Agnuside (BioDeep_00000000038)

 

Secondary id: BioDeep_00000298346

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


((1S,4AR,5S,7AS)-5-HYDROXY-1-(((2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-2-YL)OXY)-1,4A,5,7A-TETRAHYDROCYCLOPENTA[C]PYRAN-7-YL)METHYL 4-HYDROXYBENZOATE

化学式: C22H26O11 (466.1475)
中文名称: 穗花牡荆苷, 慧花牡荆苷, 牡荆油
谱图信息: 最多检出来源 Viridiplantae(plant) 45.18%

分子结构信息

SMILES: C1=COC(C2C1C(C=C2COC(=O)C3=CC=C(C=C3)O)O)OC4C(C(C(C(O4)CO)O)O)O
InChI: InChI=1S/C22H26O11/c23-8-15-17(26)18(27)19(28)22(32-15)33-21-16-11(7-14(25)13(16)5-6-30-21)9-31-20(29)10-1-3-12(24)4-2-10/h1-7,13-19,21-28H,8-9H2

描述信息

Agnuside is a benzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with the primary hydroxy group of aucubin. It is an iridoid glycoside found in several Vitex plants including Vitex agnus-castus. It has a role as a plant metabolite, an anti-inflammatory agent, a pro-angiogenic agent and a cyclooxygenase 2 inhibitor. It is a terpene glycoside, an iridoid monoterpenoid, a benzoate ester, a member of phenols, a beta-D-glucoside, a cyclopentapyran and a monosaccharide derivative. It is functionally related to an aucubin.
Agnuside is a natural product found in Crescentia cujete, Vitex peduncularis, and other organisms with data available.
See also: Chaste tree fruit (part of); Vitex negundo leaf (part of).
Isolated from Vitex agnus-castus (agnus castus). Agnuside is found in herbs and spices and fruits.
Agnuside is found in fruits. Agnuside is isolated from Vitex agnus-castus (agnus castus).
Agnuside is a compound isolated from Vitex negundo, down-regulates pro-inflammatory mediators PGE2 and LTB4, and reduces the expression of cytokines, with anti-arthritic activity[1].
Agnuside is used in the study of asthma, inflammation, and angiogenic diseases. Agnuside is an orally active compound that can be extracted from Vitex negundo[1][2][3][4].
Agnuside is a compound isolated from Vitex negundo, down-regulates pro-inflammatory mediators PGE2 and LTB4, and reduces the expression of cytokines, with anti-arthritic activity[1].

同义名列表

24 个代谢物同义名

((1S,4AR,5S,7AS)-5-HYDROXY-1-(((2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-2-YL)OXY)-1,4A,5,7A-TETRAHYDROCYCLOPENTA[C]PYRAN-7-YL)METHYL 4-HYDROXYBENZOATE; [(1S,4aR,5S,7aS)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate; [(1S,4aR,5S,7aS)-5-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate; .BETA.-D-GLUCOPYRANOSIDE, 1,4A,5,7A-TETRAHYDRO-5-HYDROXY-7-(((4-HYDROXYBENZOYL)OXY)METHYL)CYCLOPENTA(C)PYRAN-1-YL, (1.ALPHA.,4A.ALPHA.,5.ALPHA.,7A.ALPHA.)-; beta-D-GLUCOPYRANOSIDE, 1,4A,5,7A-TETRAHYDRO-5-HYDROXY-7-(((4-HYDROXYBENZOYL)OXY)METHYL)CYCLOPENTA(C)PYRAN-1-YL, (1alpha,4Aalpha,5alpha,7Aalpha)-; (5-Hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,7ah-cyclopenta[c]pyran-7-yl)methyl 4-hydroxybenzoic acid; [5-Hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate; .BETA.-D-GLUCOPYRANOSIDE, (1S,4AR,5S,7AS)-1,4A,5,7A-TETRAHYDRO-5-HYDROXY-7-(((4-HYDROXYBENZOYL)OXY)METHYL)CYCLOPENTA(C)PYRAN-1-YL; beta-D-GLUCOPYRANOSIDE, (1S,4AR,5S,7AS)-1,4A,5,7A-TETRAHYDRO-5-HYDROXY-7-(((4-HYDROXYBENZOYL)OXY)METHYL)CYCLOPENTA(C)PYRAN-1-YL; (5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl)methyl 4-hydroxybenzoate; ((1S,4aR,5S,7aS)-1-(beta-D-glucopyranosyloxy)-5-hydroxy-1,4a,5,7a-tetrahydrocyclopenta(c)pyran-7-yl)methyl 4-hydroxybenzoate; [(1S,4aR,5S,7aS)-1-(beta-D-glucopyranosyloxy)-5-hydroxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate; (-)-Buddlejoside A; AGNUSIDE (USP-RS); AGNUSIDE [USP-RS]; UNII-JB24Q0OT9G; Buddlejoside A; MEGxp0_000767; ACon1_000039; JB24Q0OT9G; Agnuside; Agnoside; Agnusid; Agnuside



