falcarindiol (BioDeep_00000407529)

Main id: BioDeep_00000000767

Secondary id: BioDeep_00000172512, BioDeep_00000229851

natural product PANOMIX_OTCML-2023 Antitumor activity


代谢物信息卡片


1,9-Heptadecadiene-4,6-diyne-3,8-diol, (3R,8S,9Z)-

化学式: C17H24O2 (260.17762039999997)
中文名称: 镰叶芹二醇, 法卡林二醇
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 9.49%

分子结构信息

SMILES: C=CC(O)C#CC#CC(O)C=CCCCCCCC
InChI: InChI=1S/C17H24O2/c1-3-5-6-7-8-9-10-14-17(19)15-12-11-13-16(18)4-2/h4,10,14,16-19H,2-3,5-9H2,1H3/b14-10+

描述信息

(+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
(+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
(+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
(+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
Falcarindiol, an orally active polyacetylenic oxylipin, activates PPARγ and increases the expression of the cholesterol transporter ABCA1 in cells. Falcarindiol induces apoptosis and autophagy. Falcarindiol has anti-inflammatory, antifungal, anticancer and antidiabetic properties[1][2]. Falcarindiol is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
Falcarindiol, an orally active polyacetylenic oxylipin, activates PPARγ and increases the expression of the cholesterol transporter ABCA1 in cells. Falcarindiol induces apoptosis and autophagy. Falcarindiol has anti-inflammatory, antifungal, anticancer and antidiabetic properties[1][2]. Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
Falcarindiol, an orally active polyacetylenic oxylipin, activates PPARγ and increases the expression of the cholesterol transporter ABCA1 in cells. Falcarindiol induces apoptosis and autophagy. Falcarindiol has anti-inflammatory, antifungal, anticancer and antidiabetic properties[1][2]. Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

同义名列表

13 个代谢物同义名

1,9-Heptadecadiene-4,6-diyne-3,8-diol, (3R,8S,9Z)-; (3R,8S,9Z)-heptadeca-1,9-dien-4,6-diyne-3,8-diol; falcarindiol; AIDS-185997; 55297-87-5; AIDS185997; C08449; Heptadeca-1,9-dien-4,6-diyne-3,8-diol; (E,3R,8S)-Heptadeca-1,9-dien-4,6-diyne-3,8-diol; Heptadeca-1,9E-dien-4,6-diyne-3R,8S-diol; (3R,8S)-Falcarindiol; 3(R),8(S),9(Z)-Falcarindiol; (+)-(3R,8S)-Falcarindiol



数据库引用编号

35 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)

