valerenic acid (BioDeep_00000288962)

Main id: BioDeep_00000007585

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


valerenic acid

化学式: C15H22O2 (234.162)
中文名称: 缬草素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C12=C(C)CC[C@]1([H])[C@H](C)CC[C@H]2/C=C(\C)/C(=O)O
InChI: InChI=1S/C15H22O2/c1-9-4-6-12(8-11(3)15(16)17)14-10(2)5-7-13(9)14/h8-9,12-13H,4-7H2,1-3H3,(H,16,17)/b11-8+/t9-,12+,13-/m1/s1

描述信息

A monocarboxylic acid that is 2-methylprop-2-enoic acid which is substituted at position 3 by a 3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl group. A bicyclic sesquiterpenoid constituent of the essential oil of the Valerian plant.
Valerenic acid ((-)-Valerenic Acid), a sesquiterpenoid, is an orally active positive allosteric modulator of GABAA receptors. Valerenic acid is also a partial agonist of the 5-HT5a receptor. Valerenic acid mediates anxiolytic activity via GABAA receptors containing the β3 subunit. Valerenic acid also exhibits potent antioxidant properties[1][2][3].

同义名列表

3 个代谢物同义名

valerenic acid; (-)-Valerenic Acid; Valerenic acid



数据库引用编号

16 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)

