Gypsogenin (BioDeep_00000000661)

 

Secondary id: BioDeep_00000868065

PANOMIX_OTCML-2023 Cytotoxicity natural product


代谢物信息卡片


(4aS,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-formyl-10-hydroxy-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

化学式: C30H46O4 (470.3396)
中文名称: 丝石竹皂苷元
谱图信息: 最多检出来源 Viridiplantae(plant) 92.24%

分子结构信息

SMILES: C1[C@@]2(C)[C@@]([H])(CC[C@]3(C)[C@]2([H])CC=C2[C@@]3(C)CC[C@]3(C(=O)O)[C@@]2([H])CC(C)(C)CC3)[C@@](C=O)(C)[C@@H](O)C1
InChI: InChI=1S/C30H46O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,18,20-23,32H,8-17H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1

描述信息

Gypsogenin is a sapogenin that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3 and an oxo group at position 23. It is a pentacyclic triterpenoid, a sapogenin, an aldehyde and a monocarboxylic acid. It is functionally related to an oleanolic acid. It is a conjugate acid of a gypsogenin(1-).
Gypsogenin is a natural product found in Silene firma, Gypsophila bicolor, and other organisms with data available.
Gypsogenin shows antiangiogenic activity and the significant cytotoxicity against H460[1].
Gypsogenin shows antiangiogenic activity and the significant cytotoxicity against H460[1].

同义名列表

21 个代谢物同义名

(4aS,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-formyl-10-hydroxy-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; Olean-12-en-28-oic acid, 3-hydroxy-23-oxo-, (3.beta.,4.alpha.)-; 3-Hydroxy-23-oxo-olean-12-en-28-oic acid, (3-beta,4-alpha)-; (3.BETA.,4.ALPHA.)-3-HYDROXY-23-OXOOLEAN-12-EN-28-OIC ACID; (3beta,4alpha)-3-Hydroxy-23-oxoolean-12-en-28-oic acid; Gypsophila paniculata saponin (swiss standard saponin); Olean-12-en-28-oic acid, 3-beta-hydroxy-23-oxo-; 3beta-hydroxy-23-oxoolean-12-en-28-oic acid; Gypsogenin (Githagenin); Gypsophilasapogenin; Saponin-gypsophila; Gypsophilasaponin; Astrantiagenin D; GYPSOGENIN [MI]; UNII-2A9SGC905J; Albasapogenin; Albsapogenin; 2A9SGC905J; Gypsogenin; Githagenin; Gypsogenin



数据库引用编号

21 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(1)

