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Rapid Analysis of Four Alkaloids in uncaria rhynchophylla by Core-Shell Column HPLC and Quantitative Analysis of Multi-Components by Single Marker(QAMS)

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Phyton-International Journal of Experimental Botany 2023年第1期92卷 285-296页

作者： Kesheng Lin Jiawen Zhou Lijuan Han Ning Li KMHD(Kangmeihuada Gene Technology Co. Ltd.)Shenzhen518128China Guangdong Province Enterprise Key Laboratory of Traditional Chinese Medicine Decoction Pieces Kangmei Pharmaceutical Co.Ltd.Jieyang515300China

As a traditional herbal medicine,the major alkaloids in uncaria rhynchophylla have been proven to have blood pressure-lowering and sedative effects.It is essential to develop an effective method for the determination of the major alkaloids in U.rhynchophylla.In this research,a rapid quantitative analysis involving multi-components analysis by a single marker strategy coupled with core-shell column HPLC was adopted to analyse four alkaloids(corynoxeine,isocorynoxeine,isorhynchophylline,rhynchophylline)in U.rhynchophylla.Isorhynchophylline was selected as the internal reference substance,the content of which was determined by the traditional external standard method.Relative correction factors(RCF)between isorhynchophylline and the other three alkaloids were calculated respectively.The results showed that the QAMS method had good robustness under different HPLC instruments.Nineteen batches of U.rhynchophylla were tested.No significant difference was observed between the results by QAMS and EMS(Correlation coefficient>0.99,p>0.05).The QAMS method could be employed as a rapid,effective technique for the quality control of U.rhynchophylla.

关键词： uncaria rhynchophylla HPLC core-shell column QAMS

Two folate-derived analogues from an aqueous decoction of uncaria rhynchophylla

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Chinese Journal of Natural Medicines 2019年第12期17卷 928-934页

作者： WANG Yue GUO Qing-Lan LI Ruo-Fei XU Cheng-Bo ZHU Cheng-Gen SHI Jian-Gong State Key Laboratory of Bioactive Substance and Function of Natural Medicines Institute of Materia Medica Chinese Academy of Medical Sciences and Peking Union Medical College

Two new folate-derived analogues,named uncarophyllofolic acids A(1)and B(2),respectively,were isolated from the uncaria rhynchophylla hook bearing stem(Gouteng in Chinese).The distinct stereochemical structures of 1 and 2 were determined by spectroscopic data analysis in combination with acidic hydrolysis and Marfey’s derivatization,along with comparison of their specific rotation and Cotton effect(CE)data with those of the biogenetically related known derivatives as well as theoretical calculations of electronic circular dichroism(ECD)spectra.A plausible biosynthetic pathway of 1 and 2,associating to folate metabolism and the previously reported orychophragines A-C from Orychophragmus violaceus,is discussed.

关键词： Rubiaceae uncaria rhynchophylla Folate derivative Uncarophyllofolic acid Folate metabolism

Two new ortho benzoquinones from uncaria rhynchophylla

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Chinese Journal of Natural Medicines 2016年第3期14卷 232-235页

作者： ZHANG Qian CHEN Lei HU Le-Jian LIU Wen-Yuan FENG Feng QU Wei Department of Natural Medicinal Chemistry China Pharmaceutical University Department of Pharmaceutical Analysis China Pharmaceutical University Key Laboratory of Biomedical Functional Materials China Pharmaceutical University

The present study was designed to determine the chemical constituents of the stems and hooks of uncaria rhynchophylla. The chemical constituents were isolated and purified from CH_2Cl_2 fraction by chromatography. Their structures were elucidated by spectroscopic analyses. Their cytotoxicity was tested using MTT method. Two new ortho benzoquinones, 3-diethylamino-5-methoxy-1, 2-benzoquinone(1) and 3-ethylamino-5-methoxy-1, 2-benzoquinone(2), together with a known compound isorhynchophyllic acid(3) were isolated from U. rhynchophylla. These compounds were evaluated for their cytotoxicity against cancer cells A549, Hep G2 and A2780. Compounds 1 and 2 were new ortho benzoquinones and showed weak antiproliferative activities on A549, Hep G2 and A2780 cells. Compound 3 significantly inhibited the proliferation of A549, Hep G2 and A2780 cells with IC_(50) values being 5.8, 12.8 and 11.8 μmol·L^(–1), respectively.

