β-Hederin (BioDeep_00000001014)

   

PANOMIX_OTCML-2023


代谢物信息卡片


(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

化学式: C41H66O11 (734.4604886000001)
中文名称: Α-常春藤素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 2.48%

分子结构信息

SMILES: C1[C@@H](C([C@H]2[C@](C1)([C@@H]1[C@@](CC2)([C@]2(C(=CC1)[C@H]1[C@@](CC2)(CCC(C1)(C)C)C(=O)O)C)C)C)(C)C)O[C@@H]1[C@@H]([C@@H]([C@@H](CO1)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)C)O)O)O
InChI: InChI=1S/C41H66O11/c1-21-28(43)30(45)31(46)33(50-21)52-32-29(44)24(42)20-49-34(32)51-27-12-13-38(6)25(37(27,4)5)11-14-40(8)26(38)10-9-22-23-19-36(2,3)15-17-41(23,35(47)48)18-16-39(22,40)7/h9,21,23-34,42-46H,10-20H2,1-8H3,(H,47,48)/t21-,23+,24-,25+,26-,27+,28+,29-,30+,31-,32-,33+,34-,38+,39-,40-,41+/m1/s1

描述信息

Beta-Hederin is a triterpenoid.
beta-Hederin is a natural product found in Hedera caucasigena, Akebia quinata, and other organisms with data available.

同义名列表

8 个代谢物同义名

(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid; (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid; Olean-12-en-28-oic acid, 3-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.alpha.-L-arabinopyranosyl]oxy]-, (3.beta.)-; (3beta)-3-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl)oxy)olean-12-en-28-oic acid; .beta.-Hederin; beta-Hederin; β-Hederin; a-Hederin



数据库引用编号

14 个数据库交叉引用编号

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)

