1.Chemical constituents of Dolomiaea souliei.
Hu WEI ; Chunnian HE ; Yong PENG ; Guoxu MA ; Peigen XIAO
China Journal of Chinese Materia Medica 2012;37(9):1249-1253
OBJECTIVETo study the chemical constituents of Dolomiaea souliei.
METHODVarious chromatographic techniques were adopted to separate the constituents, and the spectrum analysis was made to identify their structures.
RESULTSeventeen compounds were isolated and identified as: dehydrocostus lactone (1), costunolide (2), mokko lactone (3), santamarine(4), reynosin (5), 4alpha-hydroxy-4beta-methyldihydrocostol (6), sulfocostunolide A (7), beta-costic acid (8), beta-cyclocostunolide (9), vladinol A (10), ursolic acid (11), betulinic acid (12), betulin (13), dibutyl terephthalate (14), dibutyl phthalate (15), uridine (16), and emodin (17).
CONCLUSIONCompounds 6-9 and 12-17 were obtained from this genus for the first time, and compound 11 was obtained from this plant for the first time.
4-Butyrolactone ; analogs & derivatives ; chemistry ; Asteraceae ; chemistry ; Emodin ; chemistry ; Lactones ; chemistry ; Sesquiterpenes ; chemistry ; Triterpenes ; chemistry
2.Comparison on content of ligustilides in different danggui samples.
Xi LI ; Li-Hong ZHANG ; Guang-Hua LV ; Xiao-Xiao WANG ; Wei-Dong JIANG ; Yu-Qing JIN ; Zhong-Zhen ZHAO
China Journal of Chinese Materia Medica 2013;38(17):2838-2843
Bioactivity of Danggui is linked to the content of ligustilide, but the relationship between ligustilide with herb shape, cultivating areas and plant species is still unknown. The relationship was investigated by quantifying on the amounts of Z-ligustilide and E-ligustilide by HPLC-DAD-MS method, and then comparing the content of ligustilides (the sum of Z-ligustilide and E-ligustilide) among forty-four various "Danggui" samples containing thirty Chinese Danggui (CDG), six Japanese Danggui (JDG), four Korea Danggui (KDG) and four European Danggui (EDG). Results showed that the content of ligustilides in CDG samples (Angelica sinensis) was in the range of 5.63-24.53 mg x g(-1) with the mean of 11.02 mg x g(-1) (n = 30). Ligustilides amounts were varied among samples cultivated in different areas in China, i. e. 13.90 mg x g(-1) (n = 6) in Yannan, 12.51 mg x g(-1) (n = 6) in Sichuan and 10.04 mg x g(-1) (n = 13) in Gansu. It was also found that ligustilides content was related to the shape, color and fragrance of herb, e. g. the relative larger amount of ligustilides was in the small main root, long rootlet and perfumed sample. Further, ligustilides contents were estimated to be 1.00 mg x g(-1) (n = 6) in JDG samples (A. acutiloba and A. acutiloba var. sugiyamae) and 2.78 mg x g(-1) (n = 2) in EDG samples (lovage root, Levisticum officinale). However, ligustilides could not be detected in the four KDG samples (A. gigas) and two EDG samples (angelica root, A. archangelica). It has been concluded that ligustilide is significant variant among plant species, which may result in the variety of bioactivity and therapeutic effect.
4-Butyrolactone
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analogs & derivatives
;
analysis
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Angelica sinensis
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chemistry
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China
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Chromatography, High Pressure Liquid
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Drugs, Chinese Herbal
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chemistry
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Geography
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Quality Control
3.Development of gas chromatographic-mass spectrometry-pattern recognition method for the quality control of Chinese Angelica.
Xiang-lan PIAO ; Cheng-quan HONG
China Journal of Chinese Materia Medica 2008;33(16):2008-2010
OBJECTIVETo compare 39 root samples of Angelica sinensis and A. acutiloba from China and Japan for the quality control of Chinese Angelica.
METHODAn HP-5 (0.32 mm x 30 m, 0.25 microm) column was used for the GC-MS analysis. The oven temperature was programmed from 120 degrees C to 280 degrees C at a rate of 5 degrees C x min(-1). Using principal component analysis, cluster analysis, and discriminant analysis on the sample fingerprints for chemical pattern recognition research.
