harpagide (BioDeep_00000231592)
Main id: BioDeep_00000230050
PANOMIX_OTCML-2023
代谢物信息卡片
(7S)-4a,5,7-trihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl D-glucopyranoside
化学式: C15H24O10 (364.13694039999996)
中文名称: 哈巴苷, 6-表哈帕甙
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)O
InChI: InChI=1S/C15H24O10/c1-14(21)4-7(17)15(22)2-3-23-13(11(14)15)25-12-10(20)9(19)8(18)6(5-16)24-12/h2-3,6-13,16-22H,4-5H2,1H3
描述信息
Origin: Plant; SubCategory_DNP: Monoterpenoids, Harpagide monoterpenoids
Harpagide is a class of iridoid glycoside isolated from Scrophularia ningpoensis and has antiparasitic activity, which exhibits good in vitro trypanocidal activities against African trypanosomes (T.b. rhodesiense) with an IC50 of 21 μg/mL. Harpagide exerts significant antileishmanial activity against L. donovani with an IC50 value of 2.0 μg/mL. Harpagide also possess significant anti-inflammatory activities[1][2].
Harpagide is a class of iridoid glycoside isolated from Scrophularia ningpoensis and has antiparasitic activity, which exhibits good in vitro trypanocidal activities against African trypanosomes (T.b. rhodesiense) with an IC50 of 21 μg/mL. Harpagide exerts significant antileishmanial activity against L. donovani with an IC50 value of 2.0 μg/mL. Harpagide also possess significant anti-inflammatory activities[1][2].
同义名列表
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
2 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Yasuhiko Izumi, Harue Kataoka, Yuki Takada-Takatori, Yutaka Koyama, Kazuhiro Irie, Akinori Akaike, Toshiaki Kume. Isolation and Purification of Harpagogenin as an Nrf2-ARE Activator from the Tubers of Chinese Artichoke (Stachys sieboldii).
Biological & pharmaceutical bulletin.
2023; 46(11):1576-1582. doi:
10.1248/bpb.b23-00383. [PMID: 37914360] - Yuxin Xiao, Mengfei Tian, Qinglong Liu, Baoti Xu, Yang Peng, Chunjian Zhao, Chunying Li. A novel absorbent, HOF-3@PU: Preparation and application for sustainable and efficient purification of catalpol and ajugol from Rehmannia glutinosa leaves.
Natural product research.
2022 Sep; ?(?):1-7. doi:
10.1080/14786419.2022.2119968. [PMID: 36070589] - Ochuko L Erukainure, Olubunmi Atolani, Aliyu Muhammad, Sanusi B Katsayal, Osadolor O Ebhuoma, Collins U Ibeji, M Ahmed Mesaik. Targeting the initiation and termination codons of SARS-CoV-2 spike protein as possible therapy against COVID-19: the role of novel harpagide 5-O-β-D-glucopyranoside from Clerodendrum volubile P Beauv. (Labiatae).
Journal of biomolecular structure & dynamics.
2022 04; 40(6):2475-2488. doi:
10.1080/07391102.2020.1840439. [PMID: 33140706] - Heng Zhang, Junfeng Lu, Hao Liu, Lingling Guan, Shiqing Xu, Zai Wang, Yang Qiu, Honglin Liu, Liang Peng, Xiuli Men. Ajugol enhances TFEB-mediated lysosome biogenesis and lipophagy to alleviate non-alcoholic fatty liver disease.
Pharmacological research.
2021 12; 174(?):105964. doi:
10.1016/j.phrs.2021.105964. [PMID: 34732369] - Yunwei Lu, Renjuan Hao, Yingchao Hu, Yuyan Wei, Yuyan Xie, Yu Shen, Qinglin Rui, Guran Yu. Harpagide alleviate neuronal apoptosis and blood-brain barrier leakage by inhibiting TLR4/MyD88/NF-κB signaling pathway in Angiotensin II-induced microglial activation in vitro.
Chemico-biological interactions.
