1.Effects of different processing methods on traits and chemical constituents of Forsythiae Fructus.
Rong-Rong XU ; Rui LI ; Chu-Han ZHANG ; Wei TIAN ; Xin-Guo WANG ; Li-Ying NIU ; Wei FENG
China Journal of Chinese Materia Medica 2025;50(2):465-471
This study aims to investigate the correlations of the appearance traits, total antioxidant capacity, and component content of Forsythiae Fructus processed by different methods, explore the effects of different processing methods on the abovementioned three aspects of Forsythiae Fructus, and screen out the internal and external indicators that have important effects on its quality. It determined the length, diameter, stem length, chroma value L~*, a~*, b~*, and other appearance indexes and antioxidant activity of Forsythiae Fructus processed by different methods. The content of forsythiaside A, rutin, forsythin, pinoresinol, and phillygenin was determined by ultra performance liquid chromatography(UPLC). Correlation analysis, principal component analysis(PCA), orthogonal partial least squares discriminant analysis(OPLS-DA), and independent sample t-test analysis were performed on the appearance indexes and the component content. The correlation analysis showed that there were differences in the appearance traits and the component content. L~* and E~* had highly significant negative correlations with pinoresinol and phillygenin(P<0.01) and significant positive correlations with forsythiaside A(P<0.05). There were a highly significant negative correlation between a~* and forsythiaside A(P<0.01) and highly significant positive correlations of a~* with pinoresinol and phillygenin(P<0.01). There were a highly significant positive correlation between b~* and forsythiaside A(P<0.01) and highly significant negative correlations of b~* with pinoresinol and phillygenin(P<0.01). The total antioxidant capacity had highly significant negative correlations with pinoresinol and phillygenin(P<0.01). The PCA results showed that there were differences among Forsythiae Fructus samples processed by different methods. OPLS-DA marked five important indicators, which were forsythiaside A, stem length, E~*, L~*, and b~*. The results of independent sample t-test showed that the content of forsythiaside A, pinoresinol, and phillygenin, the total antioxidant capacity, and the appearance traits such as L~*, a~*, b~*, and E~* were significantly different between the Forsythiae Fructus samples processed by steaming and boiling(P<0.05). According to content determination and a related biological activity analysis, steaming is a good choice from the perspective of improving the stability of chemical constituents and antioxidant activity of Forsythiae Fructus. From the point of view of improving the stability of chemical constituents and anti-inflammatory and anti-cancer activities of Forsythiae Fructus, it is recommended to use boiling as the processing method. Based on the above analysis methods, the main indexes for the appearance traits of Forsythiae Fructus processed by different methods are powder chroma value(L~*, a~*, b~*, E~*), stem length, and total antioxidant capacity, and those for chemical constituents are the content of forsythiaside A, pinoresinol, and phillygenin. This study provides reference for seeking scientific processing methods of Forsythiae Fructus.
Forsythia/chemistry*
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Drugs, Chinese Herbal/isolation & purification*
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Fruit/chemistry*
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Antioxidants/analysis*
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Chromatography, High Pressure Liquid
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Glycosides/analysis*
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Principal Component Analysis
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Furans
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Lignans
2.A new tetralone glycoside in leaves of Cyclocarya paliurus.
Ting-Si GUO ; Qin HUANG ; Qi-Qi HU ; Fei-Bing HUANG ; Qing-Ling XIE ; Han-Wen YUAN ; Wei WANG ; Yu-Qing JIAN
China Journal of Chinese Materia Medica 2025;50(1):146-167
The chemical constituents from leaves of Cyclocarya paliurus were isolated and purified by chromatography on silica gel, C_(18) reverse-phase silica gel, and Sephadex LH-20 gel, as well as semi-preparative high-performance liquid chromatography. Six compounds were identified by UV, IR, NMR, MS, calculated ECD, and comparison with literature data as cyclopaloside D(1), boscialin(2),(5R,6S)-6-hydroxy-6-[(E)-3-hydroxybut-1-enyl]-1,1,5-trimethylcyclohexanone(3), 3S,5R-dihydroxy-6R,7-megastigmadien-9-one(4), 3S,5R-dihydroxy-6S,7-megastigmadien-9-one(5), and gingerglycolipid A(6), respectively. Among them, compound 1 was identified as a new tetralone glycoside, and compounds 2-6 were isolated from leaves of C. paliurus for the first time. Furthermore, compound 1 exhibited strong antioxidant activity, with the IC_(50) of(454.20±31.81)μmol·L~(-1) and(881.82±42.31)μmol·L~(-1) in scavenging DPPH and ABTS free radicals, respectively.
