Aloesin (BioDeep_00000000883)

   

natural product PANOMIX_OTCML-2023


代谢物信息卡片


2-acetonyl-7-hydroxy-5-methyl-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one

化学式: C19H22O9 (394.1264)
中文名称: 芦荟苦素
谱图信息: 最多检出来源 Viridiplantae(plant) 22.68%

分子结构信息

SMILES: CC(=O)Cc1cc(=O)c2c(C)cc(O)c(C3OC(CO)C(O)C(O)C3O)c2o1
InChI: InChI=1S/C19H22O9/c1-7-3-10(22)14(19-17(26)16(25)15(24)12(6-20)28-19)18-13(7)11(23)5-9(27-18)4-8(2)21/h3,5,12,15-17,19-20,22,24-26H,4,6H2,1-2H3

描述信息

Aloesin is a member of chromones.
Aloesin is a natural product found in Aloe africana, Aloe castanea, and other organisms with data available.

同义名列表

24 个代谢物同义名

2-acetonyl-7-hydroxy-5-methyl-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one; 7-hydroxy-5-methyl-2-(2-oxopropyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one; 4H-1-Benzopyran-4-one, 8-.beta.-D-glucopyranosyl-7-hydroxy-5-methyl-2-(2-oxopropyl)-; 4H-1-Benzopyran-4-one, 8-beta-D-glucopyranosyl-7-hydroxy-5-methyl-2-(2-oxopropyl)-; 8-beta-D-glucopyranosyl-7-hydroxy-5-methyl-2-(2-oxopropyl)-4H-1-benzopyran-4-one; 2-acetonyl-8-beta-d-glucopyranosyl-7-hydroxy-5-methylchromone; UNII-Y27M69Y8ES; ALOESIN [INCI]; aloe resin B; ALOESIN [MI]; aloeresin B; Y27M69Y8ES; Aloersin B; Aloeresin; Aloesin; 2-acetonyl-7-hydroxy-5-methyl-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]-4-chromenone; 2-acetonyl-7-hydroxy-5-methyl-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]chromone; AIDS-134027; 30861-27-9; NSC 631262; AIDS134027; NSC631262; C08994; Aloesin



数据库引用编号

46 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)