2021 Oct; 348(?):109653. doi:
10.1016/j.cbi.2021.109653. [PMID: 34516974] - Dan Gao, Vinh Le Ba, Rustamov Rustam, Chong Woon Cho, Seo Young Yang, Xiang Dong Su, Young Ho Kim, Jong Seong Kang. Isolation of bioactive components with soluble epoxide hydrolase inhibitory activity from Stachys sieboldii MiQ. by ultrasonic-assisted extraction optimized using response surface methodology.
Preparative biochemistry & biotechnology.
2021; 51(4):395-404. doi:
10.1080/10826068.2020.1821217. [PMID: 32940554] - Claudio Frezza, Daniela de Vita, Chiara Toniolo, Antonio Ventrone, Lamberto Tomassini, Sebastiano Foddai, Marcello Nicoletti, Marcella Guiso, Armandodoriano Bianco, Mauro Serafini. Harpagide: Occurrence in plants and biological activities - A review.
Fitoterapia.
2020 Nov; 147(?):104764. doi:
10.1016/j.fitote.2020.104764. [PMID: 33122133] - Ke Wang, Yeliang Lou, Huang Xu, Xiaoming Zhong, Zhen Huang. Harpagide from Scrophularia protects rat cortical neurons from oxygen-glucose deprivation and reoxygenation-induced injury by decreasing endoplasmic reticulum stress.
Journal of ethnopharmacology.
2020 May; 253(?):112614. doi:
10.1016/j.jep.2020.112614. [PMID: 32007630] - Zhan-Yun Shen, Bo Zhu, Quan-Long Zhang, Lu-Ping Qin. [Isolation and identification of endophytic fungi producing harpagoside and harpagide from Scrophularia ningpoensis].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2019 May; 44(10):2046-2050. doi:
10.19540/j.cnki.cjcmm.20190301.008. [PMID: 31355559] - Gülin Renda, Büşra Korkmaz, Merve Kılıç, Mine Kadıoğlu Duman, Hasan Kırmızıbekmez. Evaluation of in vivo analgesic activity of Scrophularia kotscyhana and isolation of bioactive compounds through activity-guided fractionation.
Natural product research.
2018 Aug; 32(16):1902-1910. doi:
10.1080/14786419.2017.1356829. [PMID: 28758426] - Claudio Frezza, Alessandro Venditti, Giorgia Matrone, Ilaria Serafini, Sebastiano Foddai, Armandodoriano Bianco, Mauro Serafini. Iridoid glycosides and polyphenolic compounds from Teucrium chamaedrys L.
Natural product research.
2018 Jul; 32(13):1583-1589. doi:
10.1080/14786419.2017.1392948. [PMID: 29058476] - Ewa Skrzypczak-Pietraszek, Katarzyna Reiss, Paweł Żmudzki, Jacek Pietraszek. Enhanced accumulation of harpagide and 8-O-acetyl-harpagide in Melittis melissophyllum L. agitated shoot cultures analyzed by UPLC-MS/MS.
PloS one.
2018; 13(8):e0202556. doi:
10.1371/journal.pone.0202556. [PMID: 30133513] - Claudio Frezza, Alessandro Venditti, Mirella Di Cecco, Giampiero Ciaschetti, Mauro Serafini, Armandodoriano Bianco. Iridoids and phenylethanoid glycosides from the aerial parts of Ajuga tenorei, an endemic Italian species.
Natural product research.
2017 Jan; 31(2):218-223. doi:
10.1080/14786419.2016.1218490. [PMID: 27492580] - A Venditti, C Frezza, F Maggi, G Lupidi, M Bramucci, L Quassinti, C Giuliani, K Cianfaglione, F Papa, M Serafini, A Bianco. Phytochemistry, micromorphology and bioactivities of Ajuga chamaepitys (L.) Schreb. (Lamiaceae, Ajugoideae): Two new harpagide derivatives and an unusual iridoid glycosides pattern.
Fitoterapia.
2016 Sep; 113(?):35-43. doi:
10.1016/j.fitote.2016.06.016. [PMID: 27373875] - P Schopohl, P Grüneberg, M F Melzig. The influence of harpagoside and harpagide on TNFα-secretion and cell adhesion molecule mRNA-expression in IFNγ/LPS-stimulated THP-1 cells.