Plant Leaves/chemistry*
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Glycosides/isolation & purification*
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Juglandaceae/chemistry*
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Tetralones/isolation & purification*
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Drugs, Chinese Herbal/isolation & purification*
3.Four new diglycosides from Momordicae Semen.
Cheng-Lin ZHOU ; Xiao-Bo LI ; Pei-Jun JU ; Ru DING ; Meng-Yue WANG
China Journal of Chinese Materia Medica 2025;50(6):1558-1563
The seed kernel of Momordica cochinchinensis, i.e., Momordicae Semen, is used for medicinal purposes, but to date, no research has been reported on its chemical constituents. In this study, the chemical constituents of Momordicae Semen were investigated for the first time using silica gel column chromatography, semi-preparative HPLC, HR-MS, and NMR. As a result, eight compounds were isolated and identified as: p-hydroxybenzoic acid-7-O-trehaloside(mubeside A, 1), 2,6-dimethoxyphenol-O-β-D-apiosyl-(1→2)-β-D-glucoside(mubeside B, 2), 1-O-p-methoxybenzoyl-1,4-benzenediol-4-O-β-D-apiosyl-(1→2)-β-D-glucoside(mubeside C, 3), 1-O-p-hydroxybenzoyl-1,4-benzenediol-4-O-β-D-apiosyl-(1→2)-β-D-glucoside(mubeside D, 4), gypsogenin-3-O-β-D-galactosyl-(1→2)-β-D-glucuronoside(5), quillaic acid-3-O-β-D-galactosyl-(1→2)-β-D-glucuronoside(6), violanthin(7), and kaempferitrin(8). Compounds 1-4 are new compounds, while compounds 5-8 were isolated from Momordicae Semen for the first time.
Glycosides/isolation & purification*
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Drugs, Chinese Herbal/isolation & purification*
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Molecular Structure
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Magnetic Resonance Spectroscopy
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Chromatography, High Pressure Liquid
4.Anti-cancer and anti-inflammatory effects of flavan-4-ol and flavan glycosides from the roots of Pronephrium penangianum.
Feibing HUANG ; Yong YANG ; Qingling XIE ; Hanwen YUAN ; Muhammad AAMER ; Yuqing JIAN ; Ye ZHANG ; Wei WANG
Chinese Journal of Natural Medicines (English Ed.) 2025;23(5):593-603
Five new flavan-4-ol glycosides jixueqiosides A-E (1-5) and two new flavan glycosides jixueqiosides F and G (6 and 7), along with twelve known flavan-4-ol glycosides (8-19), were isolated from the roots of Pronephrium penangianum. Comprehensive spectral analyses, X-ray single-crystal diffraction, and theoretical electronic circular dichroism (ECD) calculations established structures and absolute configurations. A single crystal structure of flavan-4-ol glycoside (14) was reported for the first time, while the characteristic ECD and NMR data for all isolated flavan-4-ol glycosides (1-5 , 8-19) were analyzed, establishing a set of empirical rules. Activity screening of these isolates showed that 8 and 9 could inhibit the proliferation of MDA-MB-231 and MCF-7 cells with IC50 values of 7.93 ? 2.85 ?mol?L-1 and 5.87 ? 1.58 ?mol?L-1 (MDA-MB-231), and 2.21 ? 1.38 ?mol?L-1 and 3.52 ? 1.55 ?mol?L-1 (MCF-7), respectively. Western blotting and flow cytometry analyses demonstrated that 8 and 9 dose-dependently induced apoptosis in MDA-MB-231 cells by up-regulating BAX, activating caspase-3 and down-regulating BCL-2. Additionally, compound 8 affected autophagy-related proteins, increasing the ratio of LC3-II/LC3-I and Beclin-1 levels to inhibit MDA-MB-231 cell proliferation. Moreover, anti-inflammatory studies indicated that 2, 3, 7, 13, 14, and 18 moderately inhibited tumor necrosis factor-a (TNF-a), interleukin-6 (IL-6), and nitric oxide (NO) release.