73 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 13 CDC25A, CDC42, CDK2, CTNNB1, MAPK8, PAK1, RAC1, SMAD2, SMAD3, TH, TUBB2B, TYR, XDH
Peripheral membrane protein 1 PAK1
Endoplasmic reticulum membrane 3 CDC42, PLP2, RAC1
Nucleus 10 CDC25A, CDK2, CTNNB1, MAPK8, PAK1, RAC1, SMAD2, SMAD3, TH, TUBB2B
cytosol 12 CDC25A, CDC42, CDK2, CTNNB1, LIPE, MAPK8, PAK1, RAC1, SMAD2, SMAD3, TH, XDH
dendrite 3 PAK1, RAC1, TH
phagocytic vesicle 1 CDC42
trans-Golgi network 1 RAC1
centrosome 4 CDC42, CDK2, CTNNB1, PAK1
nucleoplasm 7 CDC25A, CDK2, CTNNB1, MAPK8, PAK1, SMAD2, SMAD3
Cell membrane 6 CDC42, CTNNB1, LIPE, PAK1, RAC1, TNF
Lipid-anchor 2 CDC42, RAC1
Cytoplasmic side 2 CDC42, RAC1
Cleavage furrow 1 PAK1
lamellipodium 3 CTNNB1, PAK1, RAC1
ruffle membrane 2 PAK1, RAC1
Cell projection, axon 1 TH
Synapse 3 CTNNB1, MAPK8, RAC1
cell cortex 2 CTNNB1, RAC1
cell junction 1 CTNNB1
cell surface 1 TNF
glutamatergic synapse 3 CDC42, CTNNB1, RAC1
Golgi membrane 2 CDC42, INS
neuronal cell body 2 CDC42, TNF
postsynapse 1 RAC1
presynaptic membrane 1 CTNNB1
smooth endoplasmic reticulum 1 TH
synaptic vesicle 1 TH
Cytoplasm, cytosol 1 LIPE
Lysosome 1 TYR
endosome 2 CDK2, PAK1
plasma membrane 8 CDC42, CTNNB1, LTB, PAK1, PLP2, RAC1, SMAD3, TNF
terminal bouton 1 TH
Membrane 7 CDC42, CTNNB1, LIPE, LTB, PLP2, RAC1, SMAD2
axon 3 MAPK8, PAK1, TH
basolateral plasma membrane 1 CTNNB1
caveola 1 LIPE
extracellular exosome 3 CDC42, CTNNB1, RAC1
endoplasmic reticulum 1 PLP2
extracellular space 6 IGF1, IL6, INS, LTB, TNF, XDH
perinuclear region of cytoplasm 3 CTNNB1, TH, TYR
Schaffer collateral - CA1 synapse 3 CDC42, CTNNB1, TUBB2B
adherens junction 1 CTNNB1
apicolateral plasma membrane 1 CTNNB1
bicellular tight junction 1 CTNNB1
intercalated disc 1 PAK1
mitochondrion 1 TH
protein-containing complex 4 CDC42, CTNNB1, PAK1, SMAD2
intracellular membrane-bounded organelle 1 TYR
filopodium 1 CDC42
Single-pass type I membrane protein 1 TYR
Secreted 4 IGF1, IL6, INS, RAC1
extracellular region 5 IGF1, IL6, INS, RAC1, TNF
cytoplasmic side of plasma membrane 1 TH
transcription regulator complex 4 CDK2, CTNNB1, SMAD2, SMAD3
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 3 CDC42, CDK2, PAK1
nuclear membrane 1 PAK1
external side of plasma membrane 1 TNF
dendritic spine 2 CDC42, RAC1
perikaryon 1 TH
Z disc 2 CTNNB1, PAK1
beta-catenin destruction complex 1 CTNNB1
cytoplasmic vesicle 2 RAC1, TH
microtubule cytoskeleton 1 TUBB2B
Wnt signalosome 1 CTNNB1
Melanosome membrane 2 TH, TYR
midbody 2 CDC42, PAK1
apical part of cell 2 CDC42, CTNNB1
cell-cell junction 3 CDC42, CTNNB1, PAK1
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
spindle midzone 1 CDC42
Single-pass type II membrane protein 2 LTB, TNF
postsynaptic membrane 1 CTNNB1
Cell projection, lamellipodium 2 PAK1, RAC1
Cell projection, ruffle membrane 1 PAK1
Cytoplasm, perinuclear region 1 TH
Membrane raft 1 TNF
Cell junction, focal adhesion 1 PAK1
Cytoplasm, cytoskeleton 2 CTNNB1, TUBB2B
Cytoplasm, cytoskeleton, spindle 1 CDC42
focal adhesion 4 CDC42, CTNNB1, PAK1, RAC1
microtubule 1 TUBB2B
Cell junction, adherens junction 1 CTNNB1
flotillin complex 1 CTNNB1
Peroxisome 1 XDH
sarcoplasmic reticulum 1 XDH
secretory granule 1 CDC42
