Soyasapogenol B (BioDeep_00000000555)

 

Secondary id: BioDeep_00000285579, BioDeep_00000862470

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


(3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-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-icosahydropicene-3,9-diol

化学式: C30H50O3 (458.376)
中文名称: 大豆甾醇B, 大豆皂醇B, 大豆甾醇 B
谱图信息: 最多检出来源 Viridiplantae(plant) 23.52%

分子结构信息

SMILES: CC1(C)CC(O)C2(C)CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(CO)C5CCC43C)C2C1
InChI: InChI=1S/C30H50O3/c1-25(2)16-20-19-8-9-22-27(4)12-11-23(32)28(5,18-31)21(27)10-13-30(22,7)29(19,6)15-14-26(20,3)24(33)17-25/h8,20-24,31-33H,9-18H2,1-7H3/t20-,21+,22+,23-,24+,26+,27-,28+,29+,30+/m0/s1

描述信息

Soyasapogenol b-1, also known as 24-hydroxysophoradiol, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Soyasapogenol b-1 is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Soyasapogenol b-1 can be synthesized from oleanane. Soyasapogenol b-1 is also a parent compound for other transformation products, including but not limited to, soyasapogenol B 3-O-beta-glucuronide, soyasaponin III, and soyasaponin I. Soyasapogenol b-1 can be found in soy bean, which makes soyasapogenol b-1 a potential biomarker for the consumption of this food product.
Soyasapogenol B is a pentacyclic triterpenoid that is oleanane containing a double bond between positions 12 and 13 and substituted by hydroxy groups at the 3beta, 22beta and 24-positions. It derives from a hydride of an oleanane.
Soyasapogenol B is a natural product found in Astragalus mongholicus, Melilotus messanensis, and other organisms with data available.
See also: Trifolium pratense flower (part of); Medicago sativa whole (part of).
Soyasapogenol B, also known as 24-hydroxysophoradiol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Soyasapogenol B is an extremely weak basic (essentially neutral) compound (based on its pKa). Soyasapogenol B is found in alfalfa. Soyasapogenol B is a constituent of soya bean saponin, Medicago, Astragalus, and Trifolium species.
Soyasapogenol B, an ingredient of soybean, exerts anti-proliferative, anti-metastatic activities. Soyasapogenol B triggers endoplasmic reticulum stress, which mediates apoptosis and autophagy in colorectal cancer[1][2].
Soyasapogenol B, an ingredient of soybean, exerts anti-proliferative, anti-metastatic activities. Soyasapogenol B triggers endoplasmic reticulum stress, which mediates apoptosis and autophagy in colorectal cancer[1][2].

同义名列表

32 个代谢物同义名

(3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-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-icosahydropicene-3,9-diol; (3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,9-diol; 4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,9-diol; OLEAN-12-ENE-3,22,23-TRIOL, (3.BETA.,4.BETA.,22.BETA.)-; Olean-12-ene-3,22,23-triol, (3beta,4beta,22beta)-; (3beta,4beta,22beta)-Olean-12-ene-3,22,23-triol; Olean-12-ene-3,22,24-triol, (3beta,22beta)-; 3.BETA.,22.BETA.,24-TRIHYDROXYOLEAN-12-ENE; (3beta,22beta)-olean-12-ene-3,22,24-triol; 3beta,22beta,24-TRIHYDROXYOLEAN-12-ENE; OLEAN-12-ENE-3.BETA.,22.BETA.,24-TRIOL; (3Β,4β,22β)-olean-12-ene-3,22,23-triol; OLEAN-12-EN-3.BETA.,22.BETA.,24-TRIOL; OLEAN-12-ENE-3beta,22beta,24-TRIOL; OLEAN-12-EN-3beta,22beta,24-TRIOL; 3Β,22β,24-trihydroxyolean-12-ene; Soyasapogenol B, >=98\\% (HPLC); 3-Bromopropylisocyanate,98\\%; Olean-12-ene-3β,22β,24-triol; Olean-12-en-3β,22β,24-triol; 24-hydroxysophoradiol; SOYASAPOGENOL B(P); Soyasapogenol B-1; Soyasapogenol M2; Soyasapogenol B; soyasapogenol-B; SOYASAPOGENOL I; UNII-1EZ10D7E2F; soyasapogenin B; SOYASAPOGENIN; 1EZ10D7E2F; Soyasapogenol B



数据库引用编号

25 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

52 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(52)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

