Coniferaldehyde (BioDeep_00000000189)

 

Secondary id: BioDeep_00000269040, BioDeep_00000861087

natural product human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enal

化学式: C10H10O3 (178.062991)
中文名称: 4-羟基-3-甲氧基肉桂醛, 松柏醛
谱图信息: 最多检出来源 Viridiplantae(plant) 0.65%

Reviewed

Last reviewed on 2024-09-04.

Cite this Page

Coniferaldehyde. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/coniferaldehyde (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000000189). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: c1(c(ccc(c1)/C=C/C=O)O)OC
InChI: InChI=1/C10H10O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-7,12H,1H3/b3-2+

描述信息

Coniferaldehyde (CAS: 458-36-6), also known as 4-hydroxy-3-methoxycinnamaldehyde or ferulaldehyde, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Coniferaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, coniferaldehyde is found, on average, in the highest concentration within sherries. Coniferaldehyde has also been detected, but not quantified in, several different foods, such as highbush blueberries, lima beans, Chinese cabbages, loquats, and greenthread tea. This could make coniferaldehyde a potential biomarker for the consumption of these foods. BioTransformer predicts that coniferaldehyde is a product of caffeic aldehyde metabolism via a catechol-O-methylation-pattern2 reaction catalyzed by the enzyme catechol O-methyltransferase (PMID: 30612223).
Coniferyl aldehyde, also known as 4-hydroxy-3-methoxycinnamaldehyde or 4-hm-ca, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Coniferyl aldehyde is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Coniferyl aldehyde can be found in a number of food items such as pear, common walnut, kelp, and citrus, which makes coniferyl aldehyde a potential biomarker for the consumption of these food products. Coniferyl aldehyde is a low molecular weight phenolic compound susceptible to be extracted from cork stoppers into wine .
Coniferyl aldehyde is a member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3. It has a role as an antifungal agent and a plant metabolite. It is a member of cinnamaldehydes, a phenylpropanoid and a member of guaiacols. It is functionally related to an (E)-cinnamaldehyde.
4-Hydroxy-3-methoxycinnamaldehyde is a natural product found in Pandanus utilis, Microtropis japonica, and other organisms with data available.
A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3.
Acquisition and generation of the data is financially supported in part by CREST/JST.
Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells[1].
Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells

Coniferaldehyde. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=458-36-6 (retrieved 2024-09-04) (CAS RN: 458-36-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

47 个代谢物同义名

E-Coniferyl aldehyde; trans-Coniferaldehyde; trans-Coniferyl aldehyde; InChI=1/C10H10O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-7,12H,1H3/b3-2; 2-Propenal, 3-(4-hydroxy-3-methoxyphenyl)-, (2E)-; 2-Propenal, 3-(4-hydroxy-3-methoxyphenyl), (E)-; (E)-3-(4-Hydroxy-3-methoxyphenyl)acrylaldehyde; (2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenal; (2e)-3-(4-Hydroxy-3-Methoxyphenyl)prop-2-Enal; (E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enal; (e)-3-(4-Hydroxy-m-methoxyphenyl)prop-2-enal; (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enal; 3-(4-Hydroxy-3-methoxyphenyl)acrylaldehyde; 3-(4-Hydroxy-3-methoxyphenyl)prop-2-enal; 4-Hydroxy-3-methoxy-trans-cinnamaldehyde; 3-(4-Hydroxy-3-methoxyphenyl)-2-propenal; 4-Hydroxy-3-methoxycinnamaldehyde, 98\\%; (2E)-4-Hydroxy-3-methoxycinnamaldehyde; 3-(4-Hydroxy-3-methoxyphenyl)acrolein; 3-(4-Hydroxy-3-methoxyphenyl)propenal; 5DF06912-B0DD-4C76-B493-29D29F746430; 4-hydroxy-3-methoxycinnamic aldehyde; 2-Methoxy-4-(3-oxo-1-propenyl)phenol; Cinnamaldehyde, 4-hydroxy-3-methoxy-; 3-Methoxy-4-hydroxycinnamaldehyde; 4-Hydroxy-3-methoxycinnamaldehyde; 4-Hydroxy3-Methoxy Cinnamaldehyde; 4-Hydroxy-3-methoxyzimtaldehyde; 3-BIPHENYL-3-AMINO-ACETICACID; coniferaldehyde, (E)-isomer; trans-coniferyl aldehyde; Trans-Coniferylaldehyde; (e)-Coniferyl aldehyde; trans-Coniferaldehyde; e-Coniferyl aldehyde; Coniferylic aldehyde; trans-Ferulaldehyde; (E)-coniferaldehyde; coniferyl aldehyde; p-Coniferaldehyde; (E)-Ferulaldehyde; coniferylaldehyde; Ferulic Aldehyde; Ferulyl aldehyde; UNII-06TPT01AD5; coniferaldehyde; Ferulaldehyde; 06TPT01AD5; 4-HM-CA



