1.Effect of origin, tree age, and harvesting time on content of flavonoids and terpene lactones in Ginkgo Folium.
Fu-Juan SHI ; Chao-Jie YANG ; Xiu-Fen CHEN ; Mi-Ji-Ti MAIHELIYA ; Miao-Miao HUANG ; Xue-Jiao WEI ; Kun WANG ; Chun-Sheng LIU ; Yao-Jun YANG
China Journal of Chinese Materia Medica 2022;47(15):4055-4065
The content of total flavonol glycosides in Ginkgo Folium in the planting bases was determined by high performance liquid chromatography(HPLC).The samples were extracted by reflux with methanol-25% hydrochloric acid.The HPLC conditions were as follows: Agilent ZORBAX SB-C_(18) column(4.6 mm×250 mm, 5 μm), isocratic elution with mobile phase of 0.4% phosphoric acid solution-methanol(45∶55), flow rate of 1 mL·min~(-1), column temperature of 30 ℃, detection wavelength of 360 nm, and injection vo-lume of 10 μL.A method for the determination of terpene lactones in Ginkgo Folium was established based on ultra-high performance liquid chromatograph-triple-quadrupole/linear ion-trap tandem mass spectrometry(UPLC-QTRAP-MS/MS).The UPLC conditions were as below: gradient elution with acetonitrile-0.1% formic acid, flow rate of 0.2 mL·min~(-1), column temperature of 30 ℃, sample chamber temperature of 10 ℃, and injection volume of 10 μL.The ESI~+and multiple reaction monitoring(MRM) were adopted for the MS.The above methods were used to determine the content of total flavonol glycosides and terpene lactones in 99 batches of Ginkgo Folium from 6 planting bases, and the results were statistically analyzed.The content of flavonoids and terpene lactones in Ginkgo Folium from different origins, from trees of different ages, harvested at different time, from trees of different genders, and processed with different methods was compared.The results showed that the content of total flavonol glucosides in 99 Ginkgo Folium samples ranged from 0.38% to 2.08%, and the total content of the four terpene lactones was in the range of 0.03%-0.87%.The method established in this study is simple and reliable, which can be used for the quantitative analysis of Ginkgo Folium.The research results lay a basis for the quality control of Ginkgo Folium.
Chromatography, High Pressure Liquid/methods*
;
Flavonoids/analysis*
;
Flavonols
;
Ginkgo biloba
;
Glycosides/analysis*
;
Lactones/analysis*
;
Methanol
;
Plant Leaves/chemistry*
;
Tandem Mass Spectrometry/methods*
;
Terpenes/analysis*
;
Trees
2.Terpenoids from fruits of Amomum villosum and their hypoglycemic activity.
Min DING ; Sheng-Li WU ; Xiao-Feng HE ; Xue-Mei ZHANG ; Chang-An GENG
China Journal of Chinese Materia Medica 2022;47(21):5849-5854
Eight terpenoids were isolated from the fruits of Amomum villosum by silica gel, Sephadex LH-20, Rp-C_(18), MCI GEL CHP20 P column chromatography, preparative TLC, and HPLC. Their structures were identified by HR-ESI-MS, ~1H and ~(13)C-NMR, IR, UV, [α]_D, and ECD spectroscopic data as kravanhin A 3-O-β-D-glucopyranoside(1), kravanhin B(2), 6-eudesmene-1β,4β-diol(3), oplodiol(4), vicodiol(5),(1R,2S,4R,7S)-vicodiol 9-O-β-D-glucopyranoside(6),(1R,2S,4S,5R)-angelicoidenol 2-O-β-D-glucopyranoside(7), and(1S,2S,4R,6S)-bornane-2,6-diol 2-O-β-D-glucopyranoside(8). Compound 1 was a new compound, and compounds 2-5 were isolated from A. villosum for the first time. Their hypoglycemic activity was tested based on STC-1 cell model and two enzymatic models(GPa and PTP1 B). The results showed that compounds 1, 7, and 8 could stimulate GLP-1 with the secretion rates of 692.8%, 398.6%, and 483.3% at 25.0 μmol·L~(-1), and compound 6 showed inhibitory activity against GPa with an IC_(50) value of 78.6 μmol·L~(-1).
