Osajin (BioDeep_00000002495)

   

natural product PANOMIX_OTCML-2023


代谢物信息卡片


4H,8H-Benzo(1,2-b:3,4-b)dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)- (8CI)

化学式: C25H24O5 (404.1624)
中文名称: β-香树脂醇, 奥沙京
谱图信息: 最多检出来源 Viridiplantae(plant) 20.83%

Reviewed

Last reviewed on 2024-08-14.

Cite this Page

Osajin. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/osajin (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000002495). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C12OC(C)(C)C=CC=1C1OC=C(C3=CC=C(O)C=C3)C(=O)C=1C(O)=C2C/C=C(/C)\C
InChI: InChI=1S/C25H24O5/c1-14(2)5-10-17-21(27)20-22(28)19(15-6-8-16(26)9-7-15)13-29-24(20)18-11-12-25(3,4)30-23(17)18/h5-9,11-13,26-27H,10H2,1-4H3

描述信息

Osajin is a member of isoflavanones.
Osajin is a natural product found in Deguelia hatschbachii, Euchresta japonica, and other organisms with data available.
Origin: Plant, Pyrans

Osajin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=482-53-1 (retrieved 2024-08-14) (CAS RN: 482-53-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

36 个代谢物同义名

4H,8H-Benzo(1,2-b:3,4-b)dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)- (8CI); 4H,8H-BENZO(1,2-B:3,4-B)DIPYRAN-4-ONE, 5-HYDROXY-3-(4-HYDROXYPHENYL)-8,8-DIMETHYL-6-(3-METHYL-2-BUTEN-1-YL)-; 5-Hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H-benzo[1,2-b:3,4-b]dipyran-4-one; 4H,8H-benzo(1,2-b:3,4-b)dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-; 4H,8H-BENZO(1,2-B:3,4-B)DIPYRAN-4-ONE, 5-HYDROXY-3-(4-HYDROXYPHENYL)-8,8-DIMETHYL-6-(3-METHYL-2-BUTENYL)-; 4H,8H-BENZO(1,2-B:3,4-B)DIPYRAN-4-ONE, 5-HYDROXY-3-(P-HYDROXYPHENYL)-8,8-DIMETHYL-6-(3-METHYL-2-BUTENYL)-; 5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-h]chromen-4-one; 5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-4H,8H-pyrano[2,3-f]chromen-4-one; 4H,2-b:3,4-b]dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-; 4H,2-b:3,4-b]dipyran-4-one, 5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-; 5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one; Osajin, >=95\\% (LC/MS-ELSD); 1-adamantylmethacrylate; 5-O-demethylscandinone; Spectrum5_000034; Spectrum2_000175; Spectrum4_001527; Spectrum3_000225; 3-deoxypomiferin; UNII-83R5N9X74B; OSAJIN [INCI]; Oprea1_003228; MEGxp0_001415; Oprea1_066678; DivK1c_006293; KBio1_001237; KBio3_001369; KBio2_000714; KBio2_003282; ACon1_002463; KBio2_005850; OSAJIN [MI]; 83R5N9X74B; Osajin; 5-Hydroxy-3- (4-hydroxyphenyl) -8,8-dimethyl-6- (3-methyl-2-butenyl) -4H,8H-benzo [ 1,2-b:3,4-b ] dipyran-4-one; Osajin



数据库引用编号

69 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)

