MOMORDIN IIB (BioDeep_00000230638)

Main id: BioDeep_00000230830

 

PANOMIX_OTCML-2023


代谢物信息卡片


(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

化学式: C42H66O14 (794.4452336)
中文名称: 竹节人参皂苷 IVA
谱图信息: 最多检出来源 () 0%

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@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O)CO)C)C)C)(C)C)O[C@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O)C(=O)O
InChI: InChI=1S/C42H66O14/c1-37(2)14-16-42(36(52)56-34-30(48)27(45)26(44)22(19-43)53-34)17-15-40(6)20(21(42)18-37)8-9-24-39(5)12-11-25(38(3,4)23(39)10-13-41(24,40)7)54-35-31(49)28(46)29(47)32(55-35)33(50)51/h8,21-32,34-35,43-49H,9-19H2,1-7H3,(H,50,51)/t21-,22+,23-,24+,25-,26+,27-,28-,29-,30+,31+,32-,34-,35+,39-,40+,41+,42-/m0/s1

描述信息

Chikusetsusaponin-IVa is a triterpenoid saponin. It has a role as a metabolite.
Chikusetsusaponin iva is a natural product found in Swartzia simplex, Anredera baselloides, and other organisms with data available.
See also: Calendula Officinalis Flower (part of).
Chikusetsusaponin IVa a major active ingredient of triterpenoid saponins, exerts antithrombotic effects, including minor hemorrhagic events. This appears to be important for the development of new therapeutic agents. a novel AMPK activator that is capable of bypassing defective insulin signalling and could be useful for the treatment of T2DM or other metabolic disorders. IC50 Value: 199.4 ± 9.1 μM (inhibiting thrombin-induced fibrinogen clotting) Target: In vitro: Using biochemical and pharmacological methods, it proves that chikusetsusaponin IVa prolongs the recalcification time, prothrombin time, activated partial thromboplastin time, and thrombin time of normal human plasma in a dose-dependent manner; inhibits the amidolytic activity of thrombin and factor Xa upon synthetic substrates S2238 and S2222; inhibits thrombin-induced fibrinogen clotting (50\\% inhibition concentration, 199.4 ± 9.1 μM); inhibits thrombin- and collagen-induced platelet aggregation. Chikusetsusaponin IVa can also preferentially inhibits thrombin in a competitive manner (K(i)=219.6 μM) [1]. Chikusetsusaponin IVa suppresses the production of iNOS, COX-2, IL-1β, IL-6, and TNF-α in LPS-stimulated THP-1 cells likely by inhibiting NF-κB activation and ERK, JNK, and p38 signal pathway phosphorylation [2]. In vivo: Studies were performed on type 2 diabetic mellitus (T2DM) rats given CHS for 28 days to test the antihyperglycemic activity. Oral administration of CHS dose-dependently increased the level of serum insulin and decreased the rise in blood glucose level [3].
Chikusetsusaponin IVa a major active ingredient of triterpenoid saponins, exerts antithrombotic effects, including minor hemorrhagic events. This appears to be important for the development of new therapeutic agents. a novel AMPK activator that is capable of bypassing defective insulin signalling and could be useful for the treatment of T2DM or other metabolic disorders. IC50 Value: 199.4 ± 9.1 μM (inhibiting thrombin-induced fibrinogen clotting) Target: In vitro: Using biochemical and pharmacological methods, it proves that chikusetsusaponin IVa prolongs the recalcification time, prothrombin time, activated partial thromboplastin time, and thrombin time of normal human plasma in a dose-dependent manner; inhibits the amidolytic activity of thrombin and factor Xa upon synthetic substrates S2238 and S2222; inhibits thrombin-induced fibrinogen clotting (50\% inhibition concentration, 199.4 ± 9.1 μM); inhibits thrombin- and collagen-induced platelet aggregation. Chikusetsusaponin IVa can also preferentially inhibits thrombin in a competitive manner (K(i)=219.6 μM) [1]. Chikusetsusaponin IVa suppresses the production of iNOS, COX-2, IL-1β, IL-6, and TNF-α in LPS-stimulated THP-1 cells likely by inhibiting NF-κB activation and ERK, JNK, and p38 signal pathway phosphorylation [2]. In vivo: Studies were performed on type 2 diabetic mellitus (T2DM) rats given CHS for 28 days to test the antihyperglycemic activity. Oral administration of CHS dose-dependently increased the level of serum insulin and decreased the rise in blood glucose level [3].