51 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

  • Likang Zhao, Changkai Li, Meng Zhang, Honglian Li, Shengli Ding, Xi Zhao, Lianjuan Yang, Jia Liu, Qing X Li, Risong Na. Design, Synthesis, and Antifungal Activity of Polyacetylenic Alcohol Derivatives and Stereoisomers against Phytopathogenic Fungi. Journal of agricultural and food chemistry. 2023 Jun; ?(?):. doi: 10.1021/acs.jafc.3c00924. [PMID: 37261403]
  • Siyue Kan, Jingwen Tan, Qing Cai, Lulu An, Zhiqin Gao, Hong Yang, Siyu Liu, Risong Na, Lianjuan Yang. Synergistic activity of the combination of falcarindiol and itraconazole in vitro against dermatophytes. Frontiers in cellular and infection microbiology. 2023; 13(?):1128000. doi: 10.3389/fcimb.2023.1128000. [PMID: 37207188]
  • 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]
  • Kyung-Ran Park, Hyun Hee Leem, Yoon-Ju Kwon, Il Keun Kwon, Jin Tae Hong, Hyung-Mun Yun. Falcarindiol Stimulates Apoptotic and Autophagic Cell Death to Attenuate Cell Proliferation, Cell Division, and Metastasis through the PI3K/AKT/mTOR/p70S6K Pathway in Human Oral Squamous Cell Carcinomas. The American journal of Chinese medicine. 2022; 50(1):295-311. doi: 10.1142/s0192415x22500112. [PMID: 34931585]
  • Chaoyue Zhao, Hongda Zheng, Liman Zhou, Hongrui Ji, Lu Zhao, Wengong Yu, Qianhong Gong. Falcarindiol Isolated from Notopterygium incisum Inhibits the Quorum Sensing of Pseudomonas aeruginosa. Molecules (Basel, Switzerland). 2021 Sep; 26(19):. doi: 10.3390/molecules26195896. [PMID: 34641440]
  • Chong-Zhi Wang, Yun Luo, Wei-Hua Huang, Jinxiang Zeng, Chun-Feng Zhang, Mallory Lager, Wei Du, Ming Xu, Chun-Su Yuan. Falcarindiol and dichloromethane fraction are bioactive components in Oplopanax elatus: Colorectal cancer chemoprevention via induction of apoptosis and G2/M cell cycle arrest mediated by cyclin A upregulation. Journal of applied biomedicine. 2021; 19(2):113-124. doi: 10.32725/jab.2021.013. [PMID: 34754259]
  • 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]
  • 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]
  • Ju Eun Jeon, Jung-Gun Kim, Curt R Fischer, Niraj Mehta, Cosima Dufour-Schroif, Kimberly Wemmer, Mary Beth Mudgett, Elizabeth Sattely. A Pathogen-Responsive Gene Cluster for Highly Modified Fatty Acids in Tomato. Cell. 2020 01; 180(1):176-187.e19. doi: 10.1016/j.cell.2019.11.037. [PMID: 31923394]
  • A Djebara, M L Ciavatta, V Mathieu, M Colin, F Bitam, M Carbone, M Gavagnin. Oxygenated C17 polyacetylene metabolites from Algerian Eryngium tricuspidatum L. roots: Structure and biological activity. Fitoterapia. 2019 Oct; 138(?):104355. doi: 10.1016/j.fitote.2019.104355. [PMID: 31520650]
  • Emma Pipó-Ollé, Prasad Walke, Martine K Notabi, Rime B El-Houri, Morten Østergaard Andersen, David Needham, Eva C Arnspang. Uptake of New Lipid-coated Nanoparticles Containing Falcarindiol by Human Mesenchymal Stem Cells. Journal of visualized experiments : JoVE. 2019 02; ?(144):. doi: 10.3791/59094. [PMID: 30799864]
  • 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]
  • Lin Xiao, Yuan-Ming Zhou, Xiang-Fei Zhang, Feng-Yu Du. Notopterygium incisum extract and associated secondary metabolites inhibit apple fruit fungal pathogens. Pesticide biochemistry and physiology. 2018 Sep; 150(?):59-65. doi: 10.1016/j.pestbp.2018.07.001. [PMID: 30195388]
  • 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]
  • Wei Sun, Yi-Sheng He, Ling-Hui Xu, Bi-Ying Zhang, Lian-Wen Qi, Jie Yang, Ping Li, Xiao-Dong Wen. Pharmacokinetic profiles of falcarindiol and oplopandiol in rats after oral administration of polyynes extract of Oplopanax elatus. Chinese journal of natural medicines. 2016 Sep; 14(9):714-720. doi: 10.1016/s1875-5364(16)30085-1. [PMID: 27667518]
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  • 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]
  • Jin-Long Li, Li-Xin Gao, Fan-Wang Meng, Chun-Lan Tang, Ru-Jun Zhang, Jing-Ya Li, Cheng Luo, Jia Li, Wei-Min Zhao. PTP1B inhibitors from stems of Angelica keiskei (Ashitaba). Bioorganic & medicinal chemistry letters. 2015; 25(10):2028-32. doi: 10.1016/j.bmcl.2015.04.003. [PMID: 25891102]
  • Xin Liu, Olaf Kunert, Martina Blunder, Nanang Fakhrudin, Stefan M Noha, Clemens Malainer, Andreas Schinkovitz, Elke H Heiss, Atanas G Atanasov, Manfred Kollroser, Daniela Schuster, Verena M Dirsch, Rudolf Bauer. Polyyne hybrid compounds from Notopterygium incisum with peroxisome proliferator-activated receptor gamma agonistic effects. Journal of natural products. 2014 Nov; 77(11):2513-21. doi: 10.1021/np500605v. [PMID: 25333853]
  • Chong-Zhi Wang, Zhiyu Zhang, Wei-Hua Huang, Guang-Jian Du, Xiao-Dong Wen, Tyler Calway, Chunhao Yu, Rachael Nass, Jing Zhao, Wei Du, Shao-Ping Li, Chun-Su Yuan. Identification of potential anticancer compounds from Oplopanax horridus. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2013 Aug; 20(11):999-1006. doi: 10.1016/j.phymed.2013.04.013. [PMID: 23746754]