43 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 12 ANXA5, AR, BCL2, CA1, CA2, ELANE, FASN, GDF15, MSMP, PTEN, PTGS2, RPS6KA3
Peripheral membrane protein 3 ACHE, ANXA5, PTGS2
Endoplasmic reticulum membrane 2 BCL2, PTGS2
Mitochondrion membrane 1 ABCG2
Nucleus 8 ACHE, AR, BCL2, FASLG, GDF15, JUND, PTEN, RPS6KA3
cytosol 9 ANXA5, AR, BCL2, CA1, CA2, ELANE, FASN, PTEN, RPS6KA3
mitochondrial membrane 1 ABCG2
phagocytic vesicle 1 ELANE
nucleoplasm 5 ABCG2, AR, JUND, PTEN, RPS6KA3
RNA polymerase II transcription regulator complex 1 JUND
Cell membrane 4 ABCG2, ACHE, CA2, FASLG
Multi-pass membrane protein 1 ABCG2
Synapse 2 ACHE, RPS6KA3
cell surface 2 ACHE, ELANE
Golgi apparatus 3 ACHE, FASN, GDF15
Golgi membrane 1 INS
neuromuscular junction 1 ACHE
sarcolemma 1 ANXA5
plasma membrane 8 ABCG2, ACHE, AR, BCHE, CA2, FASLG, FASN, PTEN
Membrane 7 ABCG2, ACHE, ANXA5, AR, BCL2, FASLG, FASN
apical plasma membrane 2 ABCG2, PTEN
caveola 2 FASLG, PTGS2
extracellular exosome 7 ANXA5, CA1, CA2, ELANE, FASLG, FASN, GDF15
endoplasmic reticulum 2 BCL2, PTGS2
extracellular space 8 ACHE, BCHE, ELANE, FASLG, GDF15, IL6, INS, MSMP
lysosomal lumen 1 FASLG
perinuclear region of cytoplasm 2 ACHE, FASLG
mitochondrion 1 BCL2
protein-containing complex 3 AR, BCL2, PTGS2
Microsome membrane 1 PTGS2
postsynaptic density 1 PTEN
Secreted 7 ACHE, BCHE, FASLG, GDF15, IL6, INS, MSMP
extracellular region 10 ACHE, ANXA5, BCHE, ELANE, ELN, FASLG, GDF15, IL6, INS, PTEN
cytoplasmic side of plasma membrane 1 PTEN
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
Extracellular side 1 ACHE
Cytoplasmic vesicle lumen 1 FASLG
transcription regulator complex 1 JUND
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 ANXA5, FASLG
Secreted, extracellular space, extracellular matrix 1 ELN
dendritic spine 1 PTEN
nucleolus 1 RPS6KA3
apical part of cell 1 CA2
Single-pass type II membrane protein 1 FASLG
Apical cell membrane 1 ABCG2
Membrane raft 1 ABCG2
pore complex 1 BCL2
focal adhesion 1 ANXA5
extracellular matrix 1 ELN
basement membrane 1 ACHE
Cell projection, dendritic spine 1 PTEN
Nucleus, PML body 1 PTEN
PML body 1 PTEN
collagen-containing extracellular matrix 3 ANXA5, ELANE, ELN
secretory granule 1 ELANE
nuclear speck 1 AR
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Cell projection, neuron projection 1 PTEN
Zymogen granule membrane 1 ANXA5
neuron projection 2 PTEN, PTGS2
chromatin 2 AR, JUND
cell projection 1 PTEN
brush border membrane 1 ABCG2
blood microparticle 1 BCHE
Lipid-anchor, GPI-anchor 1 ACHE
endosome lumen 1 INS
Melanosome 1 FASN
side of membrane 1 ACHE
myelin sheath 2 BCL2, CA2
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 4 BCHE, IL6, INS, PTGS2
transcription repressor complex 2 ELANE, JUND
specific granule lumen 1 ELANE
transport vesicle 1 INS
Schmidt-Lanterman incisure 1 PTEN
azurophil granule lumen 1 ELANE
Lysosome lumen 1 FASLG
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
nuclear envelope lumen 1 BCHE
vesicle membrane 1 ANXA5
synaptic cleft 1 ACHE
external side of apical plasma membrane 1 ABCG2
Cytoplasmic vesicle, phagosome 1 ELANE
elastic fiber 1 ELN
ribosome 1 RPS6KA3
transcription factor AP-1 complex 1 JUND
interleukin-6 receptor complex 1 IL6
myelin sheath adaxonal region 1 PTEN
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
[Isoform alpha]: Secreted 1 PTEN
[Isoform H]: Cell membrane 1 ACHE
[Tumor necrosis factor ligand superfamily member 6, soluble form]: Secreted 1 FASLG
[FasL intracellular domain]: Nucleus 1 FASLG
glycogen granule 1 FASN