数据库引用编号

24 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)

57 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 AIMP2, BCL2, DCTN4, GJA1, HIF1A, IL18, NLRP3, PIK3CA, PTGS2, SMAD2, SMAD4, STAT3, VEGFA
Peripheral membrane protein 1 PTGS2
Endoplasmic reticulum membrane 3 BCL2, GJA1, PTGS2
Nucleus 11 AIMP2, BCL2, DCTN4, GATA3, GJA1, HIF1A, NLRP3, SMAD2, SMAD4, STAT3, VEGFA
cytosol 11 AIMP2, BCL2, DCTN4, GJA1, HIF1A, IL18, NLRP3, PIK3CA, SMAD2, SMAD4, STAT3
nuclear body 1 HIF1A
centrosome 2 DCTN4, SMAD4
nucleoplasm 6 GATA3, GJA1, HIF1A, SMAD2, SMAD4, STAT3
RNA polymerase II transcription regulator complex 3 HIF1A, SMAD4, STAT3
Cell membrane 2 GJA1, GJA8
lamellipodium 1 PIK3CA
Multi-pass membrane protein 2 GJA1, GJA8
Golgi apparatus membrane 1 NLRP3
cell cortex 1 DCTN4
cell junction 1 GJA1
cell surface 1 VEGFA
Golgi apparatus 2 GJA1, VEGFA
Golgi membrane 2 GJA1, NLRP3
Cytoplasm, cytosol 3 AIMP2, IL18, NLRP3
plasma membrane 5 GJA1, GJA8, IGHE, PIK3CA, STAT3
Membrane 5 AIMP2, BCL2, NLRP3, SMAD2, VEGFA
apical plasma membrane 1 GJA1
caveola 1 PTGS2
extracellular exosome 1 TIMP1
endoplasmic reticulum 5 BCL2, GJA1, NLRP3, PTGS2, VEGFA
extracellular space 7 IGHE, IL10, IL18, IL2, IL4, TIMP1, VEGFA
perinuclear region of cytoplasm 1 PIK3CA
adherens junction 1 VEGFA
gap junction 1 GJA1
intercalated disc 2 GJA1, PIK3CA
mitochondrion 3 BCL2, GJA1, NLRP3
protein-containing complex 4 BCL2, HIF1A, PTGS2, SMAD2
intracellular membrane-bounded organelle 1 GJA1
Microsome membrane 1 PTGS2
Single-pass type I membrane protein 1 IGHE
Secreted 7 IL10, IL18, IL2, IL4, NLRP3, TIMP1, VEGFA
extracellular region 8 IGHE, IL10, IL18, IL2, IL4, NLRP3, TIMP1, VEGFA
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
transcription regulator complex 3 SMAD2, SMAD4, STAT3
motile cilium 1 HIF1A
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 DCTN4
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
Secreted, extracellular space, extracellular matrix 1 VEGFA
axon cytoplasm 1 HIF1A
Membrane raft 1 GJA1
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 DCTN4
focal adhesion 2 DCTN4, GJA1
extracellular matrix 2 TIMP1, VEGFA
basement membrane 1 TIMP1
collagen trimer 1 TIMP1
secretory granule 1 VEGFA
Cell junction, gap junction 2 GJA1, GJA8
connexin complex 2 GJA1, GJA8
contractile muscle fiber 1 GJA1
fascia adherens 1 GJA1
intermediate filament 1 GJA1
lateral plasma membrane 1 GJA1
nuclear speck 1 HIF1A
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 1 NLRP3
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Cytoplasm, myofibril, sarcomere 1 DCTN4
sarcomere 1 DCTN4
neuron projection 1 PTGS2
chromatin 5 GATA3, HIF1A, SMAD2, SMAD4, STAT3
IgE immunoglobulin complex 1 IGHE
spindle pole 1 DCTN4
Cytoplasm, cell cortex 1 DCTN4
[Isoform 2]: Cell membrane 1 IGHE
Endomembrane system 1 NLRP3
microtubule organizing center 1 NLRP3
Golgi-associated vesicle membrane 1 GJA1
Nucleus speckle 1 HIF1A
euchromatin 1 HIF1A
myelin sheath 1 BCL2
stress fiber 1 DCTN4
endoplasmic reticulum lumen 2 PTGS2, TIMP1
platelet alpha granule lumen 2 TIMP1, VEGFA
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
dynactin complex 1 DCTN4
kinetochore 1 DCTN4
tight junction 1 GJA1
cytoplasmic dynein complex 1 DCTN4
Cytoplasm, cytoskeleton, stress fiber 1 DCTN4
heteromeric SMAD protein complex 2 SMAD2, SMAD4
SMAD protein complex 2 SMAD2, SMAD4
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
activin responsive factor complex 2 SMAD2, SMAD4
cell-cell contact zone 1 GJA1
[Isoform 3]: Cell membrane 1 IGHE
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
BAD-BCL-2 complex 1 BCL2
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
homomeric SMAD protein complex 1 SMAD2