Fitoterapia.
2016 Apr; 110(?):157-65. doi:
10.1016/j.fitote.2016.03.005. [PMID: 26979254] - Gang Cao, Xin Wu, Qinglin Li, Hao Cai, Baochang Cai, Xuemei Zhu. Influence of processing procedure on the quality of Radix Scrophulariae: a quantitative evaluation of the main compounds obtained by accelerated solvent extraction and high-performance liquid chromatography.
Journal of separation science.
2015 Feb; 38(3):390-4. doi:
10.1002/jssc.201401141. [PMID: 25431110] - Yukun Feng, Zhenzhen Liu, Ying Peng, Lunhui Zhang, Ping Ju, Kaishun Bi, Xiaohui Chen. Validated LC-MS method for simultaneous quantitation of catalpol and harpagide in rat plasma: application to a comparative pharmacokinetic study in normal and diabetic rats after oral administration of Zeng-Ye-Decoction.
Biomedical chromatography : BMC.
2013 Nov; 27(11):1503-10. doi:
10.1002/bmc.2949. [PMID: 23754598] - Jie Zhong, Zhao-dan Tan, Tian-ming Wang, Rong Shi, Yue-ming Ma. [Absorption and pharmacokinetics of radix rehmanniae in rats].
Yao xue xue bao = Acta pharmaceutica Sinica.
2013 Sep; 48(9):1464-70. doi:
. [PMID: 24358782] - Bin-Yu Wen, Jian-Rong Li. [Pharmacokinetics of 8-O-acetylharpagide and harpagide after oral administration of Ajuga decumbens extract in beagle dog].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2013 Jun; 38(12):2015-8. doi:
NULL. [PMID: 24066603] - Binyu Wen, Rong He, Pengyue Li, Qihua Xu, Yanli Lu, Bo Peng, Jianrong Li. Pharmacokinetics of 8-O-acetylharpagide and harpagide after oral administration of Ajuga decumbens Thunb extract in rats.
Journal of ethnopharmacology.
2013 May; 147(2):503-8. doi:
10.1016/j.jep.2013.03.048. [PMID: 23545457] - A Venditti, A M Serrilli, M Di Cecco, G Ciaschetti, T Andrisano, A Bianco. Phytochemical composition of polar fraction of Stachys germanica L. subsp. salviifolia (Ten.) Gams, a typical plant of Majella National Park.
Natural product research.
2013; 27(2):190-3. doi:
10.1080/14786419.2012.661732. [PMID: 22372659] - Yun'e Bai, Pengfei Yuan, Qinghui Wang, Suli Wang, Yuewei Ge, Zhengri Niu, Mingying Shang, Guangxue Liu, Chen Li, Shaoqing Cai. [Determination of harpagide and harpagoside in Scrophulariae Radix by HPLC-UV].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2011 Oct; 36(19):2697-702. doi:
. [PMID: 22242433] - Liuqiang Zhang, Li Feng, Qi Jia, Jinwen Xu, Rui Wang, Zhengtao Wang, Yingchun Wu, Yiming Li. Effects of β-glucosidase hydrolyzed products of harpagide and harpagoside on cyclooxygenase-2 (COX-2) in vitro.
Bioorganic & medicinal chemistry.
2011 Aug; 19(16):4882-6. doi:
10.1016/j.bmc.2011.06.069. [PMID: 21775152] - Maryam Modarai, Andy Suter, Andreas Kortenkamp, Michael Heinrich. The interaction potential of herbal medicinal products: a luminescence-based screening platform assessing effects on cytochrome P450 and its use with devil's claw (Harpagophyti radix) preparations.
The Journal of pharmacy and pharmacology.
2011 Mar; 63(3):429-38. doi:
10.1111/j.2042-7158.2010.01235.x. [PMID: 21749392] - Xuemei Zhang, Rui Wang, Rui An, Ximin Wu, Xinhong Wang, Yiming Li. [Simultaneous determination of five constituents in Scrophularia ningpoensis by HPLC].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2011 Mar; 36(6):709-11. doi:
. [PMID: 21710734] - Raju Gautam, Sanjay M Jachak, Arvind Saklani. Anti-inflammatory effect of Ajuga bracteosa Wall Ex Benth. mediated through cyclooxygenase (COX) inhibition.
