Dihydrocapsaicin (BioDeep_00000000325)

 

Secondary id: BioDeep_00000398299, BioDeep_00000866905

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


Dihydrocapsaicin, Nonanamide, 8-methyl-N-vanillyl- (7CI,8CI); 6,7-Dihydrocapsaicin; Capsaicin, dihydro-; Dihydrocapsaicin

化学式: C18H29NO3 (307.2147324)
中文名称: 二氢辣椒碱, 二氢辣椒素, 辣椒素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 1.38%

分子结构信息

SMILES: C1=CC(CNC(=O)CCCCCCC(C)C)=CC(OC)=C1O
InChI: InChI=1S/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)

描述信息

Dihydrocapsaicin is found in pepper (C. annuum). It is a potential nutriceutical. Dihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin it is an irritant. Dihydrocapsaicin accounts for about 22\\\\\% of the total capsaicinoids mixture and has about the same pungency as capsaicin. Pure dihydrocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. It is soluble in dimethyl sulfoxide and 100 \\\\\% ethanol.
Dihydrocapsaicin is a capsaicinoid.
Dihydrocapsaicin is a natural product found in Capsicum pubescens, Capsicum annuum, and Ganoderma lucidum with data available.
See also: Capsicum (part of); Paprika (part of); Habanero (part of) ... View More ...
Potential nutriceutical
Dihydrocapsaicin, a capsaicin, is a potent and selective TRPV1 (transient receptor potential vanilloid channel 1) agonist. Dihydrocapsaicin reduces AIF, Bax, and Caspase-3 expressions, and increased Bcl-2, Bcl-xL and p-Akt levels. Dihydrocapsaicin enhances the hypothermia-induced neuroprotection following ischemic stroke via PI3K/Akt regulation in rat[1][2][3].
Dihydrocapsaicin, a capsaicin, is a potent and selective TRPV1 (transient receptor potential vanilloid channel 1) agonist. Dihydrocapsaicin reduces AIF, Bax, and Caspase-3 expressions, and increased Bcl-2, Bcl-xL and p-Akt levels. Dihydrocapsaicin enhances the hypothermia-induced neuroprotection following ischemic stroke via PI3K/Akt regulation in rat[1][2][3].
Dihydrocapsaicin, a capsaicin, is a potent and selective TRPV1 (transient receptor potential vanilloid channel 1) agonist. Dihydrocapsaicin reduces AIF, Bax, and Caspase-3 expressions, and increased Bcl-2, Bcl-xL and p-Akt levels. Dihydrocapsaicin enhances the hypothermia-induced neuroprotection following ischemic stroke via PI3K/Akt regulation in rat[1][2][3].

同义名列表

31 个代谢物同义名

Dihydrocapsaicin, Nonanamide, 8-methyl-N-vanillyl- (7CI,8CI); 6,7-Dihydrocapsaicin; Capsaicin, dihydro-; Dihydrocapsaicin; Dihydrocapsaicin, United States Pharmacopeia (USP) Reference Standard; Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-; Nonanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-; N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-Nonanamide; N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methylnonanamide; N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide; DIHYDROCAPSAICIN (CONSTITUENT OF CAPSICUM) [DSC]; N-(4-hydroxy-3-methoxybenzyl)-8-methylnonanamide; Dihydrocapsaicin, from Capsicum sp., >=85\\%; DIHYDROCAPSAICIN (CONSTITUENT OF CAPSICUM); Dihydrocapsaicin, analytical standard; Nonanamide, 8-methyl-N-vanillyl-; 8-methyl-N-vanillyl-nonanamide; 8-Methyl-N-vanillylnonanamide; 8-Methyl-N-vanillyl-nonamide; XJQPQKLURWNAAH-UHFFFAOYSA-N; DIHYDROCAPSAICIN [USP-RS]; DIHYDROCAPSAICIN (USP-RS); 8-methyl dihydrocapsaicin; Dihydrocapsaicin,(S); 6,7-Dihydrocapsaicin; CAPSAICIN, DIHYDRO-; dihydro capsaicin; Dihydrocapsacine; Dihydrocapsaicin; UNII-W9BV32M08A; Lopac0_000782; Tox21_500782; NA 18:4;O2; W9BV32M08A