52 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 11 ASL, CASP12, CASP3, CASP9, ERN1, GFAP, HPGDS, MAPK8, PPARG, PRKAA2, TH
Endosome membrane 1 SLC6A4
Endoplasmic reticulum membrane 2 ERN1, HMOX1
Nucleus 7 CASP3, CASP9, HMOX1, MAPK8, PPARG, PRKAA2, TH
cytosol 11 ASL, CASP3, CASP9, GFAP, HMOX1, HPGDS, MAPK8, PPARG, PRKAA2, SLC2A4, TH
dendrite 4 HTR1D, HTR5A, PRKAA2, TH
trans-Golgi network 1 SLC2A4
nucleoplasm 6 CASP3, HMOX1, HPGDS, MAPK8, PPARG, PRKAA2
RNA polymerase II transcription regulator complex 1 PPARG
Cell membrane 6 HTR1D, HTR5A, P2RY4, SLC2A4, SLC6A4, TNF
Cytoplasmic side 1 HMOX1
Cell projection, axon 1 TH
Multi-pass membrane protein 5 HTR1D, HTR5A, P2RY4, SLC2A4, SLC6A4
Synapse 3 HTR1D, MAPK8, SLC6A4
cell surface 2 ADIPOQ, TNF
glutamatergic synapse 2 CASP3, P2RY4
Golgi apparatus 1 PRKAA2
neuronal cell body 3 CASP3, PRKAA2, TNF
presynaptic membrane 1 SLC6A4
sarcolemma 1 SLC2A4
smooth endoplasmic reticulum 1 TH
synaptic vesicle 1 TH
Presynapse 2 SLC2A4, SLC6A4
plasma membrane 6 HTR1D, HTR5A, P2RY4, SLC2A4, SLC6A4, TNF
terminal bouton 1 TH
Membrane 4 HMOX1, PRKAA2, SLC2A4, SLC6A4
apical plasma membrane 1 P2RY4
axon 3 MAPK8, PRKAA2, TH
basolateral plasma membrane 1 P2RY4
extracellular exosome 2 ASL, SLC2A4
endoplasmic reticulum 4 ADIPOQ, CASP12, ERN1, HMOX1
extracellular space 4 ADIPOQ, CXCL8, HMOX1, TNF
perinuclear region of cytoplasm 4 HMOX1, PPARG, SLC2A4, TH
mitochondrion 3 CASP9, ERN1, TH
protein-containing complex 1 CASP9
intracellular membrane-bounded organelle 2 HPGDS, PPARG
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 ERN1
Secreted 2 ADIPOQ, CXCL8
extracellular region 3 ADIPOQ, CXCL8, TNF
cytoplasmic side of plasma membrane 1 TH
mitochondrial outer membrane 1 HMOX1
astrocyte end-foot 1 GFAP
external side of plasma membrane 2 SLC2A4, TNF
multivesicular body 1 SLC2A4
T-tubule 1 SLC2A4
perikaryon 2 HTR5A, TH
cytoplasmic vesicle 1 TH
Melanosome membrane 1 TH
clathrin-coated pit 1 SLC2A4
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 SLC6A4
presynaptic active zone membrane 1 P2RY4
Cytoplasm, perinuclear region 2 SLC2A4, TH
Membrane raft 3 SLC2A4, SLC6A4, TNF
Cell junction, focal adhesion 1 SLC6A4
focal adhesion 1 SLC6A4
collagen trimer 1 ADIPOQ
sarcoplasmic reticulum 1 SLC2A4
collagen-containing extracellular matrix 1 ADIPOQ
intermediate filament 1 GFAP
nuclear speck 1 PRKAA2
nuclear inner membrane 1 ERN1
receptor complex 1 PPARG
Cell projection, neuron projection 1 SLC6A4
neuron projection 2 SLC6A4, TH
chromatin 1 PPARG
cell projection 1 GFAP
phagocytic cup 1 TNF
Endomembrane system 2 SLC2A4, SLC6A4
Cytoplasmic vesicle membrane 1 SLC2A4
cytoplasmic stress granule 1 PRKAA2
cell body 1 GFAP
intermediate filament cytoskeleton 1 GFAP
clathrin-coated vesicle 1 SLC2A4
trans-Golgi network transport vesicle 1 SLC2A4
Single-pass type IV membrane protein 1 HMOX1
apoptosome 1 CASP9
vesicle membrane 1 SLC2A4
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
postsynaptic specialization membrane 1 HTR5A
nucleotide-activated protein kinase complex 1 PRKAA2
AIP1-IRE1 complex 1 ERN1
Ire1 complex 1 ERN1
IRE1-RACK1-PP2A complex 1 ERN1
IRE1-TRAF2-ASK1 complex 1 ERN1
cytoplasmic side of lysosomal membrane 1 GFAP
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle 1 TH
insulin-responsive compartment 1 SLC2A4
serotonergic synapse 1 SLC6A4
NLRP1 inflammasome complex 1 CASP12
caspase complex 1 CASP9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Natalie E Pinder, Isaac Y Ligocki, Brent M Horton, John E Hoover. Valerenic acid reduces anxiety-like behavior in young adult, female (C57BL/6J) mice. Behavioural brain research. 2024 02; 457(?):114717. doi: 10.1016/j.bbr.2023.114717. [PMID: 37852540]