同义名列表

18 个代谢物同义名

(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid; .BETA.-D-GLUCOPYRANOSIDURONIC ACID, (3.BETA.)-28-(.BETA.-D-GLUCOPYRANOSYLOXY)-28-OXOOLEAN-12-EN-3-YL; beta-D-Glucopyranosiduronic acid, (3beta)-28-(beta-D-glucopyranosyloxy)-28-oxoolean-12-en-3-yl; OLEANOLIC ACID 3-O-(.BETA.-D-GLUCURONOPYRANOSYL)-28-O-.BETA.-D-GLUCOPYRANOSIDE; 3-O-.BETA.-D-GLUCURONOPYRANOSYL)OLEANOLIC ACID 28-O-.BETA.-D-GLUCOPYRANOSIDE; OLEANOLIC ACID 3-O-(beta-D-GLUCURONOPYRANOSYL)-28-O-beta-D-GLUCOPYRANOSIDE; 3-O-beta-D-GLUCURONOPYRANOSYL)OLEANOLIC ACID 28-O-beta-D-GLUCOPYRANOSIDE; chikusetsu saponin IVa; Chikusetsusaponin-IVa; chikusetsusaponin IVa; Chikusetsu saponin a; UNII-T3FU6ZPR5V; Calenduloside F; SILPHIOSIDE G; MOMORDIN IIB; T3FU6ZPR5V; Oleanolic acid 3-O-[beta-D-glucuronopyranosyl]-28-O-bet.-D-glucopyranoside; b-D-Glucopyranosiduronic acid, (3b)-28-(b-D-glucopyranosyloxy)-28-oxoolean-12-en-3-yl



数据库引用编号

10 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)