fascia adherens 1 CTNNB1
lateral plasma membrane 1 CTNNB1
nuclear inner membrane 1 SMAD3
ruffle 1 PAK1
receptor complex 1 SMAD3
neuron projection 2 CDC42, TH
chromatin 2 SMAD2, SMAD3
phagocytic cup 1 TNF
cell periphery 1 CTNNB1
mitotic spindle 2 CDC42, TUBB2B
Chromosome 1 PAK1
cytoskeleton 1 RAC1
Cytoplasm, cytoskeleton, cilium basal body 1 CTNNB1
cytoplasmic ribonucleoprotein granule 2 CDC42, RAC1
spindle pole 1 CTNNB1
chromosome, telomeric region 1 CDK2
actin filament 1 PAK1
postsynaptic density, intracellular component 1 CTNNB1
microvillus membrane 1 CTNNB1
intercellular bridge 1 TUBB2B
nuclear envelope 1 CDK2
Recycling endosome membrane 1 RAC1
Endomembrane system 1 CTNNB1
endosome lumen 1 INS
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
leading edge membrane 1 CDC42
Nucleus, nucleoplasm 1 PAK1
Cell projection, dendrite 2 CDC42, RAC1
Melanosome 2 RAC1, TYR
euchromatin 1 CTNNB1
exocytic vesicle 1 IGF1
secretory granule lumen 1 INS
secretory granule membrane 1 RAC1
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 IL6, INS
male germ cell nucleus 1 CDK2
platelet alpha granule lumen 1 IGF1
transport vesicle 1 INS
beta-catenin-TCF complex 1 CTNNB1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
presynaptic active zone cytoplasmic component 1 CTNNB1
Cajal body 1 CDK2
heteromeric SMAD protein complex 2 SMAD2, SMAD3
SMAD protein complex 2 SMAD2, SMAD3
protein-DNA complex 1 CTNNB1
ficolin-1-rich granule membrane 1 RAC1
basal dendrite 1 MAPK8
condensed chromosome 1 CDK2
catenin complex 1 CTNNB1
Nucleus, Cajal body 1 CDK2
X chromosome 1 CDK2
Y chromosome 1 CDK2
activin responsive factor complex 1 SMAD2
cyclin-dependent protein kinase holoenzyme complex 1 CDK2
cyclin E1-CDK2 complex 1 CDK2
cyclin E2-CDK2 complex 1 CDK2
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
NADPH oxidase complex 1 RAC1
alphav-beta3 integrin-IGF-1-IGF1R complex 1 IGF1
insulin-like growth factor binding protein complex 1 IGF1
insulin-like growth factor ternary complex 1 IGF1
interleukin-6 receptor complex 1 IL6
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle 1 TH
beta-catenin-TCF7L2 complex 1 CTNNB1
cyclin A2-CDK2 complex 1 CDK2
cyclin A1-CDK2 complex 1 CDK2
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1
Golgi transport complex 1 CDC42
storage vacuole 1 CDC42
Cell projection, invadopodium 1 PAK1
homomeric SMAD protein complex 1 SMAD2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Xin-Yu Kong, Tong-Tong Chen, Hong-Wu Zhang, Hong-Mei Jia, Meng Yu, Zhong-Mei Zou. Characterization of the metabolism of aloin A/B and aloesin in rats using ultra-high performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry. Biomedical chromatography : BMC. 2022 Dec; 36(12):e5483. doi: 10.1002/bmc.5483. [PMID: 35975594]
  • Emily G Hicks, Sylvie E Kandel, Jed N Lampe. Identification of Aloe-derived natural products as prospective lead scaffolds for SARS-CoV-2 main protease (Mpro) inhibitors. Bioorganic & medicinal chemistry letters. 2022 06; 66(?):128732. doi: 10.1016/j.bmcl.2022.128732. [PMID: 35427739]
  • Hans Wilhelm Rauwald, Ralf Maucher, Gerd Dannhardt, Kenny Kuchta. Dihydroisocoumarins, Naphthalenes, and Further Polyketides from Aloe vera and A. plicatilis: Isolation, Identification and Their 5-LOX/COX-1 Inhibiting Potency. Molecules (Basel, Switzerland). 2021 Jul; 26(14):. doi: 10.3390/molecules26144223. [PMID: 34299499]
