(-)-Kaur-16-en-19-oic acid (BioDeep_00000003807)

 

Secondary id: BioDeep_00000175037, BioDeep_00000229914, BioDeep_00000420936

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

化学式: C20H30O2 (302.224568)
中文名称: 异贝壳杉烯酸, 异贝壳杉烯酸
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.33%

分子结构信息

SMILES: C1C[C@]([C@@H]2[C@@](C1)([C@H]1[C@@]3(CC2)C[C@@H](CC1)C(=C)C3)C)(C(=O)O)C
InChI: InChI=1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)

描述信息

(-)-kaur-16-en-19-oic acid, also known as ent-kaurenoic acid or ent-kaur-16-en-19-oate, is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D (-)-kaur-16-en-19-oic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (-)-kaur-16-en-19-oic acid can be found in sugar apple and sunflower, which makes (-)-kaur-16-en-19-oic acid a potential biomarker for the consumption of these food products.
Kaurenoic acid is a diterpene from Sphagneticola trilobata, inhibits Inflammatory Pain by the inhibition of cytokine production and activation of the NO–cyclic GMP–PKG–ATP-sensitive potassium channel signaling pathway[1].
Kaurenoic acid is a diterpene from Sphagneticola trilobata, inhibits Inflammatory Pain by the inhibition of cytokine production and activation of the NO–cyclic GMP–PKG–ATP-sensitive potassium channel signaling pathway[1].

同义名列表

27 个代谢物同义名

(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid; (5beta,8alpha,9beta,10alpha,13alpha)-kaur-16-en-18-oic acid; (5beta,8alpha,9beta,10alpha,13alpha)-Kaur-16-en-18-Oate; (5b,8a,9b,10a,13a)-Kaur-16-en-18-Oic acid; (5Β,8α,9β,10α,13α)-kaur-16-en-18-Oic acid; (5b,8a,9b,10a,13a)-Kaur-16-en-18-Oate; (5Β,8α,9β,10α,13α)-kaur-16-en-18-Oate; ent-Kaur-16(17)-en-19-oic acid; 3beta-hydroxy-kaurenoic acid; ent-Kaur-16-en-19-oic acid; (-)-Kaur-16-en-19-oic acid; ent-Kaur-16(17)-en-19-Oate; ent-kaur-16-en-18-oic acid; (-)-Kaur-16-en-19-Oate; ent-Kaur-16-en-19-Oate; kaur-16-en-18-oic acid; Ent-kaurenoic acid; Kauren-19-oic acid; Kaur-16-en-18-Oate; Argyrophilic acid; Kaurenoic acid; Kauren-19-Oate; ent-Kaurenoate; Kaurenic acid; Cunabic acid; kaurenoate; Kaurenate



数据库引用编号

20 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)