RESULTZ-Ligustilide was the key principle distinguishing Chin samples from Japan. Moreover, using discriminant analysis, seven samples (four of A. sinensis, three of A. acutiloba) were validated. All samples tested were successfully classified according to their species origin.
4-Butyrolactone ; analogs & derivatives ; chemistry ; Angelica sinensis ; chemistry ; Cluster Analysis ; Discriminant Analysis ; Gas Chromatography-Mass Spectrometry ; methods ; Principal Component Analysis
4.Research progress studies on pharmacology and pharmacokinetics of ligustilide.
Ai-Hua ZUO ; Li WANG ; Hong-Bin XIAO
China Journal of Chinese Materia Medica 2012;37(22):3350-3353
Ligustilide is contained highly or around 1% in such umbelliferous plants as Angelica sinensis and Ligusticum chuanxiong, is one of main bioactive constituents. It shows many pharmacological activities related to their efficacy. At present, ligustilide has attracted extensive attention and more and more studies have been reported, indicating that it is a promising compound. This essay summarizes the progress of pharmacological effects of ligustilide on neuroprotection, vasodilatation, anti-caner and anti-tumor, analgesia and anti-inflammation, and pharmacokinetics including absorption, distribution, metabolism and excretion, providing basis for further studies and development of ligustilide.
4-Butyrolactone
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analogs & derivatives
;
pharmacokinetics
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pharmacology
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Angelica sinensis
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chemistry
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Animals
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Drugs, Chinese Herbal
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pharmacokinetics
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pharmacology
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Humans
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Ligusticum
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chemistry
5.Effect of ligustilide on oxygen and glucose deprivation/reperfusion-induced mitochondria fission in PC12 cells.
Qian WU ; Ning WANG ; Jiao LIU ; Zhi-Guo MAO ; Yan-Xiang WANG
China Journal of Chinese Materia Medica 2020;45(16):3931-3937
This study aimed to investigate the effect and mechanism of ligustilide, the main active ingredient in Ligusticum wallichii, on mitochondria fission after PC12 cell injury induced by oxygen and glucose deprivation/reperfusion(OGD/R). In the experiment, an OGD/R model was established in vitro, and PC12 cells were pre-treated with ligustilide for 3 h, and then the cell viability was detected by CCK-8 method. The effect of different concentrations of ligustilide on the morphology of PC12 cells after OGD/R injury was observed under an inverted microscope. Transmission electron microscopy was used to observe the mitochondrial fission of PC12 cells after OGD/R injury. DCFH-DA immunofluorescence staining method was used to detect intracellular reactive oxygen species(ROS) changes. Changes in mitochondria membrane potential(MMP) were detected by flow cytometry. Hochest 33258 was used to observe the apoptosis of PC12 cells. Western blot was used to detect changes in cytochrome C(Cyt C) content in mitochondria and cytoplasm, and mitochondrial fission-related proteins Drp 1 and Fis 1. All results showed that compared with the model group, ligustilide significantly increased the survival rate of PC12 cells and the number of cells. Further experiments showed that ligustilide inhibited the release of ROS and decline of mitochondrial membrane potential in PC12 cells after OGD/R injury. Moreover, ligustilide reduced the release of Cyt C and promoted the expressions of Drp1 and Fis1 in mitochondrial fission proteins. Verification experiments showed that mitochondrial fission inhibitor mdivi-1 decreased cell survival rate and inhibited fission. The results indicated that ligustilide exerted neuro-protective effects by promoting mitochondrial fission and reducing cell damage. It preliminary proves that the mechanism of ligustilide on ischemic brain injury may be related to the promotion of mitochondrial fission and the maintenance of cell homeostasis.
4-Butyrolactone
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analogs & derivatives
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Animals
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Apoptosis
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Cell Survival
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Glucose
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Mitochondria
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Oxygen
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PC12 Cells
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Rats
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Reactive Oxygen Species
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Reperfusion Injury
6.Chemical constituents of Spatholobus suberectus.
