1-Hederin (BioDeep_00000000040)

 

Secondary id: BioDeep_00000175914, BioDeep_00000861028

PANOMIX_OTCML-2023


代谢物信息卡片


(4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-(((2S,3R,4S,5S)-4,5-Dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

化学式: C41H66O12 (750.4554036000001)
中文名称: Alpha常春藤苷, α-常春藤皂苷, α-常春藤苷, ALPHA-常春藤皂甙
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 1.82%

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)CO)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/C41H66O12/c1-21-28(44)30(46)31(47)33(51-21)53-32-29(45)24(43)19-50-34(32)52-27-11-12-37(4)25(38(27,5)20-42)10-13-40(7)26(37)9-8-22-23-18-36(2,3)14-16-41(23,35(48)49)17-15-39(22,40)6/h8,21,23-34,42-47H,9-20H2,1-7H3,(H,48,49)

描述信息

Kalopanaxsaponin A is a triterpenoid saponin that is hederagenin attached to a 2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl residue at position 3 via a glycosidic linkage. It has been isolated from the stem bark of Kalopanax pictus. It has a role as an anti-inflammatory agent and a plant metabolite. It is a pentacyclic triterpenoid, a triterpenoid saponin, a disaccharide derivative and a hydroxy monocarboxylic acid. It is functionally related to a hederagenin.
alpha-Hederin is a natural product found in Lonicera japonica, Hedera caucasigena, and other organisms with data available.
A triterpenoid saponin that is hederagenin attached to a 2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl residue at position 3 via a glycosidic linkage. It has been isolated from the stem bark of Kalopanax pictus.
alpha-Hederin (α-Hederin), a monodesmosidic triterpenoid saponin, exhibits promising antitumor potential against a variety of human cancer cell lines. alpha-Hederin could inhibit the proliferation and induce apoptosis of gastric cancer accompanied by glutathione decrement and reactive oxygen species generation via activating mitochondrial dependent pathway[1].
alpha-Hederin (α-Hederin), a monodesmosidic triterpenoid saponin, exhibits promising antitumor potential against a variety of human cancer cell lines. alpha-Hederin could inhibit the proliferation and induce apoptosis of gastric cancer accompanied by glutathione decrement and reactive oxygen species generation via activating mitochondrial dependent pathway[1].

同义名列表

47 个代谢物同义名

(4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-(((2S,3R,4S,5S)-4,5-Dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid; (4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-(((2S,3R,4S,5S)-4,5-Dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylicacid; (4aS,6aR,6aS,6bR,8aR,9R,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-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid; (4aS,6aR,6aS,6bR,8aR,9R,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-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid; (4aS,6aR,6aS,6bR,8aR,9R,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-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylicacid; Olean-12-en-28-oic acid, 3-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.alpha.-L-arabinopyranosyl]oxy]-23-hydroxy-, (3.beta., 4.alpha.); OLEAN-12-EN-28-OIC ACID, 3-((2-O-(6-DEOXY-ALPHA-L- MANNOPYRANOSYL)-ALPHA-L-ARABINOPYRANOSYL)OXY)-23-HYDROXY-, (3-BETA,4-ALPHA)-; Olean-12-en-28-oic acid, 3-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl)oxy)-23-hydroxy-, (3-beta,4-alpha)-; (4.ALPHA.)-3.BETA.-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.ALPHA.- L-ARABINOPYRANOSYL)OXY)-23-HYDROXYOLEAN-12-EN-28-OIC ACID; (4ALPHA)-3BETA-((2-O-(6-DEOXY-ALPHA-L-MANNOPYRANOSYL)-ALPHA- L-ARABINOPYRANOSYL)OXY)-23-HYDROXYOLEAN-12-EN-28-OIC ACID; (4alpha)-3beta-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl)oxy)-23-hydroxyolean-12-en-28-oic acid; 3beta-{[2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy}-23-hydroxyolean-12-en-28-oic acid; 3-O-alpha-L-rhamnopyranosyl-(1->2)-alpha-L-arabinopyranosyl hederagenin; 4-17-00-02560 (Beilstein Handbook Reference); Rha-Ara-3beta-hederagenin; alpha-Hederine [French]; ALFA-HEDERINA [WHO-DD]; alpha-Hederin hydrate; Pulsatilla saponin A; .ALPHA.-HEDERIN [MI]; Kalopanaxsaponin A; Prosapogenin CP3b; Kizuta saponin K6; Akebia saponin PD; Akebiasaponin PD; Kizutasaponin K6; UNII-4H15F0GLV2; .alpha.-hederin; Glycoside L-E1; Koronaroside A; alpha-Hederine; ALFA-HEDERINA; Akeboside Stc; alpha-Hederin; Helixin (VAN); Sapindoside A; Hederoside C; Tauroside E; 4H15F0GLV2; Nepalin 2; α-Hederin; Hederin; Helixin; Hederagenin 3-O-alpha-L-rhamnopyranosyl(1-; 2)-alpha-L-arabinopyranoside; (+)-Kalopanaxsaponin A; (+)-Sapindoside A