103 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。

亚细胞结构定位 关联基因列表
Cytoplasm 9 ANXA5, ATG5, BDNF, CASP12, MAPK9, PNPLA2, RUNX2, SPHK1, TYRP1
Peripheral membrane protein 5 ACHE, ANXA5, ATG5, CYP1B1, SPHK1
Endosome membrane 2 SPHK1, TYRP1
Endoplasmic reticulum membrane 2 CYP1B1, PNPLA2
Nucleus 5 ACHE, MAPK9, PPARA, RUNX2, SPHK1
autophagosome 2 ATG5, MAP1LC3A
cytosol 7 ANXA5, ATG5, MAP1LC3A, MAPK9, PNPLA2, RUNX2, SPHK1
dendrite 1 BDNF
nucleoplasm 5 MAPK9, PNPLA2, PPARA, RUNX2, SPHK1
Cell membrane 4 ACHE, PNPLA2, SPHK1, TNF
Lipid-anchor 1 MAP1LC3A
Early endosome membrane 1 SPHK1
Multi-pass membrane protein 1 PNPLA2
Synapse 2 ACHE, SPHK1
cell surface 3 ACHE, ADIPOQ, TNF
glutamatergic synapse 2 ATG5, MAP1LC3A
Golgi apparatus 1 ACHE
Golgi membrane 1 INS
neuromuscular junction 1 ACHE
neuronal cell body 1 TNF
postsynapse 1 ATG5
sarcolemma 1 ANXA5
synaptic vesicle 1 BDNF
Presynapse 1 SPHK1
plasma membrane 5 ACHE, MAPK9, PNPLA2, SPHK1, TNF
Membrane 8 ACHE, ANXA5, ATG5, BDNF, CYP1B1, MMP13, PNPLA2, SPHK1
axon 3 ATG5, BDNF, CCK
extracellular exosome 2 ANXA5, RETN
endoplasmic reticulum 2 ADIPOQ, CASP12
extracellular space 8 ACHE, ADIPOQ, BDNF, CCK, INS, MMP13, RETN, TNF
perinuclear region of cytoplasm 2 ACHE, BDNF
Schaffer collateral - CA1 synapse 2 ATG5, MAPK9
mitochondrion 2 CYP1B1, MAPK9
protein-containing complex 1 ATG5
intracellular membrane-bounded organelle 3 CYP1B1, MAP1LC3A, SPHK1
Microsome membrane 1 CYP1B1
Single-pass type I membrane protein 1 TYRP1
Secreted 7 ACHE, ADIPOQ, BDNF, CCK, INS, MMP13, RETN
extracellular region 10 ACHE, ADIPOQ, ANXA5, BDNF, CCK, DNAH9, INS, MMP13, RETN, TNF
Extracellular side 1 ACHE
transcription regulator complex 1 RUNX2
motile cilium 1 DNAH9
external side of plasma membrane 2 ANXA5, TNF
Secreted, extracellular space, extracellular matrix 1 MMP13
Melanosome membrane 1 TYRP1
Membrane, clathrin-coated pit 1 SPHK1
clathrin-coated pit 1 SPHK1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 MAP1LC3A
focal adhesion 1 ANXA5
microtubule 2 DNAH9, MAP1LC3A
extracellular matrix 1 MMP13
basement membrane 1 ACHE
collagen trimer 1 ADIPOQ
intracellular vesicle 1 TYRP1
collagen-containing extracellular matrix 2 ADIPOQ, ANXA5
axoneme 2 ATG5, DNAH9
nuclear speck 1 MAPK9
Late endosome 1 MAP1LC3A
Zymogen granule membrane 1 ANXA5
chromatin 2 PPARA, RUNX2
Cytoplasmic vesicle, autophagosome membrane 1 MAP1LC3A
autophagosome membrane 1 MAP1LC3A
phagocytic cup 1 TNF
phagocytic vesicle membrane 1 ATG5
Cytoplasm, cytoskeleton, cilium axoneme 1 DNAH9
Lipid-anchor, GPI-anchor 1 ACHE
organelle membrane 1 MAP1LC3A
Endomembrane system 1 MAP1LC3A
endosome lumen 1 INS
Lipid droplet 1 PNPLA2
Preautophagosomal structure membrane 1 ATG5
Atg12-Atg5-Atg16 complex 1 ATG5
mitochondria-associated endoplasmic reticulum membrane contact site 1 ATG5
phagophore assembly site membrane 1 ATG5
Melanosome 1 TYRP1
side of membrane 1 ACHE
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 BDNF, INS, PNPLA2
specific granule lumen 1 RETN
endocytic vesicle 1 SPHK1
transport vesicle 1 INS
azurophil granule lumen 1 RETN
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
9+2 motile cilium 1 DNAH9
dynein complex 1 DNAH9
vesicle membrane 1 ANXA5
clathrin-coated endocytic vesicle membrane 1 TYRP1
synaptic cleft 1 ACHE
transferase complex 1 ATG5
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
Autolysosome 1 MAP1LC3A
endothelial microparticle 1 ANXA5
[Isoform H]: Cell membrane 1 ACHE
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
NLRP1 inflammasome complex 1 CASP12
phagophore 1 ATG5
outer dynein arm 1 DNAH9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
distal portion of axoneme 1 DNAH9