Humans
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Plant Roots/chemistry*
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Glycosides/isolation & purification*
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Anti-Inflammatory Agents/isolation & purification*
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Flavonoids/isolation & purification*
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Cell Proliferation/drug effects*
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Antineoplastic Agents, Phytogenic/isolation & purification*
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Molecular Structure
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Apoptosis/drug effects*
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Cell Line, Tumor
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Tumor Necrosis Factor-alpha/immunology*
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Drugs, Chinese Herbal/pharmacology*
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Interleukin-6/immunology*
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Animals
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Mice
5.Three new coumarins and a new coumarin glycoside from Micromelum integerrimum.
Nan-Kai CAO ; Yue-Mei CHEN ; Si-Si ZHU ; Ke-Wu ZENG ; Ming-Bo ZHAO ; Jun LI ; Peng-Fei TU ; Yong JIANG
Chinese Journal of Natural Medicines (English Ed.) 2021;19(8):621-625
Three new coumarins, integmarins A-C (1-3), and a new coumarin glycoside, integmaside A (4) were isolated from the leaves and stems of Micromelum integerrimum. Their structures were elucidated on the basis of 1D and 2D NMR and MS data, and their absolute configurations were assigned according to the ECD data of the in situ formed transition metal complexes and comparison of experimental and calculated ECD data. Compounds 1 and 2 are two rare coumarins with butyl and propyl moieties at the C-6 position; compound 3 is a novel coumarin with a highly oxidized prenyl group, and compound 4 is a rare bisdihydrofuranocoumarin glycoside.
Coumarins/isolation & purification*
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Glycosides/isolation & purification*
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Molecular Structure
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Plant Leaves/chemistry*
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Plant Stems/chemistry*
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Rutaceae/chemistry*
6.A new flavonostilbene glycoside from roots of Polygonum multiflorum.
Qiu-Jie XIE ; Shuo-Guo LI ; Xiao-Jun HUANG ; Zhen-Long WU ; Wen-Cai YE ; Ying WANG
China Journal of Chinese Materia Medica 2020;45(5):1114-1119
Polygonflavanol B(1), a new flavonostilbene glycoside, was isolated from the roots of Polygonum multiforum(Polygonaceae) by various column chromatography methods including macroporous resin HP-20, silica gel, Sephadex LH-20, and preparative HPLC. The structure with absolute configuration of the new compound was identified by its physicochemical properties, spectroscopic data, ECD calculation, and chemical method.
Fallopia multiflora/chemistry*
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Flavonols/isolation & purification*
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Glycosides/isolation & purification*
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Plant Roots/chemistry*
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Stilbenes/isolation & purification*
7.A new nor-sesquiterpene glycoside from Corydalis edulis.
Zhi-Tian PENG ; Ling-Hui CHAO ; Chao-Chao WANG ; Hui XIA ; Di-Fa LIU ; Zhang-Wei WANG ; Jiao ZHENG ; Yun-Fang ZHAO ; Peng-Fei TU ; Jun LI
China Journal of Chinese Materia Medica 2020;45(3):579-583
This study is to investigate the chemical constituents from the whole plant Corydalis edulis. The chemical constituents were separated and purified by macroporous resin D101, silica gel, Sephadex LH-20, ODS, and semi-preparative HPLC. Their structures were determined by physicochemical properties and spectroscopic data. Four compounds were isolated from the dichloromethane and water extracts of the whole plant C. edulis, and identified as 6'-β-D-xylosylicariside B2(1),(3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one(2), loliolide(3), and 5,5'-dimethoxybiphenyl-2,2'-diol(4), respectively. Compound 1 is a new compound, of which the absolute configuration was established by electronic circular dichroism(ECD) calculations. Compound 4 is obtained from the plants of Papaveraceae family for the first time. Compounds 2 and 3 are firstly isolated from the Corydalis genus.
