alpha-Ionone (BioDeep_00000009222)

 

Secondary id: BioDeep_00000019578, BioDeep_00000265891

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


(3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one

化学式: C13H20O (192.1514)
中文名称: α-紫罗酮, alpha-紫罗酮
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 10.42%

分子结构信息

SMILES: CC(=O)/C=C/C1C(C)=CCCC1(C)C
InChI: InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3/b8-7+

描述信息

alpha-Ionone, also known as (e)-alpha-ionone or trans-a-ionone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. alpha-Ionone is a potentially toxic compound. Alpha-ionone is a neutral compound. Alpha-ionone has a dry, floral, and flower taste with a cedar wood-like scent. It is a naturally occurring organic compound found in a variety of essential oils, including rose oil, flowers from Boronia megastigma (brown boronia; doi: 10.21273/hortsci.30.4.876d) and coml oil. Alpha-ionone is found in highest concentrations in corns, tea, and carrots and in lower concentrations in hyssops, peppermints, and safflowers. Alpha-ionone has also been detected in common grapes, sour cherries, common wheats, garden tomato, and wakames making beta-ionone a potential biomarker for the consumption of these foods. Alpha-ionone is used as to make Vitamins A, E and K1. It is used as a fragrance in perfumes, cosmetics and personal care products, and household cleaners and detergents. Alpha-ionone is used as a food flavoring in beverages, ice cream, baked goods and candies.
Alpha-ionone, also known as (E)-α-ionone or alpha-cyclocitrylideneacetone, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Alpha-ionone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Alpha-ionone is a sweet, floral, and fruity tasting compound and can be found in a number of food items such as tea, wild carrot, wild celery, and ginkgo nuts, which makes alpha-ionone a potential biomarker for the consumption of these food products. Alpha-ionone can be found primarily in saliva. Alpha-ionone exists in all eukaryotes, ranging from yeast to humans. Alpha-ionone is a non-carcinogenic (not listed by IARC) potentially toxic compound.
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

同义名列表

26 个代谢物同义名

(3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one; (3E)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-ON; alpha-Cyclocitrylideneacetone; alpha-Ionone, (e)-(+-)-isomer; a-Cyclocitrylideneacetone; Α-cyclocitrylideneacetone; alpha-Ionone, (e)-isomer; alpha-Ionone, (+)-iosmer; trans-alpha-Ionone; alpha-(e)-Ionone; (e)-alpha-Ionone; trans-Α-ionone; trans-a-Ionone; Α-(e)-ionone; (e)-Α-ionone; alpha-Ionone; a-(e)-Ionone; (e)-a-Ionone; alpha-Ionon; α-ionone; a-Ionone; Α-ionon; a-Ionon; alpha-Ionone; alpha-Ionone; alpha-Ionone



数据库引用编号

17 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)