12 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

  • Xiwu Rao, Ziwen Li, Qinchang Zhang, Yueyang Lai, Jianrong Liu, Liu Li, Haibo Cheng, Weixing Shen, Dongdong Sun. α-Hederin induces paraptosis by targeting GPCRs to activate Ca2+/MAPK signaling pathway in colorectal cancer. Cancer medicine. 2024 Apr; 13(8):e7202. doi: 10.1002/cam4.7202. [PMID: 38659391]
  • Dan Su, Tingting Wang, Chen Jin, Yali Liu, Abid Naeem, Zhou Liao, Mingyue Zhou, Changlian Chen, Yonggui Song, Zhifu Ai. Pulchinenosides: Correlation of surface activity-cytotoxicity and hepatocyte apoptosis mechanism study. Bioorganic & medicinal chemistry letters. 2021 07; 43(?):128080. doi: 10.1016/j.bmcl.2021.128080. [PMID: 33964439]
  • Saeideh Saadat, Mohammad Reza Aslani, Vahideh Ghorani, Rana Keyhanmanesh, Mohammad Hossein Boskabady. The effects of Nigella sativa on respiratory, allergic and immunologic disorders, evidence from experimental and clinical studies, a comprehensive and updated review. Phytotherapy research : PTR. 2021 Jun; 35(6):2968-2996. doi: 10.1002/ptr.7003. [PMID: 33455047]
  • Mohammad Nazrul Islam, Khandkar Shaharina Hossain, Partha Protim Sarker, Jannatul Ferdous, Md Abdul Hannan, Md Masudur Rahman, Dinh-Toi Chu, Md Jamal Uddin. Revisiting pharmacological potentials of Nigella sativa seed: A promising option for COVID-19 prevention and cure. Phytotherapy research : PTR. 2021 Mar; 35(3):1329-1344. doi: 10.1002/ptr.6895. [PMID: 33047412]
  • Ki-Baek Jeong, Sang-Mook You, Jin-Sung Park, Ke Luo, In-Seong Hwang, Hwankyu Lee, Young-Rok Kim. Topological analysis of single-stranded DNA with an alpha-hederin nanopore. Biosensors & bioelectronics. 2021 Jan; 171(?):112711. doi: 10.1016/j.bios.2020.112711. [PMID: 33059170]
  • Wen Gao, Ke Liu, Rui Wang, Xin-Guang Liu, Xiao-Shi Li, Ping Li, Hua Yang. Integration of targeted metabolite profiling and sequential optimization method for discovery of chemical marker combination to identify the closely-related plant species. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Aug; 61(?):152829. doi: 10.1016/j.phymed.2019.152829. [PMID: 31039532]
  • Jian Sun, Yu Feng, Yan Wang, Qing Ji, Gang Cai, Lei Shi, Yiyi Wang, Yan Huang, Jue Zhang, Qi Li. α-hederin induces autophagic cell death in colorectal cancer cells through reactive oxygen species dependent AMPK/mTOR signaling pathway activation. International journal of oncology. 2019 May; 54(5):1601-1612. doi: 10.3892/ijo.2019.4757. [PMID: 30896843]
  • Ki-Baek Jeong, Ke Luo, Hwankyu Lee, Min-Cheol Lim, Jin Yu, Soo-Jin Choi, Ki-Bum Kim, Tae-Joon Jeon, Young-Rok Kim. Alpha-Hederin Nanopore for Single Nucleotide Discrimination. ACS nano. 2019 02; 13(2):1719-1727. doi: 10.1021/acsnano.8b07797. [PMID: 30657663]
  • Dongdong Sun, Weixing Shen, Feng Zhang, Huisen Fan, Changliang Xu, Liu Li, Jiani Tan, Yunjie Miao, Haibin Zhang, Ye Yang, Haibo Cheng. α-Hederin inhibits interleukin 6-induced epithelial-to-mesenchymal transition associated with disruption of JAK2/STAT3 signaling in colon cancer cells. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 May; 101(?):107-114. doi: 10.1016/j.biopha.2018.02.062. [PMID: 29477470]
  • Dongdong Sun, Weixing Shen, Feng Zhang, Huisen Fan, Jiani Tan, Liu Li, Changliang Xu, Haibin Zhang, Ye Yang, Haibo Cheng. α-Hederin Arrests Cell Cycle at G2/M Checkpoint and Promotes Mitochondrial Apoptosis by Blocking Nuclear Factor-κB Signaling in Colon Cancer Cells. BioMed research international. 2018; 2018(?):2548378. doi: 10.1155/2018/2548378. [PMID: 30363706]
  • Heena Tabassum, Asad Ahmad, Iffat Z Ahmad. Nigella sativa L. and Its Bioactive Constituents as Hepatoprotectant: A Review. Current pharmaceutical biotechnology. 2018; 19(1):43-67. doi: 10.2174/1389201019666180427110007. [PMID: 29701149]
  • An-Guo Wu, Wu Zeng, Vincent Kam-Wai Wong, Yi-Zhun Zhu, Amy C Y Lo, Liang Liu, Betty Yuen-Kwan Law. Hederagenin and α-hederin promote degradation of proteins in neurodegenerative diseases and improve motor deficits in MPTP-mice. Pharmacological research. 2017 01; 115(?):25-44. doi: 10.1016/j.phrs.2016.11.002. [PMID: 27838509]
  • Miao Yu, Jiaxin Liu, Lin Li, Haiyan Xu, Yanyan Xing, Yunli Zhao, Zhiguo Yu. Pharmacokinetic parameters of three active ingredients hederacoside C, hederacoside D, and ɑ-hederin in Hedera helix in rats. Journal of separation science. 2016 Sep; 39(17):3292-301. doi: 10.1002/jssc.201600523. [PMID: 27377040]