数据库引用编号

21 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)

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

  • Mostafakamal Shams, Esra Arslan Yuksel, Guleray Agar, Melek Ekinci, Raziye Kul, Metin Turan, Ertan Yildirim. Biosynthesis of capsaicinoids in pungent peppers under salinity stress. Physiologia plantarum. 2023 Mar; ?(?):e13889. doi: 10.1111/ppl.13889. [PMID: 36905231]
  • Xueqin Chen, Jingyue Yu, Huan Lei, Lei Li, Xupin Liu, Bo Liu, Yanfei Xie, Haihong Fang. Exploring the Mechanism of Buyang Huanwu Decoction Alleviating Restenosis by Regulating VSMC Phenotype Switching and Proliferation by Network Pharmacology and Molecular Docking. Current computer-aided drug design. 2023 Feb; ?(?):. doi: 10.2174/1573409919666230203144207. [PMID: 36740793]
  • Uthai Wichai, Ploychanok Keawsomnuk, Saowarose Thongin, Chaiyot Mukthung, Chatchai Boonthip, Pattama Pittayakhajonwut, Pimonrat Ketsawatsomkron, Nuntavan Bunyapraphatsara, Kenjiro Muta. Cellular responses to 8-methyl nonanoic acid, a degradation by-product of dihydrocapsaicin, in 3T3-L1 adipocytes. BMC complementary medicine and therapies. 2023 Jan; 23(1):18. doi: 10.1186/s12906-023-03844-w. [PMID: 36681810]
  • Leeseul Jang, Jungwon Choi, Sullim Lee, Sanghyun Lee. Protective effects of Capsicum fruits and their constituents on damage in TNF-α-stimulated human dermal fibroblasts. Journal of the science of food and agriculture. 2022 Nov; ?(?):. doi: 10.1002/jsfa.12313. [PMID: 36325913]
  • Sangeeta Bhandari, Roktim Gogoi, Twahira Begum, Joyashree Baruah, Mohan Lal. Evaluation of ultra high-performance liquid chromatography (uHPLC) assisted capsaicinoids content in four different extracts of (Capsicum chinense Jacq.): their pharmacological potentials and genotoxicity study. Natural product research. 2022 Nov; 36(21):5638-5642. doi: 10.1080/14786419.2021.2019735. [PMID: 34937448]
  • Alaadin E El-Haddad, Ahmed S Saad, Soad Z El-Emam, Asmaa A Amer. Correlation of Chillies Capsaicinoids Contents with their Cytotoxic Effects against Hepatocarcinoma Cells. Pakistan journal of biological sciences : PJBS. 2021 Jan; 24(2):219-226. doi: 10.3923/pjbs.2021.219.226. [PMID: 33683051]
  • Catharine A Adams, Kolea Zimmerman, Kristi Fenstermacher, Mitchell G Thompson, Will Skyrud, Scott Behie, Anne Pringle. Fungal Seed Pathogens of Wild Chili Peppers Possess Multiple Mechanisms To Tolerate Capsaicinoids. Applied and environmental microbiology. 2020 01; 86(3):. doi: 10.1128/aem.01697-19. [PMID: 31732572]
  • Kesinee Nanok, Sompong Sansenya. α-Glucosidase, α-amylase, and tyrosinase inhibitory potential of capsaicin and dihydrocapsaicin. Journal of food biochemistry. 2020 01; 44(1):e13099. doi: 10.1111/jfbc.13099. [PMID: 31724206]
  • Milagros Liseth Castillo Rivera, Neuza Mariko Aymoto Hassimotto, Vanessa Bueris, Marcelo Palma Sircili, Felipe Alves de Almeida, Uelinton Manoel Pinto. Effect of Capsicum Frutescens Extract, Capsaicin, and Luteolin on Quorum Sensing Regulated Phenotypes. Journal of food science. 2019 Jun; 84(6):1477-1486. doi: 10.1111/1750-3841.14648. [PMID: 31132155]
  • Jung Eun Kim, Yeong Ji Oh, Ah Young Song, Sea C Min. Preservation of red pepper flakes using microwave-combined cold plasma treatment. Journal of the science of food and agriculture. 2019 Mar; 99(4):1577-1585. doi: 10.1002/jsfa.9336. [PMID: 30146707]
