Quillaic (BioDeep_00000000406)

 

Secondary id: BioDeep_00000264853

PANOMIX_OTCML-2023


代谢物信息卡片


(4aR,5R,6aS,6bR,8aR,9S,10S,12aR,12bR,14bS)-9-formyl-5,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid

化学式: C30H46O5 (486.3345)
中文名称: 奎拉酸, 皂皮酸, 皂树皮提取物
谱图信息: 最多检出来源 Homo sapiens(otcml) 39.23%

分子结构信息

SMILES: CC1(C)CCC2(C(=O)O)C(O)CC3(C)C(=CCC4C5(C)CCC(O)C(C)(C=O)C5CCC43C)C2C1
InChI: InChI=1S/C30H46O5/c1-25(2)13-14-30(24(34)35)19(15-25)18-7-8-21-26(3)11-10-22(32)27(4,17-31)20(26)9-12-28(21,5)29(18,6)16-23(30)33/h7,17,19-23,32-33H,8-16H2,1-6H3,(H,34,35)/t19-,20+,21+,22-,23+,26-,27-,28+,29+,30+/m0/s1

描述信息

Quillaic acid is a pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 3 and 16, an oxo group at position 23 and a carboxy group at position 28 (the 3beta,16alpha stereoisomer). It has a role as an anti-inflammatory agent and a metabolite. It is a pentacyclic triterpenoid, a hydroxy monocarboxylic acid and an aldehyde. It is a conjugate acid of a quillate. It derives from a hydride of an oleanane.
Quillaic acid is a natural product found in Silene firma, Gypsophila oldhamiana, and other organisms with data available.
A pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 3 and 16, an oxo group at position 23 and a carboxy group at position 28 (the 3beta,16alpha stereoisomer).
Quillaic acid (Quillaja sapogenin) is a natural product used in pain relief research.
Quillaic acid (Quillaja sapogenin) is a natural product used in pain relief research.

同义名列表

17 个代谢物同义名

(4aR,5R,6aS,6bR,8aR,9S,10S,12aR,12bR,14bS)-9-formyl-5,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid; (4aR,5R,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-formyl-5,10-dihydroxy-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, 3,16-dihydroxy-23-oxo-, (3.beta.,4.alpha.,16.alpha.)-; (3beta,4alpha,16alpha)-3,16-Dihydroxy-23-oxoolean-12-en-28-oic acid; OLEAN-12-EN-28-OIC ACID, 3.BETA.,16.ALPHA.-DIHYDROXY-23-OXO-; (3beta,16alpha)-3,16-dihydroxy-23-oxoolean-12-en-28-oic acid; 3 beta,16 alpha-dihydroxy-23-oxoolean-12-en-28-oic acid; 3beta,16alpha-dihydroxy-23-oxoolean-12-en-28-oic acid; Quillaic acid(Quillaja sapogenin); QUILLAIC ACID [MI]; quillaja sapogenin; (+)-quillaic acid; UNII-69O8E4G02B; Quillaic acid; 69O8E4G02B; Quillaic; Quillaic acid



