Falcarinol (BioDeep_00000625339)

Main id: BioDeep_00000629719

Secondary id: BioDeep_00000000842

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(CIS)-(-)-3-HYDROXY-1,9-HEPTADECADIEN-4,6-DIYNE

化学式: C17H24O (244.18270539999997)
中文名称: (R)-(-)-法卡诺尔, 人参炔醇
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 14.4%

分子结构信息

SMILES: C=CC(O)C#CC#CC/C=C/CCCCCCC
InChI: InChI=1S/C17H24O/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17(18)4-2/h4,10-11,17-18H,2-3,5-9,12H2,1H3/b11-10+/t17-/m1/s1

描述信息

Panaxynol is a long-chain fatty alcohol. It has a role as a metabolite.
Falcarinol is a natural product found in Chaerophyllum aureum, Cussonia arborea, and other organisms with data available.
A natural product found in Panax ginseng and Angelica japonica.

同义名列表

21 个代谢物同义名

(CIS)-(-)-3-HYDROXY-1,9-HEPTADECADIEN-4,6-DIYNE; 1,9-Heptadecadiene-4,6-diyn-3-ol, (3R,9Z)-; (Z)-(-)-1,9-heptadecadiene-4,6-diyne-3-ol; (3R,9Z)-heptadeca-1,9-dien-4,6-diyn-3-ol; (R,Z)-Heptadeca-1,9-dien-4,6-diyn-3-ol; 1,9Z-heptadecadien-4,6-diyn-3R-ol; 1,9-Heptadecadiene-4,6-diyn-3-ol; falcarinol, (Z)-isomer; Falcarinol,Panaxynol; (R)-(-)-Falcarinol; FALCARINOL [HSDB]; (3R)-faclarinol; UNII-8P1DJD416I; (-)-Falcarinol; (-)-PANAXYNOL; Falcarinol; 8P1DJD416I; panaxynol; FOH 17:6; (E,R)-Heptadeca-1,9-dien-4,6-diyne-3-ol; Heptadeca-1,9E-dien-4,6-diyne-3R-ol



数据库引用编号

18 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)