Ren-Neng TANG ; Xiao-Bo QU ; Shu-Hong GUAN ; Ping-Ping XU ; Yang-Yang SHI ; De-An GUO
Chinese Journal of Natural Medicines (English Ed.) 2012;10(1):32-35
AIM:
To investigate chemical constituents of Spatholobus suberectus Dunn.
METHODS:
Isolation and purification were carried out by column chromatographic methods. Compounds were characterized based on their physical characteristics and spectra data.
RESULTS:
Seventeen compounds were isolated from ethanol extract of S. suberectus. The structures were elucidated as prestegane B (1), (2R, 3R)-buteaspermanol (2), (+)-medioresinol (3), (2R, 3R)-3,7-dihydroxyflavanone (4), benzeneethanol (5), 4, 7, 2'-trihydroxy-4'-methoxyisoflavanol (6), naringenin (7), blumenol A (8), protocatechuic acid ethyl ester (9), liquiritigenin (10), 7, 4'-dihydroxy-8-methoxy-isoflavone (11), 3, 5, 7, 3', 5'-pentahydroxyflavanone (12), protocatechuic acid (13), glycyroside (14), 8-methylretusin-7-O-β-D-glucopyranoside (15), 3, 3', 4', 5, 6, 7, 8-heptahydroxyflavan (16), and dulcisflavan (17).
CONCLUSION
All compounds are firstly isolated from the title plant and compounds 1, 3 were isolated from the Spatholobus genus for the first time.
4-Butyrolactone
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analogs & derivatives
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chemistry
;
isolation & purification
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Fabaceae
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chemistry
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Lignans
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chemistry
;
isolation & purification
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Molecular Structure
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Plant Extracts
;
chemistry
7.Mitophagy mediated by ligustilide relieves OGD/R-induced injury in HT22 cells.
Qian WU ; Jiao LIU ; Li-Yu TIAN ; Ning WANG
China Journal of Chinese Materia Medica 2022;47(7):1897-1903
Mitochondrion, as the main energy-supply organelle, is the key target region that determines neuronal survival and death during ischemia. When an ischemic stroke occurs, timely removal of damaged mitochondria is very important for improving mitochondrial function and repairing nerve damage. This study investigated the effect of ligustilide(LIG), an active ingredient of Chinese medicine, on mitochondrial function and mitophagy based on the oxygen and glucose deprivation/reperfusion(OGD/R)-induced injury model in HT22 cells. By OGD/R-induced injury model was induced in vitro, HT22 cells were pre-treated with LIG for 3 h, and the cell viability was detected by the CCK-8 assay. Immunofluorescence and flow cytometry were used to detect indicators related to mitochondrial function, such as mitochondrial membrane potential, calcium overload, and reactive oxygen species(ROS). Western blot was used to detect the expression of dynamin-related protein 1(Drp1, mitochondrial fission protein) and cleaved caspase-3(apoptotic protein). Immunofluorescence was used to observe the co-localization of the translocase of outer mitochondrial membrane 20(TOMM20, mitochondrial marker) and lysosome-associated membrane protein 2(LAMP2, autophagy marker). The results showed that LIG increased the cell viability of HT22 cells as compared with the conditions in the model group. Furthermore, LIG also inhibited the ROS release, calcium overload, and the decrease in mitochondrial membrane potential in HT22 cells after OGD/R-induced injury, facilitated Drp1 expression, and promoted the co-localization of TOMM20 and LAMP2. The findings indicate that LIG can improve the mitochondrial function after OGD/R-induced injury and promote mitophagy. When mitophagy inhibitor mdivi-1 was administered, the expression of apoptotic protein increased, suggesting that the neuroprotective effect of LIG may be related to the promotion of mitophagy.
4-Butyrolactone/analogs & derivatives*
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Apoptosis
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Calcium/pharmacology*
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Glucose/metabolism*
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Humans
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Mitochondrial Proteins
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Mitophagy
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Reactive Oxygen Species/metabolism*
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Reperfusion Injury/genetics*
8.Studies on the chemical constituents in herbs of Hemistepta lyrata.
Zhong-jie ZOU ; Jun-shan YANG ; Jian-hua JU
China Journal of Chinese Materia Medica 2006;31(10):812-813
OBJECTIVETo investigate the chemical constituents of Hemistepta lyrata.