文献列表

  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Mami Sogame, Yoko Naraki, Takahiro Sasaki, Masaharu Seki, Kazuyoshi Yokota, Sayaka Masada, Takashi Hakamatsuka. Quality Assessment of Medicinal Product and Dietary Supplements Containing Vitex agnus-castus by HPLC Fingerprint and Quantitative Analyses. Chemical & pharmaceutical bulletin. 2019; 67(6):527-533. doi: 10.1248/cpb.c18-00725. [PMID: 31155557]
  • Rachumallu Ramakrishna, Manisha Bhateria, Rajbir Singh, Santosh Kumar Puttrevu, Rabi Sankar Bhatta. Plasma pharmacokinetics, bioavailability and tissue distribution of agnuside following peroral and intravenous administration in mice using liquid chromatography tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2016 Jun; 125(?):154-64. doi: 10.1016/j.jpba.2016.02.047. [PMID: 27018507]
  • Masahiro Fukahori, Shojiro Kobayashi, Yoko Naraki, Takahiro Sasaki, Hideki Oka, Masaharu Seki, Sayaka Masada-Atsumi, Takashi Hakamatsuka, Yukihiro Goda. Quality evaluation of medicinal products and health foods containing chaste berry (Vitex agnus-castus) in Japanese, European and American markets. Chemical & pharmaceutical bulletin. 2014; 62(4):379-85. doi: 10.1248/cpb.c13-00588. [PMID: 24695348]
  • Donna E Webster, Ying He, Shao-Nong Chen, Guido F Pauli, Norman R Farnsworth, Zaijie Jim Wang. Opioidergic mechanisms underlying the actions of Vitex agnus-castus L. Biochemical pharmacology. 2011 Jan; 81(1):170-7. doi: 10.1016/j.bcp.2010.09.013. [PMID: 20854795]
  • Yuan Hu, Ting-Ting Hou, Qiao-Yan Zhang, Hai-Liang Xin, Han-Chen Zheng, Khalid Rahman, Lu-Ping Qin. Evaluation of the estrogenic activity of the constituents in the fruits of Vitex rotundifolia L. for the potential treatment of premenstrual syndrome. The Journal of pharmacy and pharmacology. 2007 Sep; 59(9):1307-12. doi: 10.1211/jpp.59.9.0016. [PMID: 17883902]
  • Chenchugari Sridhar, Gottumukkala V Subbaraju, Yenamandra Venkateswarlu, Raju T Venugopal. New acylated iridoid glucosides from Vitex altissima. Journal of natural products. 2004 Dec; 67(12):2012-6. doi: 10.1021/np040117r. [PMID: 15620243]
  • A Suksamrarn, S Kumpun, K Kirtikara, B Yingyongnarongkul, S Suksamrarn. Iridoids with anti-inflammatory activity from Vitex peduncularis. Planta medica. 2002 Jan; 68(1):72-3. doi: 10.1055/s-2002-20048. [PMID: 11842334]