Fruit/chemistry*
;
Terpenes/analysis*
;
Amomum
;
Hypoglycemic Agents/analysis*
;
Chromatography, High Pressure Liquid
3.Accumulation and biosynthetic of curcuminoids and terpenoids in turmeric rhizome in different development periods.
Jing-Ru SUN ; Jun-Ling BU ; Guang-Hong CUI ; Ying MA ; Huan ZHAO ; Ya-Ping MAO ; Wen ZENG ; Juan GUO ; Lu-Qi HUANG
China Journal of Chinese Materia Medica 2019;44(5):927-934
The dynamic accumulation rule of active substances in medicinal plants is of great value not only for medicinal material production and application,but also for the genetic mechanism study on the formation of medicinal ingredients,especially vital to guide medicinal material collection as well as experiment material selection and candidate gene screening in the analysis of biosynthesis pathway. This study investigated the accumulation of curcumins and terpenoids,and the biosynthesis of these metabolites,which are the active metabolites in Curcuma longa,a commonly used traditional Chinese medicine. Rhizoma of C. longa from leaf growing period,rhizome swelling period and dry matter accumulating period were used as experimental materials,to analyze the changes of metabolites and biosynthesis in the three periods by comparative transcriptome and metabolomes analysis.The results indicated that terpenoids accumulation and biosynthesis mainly occurred in leaf growing period,while curcumin accumulation and biosynthesis mainly occurred in dry matter accumulating period. Therefore,we suggested that turmeric rhizomes in leaf growth period were suitable for terpenoids biosynthetic pathway characterization,and rhizome in accumulation of dry matter period was suitable for curcuminoid biosynthesis pathway characterization. This study provides references for medicinal materialproduction and application,as well as biopathway analysis of active compounds for C. longa.
Curcuma
;
chemistry
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Curcumin
;
analysis
;
Phytochemicals
;
analysis
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Plants, Medicinal
;
chemistry
;
Rhizome
;
chemistry
;
Terpenes
;
analysis
4.Analysis of chemical components of Huanbei Zhike Prescription based on UPLC-Q-TOF-MS/MS technology.
Wen-Xia ZHANG ; Min FENG ; Yu-Lu MIAO ; Wen-Zhi ZHANG ; Yuan-Yuan LI ; Li-Guo TONG ; Pan HE ; Yan NI
China Journal of Chinese Materia Medica 2019;44(14):3022-3034
To characterize the chemical constituents of Huanbei Zhike Prescription by ultra-high performance liquid chromatography-time of flight mass spectrometry( UPLC-Q-TOF-MS/MS). A Thermo Syncronls C18 column( 2. 1 mm×100 mm,1. 7 μm) was used with methanol( A)-0. 1% formic acid solution( B) as the mobile phase for gradient elution. The injection volume was 2 μL; the column temperature was 40 ℃; the flow rate was 0. 3 m L·min-1; and electrospray ionization( ESI) source was used to collect data in positive and negative ion modes. The ion scanning range was m/z 50-1 200,with capillary voltage of 3 000 V,ion source temperature of100 ℃,atomization gas flow rate of 50 L·h-1,desolvent gas flow rate of 800 L·h-1,desolvent temperature of 400 ℃,cone hole voltage of 40 V,with argon as the collision gas and the collision energy was 20-35 V. The excimer ion peak information was analyzed by Waters UNIFI data processing software. The molecular formula with error within 1×10-5 was compared with the data in database to identify the compounds. The secondary fragment ion information of the target compound was selected,and then compared with the retention time and fragmentation patterns provided by the database and the existing literature to further confirm the compositions and structures of the compounds. A total of 68 main compounds in Huanbei Zhike Prescription were identified,including 38 flavonoids,10 organic acids,6 terpenoids and 10 nitrogen-containing compounds,of which 12 compounds were verified by the control substances. This method is rapid and accurate,which provides a new strategy for the qualitative analysis of the chemical constituents of Huanbei Zhike Prescription,and lays a foundation for the further study and quality control of the compound pharmacodynamic substance.