  • Meron Hiruy, Daniel Bisrat, Avijit Mazumder, Kaleab Asres. Two chromones with antimicrobial activity from the leaf latex of Aloe monticola Reynolds. Natural product research. 2021 Mar; 35(6):1052-1056. doi: 10.1080/14786419.2019.1614581. [PMID: 31137974]
  • Chang Peng, WeiJia Zhang, Xue Shen, YueMei Yuan, Yan Li, Wei Zhang, MeiCun Yao. Post-transcriptional regulation activity through alternative splicing involved in the effects of Aloe vera on the Wnt/β-catenin and Notch pathways in colorectal cancer cells. Journal of pharmacological sciences. 2020 Jul; 143(3):148-155. doi: 10.1016/j.jphs.2020.03.006. [PMID: 32268968]
  • Chang Peng, WeiJia Zhang, Cong Dai, Wa Li, Xue Shen, YueMei Yuan, Li Yan, Wei Zhang, MeiCun Yao. Study of the aqueous extract of Aloe vera and its two active components on the Wnt/β-catenin and Notch signaling pathways in colorectal cancer cells. Journal of ethnopharmacology. 2019 Oct; 243(?):112092. doi: 10.1016/j.jep.2019.112092. [PMID: 31319122]
  • Luigi Lucini, Marco Pellizzoni, Roberto Pellegrino, Gian Pietro Molinari, Giuseppe Colla. Phytochemical constituents and in vitro radical scavenging activity of different Aloe species. Food chemistry. 2015 Mar; 170(?):501-7. doi: 10.1016/j.foodchem.2014.08.034. [PMID: 25306376]
  • Mesfin Yimam, Lidia Brownell, Qi Jia. In vivo safety evaluation of UP780, a standardized composition of aloe chromone aloesin formulated with an Aloe vera inner leaf fillet. Regulatory toxicology and pharmacology : RTP. 2014 Aug; 69(3):390-7. doi: 10.1016/j.yrtph.2014.05.001. [PMID: 24830776]
  • Mesfin Yimam, Jifu Zhao, Brandon Corneliusen, Mandee Pantier, Lidia Alfaro Brownell, Qi Jia. UP780, a chromone-enriched aloe composition improves insulin sensitivity. Metabolic syndrome and related disorders. 2013 Aug; 11(4):267-75. doi: 10.1089/met.2012.0135. [PMID: 23573999]
  • Xiao-Fang Wu, Jin-Zhi Wan, Bing-Jun Luo, Miao-Rong Yang, Wen-Jing Ding, Jia-Sheng Zhong. [A novel naphthalene derivative from Aloe barbadensis]. Yao xue xue bao = Acta pharmaceutica Sinica. 2013 May; 48(5):723-7. doi: . [PMID: 23888696]
  • M Rendon, S Horwitz. Topical treatment of hyperpigmentation disorders. Annales de dermatologie et de venereologie. 2012 Dec; 139 Suppl 4(?):S153-8. doi: 10.1016/s0151-9638(12)70128-x. [PMID: 23522631]
  • Lucia Steenkamp, Kgama Mathiba, Paul Steenkamp, Vuyisile Phehane, Robin Mitra, Steven Heggie, Dean Brady. Biocatalytic conversion of aloeresin A to aloesin. Journal of industrial microbiology & biotechnology. 2012 Jul; 39(7):1091-7. doi: 10.1007/s10295-012-1101-5. [PMID: 22374229]
  • Barry Lynch, Ryan Simon, Ashley Roberts. Subchronic toxicity evaluation of aloesin. Regulatory toxicology and pharmacology : RTP. 2011 Nov; 61(2):161-71. doi: 10.1016/j.yrtph.2011.07.005. [PMID: 21784118]
  • Mi-Young Park, Hoon-Jeong Kwon, Mi-Kyung Sung. Dietary aloin, aloesin, or aloe-gel exerts anti-inflammatory activity in a rat colitis model. Life sciences. 2011 Mar; 88(11-12):486-92. doi: 10.1016/j.lfs.2011.01.010. [PMID: 21277867]
