Soyasaponin I (BioDeep_00000000599)

 

Secondary id: BioDeep_00000291751, BioDeep_00000859618

human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds natural product


代谢物信息卡片


(2S,3S,4S,5R,6R)-6-{[(3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-5-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

化学式: C48H78O18 (942.5187888)
中文名称: 大豆皂苷 BB, 大豆皂苷Bb
谱图信息: 最多检出来源 Homo sapiens(feces) 0.63%

分子结构信息

SMILES: CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4CCC5(C(C4(C)CO)CCC6(C5CC=C7C6(CCC8(C7CC(CC8O)(C)C)C)C)C)C)C(=O)O)O)O)CO)O)O)O)O)O
InChI: InChI=1S/C48H78O18/c1-21-29(52)31(54)35(58)40(61-21)65-37-32(55)30(53)24(19-49)62-41(37)66-38-34(57)33(56)36(39(59)60)64-42(38)63-28-12-13-45(5)25(46(28,6)20-50)11-14-48(8)26(45)10-9-22-23-17-43(2,3)18-27(51)44(23,4)15-16-47(22,48)7/h9,21,23-38,40-42,49-58H,10-20H2,1-8H3,(H,59,60)/t21-,23-,24+,25+,26+,27+,28-,29-,30-,31+,32-,33-,34-,35+,36-,37+,38+,40-,41-,42+,44+,45-,46+,47+,48+/m0/s1

描述信息

Soyasaponin I is a triterpenoid saponin that is composed of soyasapogenol B having an alpha-L-rhamnopyranosyl-(1->2)-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid moiety attached at the 3-position via a glycosidic linkage. It has a role as a sialyltransferase inhibitor. It is a pentacyclic triterpenoid, a triterpenoid saponin, a trisaccharide derivative and a carbohydrate acid derivative. It is functionally related to a soyasapogenol B. It is a conjugate acid of a soyasaponin I(1-).
Soyasaponin I is a natural product found in Crotalaria albida, Hedysarum polybotrys, and other organisms with data available.
A triterpenoid saponin that is composed of soyasapogenol B having an alpha-L-rhamnopyranosyl-(1->2)-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid moiety attached at the 3-position via a glycosidic linkage.
Azukisaponin V is found in pulses. Azukisaponin V is isolated from seeds of azuki bean (Vigna angularis).
soyasaponin Bb is a soyasaponin isolated from Phaseolus vulgaris, acting as an aldose reductase differential inhibitor (ARDI)[1].
soyasaponin Bb is a soyasaponin isolated from Phaseolus vulgaris, acting as an aldose reductase differential inhibitor (ARDI)[1].

同义名列表

27 个代谢物同义名

(2S,3S,4S,5R,6R)-6-{[(3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-5-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid; (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylic acid; 5-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-3,4-dihydroxy-6-[[9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]oxane-2-carboxylic acid; beta-D-Glucopyranosiduronic acid, (3beta,4beta,22beta)-22,23-dihydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-beta-D-galactopyranosyl-(1-2)-; (3beta,4beta,22beta)-22,23-Dihydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid; b-D-Glucopyranosiduronic acid, (3b,4b,22b)-22,23-dihydroxyolean-12-en-3-yl O-6-deoxy-.alpha.-L-mannopyranosyl-(1.2)-O-.beta.-D-galactopyranosyl-(1.2)-; (3beta,22beta)-22,24-dihydroxyolean-12-en-3-yl 6-deoxy-alpha-L-mannopyranosyl-(1->2)-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid; (3beta,22beta)-22,24-dihydroxyolean-12-en-3-yl alpha-L-rhamnopyranosyl-(1->2)-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid; (3Β,4β,22β)-22,23-dihydroxyolean-12-en-3-yl O-6-deoxy-α-L-mannopyranosyl-(1→2)-O-β-D-galactopyranosyl-(1→2)-β-D-glucopyranosiduronic acid; (3beta,22beta)-22,24-Dihydroxyolean-12-en-3-yl alpha-L-rhamnopyranosyl-(1->2)-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronate; (3Β,22β)-22,24-dihydroxyolean-12-en-3-yl α-L-rhamnopyranosyl-(1->2)-β-D-galactopyranosyl-(1->2)-β-D-glucopyranosiduronic acid; (3b,22b)-22,24-Dihydroxyolean-12-en-3-yl a-L-rhamnopyranosyl-(1->2)-b-D-galactopyranosyl-(1->2)-b-D-glucopyranosiduronic acid; (3Β,22β)-22,24-dihydroxyolean-12-en-3-yl α-L-rhamnopyranosyl-(1->2)-β-D-galactopyranosyl-(1->2)-β-D-glucopyranosiduronate; (3b,22b)-22,24-Dihydroxyolean-12-en-3-yl a-L-rhamnopyranosyl-(1->2)-b-D-galactopyranosyl-(1->2)-b-D-glucopyranosiduronate; Oleanane, b-D-glucopyranosiduronic acid deriv.; Soyasaponin Bb(Soyasaponin I); Soybean saponin fraction B1; PTDAHAWQAGSZDD-IOVCITQVSA-N; Soyasaponin b-I; Soyasaponin Bb; Soyasaponin-Bb; soyasaponin 1; SOYASAPONIN I; SoyasaponinBb; Soysaponin I; SCM 3B; Soyasaponin I