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

  • Shivani Puri, Prithvi Pal Singh, Prateek Singh Bora, Upendra Sharma. Chemometric guided isolation of new triterpenoid saponins as acetylcholinesterase inhibitors from seeds of Achyranthes bidentata Blume. Fitoterapia. 2024 Jun; 175(?):105925. doi: 10.1016/j.fitote.2024.105925. [PMID: 38537885]
  • Tong Niu, Jinqian Yu, Zhenqiang Wang, Chuangchuang Wang, Yingjian Guo, Jian Li, Xiao Wang. Purification of triterpenoid saponins and 25R/25S-inokosterone from Achyranthes bidentata Bl. by high-speed countercurrent chromatography coupled silver nitrate coordination. Journal of separation science. 2024 Apr; 47(7):e2300901. doi: 10.1002/jssc.202300901. [PMID: 38605456]
  • Xiang Guo, Jinyu Ji, Jingkai Zhang, Xiaoqiang Hou, Xianyun Fu, Yanan Luo, Zhigang Mei, Zhitao Feng. Anti-inflammatory and osteoprotective effects of Chikusetsusaponin Ⅳa on rheumatoid arthritis via the JAK/STAT signaling pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Dec; 93(?):153801. doi: 10.1016/j.phymed.2021.153801. [PMID: 34758437]
  • Jie Yang, Yuanyuan Ling, Di Hua, Chenglei Zhao, Xiaoyan Sun, Xueting Cai, Jiao Chen, Chunping Hu, Peng Cao. IL-6R blockade by chikusetsusaponin IVa butyl ester inhibits Th17 cell differentiation and ameliorates collagen-induced arthritis. Cellular & molecular immunology. 2021 06; 18(6):1584-1586. doi: 10.1038/s41423-021-00651-6. [PMID: 33637959]
  • Qian Xie, Yang Liu, Ying Long, Zhou Wang, Sai Jiang, Rida Ahmed, Muhammad Daniyal, Bin Li, Bin Liu, Wei Wang. Hybrid-cell membrane-coated nanocomplex-loaded chikusetsusaponin IVa methyl ester for a combinational therapy against breast cancer assisted by Ce6. Biomaterials science. 2021 Apr; 9(8):2991-3004. doi: 10.1039/d0bm02211j. [PMID: 33651044]
  • Anmin Shao, Jianping Fei, Shuquan Feng, Jiandong Weng. Chikusetsu saponin IVa alleviated sevoflurane-induced neuroinflammation and cognitive impairment by blocking NLRP3/caspase-1 pathway. Pharmacological reports : PR. 2020 Aug; 72(4):833-845. doi: 10.1007/s43440-020-00078-2. [PMID: 32124392]
  • Van Mai Do, Cong Luan Tran, Tan Phat Nguyen. Polysciosides J and K, two new oleanane-type triterpenoid saponins from the leaves of Polyscias fruticosa (L.) harms. cultivating in An Giang Province, Viet Nam. Natural product research. 2020 May; 34(9):1250-1255. doi: 10.1080/14786419.2018.1557657. [PMID: 30663359]
  • Jia Cui, Jialin Duan, Jianjie Chu, Chao Guo, Miaomiao Xi, Yi Li, Yan Weng, Guo Wei, Ying Yin, Aidong Wen, Boling Qiao. Chikusetsu saponin IVa protects pancreatic β cell against intermittent high glucose-induced injury by activating Wnt/β-catenin/TCF7L2 pathway. Aging. 2020 01; 12(2):1591-1609. doi: 10.18632/aging.102702. [PMID: 31969494]
  • Navneet Kishore, Pradeep Kumar, Karuna Shanker, Akhilesh Kumar Verma. Human disorders associated with inflammation and the evolving role of natural products to overcome. European journal of medicinal chemistry. 2019 Oct; 179(?):272-309. doi: 10.1016/j.ejmech.2019.06.034. [PMID: 31255927]
  • Si-Wen Zheng, Sheng-Yuan Xiao, Jia Wang, Wei Hou, Ying-Ping Wang. Inhibitory Effects of Ginsenoside Ro on the Growth of B16F10 Melanoma via Its Metabolites. Molecules (Basel, Switzerland). 2019 Aug; 24(16):. doi: 10.3390/molecules24162985. [PMID: 31426477]
  • Yi Tao, Surun Huang, Jizhong Yan, Baochang Cai. Determination of major components from Radix Achyranthes bidentate using ultra high performance liquid chromatography with triple quadrupole tandem mass spectrometry and an evaluation of their anti-osteoporosis effect in vitro. Journal of separation science. 2019 Jul; 42(13):2214-2221. doi: 10.1002/jssc.201900146. [PMID: 31037819]