文献列表

  • Shih-Yin Huang, Guan-Jhong Huang, Po-Fan Hsieh, Hsi-Chin Wu, Wen-Chin Huang. Osajin displays potential antiprostate cancer efficacy via impairment of fatty acid synthase and androgen receptor expression. The Prostate. 2019 09; 79(13):1543-1552. doi: 10.1002/pros.23876. [PMID: 31299104]
  • Nattiya Chaichamnong, Prapapan Temkitthawon, Nantaka Khorana, Prompan Pitpakdeeanan, Pornnarin Taepavarapruk, Nitra Nuengchamnong, Yuthana Siriwattanasathien, Apichart Suksamrarn, Kornkanok Ingkaninan. Phosphodiesterase 5 Inhibitors from Derris scandens. Planta medica. 2018 Oct; 84(15):1134-1140. doi: 10.1055/a-0619-5547. [PMID: 29702722]
  • Esra Dilek, Hüseyin Serkan Erol, Ahmet Cakir, Murat Koc, Mesut Bünyami Halici. Natural product inhibitors of carbonic anhydrase I and II isoenzymes: osajin and pomiferin. Archives of physiology and biochemistry. 2017 Oct; 123(4):219-224. doi: 10.1080/13813455.2017.1303742. [PMID: 28338341]
  • Giovanni Ribaudo, Mario Angelo Pagano, Valeria Pavan, Marco Redaelli, Maira Zorzan, Raffaele Pezzani, Carla Mucignat-Caretta, Tiziano Vendrame, Sergio Bova, Giuseppe Zagotto. Semi-synthetic derivatives of natural isoflavones from Maclura pomifera as a novel class of PDE-5A inhibitors. Fitoterapia. 2015 Sep; 105(?):132-8. doi: 10.1016/j.fitote.2015.06.020. [PMID: 26136059]
  • Hyung-In Moon. Effect of osajin and pomiferin on antidiabetic effects from normal and streptozotocin-induced diabetic rats. Natural product communications. 2014 Dec; 9(12):1723-4. doi: . [PMID: 25632468]
  • Yan Wang, Marcus J Curtis-Long, Heung Joo Yuk, Dae Wook Kim, Xue Fei Tan, Ki Hun Park. Bacterial neuraminidase inhibitory effects of prenylated isoflavones from roots of Flemingia philippinensis. Bioorganic & medicinal chemistry. 2013 Nov; 21(21):6398-404. doi: 10.1016/j.bmc.2013.08.049. [PMID: 24054487]
  • Tsung-Teng Huang, Fu-Guo Liu, Chia-Fong Wei, Chia-Chen Lu, Chang-Chieh Chen, Hung-Chi Lin, David M Ojcius, Hsin-Chih Lai. Activation of multiple apoptotic pathways in human nasopharyngeal carcinoma cells by the prenylated isoflavone, osajin. PloS one. 2011 Apr; 6(4):e18308. doi: 10.1371/journal.pone.0018308. [PMID: 21532751]
  • Atmakur Hymavathi, Peta Devanand, Katragadda Suresh Babu, Thonthula Sreelatha, Usha Rani Pathipati, Janaswamy Madhusudana Rao. Vapor-phase toxicity of Derris scandens Benth.-derived constituents against four stored-product pests. Journal of agricultural and food chemistry. 2011 Mar; 59(5):1653-7. doi: 10.1021/jf104411h. [PMID: 21314138]
  • A Kumar, S Lingadurai, A Jain, N R Barman. Erythrina variegata Linn: A review on morphology, phytochemistry, and pharmacological aspects. Pharmacognosy reviews. 2010 Jul; 4(8):147-52. doi: 10.4103/0973-7847.70908. [PMID: 22228954]
  • T Sreelatha, A Hymavathi, V Rama Subba Rao, P Devanand, P Usha Rani, J Madhusudana Rao, K Suresh Babu. A new benzil derivative from Derris scandens: Structure-insecticidal activity study. Bioorganic & medicinal chemistry letters. 2010 Jan; 20(2):549-53. doi: 10.1016/j.bmcl.2009.11.103. [PMID: 19969457]
  • James V Gruber, Robert Holtz. Examining the genomic influence of skin antioxidants in vitro. Mediators of inflammation. 2010; 2010(?):. doi: 10.1155/2010/230450. [PMID: 20706672]