  • Jun Yoshida, Hiroko Seino, Yoshiaki Ito, Toshimitsu Nakano, Takumi Satoh, Yoshiko Ogane, Saori Suwa, Hiroyuki Koshino, Ken-Ichi Kimura. Inhibition of glycogen synthase kinase-3β by falcarindiol isolated from Japanese Parsley (Oenanthe javanica). Journal of agricultural and food chemistry. 2013 Aug; 61(31):7515-21. doi: 10.1021/jf401042m. [PMID: 23895038]
  • Juan David Guzman, Dimitrios Evangelopoulos, Antima Gupta, Jose M Prieto, Simon Gibbons, Sanjib Bhakta. Antimycobacterials from lovage root (Ligusticum officinale Koch). Phytotherapy research : PTR. 2013 Jul; 27(7):993-8. doi: 10.1002/ptr.4823. [PMID: 22899555]
  • Taryn O'Neill, John A Johnson, Duncan Webster, Christopher A Gray. The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins. Journal of ethnopharmacology. 2013 May; 147(1):232-7. doi: 10.1016/j.jep.2013.03.009. [PMID: 23501157]
  • Randi Seljåsen, Gjermund Vogt, Elisabeth Olsen, Per Lea, Lars Arne Høgetveit, Torgeir Tajet, Richard Meadow, Gunnar B Bengtsson. Influence of field attack by carrot psyllid (Trioza apicalis Förster) on sensory quality, antioxidant capacity and content of terpenes, falcarindiol and 6-methoxymellein of carrots (Daucus carota L.). Journal of agricultural and food chemistry. 2013 Mar; 61(11):2831-8. doi: 10.1021/jf303979y. [PMID: 23414489]
  • Atanas G Atanasov, Martina Blunder, Nanang Fakhrudin, Xin Liu, Stefan M Noha, Clemens Malainer, Matthias P Kramer, Amina Cocic, Olaf Kunert, Andreas Schinkovitz, Elke H Heiss, Daniela Schuster, Verena M Dirsch, Rudolf Bauer. Polyacetylenes from Notopterygium incisum--new selective partial agonists of peroxisome proliferator-activated receptor-gamma. PloS one. 2013; 8(4):e61755. doi: 10.1371/journal.pone.0061755. [PMID: 23630612]
  • 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]
  • Jin Woo Lee, Cheong-Yong Yun, Eunmiri Roh, Chul Lee, Qinghao Jin, Kwon Ki Bang, Sang-Hun Jung, Dongho Lee, Mi Kyeong Lee, Youngsoo Kim, Bang Yeon Hwang. Melanogenesis inhibitory bisabolane-type sesquiterpenoids from the roots of Angelica koreana. Bioorganic & medicinal chemistry letters. 2012 Apr; 22(8):2927-31. doi: 10.1016/j.bmcl.2012.02.047. [PMID: 22450129]
  • Xing Su, Xiang-kun Li, Tao Wu, Tong Zhang, Zhen-tao Wang. [Fingerprint analysis of Glehniae Radix by TLC]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2012 Feb; 35(2):210-3. doi: . [PMID: 22822664]
  • Ki-Eun Bae, Young-Woong Choi, Sang-Tae Kim, Young-Kyoon Kim. Components of rhizome extract of Cnidium officinale Makino and their in vitro biological effects. Molecules (Basel, Switzerland). 2011 Oct; 16(10):8833-47. doi: 10.3390/molecules16108833. [PMID: 22019572]
  • 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]
  • Tomokazu Ohnuma, Eisaburo Anan, Rika Hoashi, Yuika Takeda, Takahito Nishiyama, Kenichiro Ogura, Akira Hiratsuka. Dietary diacetylene falcarindiol induces phase 2 drug-metabolizing enzymes and blocks carbon tetrachloride-induced hepatotoxicity in mice through suppression of lipid peroxidation. Biological & pharmaceutical bulletin. 2011; 34(3):371-8. doi: 10.1248/bpb.34.371. [PMID: 21372387]
  • Seika Mitsui, Kan Torii, Hajime Fukui, Kunio Tsujimura, Akira Maeda, Mitsuhiko Nose, Akito Nagatsu, Hajime Mizukami, Akimichi Morita. The herbal medicine compound falcarindiol from Notopterygii Rhizoma suppresses dendritic cell maturation. The Journal of pharmacology and experimental therapeutics. 2010 Jun; 333(3):954-60. doi: 10.1124/jpet.109.162305. [PMID: 20215408]
  • Taichi Inui, Yuehong Wang, Dejan Nikolic, David C Smith, Scott G Franzblau, Guido F Pauli. Sesquiterpenes from Oplopanax horridus. Journal of natural products. 2010 Apr; 73(4):563-7. doi: 10.1021/np900674d. [PMID: 20218656]
  • 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]
  • Laetitia Meot-Duros, Stéphane Cérantola, Hélène Talarmin, Christophe Le Meur, Gaëtan Le Floch, Christian Magné. New antibacterial and cytotoxic activities of falcarindiol isolated in Crithmum maritimum L. leaf extract. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2010 Feb; 48(2):553-7. doi: 10.1016/j.fct.2009.11.031. [PMID: 19922760]
  • Ludger Schmiech, Carole Alayrac, Bernhard Witulski, Thomas Hofmann. Structure determination of bisacetylenic oxylipins in carrots (Daucus carota L.) and enantioselective synthesis of falcarindiol. Journal of agricultural and food chemistry. 2009 Nov; 57(22):11030-40. doi: 10.1021/jf9031475. [PMID: 19845355]
  • 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]
  • Tomokazu Ohnuma, Takao Komatsu, Shinji Nakayama, Takahito Nishiyama, Kenichiro Ogura, Akira Hiratsuka. Induction of antioxidant and phase 2 drug-metabolizing enzymes by falcarindiol isolated from Notopterygium incisum extract, which activates the Nrf2/ARE pathway, leads to cytoprotection against oxidative and electrophilic stress. Archives of biochemistry and biophysics. 2009 Aug; 488(1):34-41. doi: 10.1016/j.abb.2009.06.006. [PMID: 19527678]
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