1.Two new protoberberine alkaloids from Stephania hernandifolia.
Wei-Hua DAI ; Xin-Tao CUI ; Yu-Jiao TU ; Lei JIANG ; Lin YUAN
China Journal of Chinese Materia Medica 2025;50(5):1231-1235
The 95% ethanol extract of Stephania hernandifolia was isolated and purified by column chromatography on silica gel and Sephadex LH-20, RP-18 medium-pressure liquid chromatography, and semi-preparative high performance liquid chromatography. The chemical structures of the compounds were identified by NMR and high-resolution mass spectrometry. Four alkaloids were isolated and identified as(-)-8-oxo-2,3,4,10,11-pentamethoxyberberine(1),(-)-8-oxo-11-hydroxy-2,3,4,10-tetramethoxyberberine(2), N-trans-feruloyl tyramine(3), and N-cis-feruloyl tyramine(4). Compounds 1 and 2 were new protoberberine alkaloids, while compounds 3 and 4 were amide alkaloids. All the four compounds were separated from this plant for the first time. The inhibitory activities of compounds 1, 3, and 4 against α-glycosidase were measured by the enzymatic reaction in vitro with 4-nitrophenyl-α-D-glucopyranoside(PNPG) as the substrate. Compounds 3 and 4 showed inhibitory activities against α-glucosidase, with median inhibition concentration(IC_(50)) values of(7.09±0.42) and(31.25±1.14) μmol·L~(-1), respectively.
Berberine Alkaloids/isolation & purification*
;
Stephania/chemistry*
;
Drugs, Chinese Herbal/isolation & purification*
;
Molecular Structure
;
alpha-Glucosidases/metabolism*
;
Chromatography, High Pressure Liquid
;
Alkaloids/isolation & purification*
2.Research progress in chemical constituents and processing methods of Aconiti Lateralis Radix Praeparata.
Jia-Hao HU ; Wen-Ru LI ; Qing-Xin SHI ; Cheng-Wu SONG
China Journal of Chinese Materia Medica 2025;50(6):1458-1470
This article aims to study the processing methods by exploring the main chemical constituents of Aconiti Lateralis Radix Praeparata and the toxicity-attenuating mechanisms. The relevant articles were retrieved from multiple databases with the time interval of 1960-2024, and the chemical constituents of Aconiti Lateralis Radix Praeparata and the toxicity-attenuating mechanisms of its processing methods were summarized. The review revealed that the chemical constituents of Aconiti Lateralis Radix Praeparata included 32 diester-type alkaloids, 36 monoester-type alkaloids, 43 alkanolamine-type alkaloids, and 8 lipid-type alkaloids. At the same time, other chemical constituents such as water-soluble alkaloids were also studied, and their pharmacological activities were summarized. The toxicity-attenuating mechanisms of the processing methods included constituent loss, hydrolysis, ester exchange, and ion-pair action. The processing methods of Aconiti Lateralis Radix Praeparata have developed from being traditional to modern, with simplified operation and increased retention amounts of active constituents, which have improved the efficacy of processed Aconiti Lateralis Radix Praeparata products and have facilitated the industrial production. However, the existing processing methods of Aconiti Lateralis Radix Praeparata cannot completely solve the problem of possible reduction in efficacy during toxicity attenuation. More toxicity-attenuating mechanisms and lipid-type alkaloids of Aconiti Lateralis Radix Praeparata should be explored, which is expected to reduce its toxicity while retaining its efficacy.
Aconitum/toxicity*
;
Drugs, Chinese Herbal/isolation & purification*
;
Alkaloids/chemistry*
;
Animals
;
Humans
3.A new amide alkaloid from Cannabis Fructus.
Rui-Wen XU ; Yong-Zhuo ZHAO ; Yu-Guo MA ; Hui LIU ; Yan-Jun SUN ; Wei-Sheng FENG ; Hui CHEN
China Journal of Chinese Materia Medica 2025;50(11):3043-3048
Eight amide alkaloids(1-8) were isolated from the 70% ethanol extract of Cannabis Fructus using silica gel column chromatography, MCI column chromatography, and semi-preparative high-performance liquid chromatography(HPLC). Their structures were identified as hempspiramide A(1), N-[(4-hydroxyphenyl)ethyl]formamide(2), N-acetyltyramide(3), N-trans-p-coumaroyltyramine(4), N-trans-caffeoyltyramine(5), N-trans-feruloyltyramine(6), N-cis-p-coumaroyltyramine(7), N-cis-feruloyltyramine(8) by using spectroscopic methods such as NMR and MS. Among these compounds, compound 1 was a new amide alkaloid, while compounds 2 and 3 were isolated from Cannabis Fructus for the first time. Some of the isolates were assayed for their α-glucosidase inhibitory activity. Compounds 5-7 displayed significant inhibitory activity against α-glucosidase with IC_(50) values ranging from 1.07 to 4.63 μmol·L~(-1).