  • I Orhan, F S Senol, M Kartal, M Dvorská, M Zemlicka, K Smejkal, P Mokrý. Cholinesterase inhibitory effects of the extracts and compounds of Maclura pomifera (Rafin.) Schneider. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2009 Aug; 47(8):1747-51. doi: 10.1016/j.fct.2009.04.023. [PMID: 19394400]
  • Hua Li, Meihua Yang, Xiaojun Ma. [Flavonoids from roots of Flemingia philippinensis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Mar; 34(6):724-6. doi: . [PMID: 19624015]
  • Vaclav Diopan, Petr Babula, Violetta Shestivska, Vojtech Adam, Milan Zemlicka, Margita Dvorska, Jaromir Hubalek, Libuse Trnkova, Ladislav Havel, Rene Kizek. Electrochemical and spectrometric study of antioxidant activity of pomiferin, isopomiferin, osajin and catalposide. Journal of pharmaceutical and biomedical analysis. 2008 Sep; 48(1):127-33. doi: 10.1016/j.jpba.2008.05.025. [PMID: 18597965]
  • Il Hong Son, Ill-Min Chung, Sung Ik Lee, Hyun Duk Yang, Hyung-In Moon. Pomiferin, histone deacetylase inhibitor isolated from the fruits of Maclura pomifera. Bioorganic & medicinal chemistry letters. 2007 Sep; 17(17):4753-5. doi: 10.1016/j.bmcl.2007.06.060. [PMID: 17662606]
  • J Fránová, M Pavlík. [Testing of antidiabetic and antioxidative effect of the flavonoid osajin in an experiment]. Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti. 2007 Jul; 56(4):200-4. doi: . [PMID: 17969319]
  • William L Whaley, Jeremy D Rummel, Niksa Kastrapeli. Interactions of genistein and related isoflavones with lipid micelles. Langmuir : the ACS journal of surfaces and colloids. 2006 Aug; 22(17):7175-84. doi: 10.1021/la0606502. [PMID: 16893213]
  • J Necas, L Bartosíková, T Florian, J Klusáková, V Suchý, E M B Naggar, E Janostíková, T Bartosík, M Lisková. [Protective effects of the flavonoids osajin and pomiferin on heart ischemia-reperfusion]. Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti. 2006 Jul; 55(4):168-74. doi: . [PMID: 16921735]
  • Tomas Florian, Jiri Necas, Lenka Bartosikova, Jarmila Klusakova, Vaclav Suchy, Elmoataz B El Naggara, Eva Janostikova, Tomas Bartosik. Effects of prenylated isoflavones osajin and pomiferin in premedication on heart ischemia-reperfusion. Biomedical papers of the Medical Faculty of the University Palacky, Olomouc, Czechoslovakia. 2006 Jul; 150(1):93-100. doi: 10.5507/bp.2006.013. [PMID: 16936909]
  • L Bartosíková, J Necas, V Suchý, E Janostíková, T Bartosík, J Jurica, T Florian, J Klusáková, M Frydrych. Protective effects of osajin in ischemia-reperfusion of laboratory rat kidney. Die Pharmazie. 2006 Jun; 61(6):552-5. doi: . [PMID: 16826976]
  • Young-Ji Shiao, Chuen-Neu Wang, Wan-Yu Wang, Yun-Lian Lin. Neuroprotective flavonoids from Flemingia macrophylla. Planta medica. 2005 Sep; 71(9):835-40. doi: 10.1055/s-2005-871297. [PMID: 16206038]
  • Dagmar Veselá, Renáta Kubínová, Jan Muselík, Milan Zemlicka, Václav Suchý. Antioxidative and EROD activities of osajin and pomiferin. Fitoterapia. 2004 Mar; 75(2):209-11. doi: 10.1016/j.fitote.2003.12.005. [PMID: 15030927]
  • Rong Tsao, Raymond Yang, J Christopher Young. Antioxidant isoflavones in Osage orange, Maclura pomifera (Raf.) Schneid. Journal of agricultural and food chemistry. 2003 Oct; 51(22):6445-51. doi: 10.1021/jf0342369. [PMID: 14558760]