94 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 6 AIMP2, COL1A1, GPBAR1, HAS1, KRT1, MMP3
Golgi apparatus, trans-Golgi network membrane 1 HAS3
Peripheral membrane protein 1 CYP1B1
Endoplasmic reticulum membrane 2 CYP1B1, HAS2
Nucleus 7 AIMP2, FLG, HAS3, JUND, KRT1, MMP3, NR1H4
cytosol 4 AIMP2, FLG, KRT1, MMP3
nucleoplasm 2 JUND, NR1H4
RNA polymerase II transcription regulator complex 2 JUND, NR1H4
Cell membrane 5 GPBAR1, GPRC5A, HAS2, HAS3, KRT1
Cytoplasmic granule 1 FLG
Multi-pass membrane protein 6 GPBAR1, GPRC5A, HAS1, HAS2, HAS3, UCP1
Golgi apparatus membrane 2 HAS2, HAS3
glutamatergic synapse 1 FLG
Golgi apparatus 4 ATRN, HAS1, HAS2, HAS3
Golgi membrane 2 HAS2, HAS3
mitochondrial inner membrane 1 UCP1
postsynapse 1 FLG
Cytoplasm, cytosol 1 AIMP2
Lysosome 1 HAS2
plasma membrane 8 ATRN, FLG, GPBAR1, GPRC5A, HAS1, HAS2, HAS3, KRT1
Membrane 7 AIMP2, COL1A1, CYP1B1, FLG, HAS1, HAS3, KRT1
extracellular exosome 5 ATRN, COL1A2, GPRC5A, KRT1, MMP9
extracellular space 9 ATRN, COL1A1, COL1A2, CXCL8, DEFB4B, KRT1, MMP1, MMP3, MMP9
mitochondrion 3 CYP1B1, MMP3, UCP1
intracellular membrane-bounded organelle 2 CYP1B1, GPRC5A
Microsome membrane 1 CYP1B1
Single-pass type I membrane protein 1 ATRN
Secreted 4 COL1A2, CXCL8, DEFB4B, MMP3
extracellular region 9 COL1A1, COL1A2, CXCL8, DEFB4B, FLG, KRT1, MMP1, MMP3, MMP9
[Isoform 2]: Secreted 1 ATRN
transcription regulator complex 1 JUND
Extracellular vesicle 1 HAS2
Secreted, extracellular space, extracellular matrix 4 COL1A1, COL1A2, MMP1, MMP9
cytoplasmic vesicle 2 FLG, HAS2
nucleolus 1 GPRC5A
Early endosome 1 HAS3
vesicle 2 GPRC5A, HAS2
Mitochondrion inner membrane 1 UCP1
extracellular matrix 2 MMP1, MMP3
collagen trimer 2 COL1A1, COL1A2
collagen-containing extracellular matrix 5 COL1A1, COL1A2, FLG, KRT1, MMP9
secretory granule 1 COL1A1
receptor complex 4 FLG, GPBAR1, GPRC5A, NR1H4
chromatin 2 JUND, NR1H4
cytoskeleton 1 KRT1
[Isoform 3]: Nucleus 1 NR1H4
cytoplasmic ribonucleoprotein granule 1 FLG
blood microparticle 1 KRT1
[Isoform 3]: Secreted 1 ATRN
Cornified envelope 2 FLG, KRT1
Cytoplasmic vesicle membrane 1 GPRC5A
euchromatin 1 NR1H4
hyaluranon cable 1 HAS3
plasma membrane raft 1 HAS2
ficolin-1-rich granule lumen 2 KRT1, MMP9
Golgi lumen 1 DEFB4B
endoplasmic reticulum lumen 2 COL1A1, COL1A2
transcription repressor complex 1 JUND
tertiary granule lumen 1 MMP9
[Isoform 2]: Nucleus 1 NR1H4
[Isoform 1]: Nucleus 1 NR1H4
[Isoform 1]: Cell membrane 1 ATRN
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
keratin filament 1 KRT1
[Isoform 4]: Nucleus 1 NR1H4
transcription factor AP-1 complex 1 JUND
collagen type I trimer 2 COL1A1, COL1A2
keratohyalin granule 1 FLG