METHODThe constituents of the EtOAc-soluble portions of the 95% ethanol extract were isolated and purified by means of chromatography. Compounds were identified by their physical characteristics and spectral features.
RESULTFive compounds were isolated and identified as caffeic acid (1), tracheloside (2), uracil (3), 8-carboxymethyl-p-hydroxycinnamic acid (4), and 3-O-p-coumaroylquinic acid (5).
CONCLUSIONCompounds 1-5 were isolated from this genus for the first time.
4-Butyrolactone ; analogs & derivatives ; chemistry ; isolation & purification ; Asteraceae ; chemistry ; Caffeic Acids ; chemistry ; isolation & purification ; Glucosides ; chemistry ; isolation & purification ; Plants, Medicinal ; chemistry ; Uracil ; chemistry ; isolation & purification
9.Quantitative determination of 5 active ingredients in different harvest periods of Ligusticum chuanxiong by HPLC.
Jin-Liang LIU ; Qiao-Jia FAN ; Shun-Lin ZHENG ; Jie TAN ; Juan ZHOU ; Ji-Chao YUAN ; Shi-Min YANG ; Fan-Lei KONG
China Journal of Chinese Materia Medica 2014;39(9):1650-1655
A simple and quick method is described for the determination of ferulic acid, senkyunolide I, senkyunolide H, senkyunolide A and ligustilide in rhizomes of Ligusticum chuanxiong. The 5 active ingredients in the sample was extracted using 40% ethanol and analyzed by reversed-phase high performance liquid chromatography (HPLC). Chromatography separation was performed using Agilent 1100 series HPLC system with a Symmetry C18 column and gradient elution with a mixture of three solvents : solvent A, acetonitrile, solvent B, methanol and solvent C, 1% aqueous acetic acid, 0 min to 5 min A: B: C 20: 40: 40, 5 min to 30 min A: B: C 60 to 100 : 0 : 40 to 0. The effluent was monitored using a VWD detector set at 321 nm (0-4.3 min) and 275 nm (4.31-30 min). The flow rate was set at 1 mL x min(-1) and the injection volume was 10 microL. The column temperature was maintained at 35 degrees C. The calibration curve was linear (r > or = 0.99) over the tested ranges. The average recovery was 94.44%-103.1% (n = 6). The method has been successfully applied to the analysis in different harvest periods of L. chuanxiong samples. In this paper, single-factor randomized block design to study the 5 components content of L. chuanxiong on ten collecting stages. For the L. chuanxiong collected from April 15th to May 30rd, the content of 5 ingredients increased primarily, and then decreased. Determine the appropriate harvest time has important significance to the promotion of the quality of L. chuanxiong.
4-Butyrolactone
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analogs & derivatives
;
analysis
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Acetic Acid
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chemistry
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Acetonitriles
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chemistry
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Benzofurans
;
analysis
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Chromatography, High Pressure Liquid
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methods
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Coumaric Acids
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analysis
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Ligusticum
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chemistry
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Methanol
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chemistry
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Solvents
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chemistry
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Time Factors
10.New dimeric phthalide derivative from Angelica sinensis.
Dong-min SU ; Shi-shan YU ; Hai-lin QIN
Acta Pharmaceutica Sinica 2005;40(2):141-144
AIMTo study the chemical constituents of the roots of Angelica sinensis.
METHODSSilica gel column chromatography was used to separate the chemical constituents. Their structures were elucidated by chemical and spectral analysis (IR, MS, 1D and 2D NMR, etc.).
RESULTSBesides three known phthalide derivatives, one new dimeric phthalide derivative and a pair of epimer were isolated and their structures were identified as Z-3',8',3'a,7'a-tetrahydro-6,3',7,7'a-diligustilide-8'-one (1), Z,Z'-6,6',7,3'a-diligustilide (2) and the 8-epimer (3) of 2 on the basis of spectral data.
CONCLUSIONCompound 1 is a new dimeric phthalide derivative, and compound 3 was first reported from radix Angelica
4-Butyrolactone ; analogs & derivatives ; chemistry ; isolation & purification ; Angelica sinensis ; chemistry ; Benzofurans ; Molecular Conformation ; Molecular Structure ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Stereoisomerism