  • Zhuo Liu, Hui Ouyang, Zhi-Feng Li, Yan Li, Yu-Lin Feng, Ming-Zhen He, Shi-Lin Yang. [Pharmacokinetics and tissue distribution of α-hederin sodium salt in rats]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2016 Jul; 41(13):2543-2548. doi: 10.4268/cjcmm20161329. [PMID: 28905583]
  • Kamil Wojciechowski, Marta Orczyk, Thomas Gutberlet, Thomas Geue. Complexation of phospholipids and cholesterol by triterpenic saponins in bulk and in monolayers. Biochimica et biophysica acta. 2016 Feb; 1858(2):363-73. doi: 10.1016/j.bbamem.2015.12.001. [PMID: 26654784]
  • Rong Zhu, Chun-ge Zhang, Yang Liu, Zhi-qiang Yuan, Wei-liang Chen, Shu-di Yang, Ji-zhao Li, Wen-jing Zhu, Xiao-feng Zhou, Ben-gang You, Xue-nong Zhang. CD147 monoclonal antibody mediated by chitosan nanoparticles loaded with α-hederin enhances antineoplastic activity and cellular uptake in liver cancer cells. Scientific reports. 2015 Dec; 5(?):17904. doi: 10.1038/srep17904. [PMID: 26639052]
  • Rana Keyhanmanesh, Saeideh Saadat, Mostafa Mohammadi, Amir-Ali Shahbazfar, Maryam Fallahi. The Protective Effect of α-Hederin, the Active Constituent of Nigella sativa, on Lung Inflammation and Blood Cytokines in Ovalbumin Sensitized Guinea Pigs. Phytotherapy research : PTR. 2015 Nov; 29(11):1761-7. doi: 10.1002/ptr.5429. [PMID: 26292851]
  • Lucie Havliková, Kateřina Macáková, Lubomir Opleta, Petr Solich. Rapid Determination of α-Hederin and Hederacoside C in Extracts of Hedera helix Leaves Available in the Czech Republic and Poland. Natural product communications. 2015 Sep; 10(9):1529-31. doi: . [PMID: 26594750]
  • Christian Greunke, Anne Hage-Hülsmann, Thomas Sorkalla, Nelli Keksel, Felix Häberlein, Hanns Häberlein. A systematic study on the influence of the main ingredients of an ivy leaves dry extract on the β2-adrenergic responsiveness of human airway smooth muscle cells. Pulmonary pharmacology & therapeutics. 2015 Apr; 31(?):92-8. doi: 10.1016/j.pupt.2014.09.002. [PMID: 25234924]
  • Lin Cheng, Tian-Song Xia, Yi-Fen Wang, Wenbin Zhou, Xiu-Qing Liang, Jin-Qiu Xue, Liang Shi, Ying Wang, Qiang Ding, Minhai Wang. The anticancer effect and mechanism of α-hederin on breast cancer cells. International journal of oncology. 2014 Aug; 45(2):757-63. doi: 10.3892/ijo.2014.2449. [PMID: 24842044]
  • Thomas A K Prescott, Luke P Rigby, Nigel C Veitch, Monique S J Simmonds. The haploinsufficiency profile of α-hederin suggests a caspofungin-like antifungal mode of action. Phytochemistry. 2014 May; 101(?):116-20. doi: 10.1016/j.phytochem.2014.01.022. [PMID: 24569176]
  • Joseph Lorent, Laurence Lins, Òscar Domenech, Joelle Quetin-Leclercq, Robert Brasseur, Marie-Paule Mingeot-Leclercq. Domain formation and permeabilization induced by the saponin α-hederin and its aglycone hederagenin in a cholesterol-containing bilayer. Langmuir : the ACS journal of surfaces and colloids. 2014 Apr; 30(16):4556-69. doi: 10.1021/la4049902. [PMID: 24690040]
  • Joseph Lorent, Cécile S Le Duff, Joelle Quetin-Leclercq, Marie-Paule Mingeot-Leclercq. Induction of highly curved structures in relation to membrane permeabilization and budding by the triterpenoid saponins, α- and δ-Hederin. The Journal of biological chemistry. 2013 May; 288(20):14000-14017. doi: 10.1074/jbc.m112.407635. [PMID: 23530040]
  • M Mendel, M Chłopecka, N Dziekan, W Karlik, M Wiechetek. Participation of cholinergic pathways in α-hederin-induced contraction of rat isolated stomach strips. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2012 May; 19(7):591-5. doi: 10.1016/j.phymed.2012.02.011. [PMID: 22465216]
  • Anne Wolf, Reinoud Gosens, Herman Meurs, Hanns Häberlein. Pre-treatment with α-hederin increases β-adrenoceptor mediated relaxation of airway smooth muscle. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2011 Jan; 18(2-3):214-8. doi: 10.1016/j.phymed.2010.05.010. [PMID: 20637581]
  • Geva Feller, Aleksandra Kugel, Dana Moonshine, Vered Chalifa-Caspi, Martin Scholz, Dirk Prüfer, Tatiana Rabinski, Kai J Müller, Rivka Ofir. African descents are more sensitive than European descents to the antitumor compounds α-hederin and kalopanaxsaponin I. Planta medica. 2010 Nov; 76(16):1847-51. doi: 10.1055/s-0030-1250061. [PMID: 20577945]