Journal of ethnopharmacology.
2011 Jan; 133(2):928-30. doi:
10.1016/j.jep.2010.11.003. [PMID: 21073945] - C A Elusiyan, N C Ani, C O Adewunmi, T A Olugbade. Distribution of iridiod glucosides and anti-oxidant compounds in Spathodea campanulata parts.
African journal of traditional, complementary, and alternative medicines : AJTCAM.
2011; 8(1):27-33. doi:
10.4314/ajtcam.v8i1.60491. [PMID: 22238480] - Nassima Abdelouahab Ouitas, Charles Heard. Estimation of the relative antiinflammatory efficacies of six commercial preparations of Harpagophytum procumbens (Devil's Claw).
Phytotherapy research : PTR.
2010 Mar; 24(3):333-8. doi:
10.1002/ptr.2930. [PMID: 19610038] - Jing Li, Xiaoyan Huang, Xianjie Du, Wenji Sun, Yongmin Zhang. Study of chemical composition and antimicrobial activity of leaves and roots of Scrophularia ningpoensis.
Natural product research.
2009; 23(8):775-80. doi:
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Fitoterapia.
2008 Dec; 79(7-8):595-7. doi:
10.1016/j.fitote.2008.06.009. [PMID: 18672034] - Deniz Tasdemir, Reto Brun, Scott G Franzblau, Yükselen Sezgin, Ihsan Calis. Evaluation of antiprotozoal and antimycobacterial activities of the resin glycosides and the other metabolites of Scrophularia cryptophila.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2008 Mar; 15(3):209-15. doi:
10.1016/j.phymed.2007.07.032. [PMID: 17761408] - Cyril Colas, Patrice Garcia, Marie-Agnès Popot, Yves Bonnaire, Stéphane Bouchonnet. Optimization of solid-phase extraction for the liquid chromatography-mass spectrometry analysis of harpagoside, 8-para-coumaroyl harpagide, and harpagide in equine plasma and urine.
Journal of chromatographic science.
2008 Feb; 46(2):174-83. doi:
10.1093/chromsci/46.2.174. [PMID: 18366880] - Esra Küpeli Akkol, I Irem Tatli, Zeliha S Akdemir. Antinociceptive and anti-inflammatory effects of saponin and iridoid glycosides from Verbascum pterocalycinum var. mutense Hub.-Mor.
Zeitschrift fur Naturforschung. C, Journal of biosciences.
2007 Nov; 62(11-12):813-20. doi:
10.1515/znc-2007-11-1207. [PMID: 18274283] - Cyril Colas, Stéphane Bouchonnet, Françoise Rogalewicz-Gilard, Marie-Agnès Popot, Gilles Ohanessian. Proton and sodium cation affinities of harpagide: a computational study.
The journal of physical chemistry. A.
2006 Jun; 110(23):7503-8. doi:
10.1021/jp061526u. [PMID: 16759142] - Cyril Colas, Patrice Garcia, Marie-Agnès Popot, Yves Bonnaire, Stéphane Bouchonnet. Liquid chromatography/electrospray ionization mass spectrometric characterization of Harpagophytum in equine urine and plasma.
Rapid communications in mass spectrometry : RCM.
2006; 20(22):3257-66. doi:
10.1002/rcm.2721. [PMID: 17044124] - Christoph Seger, Markus Godejohann, Li-Hong Tseng, Manfred Spraul, Anny Girtler, Sonja Sturm, Hermann Stuppner. LC-DAD-MS/SPE-NMR hyphenation. A tool for the analysis of pharmaceutically used plant extracts: identification of isobaric iridoid glycoside regioisomers from Harpagophytum procumbens.
Analytical chemistry.
2005 Feb; 77(3):878-85. doi:
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Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
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Journal of ethnopharmacology.
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Journal de pharmacie de Belgique.
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