  • Timothy J Woodman, Eduard Negoescu. A simple 1 H NMR based assay of total capsaicinoid levels in Capsicum using signal suppression in non-deuterated solvent. Journal of the science of food and agriculture. 2019 Mar; 99(4):1765-1771. doi: 10.1002/jsfa.9368. [PMID: 30226282]
  • Raihana Ridzuan, Mohd Y Rafii, Martini Mohammad Yusoff, Siti Izera Ismail, Gous Miah, Magaji Usman. Genetic diversity analysis of selected Capsicum annuum genotypes based on morphophysiological, yield characteristics and their biochemical properties. Journal of the science of food and agriculture. 2019 Jan; 99(1):269-280. doi: 10.1002/jsfa.9169. [PMID: 29851100]
  • Carlos Lopez-Ortiz, Sudip Kumar Dutta, Purushothaman Natarajan, Yadira Peña-Garcia, Venkata Abburi, Thangasamy Saminathan, Padma Nimmakayala, Umesh K Reddy. Genome-wide identification and gene expression pattern of ABC transporter gene family in Capsicum spp. PloS one. 2019; 14(4):e0215901. doi: 10.1371/journal.pone.0215901. [PMID: 31039176]
  • Chuan Zhou, Dianping Ma, Wenming Cao, Haiming Shi, Yuanrong Jiang. Fast simultaneous determination of capsaicin, dihydrocapsaicin and nonivamide for detecting adulteration in edible and crude vegetable oils by UPLC-MS/MS. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2018 Aug; 35(8):1447-1452. doi: 10.1080/19440049.2018.1457801. [PMID: 29601258]
  • A Zak, N Siwinska, M Slowikowska, H Borowicz, P Szpot, M Zawadzki, A Niedzwiedz. The detection of capsaicin and dihydrocapsaicin in horse serum following long-term local administration. BMC veterinary research. 2018 Jun; 14(1):193. doi: 10.1186/s12917-018-1518-9. [PMID: 29914499]
  • Rongwei Yan, Leilei Zhao, Junfei Tao, Yong Zou, Xinjun Xu. Preparative isolation and purification of capsaicin and dihydrocapsaicin from Capsici Fructus using supercritical fluid extraction combined with high speed countercurrent chromatography. Journal of the science of food and agriculture. 2018 May; 98(7):2498-2506. doi: 10.1002/jsfa.8736. [PMID: 29023749]
  • N Jeeatid, S Techawongstien, B Suriharn, S Chanthai, P W Bosland, S Techawongstien. Influence of water stresses on capsaicinoid production in hot pepper (Capsicum chinense Jacq.) cultivars with different pungency levels. Food chemistry. 2018 Apr; 245(?):792-797. doi: 10.1016/j.foodchem.2017.11.110. [PMID: 29287443]
  • Stanislau Bogusz, Silvia H Libardi, Fernanda Fg Dias, Janclei P Coutinho, Vivian C Bochi, Daniele Rodrigues, Arlete Mt Melo, Helena T Godoy. Brazilian Capsicum peppers: capsaicinoid content and antioxidant activity. Journal of the science of food and agriculture. 2018 Jan; 98(1):217-224. doi: 10.1002/jsfa.8459. [PMID: 28573647]
  • Venu Perla, Marjan Nadimi, Rishi Reddy, Gerald R Hankins, Padma Nimmakayala, Robert T Harris, Jagan Valluri, Cristian Sirbu, Umesh K Reddy. Effect of ghost pepper on cell proliferation, apoptosis, senescence and global proteomic profile in human renal adenocarcinoma cells. PloS one. 2018; 13(10):e0206183. doi: 10.1371/journal.pone.0206183. [PMID: 30379886]