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

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PharmGKB(0)

71 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

  • Shugao Han, Xi Yang, Jing Zhuang, Qing Zhou, Jingjing Wang, Lixin Ru, Furong Niu, Wei Mao. α-Hederin promotes ferroptosis and reverses cisplatin chemoresistance in non-small cell lung cancer. Aging. 2024 Jan; 16(2):1298-1317. doi: 10.18632/aging.205408. [PMID: 38244586]
  • Dandan Meng, Meng Ren, Maofeng Li, Min Wang, Wei Geng, Qingxin Shang. Molecular mechanism of α-Hederin in tumor progression. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2024 Jan; 170(?):116097. doi: 10.1016/j.biopha.2023.116097. [PMID: 38160624]
  • Jinbao Chen, Jian Xu, Jiahua Yang, Yueping Zhan, Sen Li, Linlin Jia, Wentao Wu, Xianke Si, Die Zhang, Kun Yu, Peihao Yin, Yijun Cao, Wanli Deng, Ke Xu, Wei Li. α‑hederin overcomes hypoxia‑mediated drug resistance in colorectal cancer by inhibiting the AKT/Bcl2 pathway. International journal of oncology. 2023 03; 62(3):. doi: 10.3892/ijo.2023.5481. [PMID: 36704835]
  • Hui Feng, Jiani Tan, Qijuan Wang, Tingting Zhou, Liu Li, Dongdong Sun, Minmin Fan, Haibo Cheng, Weixing Shen. α-hederin regulates glucose metabolism in intestinal epithelial cells by increasing SNX10 expression. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Mar; 111(?):154677. doi: 10.1016/j.phymed.2023.154677. [PMID: 36724620]
  • Yue Wu, Dongliang Wang, Yuqing Lou, Xiyu Liu, Pinzheng Huang, Mingming Jin, Gang Huang. Regulatory mechanism of α-hederin upon cisplatin sensibility in NSCLC at safe dose by destroying GSS/GSH/GPX2 axis-mediated glutathione oxidation-reduction system. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Jun; 150(?):112927. doi: 10.1016/j.biopha.2022.112927. [PMID: 35398749]
  • Linna Cao, Yiwei Zhang, Jinxia Mi, Zhanhao Shi, Zhaoqin Fang, Dongwei Jia, Zhiqiang Pan, Peike Peng. α-Hederin inhibits the platelet activating factor-induced metastasis of HCC cells through disruption of PAF/PTAFR axis cascaded STAT3/MMP-2 expression. Pharmacological research. 2022 04; 178(?):106180. doi: 10.1016/j.phrs.2022.106180. [PMID: 35288308]
  • Feng Dong, Yanhua Pu, Yanfei Lv, Xiujuan Liu, Yimin Cao. Protective effect of Pulsatilla saponin A on acute myocardial infarction via miR-24-3p/p16. Toxicology mechanisms and methods. 2022 Jan; 32(1):27-36. doi: 10.1080/15376516.2021.1963364. [PMID: 34412561]
  • Cong Fang, Yahui Liu, Lanying Chen, Yingying Luo, Yaru Cui, Ni Zhang, Peng Liu, Mengjing Zhou, Yongyan Xie. α-Hederin inhibits the growth of lung cancer A549 cells in vitro and in vivo by decreasing SIRT6 dependent glycolysis. Pharmaceutical biology. 2021 Dec; 59(1):11-20. doi: 10.1080/13880209.2020.1862250. [PMID: 33356727]
  • 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]
  • Namrta Choudhry, Xin Zhao, Dan Xu, Mark Zanin, Weisan Chen, Zifeng Yang, Jianxin Chen. Chinese Therapeutic Strategy for Fighting COVID-19 and Potential Small-Molecule Inhibitors against Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2). Journal of medicinal chemistry. 2020 11; 63(22):13205-13227. doi: 10.1021/acs.jmedchem.0c00626. [PMID: 32845145]