Chromatography, High Pressure Liquid
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Drugs, Chinese Herbal
;
chemistry
;
Flavonoids
;
analysis
;
Tandem Mass Spectrometry
;
Terpenes
;
analysis
5.Study on superposition law of drug bitterness based on tongue taste evaluation and electronic tongue evaluation.
Xue-Lin LI ; Yao ZHANG ; Peng-Ju CHEN ; Jun-Han SHI ; Jing YAO ; Qing-Xiao WANG ; Xin-Jing GUI ; Lu ZHANG ; Ke-Han WANG ; Jing MA ; Yan-Li WANG ; Rui-Xin LIU
China Journal of Chinese Materia Medica 2019;44(23):5134-5142
Traditional Chinese medicine( TCM) decoction contains complex bitterness. In this paper,the simple mixing of TCM monomer bitter substances is used as the entry point to study the law of bitterness superposition. With berberine hydrochloride( alkaloids),geniposide( terpenoids),and arbutin( glycosides) as mother liquor,sophoridine( alkaloids),gentiopicroside( terpenoids),and puerarin( glycosides) as additive substances,these different additive substances were mixed with different mother liquor according to concentration gradients to form different liquid mixtures. The bitterness of the additive solution and the mixtures was evaluated by traditional human taste panel method( THTPM) and electronic tongue; the bitterness-concentration fitting model of the additive solution and the liquid mixtures was established by Weibull and logarithmic curves. By comparing and analyzing the bitterness-concentration model and the bitterness difference( ΔI_0/ΔI_e) of the additive solution and the mixture,the influence of mother liquor on the bitterness of the mixture was investigated. The results showed that both the additive solution bitterness model and the liquid mixture bitterness model were consistent with the Weibull model and the logarithmic model( THTPM: R~2≥0. 887 0,P<0. 01; electronic tongue test:R~2≥0. 753 2,P<0. 05). The fitting degree of the Weibull model was generally higher than that of the logarithmic model; the bitterness difference( ΔI_0) was monotonously decreasing; the fitting equation of tongue bitterness and electronic tongue bitterness: R~2≥0. 874 2,P<0. 01. In this article,through the superposition of different kinds of TCM bitter substances,THTPM and electronic tongue test was combined. It was found that the bitterness after superposition was still in Weibull or logarithmic relationship with the concentration of additive substances; THTPM showed that the effect of bitter mother liquor on the bitterness of the mixture decreased with the increase of the concentration of the additive; the bitterness of the electronic tongue was obviously related to the bitterness of THTPM. However,further verification is needed later by optimizing the concentration gradient and expanding the sample size.
Alkaloids/analysis*
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Electronic Nose
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Glycosides/analysis*
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Humans
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Medicine, Chinese Traditional
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Taste
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Terpenes/analysis*
6.Arabidopsis thaliana as Bioindicator of Fungal VOCs in Indoor Air.