  • Magda L Arce-Rodríguez, Neftalí Ochoa-Alejo. An R2R3-MYB Transcription Factor Regulates Capsaicinoid Biosynthesis. Plant physiology. 2017 Jul; 174(3):1359-1370. doi: 10.1104/pp.17.00506. [PMID: 28483879]
  • Padma Nimmakayala, Venkata L Abburi, Thangasamy Saminathan, Suresh B Alaparthi, Aldo Almeida, Brittany Davenport, Marjan Nadimi, Joshua Davidson, Krittika Tonapi, Lav Yadav, Sridhar Malkaram, Gopinath Vajja, Gerald Hankins, Robert Harris, Minkyu Park, Doil Choi, John Stommel, Umesh K Reddy. Genome-wide Diversity and Association Mapping for Capsaicinoids and Fruit Weight in Capsicum annuum L. Scientific reports. 2016 11; 6(?):38081. doi: 10.1038/srep38081. [PMID: 27901114]
  • Le Xie, Guang-Hong Xiang, Tao Tang, Yan Tang, Ling-Yun Zhao, Dong Liu, You-Ren Zhang, Jin-Tian Tang, Shen Zhou, Da-Hua Wu. Capsaicin and dihydrocapsaicin induce apoptosis in human glioma cells via ROS and Ca2+‑mediated mitochondrial pathway. Molecular medicine reports. 2016 Nov; 14(5):4198-4208. doi: 10.3892/mmr.2016.5784. [PMID: 27748914]
  • Qingqing Yang, Jianguo Zhu, Fei Ma, Peiwu Li, Liangxiao Zhang, Wen Zhang, Xiaoxia Ding, Qi Zhang. Quantitative determination of major capsaicinoids in serum by ELISA and time-resolved fluorescent immunoassay based on monoclonal antibodies. Biosensors & bioelectronics. 2016 Jul; 81(?):229-235. doi: 10.1016/j.bios.2016.02.074. [PMID: 26954788]
  • Chiara Bignardi, Antonella Cavazza, Massimiliano Rinaldi, Claudio Corradini. Correlation between different markers for the assessment of red chilli pepper powders stability during shelf-life. International journal of food sciences and nutrition. 2016 Jun; 67(4):391-9. doi: 10.3109/09637486.2016.1164671. [PMID: 27045952]
  • Fei Ma, Qingqing Yang, Bertrand Matthäus, Peiwu Li, Qi Zhang, Liangxiao Zhang. Simultaneous determination of capsaicin and dihydrocapsaicin for vegetable oil adulteration by immunoaffinity chromatography cleanup coupled with LC-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2016 May; 1021(?):137-144. doi: 10.1016/j.jchromb.2015.12.017. [PMID: 26739369]
  • Dimin Wang, Fanhua Meng, Lin Yu, Lu Sun, Lili Sun, Jifen Guo. A sensitive LC-MS/MS method for quantifying capsaicin and dihydrocapsaicin in rabbit plasma and tissue: application to a pharmacokinetic study. Biomedical chromatography : BMC. 2015 Apr; 29(4):496-503. doi: 10.1002/bmc.3302. [PMID: 25088519]
  • Mónika Kuzma, Krisztina Fodor, Borbála Boros, Pál Perjési. Development and validation of an HPLC-DAD analysis for pharmacopoeial qualification of industrial Capsicum extracts. Journal of chromatographic science. 2015 Jan; 53(1):16-23. doi: 10.1093/chromsci/bmu004. [PMID: 24557717]
  • George F Antonious. Elevating concentrations of capsaicin and dihydrocapsaicin in hot peppers using recycled waste. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2015; 50(7):523-32. doi: 10.1080/03601234.2015.1018765. [PMID: 25996816]
  • Xiuli Ma, Wenhua Ji, Lingxiao Chen, Xiao Wang, Jianhua Liu, Xueyong Wang. Molecularly imprinted polymers with synthetic dummy templates for the preparation of capsaicin and dihydrocapsaicin from chili peppers. Journal of separation science. 2015 Jan; 38(1):100-7. doi: 10.1002/jssc.201400911. [PMID: 25348490]