9 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

  • Kézia Cristine Barbosa Ferreira, Ana Beatriz Caribé Dos Santos Valle, Ana Cristina Moura Gualberto, Davi Trombini Aleixo, Lívia Mara Silva, Milena Maciel Santos, Danilo de Souza Costa, Letícia Ludmilla Oliveira, Jacy Gameiro, Guilherme Diniz Tavares, Ademar Alves da Silva Filho, José Otávio do Amaral Corrêa, Frederico Pittella. Kaurenoic acid nanocarriers regulates cytokine production and inhibit breast cancer cell migration. Journal of controlled release : official journal of the Controlled Release Society. 2022 12; 352(?):712-725. doi: 10.1016/j.jconrel.2022.10.048. [PMID: 36374787]
  • Helena Quintero-Pertuz, Ruben Veas-Albornoz, Ileana Carrillo, Fabiola González-Herrera, Michel Lapier, Eduino Carbonó-Delahoz, Esther Del Olmo, Arturo San Feliciano, Ulrike Kemmerling, Claudio Olea-Azar, Carla Delporte, Juan D Maya. Trypanocidal effect of alcoholic extract of Castanedia santamartensis (Asteraceae) leaves is based on altered mitochondrial function. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Apr; 148(?):112761. doi: 10.1016/j.biopha.2022.112761. [PMID: 35240521]
  • Miwa Maeda, Mayu Suzuki, Hiroyuki Fuchino, Norika Tanaka, Takahiro Kobayashi, Ryosuke Isogai, Irmanida Batubara, Dyah Iswantini, Michiyo Matsuno, Nobuo Kawahara, Mamoru Koketsu, Akie Hamamoto, Hiroshi Takemori. Diversity of Adenostemma lavenia, multi-potential herbs, and its kaurenoic acid composition between Japan and Taiwan. Journal of natural medicines. 2022 Jan; 76(1):132-143. doi: 10.1007/s11418-021-01565-3. [PMID: 34510371]
  • Sergio M Borghi, Sandra S Mizokami, Thacyana T Carvalho, Fernanda S Rasquel-Oliveira, Camila R Ferraz, Victor Fattori, Thiago H Hayashida, Jean P S Peron, Doumit Camilios-Neto, Sergio R Ambrosio, Nilton S Arakawa, Rubia Casagrande, Waldiceu A Verri. The diterpene from Sphagneticola trilobata (L.) Pruski, kaurenoic acid, reduces lipopolysaccharide-induced peritonitis and pain in mice. Journal of ethnopharmacology. 2021 Jun; 273(?):113980. doi: 10.1016/j.jep.2021.113980. [PMID: 33652112]
  • Jingwen Xu, Zhe Wang, Lianlian Sun, Yi Wang, Yihai Wang, Xiangjiu He. (3α)-3-(tiglinoyloxy)-ent-kaur-16-en-19-oic acid, isolated from Wedelia trilobata L., exerts an anti-inflammatory effect via the modulation of NF-κB, MAPK and mTOR pathway and autophagy in LPS-stimulated macrophages. Toxicology in vitro : an international journal published in association with BIBRA. 2021 Jun; 73(?):105139. doi: 10.1016/j.tiv.2021.105139. [PMID: 33705895]
  • Ju Sung Lee, Norman G Quilantang, Dae-Hyun Hahm, Ki Sung Kang, Sonia D Jacinto, Yu-Jin Choi, Sang Cheon Lee, Sanghyun Lee. Optimization of Extraction Conditions of Continentalic and Kaurenoic Acids from Aralia continentalis by HPLC/UV and Their Validation. Journal of chromatographic science. 2020 Jul; 58(7):672-677. doi: 10.1093/chromsci/bmaa019. [PMID: 32448886]
  • Rosa Mariana Montiel-Ruiz, Marcos Córdova-de la Cruz, Manasés González-Cortázar, Alejandro Zamilpa, Abraham Gómez-Rivera, Ricardo López-Rodríguez, Carlos Ernesto Lobato-García, Ever A Blé-González. Antinociceptive Effect of Hinokinin and Kaurenoic Acid Isolated from Aristolochia odoratissima L. Molecules (Basel, Switzerland). 2020 Mar; 25(6):. doi: 10.3390/molecules25061454. [PMID: 32213823]
  • Qun Peng, Jianyuan Chen, Hanying Duan, Chao Wang. Determination of Kaurenoic Acid in Acanthopanax trifoliatus by Ultra-High Performance Liquid Chromatography Coupled with Tandem Mass Spectrometry (UHPLC-MS/MS). Scientific reports. 2020 02; 10(1):3378. doi: 10.1038/s41598-020-60426-3. [PMID: 32099028]
  • Riwon Hong, Kyoung Soo Kim, Gwang Muk Choi, Mijung Yeom, Bombi Lee, Sanghyun Lee, Ki Sung Kang, Hyang Sook Lee, Hi-Joon Park, Dae-Hyun Hahm. Continentalic Acid Rather Than Kaurenoic Acid Is Responsible for the Anti-Arthritic Activity of Manchurian Spikenard In Vitro and In Vivo. International journal of molecular sciences. 2019 Nov; 20(21):. doi: 10.3390/ijms20215488. [PMID: 31690022]
  • Diéssica Padilha Dalenogare, Paula Ronsani Ferro, Samira Dal Toé De Prá, Flávia Karine Rigo, Caren Tatiane de David Antoniazzi, Amanda Spring de Almeida, Adriani Paganini Damiani, Giulia Strapazzon, Thanielly Thais de Oliveira Sardinha, Nathália Coral Galvani, Aline Augusti Boligon, Vanessa Moraes de Andrade, Evelyne da Silva Brum, Sara Marchesan Oliveira, Gabriela Trevisan. Antinociceptive activity of Copaifera officinalis Jacq. L oil and kaurenoic acid in mice. Inflammopharmacology. 2019 Aug; 27(4):829-844. doi: 10.1007/s10787-019-00588-3. [PMID: 31098702]