数据库引用编号

22 个数据库交叉引用编号

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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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173 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

  • Manami Sakanishi, Soo Yeon Chung, Kentaro Fujiwara, Mareshige Kojoma, Toshiya Muranaka, Hikaru Seki. Disruption of a licorice cellulose synthase-derived glycosyltransferase gene demonstrates its in planta role in soyasaponin biosynthesis. Plant cell reports. 2023 Dec; 43(1):15. doi: 10.1007/s00299-023-03095-6. [PMID: 38135741]
  • Wei-Ting Tsai, Yuki Nakamura, Taiki Akasaka, Yoshinori Katakura, Yasutake Tanaka, Bungo Shirouchi, Zhe Jiang, Xingyu Yuan, Masao Sato. Soyasaponin ameliorates obesity and reduces hepatic triacylglycerol accumulation by suppressing lipogenesis in high-fat diet-fed mice. Journal of food science. 2021 May; 86(5):2103-2117. doi: 10.1111/1750-3841.15696. [PMID: 33864648]
  • Junbin Chen, Hidayat Ullah, Zhongdaixi Zheng, Xiangfu Gu, Chuhong Su, Lingyu Xiao, Xinglong Wu, Fei Xiong, Qing Li, Longying Zha. Soyasaponins reduce inflammation by downregulating MyD88 expression and suppressing the recruitments of TLR4 and MyD88 into lipid rafts. BMC complementary medicine and therapies. 2020 Jun; 20(1):167. doi: 10.1186/s12906-020-2864-2. [PMID: 32493316]
  • Qunying Xie, Xiangfu Gu, Junbin Chen, Minshun Liu, Fei Xiong, Xinglong Wu, Yajie Zhang, Fengping Chen, Honger Chen, Meijuan Li, Suxia Sun, Xinwei Chu, Longying Zha. Soyasaponins Reduce Inflammation and Improve Serum Lipid Profiles and Glucose Homeostasis in High Fat Diet-Induced Obese Mice. Molecular nutrition & food research. 2018 10; 62(19):e1800205. doi: 10.1002/mnfr.201800205. [PMID: 30070430]
  • Edward C MacDonell, Istvan Rajcan. Identification of quantitative trait loci associated with soyasaponin I concentration in soybean seed. TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik. 2018 Oct; 131(10):2157-2165. doi: 10.1007/s00122-018-3144-0. [PMID: 30051334]
  • Safa M Shams Eldin, Mohamed M Radwan, Amira S Wanas, Abdel-Azim M Habib, Fahima F Kassem, Hala M Hammoda, Shabana I Khan, Michael L Klein, Khaled M Elokely, Mahmoud A ElSohly. Bioactivity-Guided Isolation of Potential Antidiabetic and Antihyperlipidemic Compounds from Trigonella stellata. Journal of natural products. 2018 05; 81(5):1154-1161. doi: 10.1021/acs.jnatprod.7b00707. [PMID: 29676912]
  • Raymond Malabed, Shinya Hanashima, Michio Murata, Kaori Sakurai. Sterol-recognition ability and membrane-disrupting activity of Ornithogalum saponin OSW-1 and usual 3-O-glycosyl saponins. Biochimica et biophysica acta. Biomembranes. 2017 Dec; 1859(12):2516-2525. doi: 10.1016/j.bbamem.2017.09.019. [PMID: 28947142]
  • Pilar Vila-Donat, Celia Fernández-Blanco, Gianni Sagratini, Guillermina Font, María-José Ruiz. Effects of soyasaponin I and soyasaponins-rich extract on the alternariol-induced cytotoxicity on Caco-2 cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2015 Mar; 77(?):44-9. doi: 10.1016/j.fct.2014.12.016. [PMID: 25542527]
  • Jing Lu, Jia-Hong Sun, Yao Tan, Yoshihiro Kano, Dan Yuan. New triterpenoid saponins from the flowers of Pueraria thomsonii. Journal of Asian natural products research. 2013; 15(10):1065-72. doi: 10.1080/10286020.2013.802690. [PMID: 24168266]
  • In-Ah Lee, Young-Jun Park, Hee-Kyung Yeo, Myung Joo Han, Dong-Hyun Kim. Soyasaponin I attenuates TNBS-Induced colitis in mice by inhibiting NF-κB pathway. Journal of agricultural and food chemistry. 2010 Oct; 58(20):10929-34. doi: 10.1021/jf102296y. [PMID: 20923188]
  • Wei Zhang, David G Popovich. Group B oleanane triterpenoid extract containing soyasaponins I and III from soy flour induces apoptosis in Hep-G2 cells. Journal of agricultural and food chemistry. 2010 May; 58(9):5315-9. doi: 10.1021/jf9037979. [PMID: 20345167]