Chromatography, High Pressure Liquid
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Corydalis/chemistry*
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Glycosides/isolation & purification*
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Molecular Structure
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Phytochemicals/isolation & purification*
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Sesquiterpenes/isolation & purification*
8.A new phenolic glycoside from honey-fried Eriobotrya japonica.
Bing-Yun LU ; Xing-Dong WU ; Yu-Ning JIA ; Jun-Ting FAN ; Ning-Hua TAN
China Journal of Chinese Materia Medica 2019;44(13):2806-2812
A total of twelve compounds were isolated from the ethyl acetate of the water extract of honey-fried Eriobotrya japonica through column chromatography over silica gel,Sephadex LH-20,RP-18,and preparative HPLC. Their structures were established by MS,1 D NMR and 2 D NMR data as japonicanoside A( 1),nerolidol-3-O-α-L-rhamnopyranosyl-( 1→2)-β-D-glucopyranoside( 2),nerolidol-3-O-α-L-rhamnopyranosyl-( l→4)-α-L-rhamnopyranosyl-( 1 → 2)-[α-L-( 4-trans-feruloyl)-rhamnopyranosyl-( 1 → 6) ]-β-D-glucopyranoside( 3),( +)-catechin( 4),(-)-epicatechin( 5),kaempferol 3-O-α-L-rhamnopyranoside( 6),quercitrin( 7),quercetin-3-O-β-D-galactopyranoside( 8),quercetin-3-O-β-glucopyranoside( 9),vanillin( 10),protocatechuic aldehyde( 11),and maltol( 12). Among them,1 is a new phenolic glycoside.
Chromatography, High Pressure Liquid
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Eriobotrya
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chemistry
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Glycosides
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chemistry
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isolation & purification
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Honey
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Magnetic Resonance Spectroscopy
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Phytochemicals
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chemistry
;
isolation & purification
9.A new antioxidant flavonoid glycoside from flowers of Hosta plantaginea.
Qing-Guang ZHOU ; Li YANG ; Jun-Wei HE ; Guo-Yue ZHONG
China Journal of Chinese Materia Medica 2019;44(15):3312-3315
Phytochemical investigation of the flowers of Hosta plantaginea led to isolate of one new flavonoid glycoside,plantanone C( 1) by silica gel,Sephadex LH-20,and RP-HPLC column chromatographies. Its structure was extensively determined on basis of HR-ESI-MS and NMR spectroscopic data. Compound 1 exhibited moderate antioxidant activity against DPPH radical scavenging activity,with an IC50 value of 240. 2 μmol·L~(-1).
Antioxidants
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analysis
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isolation & purification
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Flavonoids
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analysis
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isolation & purification
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Flowers
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chemistry
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Glycosides
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analysis
;
isolation & purification
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Hosta
;
chemistry
10.Two new C steroidal glycosides isolated from Cynanchum komarovii.
Dan ZHAO ; Shan-Shan SU ; Shao-Fei CHEN ; Xiao-Jie LU ; Gang CHEN ; Yu-Bo WANG ; Guang-Yue SU ; Yue-Hu PEI
Chinese Journal of Natural Medicines (English Ed.) 2018;16(8):610-614
The present study was designed to further investigate the C steroidal glycosides in Cynanchum plants. Two new steroidal glycosides based on a 13, 14:14, 15-disecopregnane-type aglycone, komaroside P (1) and komaroside Q (2), together with three known compounds (3-5) were isolated from the whole herbs of Cynanchum komarovii. The aglycones of compounds 1 and 2 were two new disecopregnane. Their structures were elucidated on the basis of 1D, 2D NMR spectroscopic data and acid hydrolysis. All the compounds (1-5) showed potent inhibitory activities against human leukemia cell lines (HL-60) with IC values ranging from 16.6 to 26.3 μmol·L, compared to the positive control 5-fluorouracil (6.4 μmol·L).
Cell Survival
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drug effects
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Cynanchum
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chemistry
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Drugs, Chinese Herbal
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chemistry
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isolation & purification
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pharmacology
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Glycosides
;
chemistry
;
isolation & purification
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pharmacology
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HL-60 Cells
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Humans
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Steroids
;
chemistry
;
isolation & purification
;
pharmacology

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