  • Moritz Winker, Antoine Chauveau, Martin Smieško, Olivier Potterat, Alexander Areesanan, Amy Zimmermann-Klemd, Carsten Gründemann. Immunological evaluation of herbal extracts commonly used for treatment of mental diseases during pregnancy. Scientific reports. 2023 Jun; 13(1):9630. doi: 10.1038/s41598-023-35952-5. [PMID: 37316493]
  • 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]
  • Antoine Chauveau, Andrea Treyer, Annelies Geirnaert, Lea Bircher, Angela Babst, Vanessa Fabienne Abegg, Ana Paula Simões-Wüst, Christophe Lacroix, Olivier Potterat, Matthias Hamburger. Intestinal permeability and gut microbiota interactions of pharmacologically active compounds in valerian and St. John's wort. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Apr; 162(?):114652. doi: 10.1016/j.biopha.2023.114652. [PMID: 37027987]
  • Sualiha Afzal, Xian Zhou, King Or, Ritesh Raju, Gerald Münch. Identification of Nrf2 Activators from the Roots of Valeriana officinalis. Planta medica. 2023 Jan; 89(1):30-45. doi: 10.1055/a-1887-2016. [PMID: 35764305]
  • Mehtap Kara, Ezgi Öztaş, Tuğçe Boran, Çiğdem Sevim, Seda Eren Keskin, Aristidis S Veskoukis, Sergei V Kuzmin, Aristides M Tsatsakis. The sesquiterpenoid valerenic acid protects neuronal cells from the detrimental effects of the fungicide benomyl on apoptosis and DNA oxidation. Human & experimental toxicology. 2022 Jan; 41(?):9603271221101038. doi: 10.1177/09603271221101038. [PMID: 35764419]
  • Maria Teresa Faleschini, Anne Maier, Sarah Fankhauser, Katharina Thasis, Simon Hebeisen, Matthias Hamburger, Veronika Butterweck. A FLIPR Assay for Discovery of GABAA Receptor Modulators of Natural Origin. Planta medica. 2019 Aug; 85(11-12):925-933. doi: 10.1055/a-0921-7602. [PMID: 31127604]
  • Jeff Wong, Leo d'Espaux, Ishaan Dev, Cas van der Horst, Jay Keasling. De novo synthesis of the sedative valerenic acid in Saccharomyces cerevisiae. Metabolic engineering. 2018 05; 47(?):94-101. doi: 10.1016/j.ymben.2018.03.005. [PMID: 29545148]
  • Ramin Nikzad-Langerodi, Katharina Arth, Valerie Klatte-Asselmeyer, Sabine Bressler, Johannes Saukel, Gottfried Reznicek, Christoph Dobeš. Quality Control of Valerianae Radix by Attenuated Total Reflection Fourier Transform Infrared (ATR-FTIR) Spectroscopy. Planta medica. 2018 Apr; 84(6-07):442-448. doi: 10.1055/s-0043-122239. [PMID: 29121679]
  • Folake A Egbewande, Niclas Nilsson, Jonathan M White, Mark J Coster, Rohan A Davis. The design, synthesis, and anti-inflammatory evaluation of a drug-like library based on the natural product valerenic acid. Bioorganic & medicinal chemistry letters. 2017 07; 27(14):3185-3189. doi: 10.1016/j.bmcl.2017.05.021. [PMID: 28558967]
  • Fahimeh Moradi-Afrapoli, Samad Nejad Ebrahimi, Martin Smiesko, Matthias Hamburger. HPLC-Based Activity Profiling for GABAA Receptor Modulators in Extracts: Validation of an Approach Utilizing a Larval Zebrafish Locomotor Assay. Journal of natural products. 2017 05; 80(5):1548-1557. doi: 10.1021/acs.jnatprod.7b00081. [PMID: 28485933]
  • Arun K Jugran, Amit Bahukhandi, Praveen Dhyani, Indra D Bhatt, Ranbeer S Rawal, Shyamal K Nandi. Impact of Altitudes and Habitats on Valerenic Acid, Total Phenolics, Flavonoids, Tannins, and Antioxidant Activity of Valeriana jatamansi. Applied biochemistry and biotechnology. 2016 Jul; 179(6):911-26. doi: 10.1007/s12010-016-2039-2. [PMID: 26971960]
  • Yun Ji Park, Mariadhas Valan Arasu, Naif Abdullah Al-Dhabi, Soon Sung Lim, Yeon Bok Kim, Sang Won Lee, Sang Un Park. Expression of Terpenoid Biosynthetic Genes and Accumulation of Chemical Constituents in Valeriana fauriei. Molecules (Basel, Switzerland). 2016 May; 21(6):. doi: 10.3390/molecules21060691. [PMID: 27240331]