关键词： uncaria rhynchophylla Ortho benzoquinones Spectroscopic identification

Pseudotargeted metabolomics for exploring the changes of neurotransmitters profile in aging rat brain and the potential neuroprotective effect of alkaloids from uncaria rhynchophylla

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Traditional Medicine Research 2022年第5期7卷 1-9页

作者： Shi-Wei Li Yi-Song Wu Shi-Fei Wu Wen-Long Wei Ming-Yang Qiu Yun Li De-An Guo College of Pharmacy Changchun University of Chinese MedicineChangchun 130117China Shanghai Research Center for Modernization of Traditional Chinese Medicine National Engineering Research Center of TCM Standardization TechnologyShanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China

Background:Aging is an essential risk factor for most neurodegenerative diseases,including Alzheimer’s disease and Parkinson’s disease.However,changes in the levels of neurotransmitters that are associated with aging are not well understood.Methods:Methods such as liquid-liquid extraction,protein precipitation,and solid-phase extraction,using 20 different extraction solvents,were evaluated to optimize the extraction of neurotransmitters.A pseudotargeted metabolomics approach was developed to detect neurotransmitters in brain tissues using ultra-high-performance liquid chromatography coupled with tandem triple quadrupole mass spectrometry.Alkaloids that crossed into the brain were used to evaluate the effect of glutamic acid-induced excitatory neurotoxicity in SH-SY5Y cells.Results:The overall extraction efficiency using protein precipitation was high.The changes in neurotransmitters’levels in the brain exhibited changes during the different growth cycles.The levels of seven neurotransmitters(aspartic acid,tyrosine,isoleucine,leucine,tryptophan,valine,andγ-aminobutyric acid)were significantly different.Meanwhile,alkaloids could reduce the excitatory neurotoxicity of glutamic acid-induced SH-SY5Y cells via suppression of oxidative stress.Conclusion:Significant differences were observed in neurotransmitter profiling between 1-and 8-month-old rats,and the discrepant neurotransmitters were associated with aging.Seven indole alkaloids from uncaria rhynchophylla,which could cross the blood-brain barrier,were screened and used to explore their protective effects against aging.uncaria rhynchophylla alkaloids exhibited a neuroprotective effect by inhibiting oxidative stress,indicating that the alkaloid could be a potential therapeutic candidate for neurological disorders caused by glutamic acid toxicity.

关键词： neurotransmitters aging uncaria rhynchophylla indole alkaloids neuroprotective effect pseudotargeted metabolomics

Indole Alkaloids Inhibiting Neural Stem Cell from uncaria rhynchophylla

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Natural Products and Bioprospecting 2017年第5期7卷 413-419页

作者： Xin Wei Li-Ping Jiang Ying Guo Afsar Khan Ya-Ping Liu Hao-Fei Yu Bei Wang Cai-Feng Ding Pei-Feng Zhu Ying-Ying Chen Yun-Li Zhao Yong-Bing Chen Yi-Fen Wang Xiao-Dong Luo State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201People’s Republic of China University of Chinese Academy of Sciences Beijing 100049People’s Republic of China Key Laboratory of Animal Models and Human Disease Mechanisms Kunming Institute of ZoologyChinese Academy of SciencesKunming 650223People’s Republic of China Department of Chemistry COMSATS Institute of Information TechnologyAbbottabad 22060Pakistan Yunnan Key Laboratory of Natural Medicinal Chemistry Kunming 650201People’s Republic of China

uncaria rhynchophylla is commonly recognized as a traditional treatment for dizziness,cerebrovascular diseases,and nervous disorders in China.Previously,the neuro-protective activities of the alkaloids from U.rhynchophylla were intensively reported.In current work,three new indole alkaloids(1–3),identified as geissoschizic acid(1),geissoschizic acid N4-oxide(2),and 3b-sitsirikine N4-oxide(3),as well as 26 known analogues were isolated from U.rhynchophylla.However,in the neural stem cells(NSCs)proliferation assay for all isolated compounds,geissoschizic acid(1),geissoschizic acid N4-oxide(2),isocorynoxeine(6),isorhynchophylline(7),(4S)-akuammigine N-oxide(8),and(4S)-rhynchophylline N-oxide(10)showed unexpected inhibitory activities at 10 μM.Unlike previous neuro-protective reports,as a warning or caution,our finding showcased a clue for possible NSCs toxicity and the neural lesions risk of U.rhynchophylla,while the structure–activity relationships of the isolated compounds were discussed also.

关键词： uncaria rhynchophylla Indole alkaloids NSCs proliferation