  • Jun Yin, Chang-Seob Seo, In Hyeok Hwang, Min Won Lee, Kwang Hoon Song. Anti-Obesity Activities of Chikusetsusaponin IVa and Dolichos lablab L. Seeds. Nutrients. 2018 Sep; 10(9):. doi: 10.3390/nu10091221. [PMID: 30177649]
  • Chengfu Yuan, Chaoqi Liu, Ting Wang, Yumin He, Zhiyong Zhou, Yaoyan Dun, Haixia Zhao, Dongming Ren, Junjie Wang, Changcheng Zhang, Ding Yuan. Chikusetsu saponin IVa ameliorates high fat diet-induced inflammation in adipose tissue of mice through inhibition of NLRP3 inflammasome activation and NF-κB signaling. Oncotarget. 2017 May; 8(19):31023-31040. doi: 10.18632/oncotarget.16052. [PMID: 28415686]
  • Ying Wang, Shi-Ping Liu, Mei-Hua Guo, Zhuo Wang. Determination and validation of chikusetsusaponin IVa in rat plasma by UPLC-MS/MS and its application to pharmacokinetic study. Biomedical chromatography : BMC. 2016 Sep; 30(9):1423-9. doi: 10.1002/bmc.3700. [PMID: 26864353]
  • Jie Yang, Shihui Qian, Xueting Cai, Wuguang Lu, Chunping Hu, Xiaoyan Sun, Yang Yang, Qiang Yu, S Paul Gao, Peng Cao. Chikusetsusaponin IVa Butyl Ester (CS-IVa-Be), a Novel IL6R Antagonist, Inhibits IL6/STAT3 Signaling Pathway and Induces Cancer Cell Apoptosis. Molecular cancer therapeutics. 2016 06; 15(6):1190-200. doi: 10.1158/1535-7163.mct-15-0551. [PMID: 26929249]
  • Yuki Kawahara, Tatsuro Hoshino, Hidetaka Morimoto, Tomofumi Shinizu, Yuji Narukawa, Hiroyuki Fuchino, Nobuo Kawahara, Fumiyuki Kiuchi. LC-MS-based quantification method for Achyranthes root saponins. Journal of natural medicines. 2016 Jan; 70(1):102-6. doi: 10.1007/s11418-015-0942-4. [PMID: 26439478]
  • Hae-Jun Lee, Ji-Sun Shin, Woo-Seok Lee, Heon-Yong Shim, Ji-Min Park, Dae-Sik Jang, Kyung-Tae Lee. Chikusetsusaponin IVa Methyl Ester Isolated from the Roots of Achyranthes japonica Suppresses LPS-Induced iNOS, TNF-α, IL-6, and IL-1β Expression by NF-κB and AP-1 Inactivation. Biological & pharmaceutical bulletin. 2016; 39(5):657-64. doi: 10.1248/bpb.b15-00572. [PMID: 27150139]
  • Xiaomei Song, Wei Wang, Xin Zhang, Yi Jiang, Xinjie Yang, Chong Deng, Zhenggang Yue, Zhishu Tang. Deglucose chikusetsusaponin IVa isolated from Rhizoma Panacis Majoris induces apoptosis in human HepG2 hepatoma cells. Molecular medicine reports. 2015 Oct; 12(4):5494-500. doi: 10.3892/mmr.2015.4035. [PMID: 26151883]
  • H Wang, J Qi, L Li, T Wu, Y Wang, X Wang, Q Ning. Inhibitory effects of Chikusetsusaponin IVa on lipopolysaccharide-induced pro-inflammatory responses in THP-1 cells. International journal of immunopathology and pharmacology. 2015 Sep; 28(3):308-17. doi: 10.1177/0394632015589519. [PMID: 26157065]
  • Yuwen Li, Tiejun Zhang, Jia Cui, Na Jia, Yin Wu, Miaomiao Xi, Aidong Wen. Chikusetsu saponin IVa regulates glucose uptake and fatty acid oxidation: implications in antihyperglycemic and hypolipidemic effects. The Journal of pharmacy and pharmacology. 2015 Jul; 67(7):997-1007. doi: 10.1111/jphp.12392. [PMID: 25677570]
  • Sainan Li, Ying Tang, Chunming Liu, Yuchi Zhang. Development of a method to screen and isolate potential α-glucosidase inhibitors from Panax japonicus C.A. Meyer by ultrafiltration, liquid chromatography, and counter-current chromatography. Journal of separation science. 2015 Jun; 38(12):2014-23. doi: 10.1002/jssc.201500064. [PMID: 25847676]
  • Jia Cui, Miao-Miao Xi, Yu-Wen Li, Jia-Lin Duan, Lei Wang, Yan Weng, Na Jia, Shan-Shan Cao, Rui-Li Li, Chao Wang, Chao Zhao, Yin Wu, Ai-Dong Wen. Insulinotropic effect of Chikusetsu saponin IVa in diabetic rats and pancreatic β-cells. Journal of ethnopharmacology. 2015 Apr; 164(?):334-9. doi: 10.1016/j.jep.2015.02.032. [PMID: 25701750]