  • Safa Y Almaghrabi, Dominic P Geraghty, Kiran D K Ahuja, Murray J Adams. Vanilloid-like agents inhibit aggregation of human platelets. Thrombosis research. 2014 Aug; 134(2):412-7. doi: 10.1016/j.thromres.2014.05.038. [PMID: 24953906]
  • Lisha Mao, Honghe Liu, Li Kang, Jie Jiang, Shicheng Liao, Guihua Liu, Pingjian Deng. [Efficiency evaluation of capsaicinoids to discriminate bio-waste oils from edible vegetable oils]. Wei sheng yan jiu = Journal of hygiene research. 2014 Jul; 43(4):614-9. doi: ". [PMID: 25199291]
  • Jia-Yi Zhao, Yan-Wei Hu, Shu-Fen Li, Ya-Rong Hu, Xin Ma, Shao-Guo Wu, Yan-Chao Wang, Ji-Juan Gao, Yan-Hua Sha, Lei Zheng, Qian Wang. Dihydrocapsaicin down-regulates apoM expression through inhibiting Foxa2 expression and enhancing LXRα expression in HepG2 cells. Lipids in health and disease. 2014 Mar; 13(?):50. doi: 10.1186/1476-511x-13-50. [PMID: 24642298]
  • Qumer Iqbal, Muhammad Amjad, Muhammad Rafique Asi, Agustin Ariño. Characterization of capsaicinoids and antioxidants in hot peppers as influenced by hybrid and harvesting stage. Plant foods for human nutrition (Dordrecht, Netherlands). 2013 Dec; 68(4):358-63. doi: 10.1007/s11130-013-0386-5. [PMID: 24081832]
  • Alberto González-Zamora, Erick Sierra-Campos, J Guadalupe Luna-Ortega, Rebeca Pérez-Morales, Juan Carlos Rodríguez Ortiz, José L García-Hernández. Characterization of different Capsicum varieties by evaluation of their capsaicinoids content by high performance liquid chromatography, determination of pungency and effect of high temperature. Molecules (Basel, Switzerland). 2013 Oct; 18(11):13471-86. doi: 10.3390/molecules181113471. [PMID: 24184818]
  • Yavuz Yardım, Zühre Sentürk. Electrochemical evaluation and adsorptive stripping voltammetric determination of capsaicin or dihydrocapsaicin on a disposable pencil graphite electrode. Talanta. 2013 Aug; 112(?):11-9. doi: 10.1016/j.talanta.2013.03.047. [PMID: 23708530]
  • Lei Zhang, Min Zhou, Guoshan Fang, Yan Tang, Zongdao Chen, Xiong Liu. Hypocholesterolemic effect of capsaicinoids by increased bile acids excretion in ovariectomized rats. Molecular nutrition & food research. 2013 Jun; 57(6):1080-8. doi: 10.1002/mnfr.201200716. [PMID: 23471827]
  • Youwen You, Cornelius E Uboh, Lawrence R Soma, Fuyu Guan, Daniel Taylor, Xiaoqing Li, Ying Liu, Jinwen Chen. Validated UHPLC-MS-MS method for rapid analysis of capsaicin and dihydrocapsaicin in equine plasma for doping control. Journal of analytical toxicology. 2013 Mar; 37(2):122-32. doi: 10.1093/jat/bks098. [PMID: 23316028]
  • Yan-Wei Hu, Xin Ma, Jin-Lan Huang, Xin-Ru Mao, Jun-Yao Yang, Jia-Yi Zhao, Shu-Fen Li, Yu-Rong Qiu, Jia Yang, Lei Zheng, Qian Wang. Dihydrocapsaicin Attenuates Plaque Formation through a PPARγ/LXRα Pathway in apoE(-/-) Mice Fed a High-Fat/High-Cholesterol Diet. PloS one. 2013; 8(6):e66876. doi: 10.1371/journal.pone.0066876. [PMID: 23840542]
  • Zeid Abdullah Alothman, Saikh Mohammad Wabaidur, Mohammad Rizwan Khan, Ayman Abdel Ghafar, Mohamed Abdelaty Habila, Yacine Badjah Hadj Ahmed. Determination of capsaicinoids in Capsicum species using ultra performance liquid chromatography-mass spectrometry. Journal of separation science. 2012 Nov; 35(21):2892-6. doi: 10.1002/jssc.201200459. [PMID: 23047709]
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