  • Zeljka Krpetić, Giorgio Scarì, Enrico Caneva, Giovanna Speranza, Francesca Porta. Gold nanoparticles prepared using cape aloe active components. Langmuir : the ACS journal of surfaces and colloids. 2009 Jul; 25(13):7217-21. doi: 10.1021/la9009674. [PMID: 19505092]
  • Mario Dell'Agli, Flavio Giavarini, Patrizia Ferraboschi, Giovanni Galli, Enrica Bosisio. Determination of aloesin and aloeresin A for the detection of aloe in beverages. Journal of agricultural and food chemistry. 2007 May; 55(9):3363-7. doi: 10.1021/jf070182h. [PMID: 17419646]
  • Dianxiu Cao, Chi Ho Yoon, Beom Soo Shin, Chul Hwan Kim, Eun Seok Park, Sun Dong Yoo. Effects of aloe, aloesin, or propolis on the pharmacokinetics of benzo[a]pyrene and 3-OH-benzo[a]pyrene in rats. Journal of toxicology and environmental health. Part A. 2005 Dec; 68(23-24):2227-38. doi: 10.1080/15287390500182164. [PMID: 16326436]
  • Akira Yagi, Satoshi Takeo. [Anti-inflammatory constituents, aloesin and aloemannan in Aloe species and effects of tanshinon VI in Salvia miltiorrhiza on heart]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2003 Jul; 123(7):517-32. doi: 10.1248/yakushi.123.517. [PMID: 12875235]
  • A Yagi, A Kabash, N Okamura, H Haraguchi, S M Moustafa, T I Khalifa. Antioxidant, free radical scavenging and anti-inflammatory effects of aloesin derivatives in Aloe vera. Planta medica. 2002 Nov; 68(11):957-60. doi: 10.1055/s-2002-35666. [PMID: 12451482]
  • Ken Jones, Jennifer Hughes, Mei Hong, Qi Jia, Steve Orndorff. Modulation of melanogenesis by aloesin: a competitive inhibitor of tyrosinase. Pigment cell research. 2002 Oct; 15(5):335-40. doi: 10.1034/j.1600-0749.2002.02014.x. [PMID: 12213089]
  • D Saccù, P Bogoni, G Procida. Aloe exudate: characterization by reversed phase HPLC and headspace GC-MS. Journal of agricultural and food chemistry. 2001 Oct; 49(10):4526-30. doi: 10.1021/jf010179c. [PMID: 11599983]
  • M Baek, J H Jeong, D H Kim. Determination of aloesin in rat plasma using a column-switching high-performance liquid chromatographic assay. Journal of chromatography. B, Biomedical sciences and applications. 2001 Apr; 754(1):121-6. doi: 10.1016/s0378-4347(00)00593-4. [PMID: 11318406]
  • K H Kim, J G Lee, J H Park, Y G Shin, S K Lee, T H Cho, S T Oh. Determination of aloesin in plasma by high-performance liquid chromatography as fluorescent 9-anthroyl derivative. Archives of pharmacal research. 1998 Dec; 21(6):651-6. doi: 10.1007/bf02976752. [PMID: 9868532]
  • M J Kim, W G Shin. Determination of aloesin in plasma by high-performance liquid chromatography. Research communications in molecular pathology and pharmacology. 1998 Jan; 99(1):125-8. doi: NULL. [PMID: 9523360]
  • B E van Wyk, M C van Rheede van Oudtshoorn, G F Smith. Geographical variation in the major compounds of Aloe ferox leaf exudate. Planta medica. 1995 Jun; 61(3):250-3. doi: 10.1055/s-2006-958066. [PMID: 7617769]
  • Q M Che, T Akao, M Hattori, K Kobashi, T Namba. Metabolism of aloesin and related compounds by human intestinal bacteria: a bacterial cleavage of the C-glucosyl bond and the subsequent reduction of the acetonyl side chain. Chemical & pharmaceutical bulletin. 1991 Mar; 39(3):704-8. doi: 10.1248/cpb.39.704. [PMID: 2070451]