41 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

  • Shabir Ahmad Ganai, Mudasir A Mir, Basit Amin Shah, Raies A Qadri, Arif Hussain Wani, Sundararaj Rajamanikandan, Awquib Sabhat. Evaluation of free radical quenching, anti-inflammatory activity together with anticancer potential of Lychnis coronaria and characterization of novel molecules from its extract through high resolution-liquid chromatography mass spectrometry coupled to structural biochemistry approach. Journal of biomolecular structure & dynamics. 2023 Feb; ?(?):1-15. doi: 10.1080/07391102.2023.2173296. [PMID: 36749717]
  • Gokay Albayrak, Serdar Demir, Halil Koyu, Sura Baykan. Anticholinesterase Compounds from Endemic Prangos uechtritzii. Chemistry & biodiversity. 2022 Nov; 19(11):e202200557. doi: 10.1002/cbdv.202200557. [PMID: 36201258]
  • Ulla Jakobsen, Morten Kobæk-Larsen, Karoline D Kjøller, Steen Antonsen, Gunnar Baatrup, Morten B Trelle. Quantification of the anti-neoplastic polyacetylene falcarinol from carrots in human serum by LC-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2022 Nov; 1210(?):123440. doi: 10.1016/j.jchromb.2022.123440. [PMID: 36088746]
  • Yan Zhao, Xialin Sun, Tingwen Zhang, Shuangli Liu, Enbo Cai, Hongyan Zhu. Study on the antidepressant effect of panaxynol through the IκB-α/NF-κB signaling pathway to inhibit the excessive activation of BV-2 microglia. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 Jun; 138(?):111387. doi: 10.1016/j.biopha.2021.111387. [PMID: 33721753]
  • Corena V Grant, Shengxin Cai, April L Risinger, Huiyun Liang, Barry R O'Keefe, John G Doench, Robert H Cichewicz, Susan L Mooberry. CRISPR-Cas9 Genome-Wide Knockout Screen Identifies Mechanism of Selective Activity of Dehydrofalcarinol in Mesenchymal Stem-like Triple-Negative Breast Cancer Cells. Journal of natural products. 2020 10; 83(10):3080-3092. doi: 10.1021/acs.jnatprod.0c00642. [PMID: 33021790]
  • Amanda Stefanson, Marica Bakovic. Dietary polyacetylene falcarinol upregulated intestinal heme oxygenase-1 and modified plasma cytokine profile in late phase lipopolysaccharide-induced acute inflammation in CB57BL/6 mice. Nutrition research (New York, N.Y.). 2020 08; 80(?):89-105. doi: 10.1016/j.nutres.2020.06.014. [PMID: 32738564]
  • Anusha Chaparala, Hossam Tashkandi, Alexander A Chumanevich, Erin E Witalison, Anthony Windust, Taixing Cui, Mitzi Nagarkatti, Prakash Nagarkatti, Lorne J Hofseth. Molecules from American Ginseng Suppress Colitis through Nuclear Factor Erythroid-2-Related Factor 2. Nutrients. 2020 Jun; 12(6):. doi: 10.3390/nu12061850. [PMID: 32575883]
  • Mirta Resetar, Xin Liu, Sonja Herdlinger, Olaf Kunert, Eva-Maria Pferschy-Wenzig, Simone Latkolik, Theresa Steinacher, Daniela Schuster, Rudolf Bauer, Verena M Dirsch. Polyacetylenes from Oplopanax horridus and Panax ginseng: Relationship between Structure and PPARγ Activation. Journal of natural products. 2020 04; 83(4):918-926. doi: 10.1021/acs.jnatprod.9b00691. [PMID: 32129622]
  • Horacio Larqué-García, Luis W Torres-Tapia, Marina Vera-Ku, Rubí Gamboa-León, Salett Novelo-Castilla, Tania I Coral-Martínez, Sergio R Peraza-Sánchez. Quantitative seasonal variation of the falcarinol-type polyacetylene (3S)-16,17-didehydrofalcarinol and its spatial tissue distribution in Tridax procumbens. Phytochemical analysis : PCA. 2020 Mar; 31(2):183-190. doi: 10.1002/pca.2878. [PMID: 31343078]
  • Dahae Lee, Jaemin Lee, Kim Long Vu-Huynh, Thi Hong Van Le, Thi Hong Tuoi Do, Gwi Seo Hwang, Jeong Hill Park, Ki Sung Kang, Minh Duc Nguyen, Noriko Yamabe. Protective Effect of Panaxynol Isolated from Panax vietnamensis against Cisplatin-Induced Renal Damage: In Vitro and In Vivo Studies. Biomolecules. 2019 12; 9(12):. doi: 10.3390/biom9120890. [PMID: 31861234]
  • Joon Hyuk Hou, Hyunjung Shin, Kyoung Hwa Jang, Chae Kyu Park, Bonsuk Koo, Hyeji Shin, Soon Hong Yuk, Ki Yong Lee. Anti-acne properties of hydrophobic fraction of red ginseng (Panax ginseng C.A. Meyer) and its active components. Phytotherapy research : PTR. 2019 Mar; 33(3):584-590. doi: 10.1002/ptr.6243. [PMID: 30506753]
  • Susan S C Cheung, David Hasman, Djamel Khelifi, Joseph Tai, Richard W Smith, Garth L Warnock. Devil's Club Falcarinol-Type Polyacetylenes Inhibit Pancreatic Cancer Cell Proliferation. Nutrition and cancer. 2019; 71(2):301-311. doi: 10.1080/01635581.2018.1559931. [PMID: 30661403]