Samantha LEE ; Richard HUNG ; Guohua YIN ; Maren A KLICH ; Casey GRIMM ; Joan W BENNETT
Mycobiology 2016;44(3):162-170
In this paper, we demonstrate the ability of Arabidopsis thaliana to detect different mixtures of volatile organic compounds (VOCs) emitted by the common indoor fungus, Aspergillus versicolor, and demonstrate the potential usage of the plant as a bioindicator to monitor fungal VOCs in indoor air. We evaluated the volatile production of Aspergillus versicolor strains SRRC 108 (NRRL 3449) and SRRC 2559 (ATCC 32662) grown on nutrient rich fungal medium, and grown under conditions to mimic the substrate encountered in the built environment where fungi would typically grow indoors (moist wallboard and ceiling tiles). Using headspace solid phase microextraction/gas chromatography-mass spectrometry, we analyzed VOC profiles of the two strains. The most abundant compound produced by both strains on all three media was 1-octen-3-ol. Strain SRRC 2559 made several terpenes not detected from strain SRRC 108. Using a split-plate bioassay, we grew Arabidopsis thaliana in a shared atmosphere with VOCs from the two strains of Aspergillus versicolor grown on yeast extract sucrose medium. The VOCs emitted by SRRC 2559 had an adverse impact on seed germination and plant growth. Chemical standards of individual VOCs from the Aspergillus versicolor mixture (2-methyl-1-butanol, 3-methyl-1-butanol, 1-octen-3-ol, limonene, and β-farnesene), and β-caryophyllene were tested one by one in seed germination and vegetative plant growth assays. The most inhibitory compound to both seed germination and plant growth was 1-octen-3-ol. Our data suggest that Arabidopsis is a useful model for monitoring indoor air quality as it is sensitive to naturally emitted fungal volatile mixtures as well as to chemical standards of individual compounds, and it exhibits relatively quick concentration- and duration-dependent responses.
Air Pollution, Indoor
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Arabidopsis*
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Aspergillus
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Atmosphere
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Biological Assay
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Fungi
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Germination
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Plants
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Spectrum Analysis
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Sucrose
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Terpenes
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Volatile Organic Compounds
;
Yeasts
7.Leojaponic acids A and B, two new homologous terpenoids, isolated from Leonurus japonicus.
Han-Kui WU ; Yan-Jun MAO ; Shan-Shan SUN ; Zhi-Yong XU ; Ya MA ; Jin-Xia CAO ; He QI ; Zhi-Fu WU ; Gang LI ; Wei-Hua YANG
Chinese Journal of Natural Medicines (English Ed.) 2016;14(4):303-307
The present study aimed at isolation and purification of the bioactive terpenoids from the herb of Leonurus japonicus by chromatographic separations such as silica gel, sephadex LH-20 and C18 reversed phase silica gel, as well as preparative HPLC. As a result, leojaponic acids A (1, C17H24O4) and B (2, C18H26O4), two homologous terpenoids, together with (-)-loliolide (3), 1-(3-ethylphenyl) ethane-1, 2-diol (4) and dibutyl phthalate (5), were isolated from the EtOH extract of L. japonicus. All the chemical structures of the isolates were elucidated on the basis of 1D and 2D NMR analyses. Compounds 1 and 2 were new terpenoids, and Compounds 3 and 4 were isolated and identified for the first time from this plant. In addition, the α-glucosidase and tyrosinase inhibitory activity of the new compounds were evaluated.
Enzyme Inhibitors
;
chemistry
;
isolation & purification
;
Fruit
;
chemistry
;
Glucosidases
;
analysis
;
antagonists & inhibitors
;
Leonurus
;
chemistry
;
Magnetic Resonance Spectroscopy
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Molecular Structure
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Plant Extracts
;
chemistry
;
isolation & purification
;
Terpenes
;
chemistry
;
isolation & purification
8.Spectroscopic characteristics of novel Psidium meroterpenoids isolated from guava leaves.
Wen OUYANG ; Xiao-ai ZHU ; Xiao-juan LIU ; Shu-min YIE ; Litchao ZHAO ; Lei SU ; Yong CAO
China Journal of Chinese Materia Medica 2015;40(14):2898-2902
Recently, novel Psidium meroterpenoids were reported in the guava leaves. According to careful analysis of the spectral data of literatures, the spectroscopic characteristics and biosynthetic pathway of Psidium meroterpenoids were summarized in this paper. The results showed that Psidium meroterpenoids had distinct spectroscopic features and reasonable biosynthetic routines, however the number order of carbon atoms was not consistent in the reported literatures. It was concluded that Psidium meroterpenoids were the characteristic chemical constituents of Psidium guajava Linn.