  • Gianni Sagratini, Yanting Zuo, Giovanni Caprioli, Gloria Cristalli, Dario Giardinà, Filippo Maggi, Laura Molin, Massimo Ricciutelli, Piero Traldi, Sauro Vittori. Quantification of soyasaponins I and betag in Italian lentil seeds by solid-phase extraction (SPE) and high-performance liquid chromatography-mass spectrometry (HPLC-MS). Journal of agricultural and food chemistry. 2009 Dec; 57(23):11226-33. doi: 10.1021/jf901707z. [PMID: 19950999]
  • Wei Zhang, Mei Ching Yeo, Fang Yin Tang, David G Popovich. Bioactive responses of Hep-G2 cells to soyasaponin extracts differs with respect to extraction conditions. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2009 Sep; 47(9):2202-8. doi: 10.1016/j.fct.2009.06.006. [PMID: 19520140]
  • Wei Zhang, Su Ping Teng, David G Popovich. Generation of group B soyasaponins I and III by hydrolysis. Journal of agricultural and food chemistry. 2009 May; 57(9):3620-5. doi: 10.1021/jf803663j. [PMID: 19338335]
  • Wei Wang, Li-Qian Hai, Yu-Ying Zhao, Hu-Biao Chen, Bin Wang, Hong Liang. [Saponins from roots of Hedysarum multijugum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Feb; 32(4):315-7. doi: . [PMID: 17455466]
  • Wesley G Taylor, Paul G Fields, Daniel H Sutherland. Insecticidal components from field pea extracts: soyasaponins and lysolecithins. Journal of agricultural and food chemistry. 2004 Dec; 52(25):7484-90. doi: 10.1021/jf0308051. [PMID: 15675793]
  • Jiang Hu, Manju B Reddy, Suzanne Hendrich, Patricia A Murphy. Soyasaponin I and sapongenol B have limited absorption by Caco-2 intestinal cells and limited bioavailability in women. The Journal of nutrition. 2004 Aug; 134(8):1867-73. doi: 10.1093/jn/134.8.1867. [PMID: 15284368]
  • Jiang Hu, Yan L Zheng, Walter Hyde, Suzanne Hendrich, Patricia A Murphy. Human fecal metabolism of soyasaponin I. Journal of agricultural and food chemistry. 2004 May; 52(9):2689-96. doi: 10.1021/jf035290s. [PMID: 15113177]
  • Hiroaki Hayashi, Pengyu Huang, Kenichiro Inoue. Up-regulation of soyasaponin biosynthesis by methyl jasmonate in cultured cells of Glycyrrhiza glabra. Plant & cell physiology. 2003 Apr; 44(4):404-11. doi: 10.1093/pcp/pcg054. [PMID: 12721381]
  • H Miyao, T Arao, M Udayama, J Kinjo, T Nohara. Kaikasaponin III and soyasaponin I, major triterpene saponins of Abrus cantoniensis, act on GOT and GPT: influence on transaminase elevation of rat liver cells concomitantly exposed to CCl4 for one hour. Planta medica. 1998 Feb; 64(1):5-7. doi: 10.1055/s-2006-957355. [PMID: 9491761]
  • G R Waller, C F Yang, L F Chen, C H Su, R M Liou, S C Wu, C C Young, M R Lee, J S Lee, C H Chou, D Kim. Can soyasaponin I and mono- and bi-desmosides isolated from mungbeans serve as growth enhancers in mungbeans and lettuce?. Advances in experimental medicine and biology. 1996; 405(?):123-39. doi: 10.1007/978-1-4613-0413-5_11. [PMID: 8910700]
  • M K Lee, Y C Ling, M Jurzysta, G R Waller. Saponins from alfalfa, clover, and mungbeans analyzed by electrospray ionization-mass spectrometry as compared with positive and negative FAB-mass spectrometry. Advances in experimental medicine and biology. 1996; 405(?):353-64. doi: 10.1007/978-1-4613-0413-5_30. [PMID: 8910718]
  • H Frøkiaer, P Møller, H Sørensen, S Sørensen. High-performance capillary electrophoresis for characterization of hapten-protein conjugates used for production of antibodies against soyasaponin I. Journal of chromatography. A. 1994 Oct; 680(2):437-45. doi: 10.1016/0021-9673(94)85141-7. [PMID: 7981825]
  • O B McManus, G H Harris, K M Giangiacomo, P Feigenbaum, J P Reuben, M E Addy, J F Burka, G J Kaczorowski, M L Garcia. An activator of calcium-dependent potassium channels isolated from a medicinal herb. Biochemistry. 1993 Jun; 32(24):6128-33. doi: 10.1021/bi00075a002. [PMID: 7685635]
  • S Tsurumi, T Takagi, T Hashimoto. A gamma-pyronyl-triterpenoid saponin from Pisum sativum. Phytochemistry. 1992 Jul; 31(7):2435-8. doi: 10.1016/0031-9422(92)83294-9. [PMID: 1368388]
  • S Southon, A J Wright, K R Price, S J Fairweather-Tait, G R Fenwick. The effect of three types of saponin on iron and zinc absorption from a single meal in the rat. The British journal of nutrition. 1988 May; 59(3):389-96. doi: 10.1079/bjn19880048. [PMID: 3395602]