代谢反应

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

49 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 7 ABL1, CGAS, MYD88, PML, SGCB, TLR4, TNK1
Peripheral membrane protein 4 CGAS, CYP1B1, PML, TNK1
Endosome membrane 3 LY96, MYD88, TLR4
Endoplasmic reticulum membrane 2 CYP1B1, PML
Nucleus 6 ABL1, BRD3, CGAS, MYD88, PML, ZNF77
cytosol 5 ABL1, BCR, CGAS, MYD88, PML
dendrite 1 ABL1
nuclear body 2 ABL1, CGAS
nucleoplasm 3 ABL1, CGAS, PML
Cell membrane 5 CD86, CGAS, GP2, TLR4, TNF
Cytoplasmic side 1 PML
Cell projection, axon 1 BCR
Early endosome membrane 1 PML
Synapse 1 BCR
cell surface 5 CD86, GP2, MYD88, TLR4, TNF
glutamatergic synapse 2 ABL1, BCR
Golgi membrane 1 INS
growth cone 1 ABL1
lysosomal membrane 1 GAA
neuronal cell body 2 ABL1, TNF
postsynapse 1 ABL1
sarcolemma 1 SGCB
Cytoplasm, cytosol 1 CGAS
Lysosome 1 GAA
endosome 1 GP2
plasma membrane 14 ABL1, BCHE, BCR, CD86, CGAS, GAA, GP2, GP5, LY96, MYD88, SGCB, TLR4, TNF, TNK1
Membrane 6 BCR, CD86, CYP1B1, GAA, TLR4, TNK1
apical plasma membrane 1 GP2
axon 1 BCR
extracellular exosome 5 BCR, CD86, GAA, GP2, GP5
Lysosome membrane 1 GAA
extracellular space 5 BCHE, GP2, IL10, INS, TNF
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 2 ABL1, TLR4
Schaffer collateral - CA1 synapse 1 BCR
mitochondrion 2 ABL1, CYP1B1
protein-containing complex 3 ABL1, BCR, MYD88
intracellular membrane-bounded organelle 2 CYP1B1, GAA
Microsome membrane 1 CYP1B1
postsynaptic density 2 ABL1, BCR
Single-pass type I membrane protein 2 CD86, TLR4
Secreted 6 BCHE, GAA, GP2, IL10, INS, LY96
extracellular region 7 BCHE, GAA, GP2, IL10, INS, LY96, TNF
centriolar satellite 1 CD86
nuclear membrane 2 ABL1, PML
external side of plasma membrane 4 CD86, GP2, TLR4, TNF
actin cytoskeleton 1 ABL1
dendritic spine 1 BCR
nucleolus 2 ABL1, PML
Early endosome 1 TLR4
recycling endosome 1 TNF
Single-pass type II membrane protein 2 SGCB, TNF
Apical cell membrane 1 GP2
Cell membrane, sarcolemma 1 SGCB
Membrane raft 2 GP2, TNF
Cytoplasm, cytoskeleton 1 SGCB
Cell projection, dendritic spine 1 BCR
Nucleus, PML body 1 PML
PML body 1 PML
Cell projection, ruffle 1 TLR4
ruffle 2 ABL1, TLR4
receptor complex 2 LY96, TLR4
Zymogen granule membrane 1 GP2
chromatin 1 BRD3
phagocytic cup 2 TLR4, TNF
Chromosome 2 BRD3, CGAS
cytoskeleton 1 SGCB
Secreted, extracellular space 1 LY96
chromosome, telomeric region 1 PML
blood microparticle 1 BCHE
Lipid-anchor, GPI-anchor 1 GP2
site of double-strand break 1 CGAS
endosome lumen 1 INS
tertiary granule membrane 1 GAA
lipopolysaccharide receptor complex 2 LY96, TLR4
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 BCHE, INS
nuclear matrix 1 PML
transport vesicle 1 INS
azurophil granule membrane 1 GAA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
nuclear envelope lumen 1 BCHE
extrinsic component of cytoplasmic side of plasma membrane 1 MYD88
ficolin-1-rich granule membrane 1 GAA
dystrophin-associated glycoprotein complex 1 SGCB
sarcoglycan complex 1 SGCB
extrinsic component of plasma membrane 1 MYD88
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
glycoprotein Ib-IX-V complex 1 GP5
autolysosome lumen 1 GAA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Fei Li, Si-Tong Wu, Ming-Hui Qu, Yi-Xiao Wang, Chun-Liu Ma, Bai-Hong Yu, Guang-Shu Wang. Studies on isolation and structural identification of saponins from the herb Hylomecon japonica and their bioactivities. Carbohydrate research. 2021 Sep; 507(?):108391. doi: 10.1016/j.carres.2021.108391. [PMID: 34271480]
  • Weixian Li, Xiaohui Ma, Guodong Li, Aili Zhang, Dong Wang, Feiyu Fan, Xiaolin Ma, Xueli Zhang, Zhubo Dai, Zigang Qian. De Novo Biosynthesis of the Oleanane-Type Triterpenoids of Tunicosaponins in Yeast. ACS synthetic biology. 2021 08; 10(8):1874-1881. doi: 10.1021/acssynbio.1c00065. [PMID: 34259519]