  • Orlagh Anderson, Joseph Beckett, Carla C Briggs, Liam A Natrass, Charles F Cranston, Elizabeth J Wilkinson, Jack H Owen, Rhodri Mir Williams, Angelos Loukaidis, Marc E Bouillon, Deiniol Pritchard, Martina Lahmann, Mark S Baird, Paul W Denny. An investigation of the antileishmanial properties of semi-synthetic saponins. RSC medicinal chemistry. 2020 Jul; 11(7):833-842. doi: 10.1039/d0md00123f. [PMID: 33479679]
  • 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]
  • Xiaohang Tong, Li Han, Huaqing Duan, Yaru Cui, Yulin Feng, Yongming Zhu, Zhong Chen, Shilin Yang. The derivatives of Pulsatilla saponin A, a bioactive compound from Pulsatilla chinensis: Their synthesis, cytotoxicity, haemolytic toxicity and mechanism of action. European journal of medicinal chemistry. 2017 Mar; 129(?):325-336. doi: 10.1016/j.ejmech.2017.02.025. [PMID: 28237662]
  • Qiang Liu, Weichang Chen, Yang Jiao, Jianquan Hou, Qingyu Wu, Yanli Liu, Xiaofei Qi. Pulsatilla saponin A, an active molecule from Pulsatilla chinensis, induces cancer cell death and inhibits tumor growth in mouse xenograft models. The Journal of surgical research. 2014 May; 188(2):387-95. doi: 10.1016/j.jss.2014.01.026. [PMID: 24576780]
  • Grace Gar-Lee Yue, Kar-Man Chan, Ming-Ho To, Ling Cheng, Kwok-Pui Fung, Ping-Chung Leung, Clara Bik-San Lau. Potent airway smooth muscle relaxant effect of cynatratoside B, a steroidal glycoside isolated from Cynanchum stauntonii. Journal of natural products. 2014 Apr; 77(4):1074-7. doi: 10.1021/np4008969. [PMID: 24761833]
  • Stefan Böttger, Katja Hofmann, Matthias F Melzig. Saponins can perturb biologic membranes and reduce the surface tension of aqueous solutions: a correlation?. Bioorganic & medicinal chemistry. 2012 May; 20(9):2822-8. doi: 10.1016/j.bmc.2012.03.032. [PMID: 22503361]
  • Tran H Quang, Nguyen T T Ngan, Chau V Minh, Phan V Kiem, Nguyen X Nhiem, Bui H Tai, Nguyen P Thao, Nguyen H Tung, Seok B Song, Young H Kim. Anti-inflammatory triterpenoid saponins from the stem bark of Kalopanax pictus. Journal of natural products. 2011 Sep; 74(9):1908-15. doi: 10.1021/np200382s. [PMID: 21870831]
  • M Sautour, A-C Mitaine-Offer, T Miyamoto, A Dongmo, M-A Lacaille-Dubois. Antifungal steroid saponins from Dioscorea cayenensis. Planta medica. 2004 Jan; 70(1):90-2. doi: 10.1055/s-2004-815467. [PMID: 14765305]
  • Y Mimaki, A Yokosuka, M Kuroda, M Hamanaka, C Sakuma, Y Sashida. New bisdesmosidic triterpene saponins from the roots of Pulsatilla chinensis. Journal of natural products. 2001 Sep; 64(9):1226-9. doi: 10.1021/np010252t. [PMID: 11575962]
  • Y Mimaki, M Kuroda, T Asano, Y Sashida. Triterpene saponins and lignans from the roots of Pulsatilla chinensis and their cytotoxic activity against HL-60 cells. Journal of natural products. 1999 Sep; 62(9):1279-83. doi: 10.1021/np9901837. [PMID: 10514313]