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

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。

亚细胞结构定位 关联基因列表
Cytoplasm 11 ANXA5, CASP3, MAPK8, MSMP, MYD88, NOS2, PTGS1, PTGS2, SGCB, TLR4, TYR
Peripheral membrane protein 4 ANXA5, CYP1B1, PTGS1, PTGS2
Endosome membrane 3 LY96, MYD88, TLR4
Endoplasmic reticulum membrane 3 CYP1B1, PTGS1, PTGS2
Nucleus 5 CASP3, MAPK8, MYD88, NOS2, PARP1
cytosol 6 ANXA5, CASP3, MAPK8, MYD88, NOS2, PARP1
nuclear body 1 PARP1
nucleoplasm 4 CASP3, MAPK8, NOS2, PARP1
Cell membrane 2 TLR4, TNF
Synapse 1 MAPK8
cell surface 3 MYD88, TLR4, TNF
glutamatergic synapse 1 CASP3
Golgi apparatus 1 PTGS1
Golgi membrane 1 INS
lysosomal membrane 1 GAA
neuronal cell body 2 CASP3, TNF
sarcolemma 2 ANXA5, SGCB
Cytoplasm, cytosol 2 NOS2, PARP1
Lysosome 2 GAA, TYR
plasma membrane 8 BCHE, GAA, LY96, MYD88, NOS2, SGCB, TLR4, TNF
Membrane 5 ANXA5, CYP1B1, GAA, PARP1, TLR4
axon 1 MAPK8
caveola 1 PTGS2
extracellular exosome 3 ANXA5, GAA, PTGS1
Lysosome membrane 1 GAA
endoplasmic reticulum 1 PTGS2
extracellular space 6 BCHE, IL10, IL6, INS, MSMP, TNF
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 3 NOS2, TLR4, TYR
mitochondrion 2 CYP1B1, PARP1
protein-containing complex 3 MYD88, PARP1, PTGS2
intracellular membrane-bounded organelle 4 CYP1B1, GAA, PTGS1, TYR
Microsome membrane 3 CYP1B1, PTGS1, PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 2 TLR4, TYR
Secreted 7 BCHE, GAA, IL10, IL6, INS, LY96, MSMP
extracellular region 8 ANXA5, BCHE, GAA, IL10, IL6, INS, LY96, TNF
transcription regulator complex 1 PARP1
photoreceptor outer segment 1 PTGS1
external side of plasma membrane 3 ANXA5, TLR4, TNF
nucleolus 1 PARP1
Melanosome membrane 1 TYR
Cytoplasm, P-body 1 NOS2
P-body 1 NOS2
Early endosome 1 TLR4
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 2 SGCB, TNF
Cell membrane, sarcolemma 1 SGCB
Cytoplasm, perinuclear region 1 NOS2
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 SGCB
focal adhesion 1 ANXA5
Peroxisome 1 NOS2
peroxisomal matrix 1 NOS2
collagen-containing extracellular matrix 1 ANXA5
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Cell projection, ruffle 1 TLR4
ruffle 1 TLR4
receptor complex 2 LY96, TLR4
Zymogen granule membrane 1 ANXA5
neuron projection 2 PTGS1, PTGS2
chromatin 1 PARP1
phagocytic cup 2 TLR4, TNF
Chromosome 1 PARP1
cytoskeleton 1 SGCB
Secreted, extracellular space 1 LY96
Nucleus, nucleolus 1 PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
blood microparticle 1 BCHE
site of double-strand break 1 PARP1
nuclear envelope 1 PARP1
Endomembrane system 1 PTGS1
endosome lumen 1 INS
tertiary granule membrane 1 GAA
Melanosome 1 TYR
lipopolysaccharide receptor complex 2 LY96, TLR4
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 4 BCHE, IL6, INS, PTGS2
transport vesicle 1 INS
azurophil granule membrane 1 GAA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
nuclear envelope lumen 1 BCHE
vesicle membrane 1 ANXA5
extrinsic component of cytoplasmic side of plasma membrane 1 MYD88
protein-DNA complex 1 PARP1
ficolin-1-rich granule membrane 1 GAA
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
dystrophin-associated glycoprotein complex 1 SGCB
sarcoglycan complex 1 SGCB
extrinsic component of plasma membrane 1 MYD88
site of DNA damage 1 PARP1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
cortical cytoskeleton 1 NOS2
interleukin-6 receptor complex 1 IL6
endothelial microparticle 1 ANXA5
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
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

