transport or facilitated diffusion in the intestinal transport process of the four effective components.
Animals
;
Chromatography, High Pressure Liquid
;
Hydroxybenzoates
;
metabolism
;
Intestinal Absorption
;
Perfusion
;
Phytochemicals
;
metabolism
;
Rats
;
Rhus
;
chemistry

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