Cannabis/chemistry*
;
Alkaloids/pharmacology*
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Amides/isolation & purification*
;
Drugs, Chinese Herbal/isolation & purification*
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Fruit/chemistry*
;
Molecular Structure
;
alpha-Glucosidases/chemistry*
;
Chromatography, High Pressure Liquid
4.A new cephalotaxine-type alkaloid dimer from Cephalotaxus lanceolata.
Jia-Yang MA ; Jing WANG ; Sha CHEN ; Chun-Lei YUAN ; Jin-Yuan YANG ; Da-Hong LI ; Hui-Ming HUA
China Journal of Chinese Materia Medica 2025;50(13):3729-3741
The chemical constituents from Cephalotaxus lanceolata were isolated and purified by using multiple chromatographic techniques, including octadecylsilane(ODS), silica gel, Sephadex LH-20 column chromatography, and semi-preparative high-performance liquid chromatography(HPLC). A total of 17 compounds obtained were identified by using spectroscopic methods such as nuclear magnetic resonance(NMR), mass spectrometry(MS), and ultraviolet(UV) combined with literature data. Compound 1 was a new alkaloid dimer, named cephalancetine E. The known compounds were determined as cephalancetine A(2), 11-hydroxycephalotaxine(3), 4-hydroxycephalotaxine(4), cephalotaxine(5), epicephalotaxine(6), cephalotaxine β-N-oxide(7), acetylcephalotaxine(8), cephalotine A(9), cephalotine B(10), 11-hydroxycephalotaxine hemiketal(11), 3-deoxy-3,11-epoxy-cephalotaxine(12), cephalotaxinone(13), isocephalotaxinone(14), 2,11-epoxy-1,2-dihydro-8-oxo-cephalotaxine(15), cephalotaxamide(16), and drupacine(17), respectively. Compounds 11, 12, and 15 were isolated from the Cephalotaxus genus for the first time. The biological activity was tested for compounds 1-17. The results reveal that compound 17 displays potent inhibitory activities against three human cancer cell lines(HepG-2, MCF-7, and SH-SY5Y).
Cephalotaxus/chemistry*
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Humans
;
Cell Line, Tumor
;
Drugs, Chinese Herbal/pharmacology*
;
Harringtonines/pharmacology*
;
Molecular Structure
;
Dimerization
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Alkaloids/isolation & purification*
;
Magnetic Resonance Spectroscopy
5.Structurally novel tryptamine-derived alkaloids from the seeds of Peganum harmala and their antiviral activities against respiratory syncytial virus.
Zhongnan WU ; Yubo ZHANG ; Guocai WANG ; Qing TANG ; Yaolan LI ; Xiaoqing XIE ; Yushen LIANG ; Wen CHENG
Chinese Journal of Natural Medicines (English Ed.) 2025;23(8):972-979
Peganum harmala L. (P. harmala) is a significant economic and medicinal plant. The seeds of P. harmala have been extensively utilized in traditional Chinese medicine, Uighur medicine, and Mongolian medicine, as documented in the Drug Standard of the Ministry of Health of China. Twelve novel tryptamine-derived alkaloids (1-12) and eight known compounds (13-20) were isolated from P. harmala seeds. Compounds 1 and 2 represent the first reported instances of tryptamine-derived heteromers, comprising tryptamine and aniline fragments with previously undocumented C-3-N-1' linkage and C-3-C-4' connection, respectively. Compounds 3-5 were identified as indole-quinazoline heteromers, exhibiting a novel C-3 and NH-1' linkage between indole and quinazoline-derived fragments. Compound 6 demonstrates the dimerization pattern of C-C linked tryptamine-quinazoline dimer. Compound 8 represents a tryptamine-derived heterodimer with a distinctive carbon skeleton, featuring an unusual spiro-tricyclic ring (7) and conventional bicyclic tryptamine. Compounds 9-11 constitute novel 6/5/5/5 spiro-tetracyclic tryptamine-derived alkaloids presenting a unique ring system of tryptamine-spiro-pyrrolizine. Compounds 1-3 and 6-11 were identified as racemates. Compounds 2, 7, 9, 10, and 12 were confirmed via X-ray crystallographic analysis. All isolated compounds (1-20) exhibited varying degrees of antiviral efficacy against respiratory syncytial virus (RSV). Notably, the anti-RSV activity of compound 12 (IC50 5.01 ± 0.14 μmol·L-1) surpassed that of the positive control (ribavirin, IC50 6.23 ± 0.95 μmol·L-1), as validated through plaque reduction and immunofluorescence assays. The identification of anti-RSV compounds from P. harmala seeds may enhance the development and application of this plant in antiviral therapeutic products.