文献列表

  • Md Mahfuzur Rob, Kawsar Hossen, Kaori Ozaki, Toshiaki Teruya, Hisashi Kato-Noguchi. Phytotoxicity and Phytotoxic Substances in Calamus tenuis Roxb. Toxins. 2023 10; 15(10):. doi: 10.3390/toxins15100595. [PMID: 37888626]
  • Yukihiro Yoshida, Dai Haraguchi, Rie Ukuda-Hosokawa, Tsunaki Andou, Takashi Matsuyama, Tsuguo Kohama, Takashi Eguchi, Satoshi Ohno, Hajime Ono, Ritsuo Nishida. Synthesis and activity of 3-oxo-α-ionone analogs as male attractants for the solanaceous fruit fly, Bactrocera latifrons (Diptera: Tephritidae). Bioscience, biotechnology, and biochemistry. 2021 Nov; 85(12):2360-2367. doi: 10.1093/bbb/zbab166. [PMID: 34601560]
  • Yanting Zhong, Xiaoying Pan, Ruifeng Wang, Jiuliang Xu, Jingyu Guo, Tingxue Yang, Jianyu Zhao, Faisal Nadeem, Xiaoting Liu, Hongyan Shan, Yanjun Xu, Xuexian Li. ZmCCD10a Encodes a Distinct Type of Carotenoid Cleavage Dioxygenase and Enhances Plant Tolerance to Low Phosphate. Plant physiology. 2020 09; 184(1):374-392. doi: 10.1104/pp.20.00378. [PMID: 32586893]
  • Mika Murata, Tetsuya Kobayashi, Shigemi Seo. α-Ionone, an Apocarotenoid, Induces Plant Resistance to Western Flower Thrips, Frankliniella occidentalis, Independently of Jasmonic Acid. Molecules (Basel, Switzerland). 2019 Dec; 25(1):. doi: 10.3390/molecules25010017. [PMID: 31861560]
  • Ilya Lukin, Guido Jach, Isabell Wingartz, Peter Welters, Gerhard Schembecker. Recovery of Natural α-Ionone from Fermentation Broth. Journal of agricultural and food chemistry. 2019 Dec; 67(49):13412-13419. doi: 10.1021/acs.jafc.8b07270. [PMID: 30864443]
  • Marinella De Leo, Lorenzo Peruzzi, Carlotta Granchi, Tiziano Tuccinardi, Filippo Minutolo, Nunziatina De Tommasi, Alessandra Braca. Constituents of Polygala flavescens ssp. flavescens and Their Activity as Inhibitors of Human Lactate Dehydrogenase. Journal of natural products. 2017 07; 80(7):2077-2087. doi: 10.1021/acs.jnatprod.7b00295. [PMID: 28692289]
  • Lian Gelis, Nikolina Jovancevic, Sophie Veitinger, Bhubaneswar Mandal, Hans-Dieter Arndt, Eva M Neuhaus, Hanns Hatt. Functional Characterization of the Odorant Receptor 51E2 in Human Melanocytes. The Journal of biological chemistry. 2016 08; 291(34):17772-86. doi: 10.1074/jbc.m116.734517. [PMID: 27226631]
  • Yao Lu, Zhi-Hong Li, Lin Ma, An-Jun Deng, Feng Wu, Zhi-Hui Zhang, Hai-Lin Qin. [Study on chemical constituents from cultivated Gynura nepalensis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2014 Oct; 39(19):3777-81. doi: . [PMID: 25612439]
  • Hongyan Sun, Li Guan, Honglin Feng, Jiao Yin, Yazhong Cao, Jinghui Xi, Kebin Li. Functional characterization of chemosensory proteins in the scarab beetle, Holotrichia oblita Faldermann (Coleoptera: Scarabaeida). PloS one. 2014; 9(9):e107059. doi: 10.1371/journal.pone.0107059. [PMID: 25188038]
  • Hao Cai, Gang Cao, Li Li, Xiao Liu, Xiao-Qing Ma, Si-Cong Tu, Ya-Jing Lou, Kun-Ming Qin, Song-Lin Li, Bao-Chang Cai. Profiling and characterization of volatile components from non-fumigated and sulfur-fumigated Flos Lonicerae Japonicae using comprehensive two-dimensional gas chromatography time-of-flight mass spectrometry coupled with chemical group separation. Molecules (Basel, Switzerland). 2013 Jan; 18(2):1368-82. doi: 10.3390/molecules18021368. [PMID: 23348991]
  • Kazuya Shimizu, Toshirou Ono, Mitsuo Miyazawa. Highly selective and asymmetric reductive biotransformation of α-ionone by Epicoccum purpurascens. Journal of oleo science. 2013; 62(4):231-4. doi: 10.5650/jos.62.231. [PMID: 23535310]
  • Jia-xu Wen, De Zhao, Jun Deng. [Influence of processing methods on the chemical composition of the essential oil from Aucklandia lappa]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2012 Sep; 35(9):1397-401. doi: . [PMID: 23451492]
  • Ufuk Ozgen, Handan Sevindik, Cavit Kazaz, Demet Yigit, Ali Kandemir, Hasan Secen, Ihsan Calis. A new sulfated alpha-ionone glycoside from Sonchus erzincanicus Matthews. Molecules (Basel, Switzerland). 2010 Apr; 15(4):2593-9. doi: 10.3390/molecules15042593. [PMID: 20428066]
  • Tatsuaki Ishida, Hiroshi Enomoto, Ritsuo Nishida. New attractants for males of the solanaceous fruit fly Bactrocera latifrons. Journal of chemical ecology. 2008 Dec; 34(12):1532-5. doi: 10.1007/s10886-008-9562-8. [PMID: 19018595]
  • María del Mar Caja, Christina Preston, Michael Kempf, Peter Schreier. Flavor authentication studies of alpha-ionone, beta-ionone, and alpha-ionol from various sources. Journal of agricultural and food chemistry. 2007 Aug; 55(16):6700-4. doi: 10.1021/jf070805r. [PMID: 17630763]
  • Grant T McQuate, Young Soo Keum, Charmaine D Sylva, Qing X Li, Eric B Jang. Active ingredients in cade oil that synergize attractiveness of alpha-ionol to male Bactrocera latifrons (Diptera: Tephritidae). Journal of economic entomology. 2004 Jun; 97(3):862-70. doi: 10.1603/0022-0493(2004)097[0862:aiicot]2.0.co;2. [PMID: 15279265]
  • G T McQuate, S L Peck. Enhancement of attraction of alpha-ionol to male Bactrocera latifrons (Diptera: Tephritidae) by addition of a synergist, cade oil. Journal of economic entomology. 2001 Feb; 94(1):39-46. doi: 10.1603/0022-0493-94.1.39. [PMID: 11233131]