  • Vincent Ricigliano, Santosh Kumar, Scott Kinison, Christopher Brooks, S Eric Nybo, Joe Chappell, Dianella G Howarth. Regulation of sesquiterpenoid metabolism in recombinant and elicited Valeriana officinalis hairy roots. Phytochemistry. 2016 May; 125(?):43-53. doi: 10.1016/j.phytochem.2016.02.011. [PMID: 26920719]
  • Hyo Young Jung, Dae Young Yoo, Sung Min Nam, Jong Whi Kim, Jung Hoon Choi, Miyoung Yoo, Sanghee Lee, Yeo Sung Yoon, In Koo Hwang. Valerenic Acid Protects Against Physical and Psychological Stress by Reducing the Turnover of Serotonin and Norepinephrine in Mouse Hippocampus-Amygdala Region. Journal of medicinal food. 2015 Dec; 18(12):1333-9. doi: 10.1089/jmf.2014.3412. [PMID: 26177123]
  • Bianca A Torres-Hernández, Lisa M Del Valle-Mojica, José G Ortíz. Valerenic acid and Valeriana officinalis extracts delay onset of Pentylenetetrazole (PTZ)-Induced seizures in adult Danio rerio (Zebrafish). BMC complementary and alternative medicine. 2015 Jul; 15(?):228. doi: 10.1186/s12906-015-0731-3. [PMID: 26168917]
  • Axel Becker, Falko Felgentreff, Helmut Schröder, Beat Meier, Axel Brattström. The anxiolytic effects of a Valerian extract is based on valerenic acid. BMC complementary and alternative medicine. 2014 Jul; 14(?):267. doi: 10.1186/1472-6882-14-267. [PMID: 25066015]
  • Juliane Hintersteiner, Maximilian Haider, Denise Luger, Christoph Schwarzer, Gottfried Reznicek, Walter Jäger, Sophia Khom, Marko D Mihovilovic, Steffen Hering. Esters of valerenic acid as potential prodrugs. European journal of pharmacology. 2014 Jul; 735(?):123-31. doi: 10.1016/j.ejphar.2014.03.019. [PMID: 24680924]
  • Sung Min Nam, Jung Hoon Choi, Dae Young Yoo, Woosuk Kim, Hyo Young Jung, Jong Whi Kim, Soo-Yong Kang, Jaeil Park, Dong-Woo Kim, Wan Jae Kim, Yeo Sung Yoon, In Koo Hwang. Valeriana officinalis extract and its main component, valerenic acid, ameliorate D-galactose-induced reductions in memory, cell proliferation, and neuroblast differentiation by reducing corticosterone levels and lipid peroxidation. Experimental gerontology. 2013 Nov; 48(11):1369-77. doi: 10.1016/j.exger.2013.09.002. [PMID: 24055511]
  • Mehdi Ansari Dugaheh, Faramarz Meisami, Zahra Torabian, Fariba Sharififar. Antioxidant effect and study of bioactive components of Valeriana sisymbriifolia and Nardostachys jatamansii in comparison to Valeriana officinalis. Pakistan journal of pharmaceutical sciences. 2013 Jan; 26(1):53-8. doi: . [PMID: 23261727]
  • Lisa M Del Valle-Mojica, José G Ortíz. Anxiolytic properties of Valeriana officinalis in the zebrafish: a possible role for metabotropic glutamate receptors. Planta medica. 2012 Nov; 78(16):1719-24. doi: 10.1055/s-0032-1315240. [PMID: 22923195]
  • Chethan Sampath, Karin Haug, Sophia Thanei, Matthias Hamburger, Hartmut Derendorf, Reginald Frye, Veronika Butterweck. Pharmacokinetics of valerenic acid in rats after intravenous and oral administrations. Planta medica. 2012 Apr; 78(6):575-81. doi: 10.1055/s-0031-1298301. [PMID: 22411722]
  • Mohamad Mirzaei, Hossein Dinpanah. Three phases hollow fiber LPME combined with HPLC-UV for extraction, preconcentration and determination of valerenic acid in Valeriana officinalis. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Jul; 879(21):1870-4. doi: 10.1016/j.jchromb.2011.05.005. [PMID: 21641881]
  • Nicholas K Chow, Michael Fretz, Matthias Hamburger, Veronika Butterweck. Telemetry as a tool to measure sedative effects of a valerian root extract and its single constituents in mice. Planta medica. 2011 May; 77(8):795-803. doi: 10.1055/s-0030-1250589. [PMID: 21154200]