  • Lucas Busta, Won Cheol Yim, Evan William LaBrant, Peng Wang, Lindsey Grimes, Kiah Malyszka, John C Cushman, Patricia Santos, Dylan K Kosma, Edgar B Cahoon. Identification of Genes Encoding Enzymes Catalyzing the Early Steps of Carrot Polyacetylene Biosynthesis. Plant physiology. 2018 12; 178(4):1507-1521. doi: 10.1104/pp.18.01195. [PMID: 30333150]
  • Michiyo Takagi, Kazunori Kimura, Ken-Ichi Nakashima, Makoto Inoue. Ameliorative effect of panaxynol on the reduction in high-molecular-weight adiponectin secretion from 3T3-L1 adipocytes treated with palmitic acids. European journal of pharmacology. 2018 Feb; 820(?):138-145. doi: 10.1016/j.ejphar.2017.12.028. [PMID: 29248425]
  • Amanda L Stefanson, Marica Bakovic. Falcarinol Is a Potent Inducer of Heme Oxygenase-1 and Was More Effective than Sulforaphane in Attenuating Intestinal Inflammation at Diet-Achievable Doses. Oxidative medicine and cellular longevity. 2018; 2018(?):3153527. doi: 10.1155/2018/3153527. [PMID: 30420908]
  • Morten Kobaek-Larsen, Rime B El-Houri, Lars P Christensen, Issam Al-Najami, Xavier Fretté, Gunnar Baatrup. Dietary polyacetylenes, falcarinol and falcarindiol, isolated from carrots prevents the formation of neoplastic lesions in the colon of azoxymethane-induced rats. Food & function. 2017 Mar; 8(3):964-974. doi: 10.1039/c7fo00110j. [PMID: 28197615]
  • Gai Liu, Daowan Lai, Qi Zhi Liu, Ligang Zhou, Zhi Long Liu. Identification of Nematicidal Constituents of Notopterygium incisum Rhizomes against Bursaphelenchus xylophilus and Meloidogyne incognita. Molecules (Basel, Switzerland). 2016 Sep; 21(10):. doi: 10.3390/molecules21101276. [PMID: 27669203]
  • Chen Qu, Bin Li, Yimu Lai, Hechu Li, Anthony Windust, Lorne J Hofseth, Mitzi Nagarkatti, Prakash Nagarkatti, Xing Li Wang, Dongqi Tang, Joseph S Janicki, Xingsong Tian, Taixing Cui. Identifying panaxynol, a natural activator of nuclear factor erythroid-2 related factor 2 (Nrf2) from American ginseng as a suppressor of inflamed macrophage-induced cardiomyocyte hypertrophy. Journal of ethnopharmacology. 2015 Jun; 168(?):326-36. doi: 10.1016/j.jep.2015.04.004. [PMID: 25882312]
  • Ingrid Aguiló-Aguayo, Corina Abreu, Mohammad B Hossain, Rosa Altisent, Nigel Brunton, Inmaculada Viñas, Dilip K Rai. Exploring the effects of pulsed electric field processing parameters on polyacetylene extraction from carrot slices. Molecules (Basel, Switzerland). 2015 Mar; 20(3):3942-54. doi: 10.3390/molecules20033942. [PMID: 25738537]
  • Evy Paulsen, Thomas H Petersen, Xavier C Fretté, Klaus E Andersen, Lars P Christensen. Systemic allergic dermatitis caused by Apiaceae root vegetables. Contact dermatitis. 2014 Feb; 70(2):98-103. doi: 10.1111/cod.12122. [PMID: 24102077]
  • Mireia Corell, Emile Sheehy, Paul Evans, Nigel Brunton, Juan Valverde. Absolute configuration of falcarinol (9Z-heptadeca-1,9-diene-4,6-diyn-3-ol) from Pastinaca sativa. Natural product communications. 2013 Aug; 8(8):1123-6. doi: ". [PMID: 24079184]
  • Nihat Knispel, Elena Ostrozhenkova, Nicholas Schramek, Claudia Huber, Luis M Peña-Rodríguez, Mercedes Bonfill, Javier Palazón, Gesine Wischmann, Rosa M Cusidó, Wolfgang Eisenreich. Biosynthesis of panaxynol and panaxydol in Panax ginseng. Molecules (Basel, Switzerland). 2013 Jul; 18(7):7686-98. doi: 10.3390/molecules18077686. [PMID: 23884121]
  • Florian Herrmann, Frank Sporer, Ahmad Tahrani, Michael Wink. Antitrypanosomal properties of Panax ginseng C. A. Meyer: new possibilities for a remarkable traditional drug. Phytotherapy research : PTR. 2013 Jan; 27(1):86-98. doi: 10.1002/ptr.4692. [PMID: 22473703]
  • Lars Kjellenberg, Eva Johansson, Karl-Erik Gustavsson, Marie E Olsson. Polyacetylenes in fresh and stored carrots (Daucus carota): relations to root morphology and sugar content. Journal of the science of food and agriculture. 2012 Jun; 92(8):1748-54. doi: 10.1002/jsfa.5541. [PMID: 22190221]
  • Haoxin Li, Taryn O'Neill, Duncan Webster, John A Johnson, Christopher A Gray. Anti-mycobacterial diynes from the Canadian medicinal plant Aralia nudicaulis. Journal of ethnopharmacology. 2012 Mar; 140(1):141-4. doi: 10.1016/j.jep.2011.12.048. [PMID: 22234257]
  • Jie Li, Juan Jiang, Yimin Zheng, Linlin Wang, Yuqing Yang, Yang Hu. [Simultaneous determination of panaxynol and panaxydol in fibrous root of Panax ginseng by HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Sep; 36(17):2380-2. doi: . [PMID: 22121807]
  • Maciej Roman, Jan Cz Dobrowolski, Malgorzata Baranska, Rafal Baranski. Spectroscopic studies on bioactive polyacetylenes and other plant components in wild carrot root. Journal of natural products. 2011 Aug; 74(8):1757-63. doi: 10.1021/np200265d. [PMID: 21800857]