  • K Foubert, F Cuyckens, K Vleeschouwer, M Theunis, A Vlietinck, L Pieters, S Apers. Rapid quantification of 14 saponins of Maesa lanceolata by UPLC-MS/MS. Talanta. 2010 Jun; 81(4-5):1258-63. doi: 10.1016/j.talanta.2010.02.018. [PMID: 20441893]
  • Jens K Nielsen, Tsuneatsu Nagao, Hikaru Okabe, Tetsuro Shinoda. Resistance in the plant, Barbarea vulgaris, and counter-adaptations in flea beetles mediated by saponins. Journal of chemical ecology. 2010 Mar; 36(3):277-85. doi: 10.1007/s10886-010-9758-6. [PMID: 20177743]
  • Martin Scholz, Marta Lipinski, Marco Leupold, Heinrich Luftmann, Lena Harig, Rivka Ofir, Rainer Fischer, Dirk Prüfer, Kai J Müller. Methyl jasmonate induced accumulation of kalopanaxsaponin I in Nigella sativa. Phytochemistry. 2009 Mar; 70(4):517-22. doi: 10.1016/j.phytochem.2009.01.018. [PMID: 19282005]
  • Yu-ming Liu, Jun-shan Yang, Qing-hua Liu. [Studies on chemical constituents in the seeds of Nigella glandulifera]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 Jul; 30(13):980-3. doi: ". [PMID: 16161422]
  • A Gepdiremen, V Mshvildadze, H Süleyman, R Elias. Acute anti-inflammatory activity of four saponins isolated from ivy: alpha-hederin, hederasaponin-C, hederacolchiside-E and hederacolchiside-F in carrageenan-induced rat paw edema. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2005 Jun; 12(6-7):440-4. doi: 10.1016/j.phymed.2004.04.005. [PMID: 16008120]
  • Ilhami Gülçin, Vakhtang Mshvildadze, Akçahan Gepdiremen, Riad Elias. Antioxidant activity of saponins isolated from ivy: alpha-hederin, hederasaponin-C, hederacolchiside-E and hederacolchiside-F. Planta medica. 2004 Jun; 70(6):561-3. doi: 10.1055/s-2004-827158. [PMID: 15241892]
  • Oliver Hegener, Lars Prenner, Frank Runkel, Stephan Leonhardt Baader, Joachim Kappler, Hanns Häberlein. Dynamics of beta2-adrenergic receptor-ligand complexes on living cells. Biochemistry. 2004 May; 43(20):6190-9. doi: 10.1021/bi035928t. [PMID: 15147203]
  • Yvan Gaillard, Pierre Blaise, Alexandre Darré, Thierry Barbier, Gilbert Pépin. An unusual case of death: suffocation caused by leaves of common ivy (Hedera helix). Detection of hederacoside C, alpha-hederin, and hederagenin by LC-EI/MS-MS. Journal of analytical toxicology. 2003 May; 27(4):257-62. doi: 10.1093/jat/27.4.257. [PMID: 12820750]
  • Da Wei Li, Jin Ee Hyun, Choon Sik Jeong, Yeong Shik Kim, Eun Bang Lee. Antiinflammatory activity of alpha-hederin methyl ester from the alkaline hydrolysate of the butanol fraction of Kalopanax pictus bark extract. Biological & pharmaceutical bulletin. 2003 Apr; 26(4):429-33. doi: 10.1248/bpb.26.429. [PMID: 12673020]
  • S Muthu Kumara Swamy, Benny Tan Kwong Huat. Intracellular glutathione depletion and reactive oxygen species generation are important in alpha-hederin-induced apoptosis of P388 cells. Molecular and cellular biochemistry. 2003 Mar; 245(1-2):127-39. doi: 10.1023/a:1022807207948. [PMID: 12708752]
  • Jongwon Choi, Keun Huh, Suk-Hwan Kim, Kyung-Tae Lee, Hee-Juhn Park, Yong Nam Han. Antinociceptive and anti-rheumatoidal effects of Kalopanax pictus extract and its saponin components in experimental animals. Journal of ethnopharmacology. 2002 Feb; 79(2):199-204. doi: 10.1016/s0378-8741(01)00383-x. [PMID: 11801382]
  • Jongwon Choi, Keun Huh, Suk Hwan Kim, Kyung Tae Lee, Hyeong Kyu Lee, Hee Juhn Park. Kalopanaxsaponin A from Kalopanax pictus, a potent antioxidant in the rheumatoidal rat treated with Freund's complete adjuvant reagent. Journal of ethnopharmacology. 2002 Jan; 79(1):113-8. doi: 10.1016/s0378-8741(01)00382-8. [PMID: 11744304]
  • P Villani, T Orsière, I Sari-Minodier, G Bouvenot, A Botta. [In vitro study of the antimutagenic activity of alphahederin]. Annales de biologie clinique. 2001 May; 59(3):285-9. doi: ". [PMID: 11397676]
  • J Choi, K Huh, S H Kim, K T Lee, S H Kwon, H J Park. Toxicology of Kalopanax pictus extract and hematological effect of the isolated anti-rheumatoidal kalopanaxsaponin A on the Freunds complete adjuvant reagent-treated rat. Archives of pharmacal research. 2001 Apr; 24(2):119-25. doi: 10.1007/bf02976479. [PMID: 11339631]
  • H J Park, S H Kwon, J H Lee, K H Lee, K Miyamoto, K T Lee. Kalopanaxsaponin A is a basic saponin structure for the anti-tumor activity of hederagenin monodesmosides. Planta medica. 2001 Mar; 67(2):118-21. doi: 10.1055/s-2001-11516. [PMID: 11301855]
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