  • K Murphy, Z J Kubin, J N Shepherd, R H Ettinger. Valeriana officinalis root extracts have potent anxiolytic effects in laboratory rats. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2010 Jul; 17(8-9):674-8. doi: 10.1016/j.phymed.2009.10.020. [PMID: 20042323]
  • Monika Nell, Christoph Wawrosch, Siegrid Steinkellner, Horst Vierheilig, Brigitte Kopp, Andreas Lössl, Chlodwig Franz, Johannes Novak, Karin Zitterl-Eglseer. Root colonization by symbiotic arbuscular mycorrhizal fungi increases sesquiterpenic acid concentrations in Valeriana officinalis L. Planta medica. 2010 Mar; 76(4):393-8. doi: 10.1055/s-0029-1186180. [PMID: 19809971]
  • Francesco Occhiuto, Annalisa Pino, Dora Rita Palumbo, Stefania Samperi, Rita De Pasquale, Emanuele Sturlese, Clara Circosta. Relaxing effects of Valeriana officinalis extracts on isolated human non-pregnant uterine muscle. The Journal of pharmacy and pharmacology. 2009 Feb; 61(2):251-6. doi: 10.1211/jpp/61.02.0016. [PMID: 19178774]
  • Dietmar Benke, Andrea Barberis, Sascha Kopp, Karl-Heinz Altmann, Monika Schubiger, Kaspar E Vogt, Uwe Rudolph, Hanns Möhler. GABA A receptors as in vivo substrate for the anxiolytic action of valerenic acid, a major constituent of valerian root extracts. Neuropharmacology. 2009 Jan; 56(1):174-81. doi: 10.1016/j.neuropharm.2008.06.013. [PMID: 18602406]
  • Gabriele Trauner, Sophia Khom, Igor Baburin, Birgit Benedek, Steffen Hering, Brigitte Kopp. Modulation of GABAA receptors by valerian extracts is related to the content of valerenic acid. Planta medica. 2008 Jan; 74(1):19-24. doi: 10.1055/s-2007-993761. [PMID: 18095218]
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  • Gail D Anderson, Gary W Elmer, Eric D Kantor, Ian E Templeton, Michael V Vitiello. Pharmacokinetics of valerenic acid after administration of valerian in healthy subjects. Phytotherapy research : PTR. 2005 Sep; 19(9):801-3. doi: 10.1002/ptr.1742. [PMID: 16220575]
  • Birgit M Dietz, Gail B Mahady, Guido F Pauli, Norman R Farnsworth. Valerian extract and valerenic acid are partial agonists of the 5-HT5a receptor in vitro. Brain research. Molecular brain research. 2005 Aug; 138(2):191-7. doi: 10.1016/j.molbrainres.2005.04.009. [PMID: 15921820]
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  • Chun-Su Yuan, Sangeeta Mehendale, Yingping Xiao, Han H Aung, Jing-Tian Xie, Michael K Ang-Lee. The gamma-aminobutyric acidergic effects of valerian and valerenic acid on rat brainstem neuronal activity. Anesthesia and analgesia. 2004 Feb; 98(2):353-358. doi: 10.1213/01.ane.0000096189.70405.a5. [PMID: 14742369]
  • J J Torrado. In vitro release of valerenic and hydroxyvalerenic acids from valerian tablets. Die Pharmazie. 2003 Sep; 58(9):636-8. doi: ". [PMID: 14531459]
  • A Herrera-Arellano, G Luna-Villegas, M L Cuevas-Uriostegui, L Alvarez, G Vargas-Pineda, A Zamilpa-Alvarez, J Tortoriello. Polysomnographic evaluation of the hypnotic effect of Valeriana edulis standardized extract in patients suffering from insomnia. Planta medica. 2001 Nov; 67(8):695-9. doi: 10.1055/s-2001-18344. [PMID: 11731907]
  • X Q Gao, L Björk. Valerenic acid derivatives and valepotriates among individuals, varieties and species of Valeriana. Fitoterapia. 2000 Feb; 71(1):19-24. doi: 10.1016/s0367-326x(99)00094-5. [PMID: 11449465]
  • R Bos, H J Woerdenbag, F M van Putten, H Hendriks, J J Scheffer. Seasonal variation of the essential oil, valerenic acid and derivatives, and velopotriates in Valeriana officinalis roots and rhizomes, and the selection of plants suitable for phytomedicines. Planta medica. 1998 Mar; 64(2):143-7. doi: 10.1055/s-2006-957392. [PMID: 9556440]