文献列表

  • Luping Wang, Junyu Wang, Hong Zhao, Guoping Jiang, Xiaojie Feng, Wenxia Sui, Hongling Liu. Soyasapogenol B exhibits anti-growth and anti-metastatic activities in clear cell renal cell carcinoma. Naunyn-Schmiedeberg's archives of pharmacology. 2019 05; 392(5):551-563. doi: 10.1007/s00210-018-01607-w. [PMID: 30607469]
  • S Divya Reddy, Bandi Siva, V S Phani Babu, M Vijaya, V Lakshma Nayak, Reeta Mandal, Ashok K Tiwari, P Shashikala, K Suresh Babu. New cycloartane type-triterpenoids from the areal parts of Caragana sukiensis and their biological activities. European journal of medicinal chemistry. 2017 Aug; 136(?):74-84. doi: 10.1016/j.ejmech.2017.04.065. [PMID: 28482219]
  • Hae-Ji Lee, Su-Min Lim, Da-Bin Ko, Jin-Ju Jeong, Yun-Ha Hwang, Dong-Hyun Kim. Soyasapogenol B and Genistein Attenuate Lipopolysaccharide-Induced Memory Impairment in Mice by the Modulation of NF-κB-Mediated BDNF Expression. Journal of agricultural and food chemistry. 2017 Aug; 65(32):6877-6885. doi: 10.1021/acs.jafc.7b02569. [PMID: 28771341]
  • Kun Cheng, Hua Gao, Rong-Rong Wang, Yang Liu, Yu-Xue Hou, Xiao-Hong Liu, Kun Liu, Wei Wang. Evaluation of Extraction and Degradation Methods to Obtain Chickpeasaponin B1 from Chickpea (Cicer arietinum L.). Molecules (Basel, Switzerland). 2017 Feb; 22(2):. doi: 10.3390/molecules22020332. [PMID: 28230799]
  • Dae-Hyoung Yoo, Dong-Hyun Kim. Lactobacillus pentosus var. plantarum C29 increases the protective effect of soybean against scopolamine-induced memory impairment in mice. International journal of food sciences and nutrition. 2015; 66(8):912-8. doi: 10.3109/09637486.2015.1064865. [PMID: 26171634]
  • Shuichi Kamo, Shunsuke Suzuki, Toshiro Sato. Comparison of bioavailability (I) between soyasaponins and soyasapogenols, and (II) between group A and B soyasaponins. Nutrition (Burbank, Los Angeles County, Calif.). 2014 May; 30(5):596-601. doi: 10.1016/j.nut.2013.10.017. [PMID: 24698352]
  • Ery O Fukushima, Hikaru Seki, Satoru Sawai, Munenori Suzuki, Kiyoshi Ohyama, Kazuki Saito, Toshiya Muranaka. Combinatorial biosynthesis of legume natural and rare triterpenoids in engineered yeast. Plant & cell physiology. 2013 May; 54(5):740-9. doi: 10.1093/pcp/pct015. [PMID: 23378447]
  • Antonio Evidente, Alessio Cimmino, Mónica Fernández-Aparicio, Diego Rubiales, Anna Andolfi, Dominique Melck. Soyasapogenol B and trans-22-dehydrocam- pesterol from common vetch (Vicia sativa L.) root exudates stimulate broomrape seed germination. Pest management science. 2011 Aug; 67(8):1015-22. doi: 10.1002/ps.2153. [PMID: 21480462]
  • Massimo Confalonieri, Maria Cammareri, Elisa Biazzi, Paola Pecchia, Manuel Pedro Salema Fevereiro, Alma Balestrazzi, Aldo Tava, Clara Conicella. Enhanced triterpene saponin biosynthesis and root nodulation in transgenic barrel medic (Medicago truncatula Gaertn.) expressing a novel beta-amyrin synthase (AsOXA1) gene. Plant biotechnology journal. 2009 Feb; 7(2):172-82. doi: 10.1111/j.1467-7652.2008.00385.x. [PMID: 19055609]
  • Wei Zhang, David G Popovich. Effect of soyasapogenol A and soyasapogenol B concentrated extracts on HEP-G2 cell proliferation and apoptosis. Journal of agricultural and food chemistry. 2008 Apr; 56(8):2603-8. doi: 10.1021/jf0731550. [PMID: 18361499]
  • Sun-Ok Lee, Andrean L Simons, Patricia A Murphy, Suzanne Hendrich. Soyasaponins lowered plasma cholesterol and increased fecal bile acids in female golden Syrian hamsters. Experimental biology and medicine (Maywood, N.J.). 2005 Jul; 230(7):472-8. doi: 10.1177/153537020523000705. [PMID: 15985622]
  • 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]
  • 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]
  • J C Rowlands, M A Berhow, T M Badger. Estrogenic and antiproliferative properties of soy sapogenols in human breast cancer cells in vitro. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2002 Dec; 40(12):1767-74. doi: 10.1016/s0278-6915(02)00181-3. [PMID: 12419690]
  • M A Berhow, E D Wagner, S F Vaughn, M J Plewa. Characterization and antimutagenic activity of soybean saponins. Mutation research. 2000 Mar; 448(1):11-22. doi: 10.1016/s0027-5107(99)00225-0. [PMID: 10751618]