  • Dongli Qi, Xiaolin Yang, Jing Chen, Fei Li, Xiupu Shi, Chunfeng Zhang, Zhonglin Yang. Determination of chikusetsusaponin V and chikusetsusaponin IV in rat plasma by liquid chromatography-mass spectrometry and its application to a preliminary pharmacokinetic study. Biomedical chromatography : BMC. 2013 Nov; 27(11):1568-73. doi: 10.1002/bmc.2961. [PMID: 23832283]
  • Tabitha Dahmer, Markus Berger, Adriana Gregory Barlette, José Reck, Jéferson Segalin, Simone Verza, George González Ortega, Simone Cristina Baggio Gnoatto, Jorge Almeida Guimarães, Hugo Verli, Grace Gosmann. Antithrombotic effect of chikusetsusaponin IVa isolated from Ilex paraguariensis (Maté). Journal of medicinal food. 2012 Dec; 15(12):1073-80. doi: 10.1089/jmf.2011.0320. [PMID: 23134458]
  • Kouichi Yoshizaki, Shoji Yahara. New triterpenoid saponins from fruits specimens of Panax japonicus collected in Kumamoto and Miyazaki prefectures (1). Chemical & pharmaceutical bulletin. 2012; 60(3):354-62. doi: 10.1248/cpb.60.354. [PMID: 22382416]
  • Hsiu-Hui Chan, Tsong-Long Hwang, Mopur Vijaya Bhaskar Reddy, Ding-Tzai Li, Keduo Qian, Kenneth F Bastow, Kuo-Hsiung Lee, Tian-Shung Wu. Bioactive constituents from the roots of Panax japonicus var. major and development of a LC-MS/MS method for distinguishing between natural and artifactual compounds. Journal of natural products. 2011 Apr; 74(4):796-802. doi: 10.1021/np100851s. [PMID: 21417387]
  • Qing-lan Guo, Bin Li, Jian Li, Jing-jing Li, Li-ying Xia, Jun-xing Dong. [Triterpenoid saponins of Alternanthera philoxeroides (Mart.) Griseb]. Yao xue xue bao = Acta pharmaceutica Sinica. 2011 Apr; 46(4):428-31. doi: . [PMID: 21751496]
  • Chun Liang, Yan Ding, Huu Tung Nguyen, Jeong-Ah Kim, Hye-Jin Boo, Hee-Kyoung Kang, Mahn Cuong Nguyen, Young Ho Kim. Oleanane-type triterpenoids from Panax stipuleanatus and their anticancer activities. Bioorganic & medicinal chemistry letters. 2010 Dec; 20(23):7110-5. doi: 10.1016/j.bmcl.2010.09.074. [PMID: 20951582]
  • Ping Wang, Stacy Ownby, Zhizhen Zhang, Wei Yuan, Shiyou Li. Cytotoxicity and inhibition of DNA topoisomerase I of polyhydroxylated triterpenoids and triterpenoid glycosides. Bioorganic & medicinal chemistry letters. 2010 May; 20(9):2790-6. doi: 10.1016/j.bmcl.2010.03.063. [PMID: 20371180]
  • Xiaomei Song, Lin Li, Guangming Yang, Baochang Cai. [HPLC determination of chikusetsusaponin IVa in Rhizoma Panacis Majoris from different producing areas]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Apr; 35(7):885-7. doi: 10.4268/cjcmm20100718. [PMID: 20575392]
  • Ariya Rattanathongkom, Jung-Bum Lee, Kyoko Hayashi, Bung-orn Sripanidkulchai, Tripetch Kanchanapoom, Toshimitsu Hayashi. Evaluation of chikusetsusaponin IVa isolated from Alternanthera philoxeroides for its potency against viral replication. Planta medica. 2009 Jun; 75(8):829-35. doi: 10.1055/s-0029-1185436. [PMID: 19277947]
  • Juan Li, Ping Li, Hui-Jun Li, Yue Song, Zhi-Ming Bi, Yan-Jing Li. Simultaneous qualification and quantification of eight triterpenoids in radix achyranthis bidentatae by high-performance liquid chromatography with evaporative light scattering detection and mass spectrometric detection. Journal of separation science. 2007 Apr; 30(6):843-50. doi: 10.1002/jssc.200600341. [PMID: 17536729]
  • Shu-ping Jia, Zhi-yong Yu, Zhi-fang Hao, Jian-xin Li. [Isolation and identification of triterpenoids from root of Achyranthes bidentata in Henan]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Aug; 31(15):1244-7. doi: . [PMID: 17048567]
  • P Yang, Y Shi, Q Pan. [Chemical constituents of Hemsleya pengxianensis W.J. Chang]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1995 Sep; 20(9):551-3, 576. doi: . [PMID: 8679094]