  • 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]
  • R Gevrenova, O Joubert, Tsv Mandova, M Zaiou, Y Chapleur, M Henry. Cytotoxic effects of four Caryophyllaceae species extracts on macrophage cell lines. Pharmaceutical biology. 2014 Jul; 52(7):919-25. doi: 10.3109/13880209.2013.868492. [PMID: 24863282]
  • Kiwon Jung, Young-Won Chin, Kee dong Yoon, Hee-Sung Chae, Chul Young Kim, Hunseung Yoo, Jinwoong Kim. Anti-inflammatory properties of a triterpenoidal glycoside from Momordica cochinchinensis in LPS-stimulated macrophages. Immunopharmacology and immunotoxicology. 2013 Feb; 35(1):8-14. doi: 10.3109/08923973.2012.715165. [PMID: 22916793]
  • Michał Arabski, Aneta Węgierek-Ciuk, Grzegorz Czerwonka, Anna Lankoff, Wiesław Kaca. Effects of saponins against clinical E. coli strains and eukaryotic cell line. Journal of biomedicine & biotechnology. 2012; 2012(?):286216. doi: 10.1155/2012/286216. [PMID: 22500084]
  • Maité Rodríguez-Díaz, Carla Delporte, Carlos Cartagena, Bruce K Cassels, Patricia González, Ximena Silva, Fredy León, Ludger A Wessjohann. Topical anti-inflammatory activity of quillaic acid from Quillaja saponaria Mol. and some derivatives. The Journal of pharmacy and pharmacology. 2011 May; 63(5):718-24. doi: 10.1111/j.2042-7158.2011.01263.x. [PMID: 21492174]
  • Sylvia Arrau, Carla Delporte, Carlos Cartagena, Maité Rodríguez-Díaz, Patricia González, Ximena Silva, Bruce K Cassels, Hugo F Miranda. Antinociceptive activity of Quillaja saponaria Mol. saponin extract, quillaic acid and derivatives in mice. Journal of ethnopharmacology. 2011 Jan; 133(1):164-7. doi: 10.1016/j.jep.2010.09.016. [PMID: 20951193]
  • Qing Chen, Jian-Guang Luo, Ling-Yi Kong. Triterpenoid saponins from Gypsophila altissima L. Chemical & pharmaceutical bulletin. 2010 Mar; 58(3):412-4. doi: 10.1248/cpb.58.412. [PMID: 20190453]
  • Jian-Guang Luo, Li Ma, Ling-Yi Kong. New triterpenoid saponins with strong alpha-glucosidase inhibitory activity from the roots of Gypsophila oldhamiana. Bioorganic & medicinal chemistry. 2008 Mar; 16(6):2912-20. doi: 10.1016/j.bmc.2007.12.053. [PMID: 18194870]
  • Zahid Iqbal Rajput, Song-hua Hu, Chen-wen Xiao, Abdullah G Arijo. Adjuvant effects of saponins on animal immune responses. Journal of Zhejiang University. Science. B. 2007 Mar; 8(3):153-61. doi: 10.1631/jzus.2007.b0153. [PMID: 17323426]
  • 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]
  • Jian-Guang Luo, Ling-Yi Kong, Yoshiaki Takaya, Masatake Niwa. Two new monodesmosidic triterpene saponins from Gypsophila oldhamiana. Chemical & pharmaceutical bulletin. 2006 Aug; 54(8):1200-2. doi: 10.1248/cpb.54.1200. [PMID: 16880670]
  • Geoffrey C Kite, Melanie-Jayne R Howes, Monique S J Simmonds. Metabolomic analysis of saponins in crude extracts of Quillaja saponaria by liquid chromatography/mass spectrometry for product authentication. Rapid communications in mass spectrometry : RCM. 2004; 18(23):2859-70. doi: 10.1002/rcm.1698. [PMID: 15517552]
  • 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]
  • Ghezala Gaidi, Tomofumi Miyamoto, Véronique Laurens, Marie-Aleth Lacaille-Dubois. New acylated triterpene saponins from Silene fortunei that modulate lymphocyte proliferation. Journal of natural products. 2002 Nov; 65(11):1568-72. doi: 10.1021/np020105a. [PMID: 12444678]
  • J L Turner, S S Dritz, J J Higgins, K L Herkelman, J E Minton. Effects of a Quillaja saponaria extract on growth performance and immune function of weanling pigs challenged with Salmonella typhimurium. Journal of animal science. 2002 Jul; 80(7):1939-46. doi: 10.2527/2002.8071939x. [PMID: 12162663]
  • Ghezala Gaidi, Maria Correia, Bruno Chauffert, Jean-Luc Beltramo, Hildebert Wagner, Marie-Aleth Lacaille-Dubois. Saponins-mediated potentiation of cisplatin accumulation and cytotoxicity in human colon cancer cells. Planta medica. 2002 Jan; 68(1):70-2. doi: 10.1055/s-2002-19873. [PMID: 11842333]
  • G Francis, H P Makkar, K Becker. Effects of Quillaja saponins on growth, metabolism, egg production and muscle cholesterol in individually reared Nile tilapia (Oreochromis niloticus). Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2001 Jun; 129(2):105-14. doi: 10.1016/s1532-0456(01)00189-2. [PMID: 11423383]
  • S Hoshi, A Uchino, N Saito, K I Kusanagi, T Ihara, S Ueda. Comparison of adjuvants with respect to serum IgG antibody response in orally immunized chickens. Comparative immunology, microbiology and infectious diseases. 1999 Jan; 22(1):63-9. doi: 10.1016/s0147-9571(98)00017-4. [PMID: 10099029]