Antiviral Agents/isolation & purification*
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Tryptamines/isolation & purification*
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Peganum/chemistry*
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Seeds/chemistry*
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Alkaloids/isolation & purification*
;
Molecular Structure
;
Humans
;
Respiratory Syncytial Viruses/drug effects*
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Plant Extracts/pharmacology*
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Drugs, Chinese Herbal/pharmacology*
6.Simultaneous determination of six major isosteroidal alkaloids in Beimu by UPLC-ELSD.
Peng CHE ; Jiu-Shi LIU ; Yao-Dong QI ; Ting-Yan QIANG ; Yi-Chen SONG ; Xue-Ping WEI ; Hai-Tao LIU ; Ben-Gang ZHANG
China Journal of Chinese Materia Medica 2020;45(6):1393-1398
An UPLC method was established for the direct determination of six major bioactive isosteroidal alkaloids, namely peimisine, imperialine, sipeimine-3-D-glucoside, verticinone, verticine and hupehenine from the bulbus of Fritillaria(Beimu), a commonly used antitussive traditional Chinese medicinal(TCM) herb. An Acquity UPLC~(TM) CSH C_(18) column(2.1 mm×100 mm, 1.7 μm) was used for all analysis. The investigated six compounds were all separated with gradient mobile phase consisting of 0.02% diethylamine-water-methanol at a flow rate of 0.3 mL·min~(-1). The temperature of sample manager was set at 20 ℃. Drift tube temperature was 45 ℃, and spray parameter was 40% with injection volume of 1 μL. Then, the further quality assessment of Beimu was carried out by cluster analysis(CA) and principal component analysis(PCA). The investigated all had good linearity(r≥0.998 9) over the tested ranges. The method is simple, accurate and reproducible, and can be used for determining the content of six major bioactive isosteroidal alkaloids.
Alkaloids/isolation & purification*
;
Chromatography, High Pressure Liquid
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Drugs, Chinese Herbal/chemistry*
;
Fritillaria/chemistry*
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Phytochemicals/isolation & purification*
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Plant Roots/chemistry*
7.Three new diterpenoid alkaloids isolated from Aconitum brevicalcaratum.
Yan SHU ; Tian-Peng YIN ; Jia-Peng WANG ; Dong GAN ; Qin-Yan ZHANG ; Le CAI ; Zhong-Tao DING
Chinese Journal of Natural Medicines (English Ed.) 2018;16(11):866-870
In the present study, three new aconitine-type diterpenoid alkaloids brochyponines A-C (1-3) were isolated from the roots of Aconitum brevicalcaratum. Their structures were established on the basis of extensive spectroscopic analyses (IR, HR-ESI-MS, and 1D and 2D NMR). The NMR data of salt form for compound 1 in CDCl were also measured.
Aconitum
;
chemistry
;
Alkaloids
;
chemistry
;
isolation & purification
;
Drugs, Chinese Herbal
;
chemistry
;
isolation & purification
;
Magnetic Resonance Spectroscopy
;
Molecular Structure
;
Plant Roots
;
chemistry
8.Carbazole alkaloids isolated from the branch and leaf extracts of Clausena lansium.
Wen-Wen PENG ; Li-Xia ZHENG ; Chang-Jiu JI ; Xu-Gen SHI ; Zhong-Hua XIONG ; Xin-Chen SHANGGUAN
Chinese Journal of Natural Medicines (English Ed.) 2018;16(7):509-512
The present study carried out a phytochemical investigation of the methanol extract of the branches and leaves of Clausena lansium and afforded nine carbazole alkaloids (compounds 1-9) including two new carbazole alkaloids, claulansiums A and B (compounds 1 and 2). The new compounds were elucidated on the basis of extensive spectroscopic data (MS, NMR, IR, and UV) and the known compounds were identified by comparing spectroscopic data with those reported in literature. All the isolated compounds were tested for their cytotoxic activity against A549 and Hela cancer cell lines. Our results showed that compounds 2-6 exhibited varying degrees of cytotoxicity to cancer cells, with IC values ranging from 8.67 to 98.89 μmol·L.