  • Dilip K Rai, Nigel P Brunton, Anastasios Koidis, Ashish Rawson, Padraig McLoughlin, William J Griffiths. Characterisation of polyacetylenes isolated from carrot (Daucus carota) extracts by negative ion tandem mass spectrometry. Rapid communications in mass spectrometry : RCM. 2011 Aug; 25(15):2231-9. doi: 10.1002/rcm.5103. [PMID: 21735506]
  • Ill-Min Chung, Hong-Keun Song, Sun-Jin Kim, Hyung-In Moon. Anticomplement activity of polyacetylenes from leaves of Dendropanax morbifera Leveille. Phytotherapy research : PTR. 2011 May; 25(5):784-6. doi: 10.1002/ptr.3336. [PMID: 21520473]
  • Lars P Christensen. Aliphatic C(17)-polyacetylenes of the falcarinol type as potential health promoting compounds in food plants of the Apiaceae family. Recent patents on food, nutrition & agriculture. 2011 Jan; 3(1):64-77. doi: 10.2174/2212798411103010064. [PMID: 21114468]
  • Marco Leonti, Laura Casu, Stefan Raduner, Filippo Cottiglia, Costantino Floris, Karl-Heinz Altmann, Jürg Gertsch. Falcarinol is a covalent cannabinoid CB1 receptor antagonist and induces pro-allergic effects in skin. Biochemical pharmacology. 2010 Jun; 79(12):1815-26. doi: 10.1016/j.bcp.2010.02.015. [PMID: 20206138]
  • Evy Paulsen, Lars P Christensen, Klaus E Andersen. Dermatitis from common ivy (Hedera helix L. subsp. helix) in Europe: past, present, and future. Contact dermatitis. 2010 Apr; 62(4):201-9. doi: 10.1111/j.1600-0536.2009.01677.x. [PMID: 20236156]
  • Ivan Vucković, Vlatka Vajs, Miroslava Stanković, Vele Tesević, Slobodan Milosavljević. A new prenylated flavanonol from Seseli annuum roots showing protective effect on human lymphocytes DNA. Chemistry & biodiversity. 2010 Mar; 7(3):698-704. doi: 10.1002/cbdv.200900067. [PMID: 20232332]
  • Stig Purup, Eric Larsen, Lars P Christensen. Differential effects of falcarinol and related aliphatic C(17)-polyacetylenes on intestinal cell proliferation. Journal of agricultural and food chemistry. 2009 Sep; 57(18):8290-6. doi: 10.1021/jf901503a. [PMID: 19694436]
  • Lars P Christensen, Martin Jensen. Biomass and content of ginsenosides and polyacetylenes in American ginseng roots can be increased without affecting the profile of bioactive compounds. Journal of natural medicines. 2009 Apr; 63(2):159-68. doi: 10.1007/s11418-008-0307-3. [PMID: 19085048]
  • Andreas Schinkovitz, Michael Stavri, Simon Gibbons, Franz Bucar. Antimycobacterial polyacetylenes from Levisticum officinale. Phytotherapy research : PTR. 2008 May; 22(5):681-4. doi: 10.1002/ptr.2408. [PMID: 18350523]
  • Ji-Hua Liu, Che-Sum Lee, Kit-Ming Leung, Zhong-Kai Yan, Bai-Hua Shen, Zhong-Zhen Zhao, Zhi-Hong Jiang. Quantification of two polyacetylenes in Radix Ginseng and roots of related Panax species using a gas chromatography-mass spectrometric method. Journal of agricultural and food chemistry. 2007 Oct; 55(22):8830-5. doi: 10.1021/jf070735o. [PMID: 17722935]
  • Jette F Young, Susan J Duthie, Lesley Milne, Lars P Christensen, Garry G Duthie, Charles S Bestwick. Biphasic effect of falcarinol on caco-2 cell proliferation, DNA damage, and apoptosis. Journal of agricultural and food chemistry. 2007 Feb; 55(3):618-23. doi: 10.1021/jf0616154. [PMID: 17263451]
  • Ze-Jian Wang, Bao-Ming Nie, Hong-Zhuan Chen, Yang Lu. Panaxynol induces neurite outgrowth in PC12D cells via cAMP- and MAP kinase-dependent mechanisms. Chemico-biological interactions. 2006 Jan; 159(1):58-64. doi: 10.1016/j.cbi.2005.09.003. [PMID: 16219303]
  • Morten Kobaek-Larsen, Lars P Christensen, Werner Vach, Jelmera Ritskes-Hoitinga, Kirsten Brandt. Inhibitory effects of feeding with carrots or (-)-falcarinol on development of azoxymethane-induced preneoplastic lesions in the rat colon. Journal of agricultural and food chemistry. 2005 Mar; 53(5):1823-7. doi: 10.1021/jf048519s. [PMID: 15740080]
  • C Ozdemir, L A Schneider, R Hinrichs, G Staib, L Weber, J M Weiss, K Scharffetter-Kochanek. [Allergic contact dermatitis to common ivy (Hedera helix L.)]. Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete. 2003 Oct; 54(10):966-9. doi: 10.1007/s00105-003-0584-4. [PMID: 14513244]
  • Andreas Czepa, Thomas Hofmann. Structural and sensory characterization of compounds contributing to the bitter off-taste of carrots (Daucus carota L.) and carrot puree. Journal of agricultural and food chemistry. 2003 Jun; 51(13):3865-73. doi: 10.1021/jf034085+. [PMID: 12797757]
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