Magnetic Resonance Spectroscopy
;
Plant Leaves
;
chemistry
;
Psidium
;
chemistry
;
Spectrum Analysis
;
Terpenes
;
chemistry
9.Analysis of triterpenoids in Ganoderma lucidum by microwave-assisted continuous extraction.
Yan-fang LU ; Jing AN ; Ye JIANG
China Journal of Chinese Materia Medica 2015;40(7):1296-1299
For further improving the extraction efficiency of microwave extraction, a microwave-assisted contijuous extraction (MACE) device has been designed and utilized. By contrasting with the traditional methods, the characteristics and extraction efficiency of MACE has also been studied. The method was validated by the analysis of the triterpenoids in Ganoderma lucidum. The extraction conditions of MACE were: using 95% ethanol as solvent, microwave power 200 W and radiation time 14.5 min (5 cycles). The extraction results were subsequently compared with traditional heat reflux extraction ( HRE) , soxhlet extraction (SE), ultrasonic extraction ( UE) as well as the conventional microwave extraction (ME). For triterpenoids, the two methods based on the microwaves (ME and MACE) were in general capable of finishing the extraction in 10, 14.5 min, respectively, while other methods should consume 60 min and even more than 100 min. Additionally, ME can produce comparable extraction results as the classical HRE and higher extraction yield than both SE and UE, however, notably lower extraction yield than MASE. More importantly, the purity of the crud extract by MACE is far better than the other methods. MACE can effectively combine the advantages of microwave extraction and soxhlet extraction, thus enabling a more complete extraction of the analytes of TCMs in comparison with ME. And therefore makes the analytic result more accurate. It provides a novel, high efficient, rapid and reliable pretreatment technique for the analysis of TCMs, and it could potentially be extended to ingredient preparation or extracting techniques of TCMs.
Chemical Fractionation
;
methods
;
Drugs, Chinese Herbal
;
analysis
;
isolation & purification
;
Microwaves
;
Reishi
;
chemistry
;
Terpenes
;
analysis
;
isolation & purification
10.Relativity of commercial specification of Menthae Herba based on chemical analysis.
Dan YE ; Ming ZHAO ; Yang SHAO ; Zhen OUYANG ; Hua-sheng PENG ; Han BANG-XING ; Wei-wan-qi ZHANG ; Xue-mei GU
China Journal of Chinese Materia Medica 2015;40(2):251-257
In order to compare the differences of 35 Menthae Herba samples collected on the market and at producing areas, the contents of six total terpenoids, the essential oil and chromatographic fingerprints were analyzed, which provided evidences for drawing up the commodity specifications and grading criteria of Menthae Herba. GC-MS method was used to analyze the chemical constituents of 35 different samples. The chromatographic fingerprints obtained by using GC were then evaluated by similarity analysis, hierarchical clustering analysis and principal component analysis. The relativity between the content of six terpenoids and the essential oil were studied. In this study, the chemical profiles of 35 samples from different producing areas had significant disparity. All samples collected in the report could be categorized into four chemical types, L-menthol, pulegone, carvone and L-menthone, but the chemical profiles had no relationship with the areas. The chromatographic fingerprints of the samples from different types were dissimilar, while the different producing areas were difficult to be separated. It was indicated that the content of volatile oil was positively correlated with the content of L-menthol and the sum of six total terpenoids. The content of the essential oil, L-menthol and the sum of six total terpenoids of Menthae Herba were considered as one of the commercial specifications and grading criteria. These results in the research could be helpful to draw up the commercial specification and grading criteria of Menthae Herba from a view of chemical information.
Cluster Analysis
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Gas Chromatography-Mass Spectrometry
;
Mentha
;
chemistry
;
Oils, Volatile
;
analysis
;
Principal Component Analysis
;
Terpenes
;
analysis

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