数据库引用编号

29 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

PlantCyc(2)

代谢反应

433 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(7)

WikiPathways(0)

Plant Reactome(231)

INOH(0)

PlantCyc(195)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

444 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

  • Edouard Pesquet, Leonard Blaschek, Junko Takahashi, Masanobu Yamamoto, Antoine Champagne, Nuoendagula, Elena Subbotina, Charilaos Dimotakis, Zoltan Bascik, Shinya Kajita. Bulk and In Situ Quantification of Coniferaldehyde Residues in Lignin. Methods in molecular biology (Clifton, N.J.). 2024; 2722(?):201-226. doi: 10.1007/978-1-0716-3477-6_14. [PMID: 37897609]
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  • Thae Thae San, Yue-Hu Wang, Dong-Bao Hu, Jun Yang, Dong-Dong Zhang, Meng-Yuan Xia, Xue-Fei Yang, Yong-Ping Yang. A new sesquineolignan and four new neolignans isolated from the leaves of Piper betle, a traditional medicinal plant in Myanmar. Bioorganic & medicinal chemistry letters. 2021 01; 31(?):127682. doi: 10.1016/j.bmcl.2020.127682. [PMID: 33207281]
  • S Pramod, Thakurdas Saha, K Rekha, P B Kavi Kishor. Hevea brasiliensis coniferaldehyde-5-hydroxylase (HbCAld5H) regulates xylogenesis, structure and lignin chemistry of xylem cell wall in Nicotiana tabacum. Plant cell reports. 2021 Jan; 40(1):127-142. doi: 10.1007/s00299-020-02619-8. [PMID: 33068174]
  • Hongyu Gai, Fang Zhou, Yuxin Zhang, Jingya Ai, Jicheng Zhan, Yilin You, Weidong Huang. Coniferaldehyde ameliorates the lipid and glucose metabolism in palmitic acid-induced HepG2 cells via the LKB1/AMPK signaling pathway. Journal of food science. 2020 Nov; 85(11):4050-4060. doi: 10.1111/1750-3841.15482. [PMID: 33037652]
  • Eugene Fletcher, Kai Gao, Kevin Mercurio, Mariam Ali, Kristin Baetz. Yeast chemogenomic screen identifies distinct metabolic pathways required to tolerate exposure to phenolic fermentation inhibitors ferulic acid, 4-hydroxybenzoic acid and coniferyl aldehyde. Metabolic engineering. 2019 03; 52(?):98-109. doi: 10.1016/j.ymben.2018.11.010. [PMID: 30471359]
  • Yuri Takeda, Shiro Suzuki, Yuki Tobimatsu, Keishi Osakabe, Yuriko Osakabe, Safendrri K Ragamustari, Masahiro Sakamoto, Toshiaki Umezawa. Lignin characterization of rice CONIFERALDEHYDE 5-HYDROXYLASE loss-of-function mutants generated with the CRISPR/Cas9 system. The Plant journal : for cell and molecular biology. 2019 02; 97(3):543-554. doi: 10.1111/tpj.14141. [PMID: 30375064]
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  • Xing Li, Dongming Ma, Jianlin Chen, Gaobin Pu, Yunpeng Ji, Caiyan Lei, Zhigao Du, Benye Liu, Hechun Ye, Hong Wang. Biochemical characterization and identification of a cinnamyl alcohol dehydrogenase from Artemisia annua. Plant science : an international journal of experimental plant biology. 2012 Sep; 193-194(?):85-95. doi: 10.1016/j.plantsci.2012.05.011. [PMID: 22794921]
  • Nicolas Richet, Koffi Tozo, Dany Afif, Jacques Banvoy, Sylvain Legay, Pierre Dizengremel, Mireille Cabané. The response to daylight or continuous ozone of phenylpropanoid and lignin biosynthesis pathways in poplar differs between leaves and wood. Planta. 2012 Aug; 236(2):727-37. doi: 10.1007/s00425-012-1644-8. [PMID: 22526501]
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  • Alex Van Moerkercke, Carlos S Galván-Ampudia, Julian C Verdonk, Michel A Haring, Robert C Schuurink. Regulators of floral fragrance production and their target genes in petunia are not exclusively active in the epidermal cells of petals. Journal of experimental botany. 2012 May; 63(8):3157-71. doi: 10.1093/jxb/ers034. [PMID: 22345641]
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  • Zakir Hossain, Lisa Amyot, Brian McGarvey, Margaret Gruber, Jinwook Jung, Abdelali Hannoufa. The translation elongation factor eEF-1Bβ1 is involved in cell wall biosynthesis and plant development in Arabidopsis thaliana. PloS one. 2012; 7(1):e30425. doi: 10.1371/journal.pone.0030425. [PMID: 22272350]
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