A549 Cells
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Alkaloids
;
chemistry
;
isolation & purification
;
toxicity
;
Antineoplastic Agents
;
chemistry
;
isolation & purification
;
toxicity
;
Carbazoles
;
chemistry
;
isolation & purification
;
toxicity
;
Cell Line, Tumor
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Cell Survival
;
drug effects
;
Clausena
;
chemistry
;
HeLa Cells
;
Humans
;
Molecular Structure
;
Plant Extracts
;
chemistry
;
toxicity
;
Plant Leaves
;
chemistry
;
Plant Stems
;
chemistry
;
Plants, Medicinal
;
chemistry
9.New steroidal alkaloid and furostanol glycosides isolated from Solanum lyratum with cytotoxicity.
Yun-Ling XU ; Jia LV ; Wei-Fang WANG ; Yue LIU ; Ya-Juan XU ; Tun-Hai XU
Chinese Journal of Natural Medicines (English Ed.) 2018;16(7):499-504
Two previously undescribed steroidal compounds, 16, 23-epoxy-22, 26-epimino-cholest-22(N), 23, 25(26)-trien-3β-ol-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (1) and 26-O-β-D-glucopyranosyl-(25R)-5α-furost-20(22)-en-3β, 26-diol (2), together with 7 known ones including 26-O-β-D-glucopyranosyl-(25R)-5, 20(22)-dien-furost-3β, 26-diol (3), (25R)-5-en-spirost-3β-ol-O-β-D-glucopyranosyl-(1→4)-[α-L-rhmanopyranosyl-(1→2)]-β-D-galactopyranoside (4), funkioside D (5), aspidistrin (6), tigogenin-3-O-β-D-lucotrioside (7), desglucolanatigonin II (8), and degalactotigonin (9), were isolated from Solanum lyratum Thunb. Their cytotoxic activities were tested in two cancer cell lines by MTT method. One of the steroidal glycosides (6) showed significant cytotoxic activity against gastric cancer SGC7901 and liver cancer BEL-7402 cells.
Alkaloids
;
chemistry
;
isolation & purification
;
toxicity
;
Antineoplastic Agents
;
chemistry
;
isolation & purification
;
toxicity
;
Cell Line, Tumor
;
Cell Survival
;
drug effects
;
Glycosides
;
chemistry
;
pharmacology
;
toxicity
;
Humans
;
Inhibitory Concentration 50
;
Molecular Structure
;
Phytosterols
;
chemistry
;
isolation & purification
;
toxicity
;
Plant Extracts
;
chemistry
;
toxicity
;
Plants, Medicinal
;
chemistry
;
Solanum
;
chemistry
;
Sterols
;
chemistry
;
pharmacology
;
toxicity
10.Antibacterial sorbicillin and diketopiperazines from the endogenous fungus Penicillium sp. GD6 associated Chinese mangrove Bruguiera gymnorrhiza.
Cheng-Shi JIANG ; Zhen-Fang ZHOU ; Xiao-Hong YANG ; Le-Fu LAN ; Yu-Cheng GU ; Bo-Ping YE ; Yue-Wei GUO
Chinese Journal of Natural Medicines (English Ed.) 2018;16(5):358-365
One new sorbicillin derivative, 2-deoxy-sohirnone C (1), one new diketopiperazine alkaloid, 5S-hydroxynorvaline-S-Ile (2), and two naturally occurring diketopiperazines, 3S-hydroxylcyclo(S-Pro-S-Phe) (3) and cyclo(S-Phe-S-Gln) (4), together with three known compounds were isolated from the Chinese mangrove endophytic fungus Penicillium sp. GD6. Their structures were determined on the basis of extensive spectroscopic analyses and by comparison with literature data. The absolute configuration of 3-hydroxyl moiety in 3 was determined by Mosher's method, while the absolute stereochemistry of 2 and 4 was established by comparison with the CD spectra of natural and synthesized diketopiperazines. Compound 1 showed moderate antibacterial activity against Methicillin-resistant Staphylococcus aureus with a MIC value of 80 μg·mL.
Alkaloids
;
chemistry
;
isolation & purification
;
Anti-Bacterial Agents
;
chemistry
;
isolation & purification
;
pharmacology
;
China
;
Circular Dichroism
;
Diketopiperazines
;
chemistry
;
isolation & purification
;
Methicillin-Resistant Staphylococcus aureus
;
drug effects
;
Microbial Sensitivity Tests
;
Molecular Structure
;
Nuclear Magnetic Resonance, Biomolecular
;
Penicillium
;
chemistry
;
Resorcinols
;
chemistry
;
isolation & purification
;
pharmacology
;
Rhizophoraceae
;
microbiology
;
Wetlands

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