Agnuside (BioDeep_00000000038)

 

Secondary id: BioDeep_00000298346

human metabolite PANOMIX_OTCML-2023 Endogenous


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 (466.14750460000005)
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(otcml) 10.6%

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

23 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



数据库引用编号

20 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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34 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。



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]