  • 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]
  • An-Dong Wang, Ying Bao, Xia Wang, Mei-Chen Li, Xu-Hong Ren, Jian-Yu Liu, Yong-Nan Xu. A new triterpenoid saponin from Pulsatilla cernua predicted by NMR-based mosaic method. Natural product research. 2020 Apr; 34(7):909-914. doi: 10.1080/14786419.2018.1538995. [PMID: 30507319]
  • Halil Ibrahim Ciftci, Safiye Emirdag Ozturk, Taha F S Ali, Mohamed O Radwan, Hiroshi Tateishi, Ryoko Koga, Zeynep Ocak, Mustafa Can, Masami Otsuka, Mikako Fujita. The First Pentacyclic Triterpenoid Gypsogenin Derivative Exhibiting Anti-ABL1 Kinase and Anti-chronic Myelogenous Leukemia Activities. Biological & pharmaceutical bulletin. 2018 Apr; 41(4):570-574. doi: 10.1248/bpb.b17-00902. [PMID: 29386476]
  • Yuping Lu, Dang Van, Leah Deibert, Greg Bishop, John Balsevich. Antiproliferative quillaic acid and gypsogenin saponins from Saponaria officinalis L. roots. Phytochemistry. 2015 May; 113(?):108-20. doi: 10.1016/j.phytochem.2014.11.021. [PMID: 25534953]
  • Jian-Yu Liu, Ying-Li Guan, Li-Bo Zou, Yi-Xia Gong, Hui-Ming Hua, Yong-Nan Xu, Hui Zhang, Zong-Gui Yu, Wen-Hao Fan. Saponins with neuroprotective effects from the roots of Pulsatilla cernua. Molecules (Basel, Switzerland). 2012 May; 17(5):5520-31. doi: 10.3390/molecules17055520. [PMID: 22572934]
  • Vijay R Chidrawar, Krishnakant N Patel, Navin R Sheth, Shruti S Shiromwar, Piyush Trivedi. Antiobesity effect of Stellaria media against drug induced obesity in Swiss albino mice. Ayu. 2011 Oct; 32(4):576-84. doi: 10.4103/0974-8520.96137. [PMID: 22661858]
  • Nikoline J Nielsen, John Nielsen, Dan Staerk. New resistance-correlated saponins from the insect-resistant crucifer Barbarea vulgaris. Journal of agricultural and food chemistry. 2010 May; 58(9):5509-14. doi: 10.1021/jf903988f. [PMID: 20387830]
  • Sonia A Tucci, Emma J Boyland, Jason Cg Halford. The role of lipid and carbohydrate digestive enzyme inhibitors in the management of obesity: a review of current and emerging therapeutic agents. Diabetes, metabolic syndrome and obesity : targets and therapy. 2010 May; 3(?):125-43. doi: 10.2147/dmsott.s7005. [PMID: 21437083]
  • Fang Li, Wei Li, Hongwei Fu, Qingbo Zhang, Kazuo Koike. Pancreatic lipase-inhibiting triterpenoid saponins from fruits of Acanthopanax senticosus. Chemical & pharmaceutical bulletin. 2007 Jul; 55(7):1087-9. doi: 10.1248/cpb.55.1087. [PMID: 17603209]
  • Anna Szakiel, Max Henry. Analysis of gypsogenin saponins in homeopathic tinctures. Acta biochimica Polonica. 2007; 54(4):853-6. doi: . [PMID: 18066408]
  • J John Balsevich, Greg G Bishop, Irving Ramirez-Erosa. Analysis of bisdesmosidic saponins in Saponaria vaccaria L. by HPLC-PAD-MS: identification of new quillaic acid and gypsogenin 3-O-trisaccharides. Phytochemical analysis : PCA. 2006 Nov; 17(6):414-23. doi: 10.1002/pca.943. [PMID: 17144250]
  • Balakyz Yeskaliyeva, M Ahmed Mesaik, Ahmed Abbaskhan, Aisha Kulsoom, G Sh Burasheva, Zh A Abilov, M Iqbal Choudhary, Atta-ur-Rahman. Bioactive flavonoids and saponins from Climacoptera obtusifolia. Phytochemistry. 2006 Nov; 67(21):2392-7. doi: 10.1016/j.phytochem.2006.07.003. [PMID: 16956629]
  • M Larhsini, A Marston, K Hostettmann. Triterpenoid saponins from the roots of Silene cucubalus. Fitoterapia. 2003 Apr; 74(3):237-41. doi: 10.1016/s0367-326x(03)00031-5. [PMID: 12727487]
  • Y Kawata, H Kizu, Y Miyaichi, T Tomimori. Studies on the constituents of Clematis species. VIII. Triterpenoid saponins from the aerial part of Clematis tibetana KUNTZ. Chemical & pharmaceutical bulletin. 2001 May; 49(5):635-8. doi: 10.1248/cpb.49.635. [PMID: 11383622]