  • M Mauro, R A De Grandis, M L Campos, A Bauermeister, R G Peccinini, F R Pavan, N P Lopes, N V De Moraes. Acid diterpenes from Copaiba oleoresin (Copaifera langsdorffii): Chemical and plasma stability and intestinal permeability using Caco-2 cells. Journal of ethnopharmacology. 2019 May; 235(?):183-189. doi: 10.1016/j.jep.2019.02.017. [PMID: 30763698]
  • Leandro Marcondes-Alves, Victor Fattori, Sergio M Borghi, Yuri Lourenco-Gonzalez, Allan J C Bussmann, Elisa Y Hirooka, Rubia Casagrande, Waldiceu A Verri, Nilton S Arakawa. Kaurenoic acid extracted from Sphagneticola trilobata reduces acetaminophen-induced hepatotoxicity through inhibition of oxidative stress and pro-inflammatory cytokine production in mice. Natural product research. 2019 Mar; 33(6):921-924. doi: 10.1080/14786419.2017.1416372. [PMID: 29262719]
  • Xiunan Jiang, Yiting Shen, Haixing Wang, Caihong Wang, Xiaoxia Ye, Zheng Xiang. Determination of kaurenoic acid in rat plasma using UPLC-MS/MS and its application to a pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2019 Feb; 164(?):27-31. doi: 10.1016/j.jpba.2018.10.016. [PMID: 30339948]
  • Carlos Hg Martins, Fariza Abrão, Thaís S Moraes, Pollyanna F Oliveira, Denise C Tavares, Lizandra G Magalhães, Fábio C Galvão, Rodrigo Cs Veneziani, Sérgio R Ambrósio. Kaurenoic acid and its sodium salt derivative: antibacterial activity against Porphyromonas gingivalis and their mechanism of action. Future microbiology. 2018 11; 13(?):1585-1601. doi: 10.2217/fmb-2018-0140. [PMID: 30430852]
  • Li-Ping Dai, Ling-Xia Zhang, Ya-Lin Liu, Hong Wu, Rui-Xin Liu, Meng Zhao, Shuang-Shuang Tian, Xue Jiang, Sui-Qing Chen. Isolation and purification of diterpenoids from the aerial parts of Isodon excisoides target-guided by UPLC-LTQ-Orbitrap-MS. Natural product research. 2018 Oct; 32(20):2424-2430. doi: 10.1080/14786419.2017.1419225. [PMID: 29320879]
  • Dalyara Mendonça de Matos, Milainy Rocha Viana, Marcela Cristina de Oliveira Alvim, Lara Soares Aleixo de Carvalho, Laura Hora Rios Leite, Ademar Alves Da Silva Filho, Jorge Willian Leandro Nascimento. Pharmacokinetic profile and oral bioavailability of Kaurenoic acid from Copaifera spp. in rats. Fitoterapia. 2018 Jul; 128(?):142-147. doi: 10.1016/j.fitote.2018.05.013. [PMID: 29772297]
  • Chisato Noguchi, Sho Miyazaki, Hiroshi Kawaide, Osamu Gotoh, Yuzo Yoshida, Yuri Aoyama. Characterization of moss ent-kaurene oxidase (CYP701B1) using a highly purified preparation. Journal of biochemistry. 2018 Jan; 163(1):69-76. doi: 10.1093/jb/mvx063. [PMID: 29036583]
  • Rondinelle G Pereira, Antonio Cala, Mónica Fernández-Aparicio, José Mg Molinillo, Maria Ad Boaventura, Francisco A Macías. Gibberellic and kaurenoic hybrid strigolactone mimics for seed germination of parasitic weeds. Pest management science. 2017 Dec; 73(12):2529-2537. doi: 10.1002/ps.4650. [PMID: 28643859]
  • A D Rocha, H da S Vieira, J A Takahashi, M A D Boaventura. Synthesis of a new allelopathic agent from the biotransformation of ent-15α-hydroxy-16-kauren-19-oic acid with Fusarium proliferatum. Natural product research. 2017 Nov; 31(22):2647-2653. doi: 10.1080/14786419.2017.1290614. [PMID: 28278633]
  • Dora Lúcia Carrara Moreti, Luís Fernando Leandro, Thaís da Silva Moraes, Monique Rodrigues Moreira, Rodrigo Cassio Sola Veneziani, Sergio Ricardo Ambrosio, Brenda Paula Gomes, Carlos Henrique Gomes Martins. Mikania glomerata Sprengel extract and its major compound ent-kaurenoic acid display activity against bacteria present in endodontic infections. Anaerobe. 2017 10; 47(?):201-208. doi: 10.1016/j.anaerobe.2017.06.008. [PMID: 28627377]
  • Xin-Xin Xie, Ze-Jing Jiang, Zhi-Hong Cheng, Dao-Feng Chen. Preparative separation and quantitative determination of two kaurenoic acid isomers in root barks of Acanthopanax gracilistylus. Chinese journal of natural medicines. 2017 Aug; 15(8):625-630. doi: 10.1016/s1875-5364(17)30090-0. [PMID: 28939025]
  • Xin-Hua Ma, Zhi-Biao Wang, Lei Zhang, Wei Li, Cui-Min Deng, Tian-Hua Zhong, Guang-Yu Li, Wei-Ming Zheng, Yong-Hong Zhang. Diterpenoids from Wedelia prostrata and Their Derivatives and Cytotoxic Activities. Chemistry & biodiversity. 2017 May; 14(5):. doi: 10.1002/cbdv.201600423. [PMID: 28130826]
  • Mi Zhang, Chenxing Zhao, Weifeng Dai, Jing He, Shiyun Jiao, Baocai Li. Anti-inflammatory ent-kaurenoic acids and their glycosides from Gochnatia decora. Phytochemistry. 2017 May; 137(?):174-181. doi: 10.1016/j.phytochem.2017.02.021. [PMID: 28236453]
  • Suellen F Mota, Denilson F Oliveira, Vladimir C G Heleno, Ana Carolina F Soares, Jacob O Midiwo, Elaine A Souza. Methyl and p-Bromobenzyl Esters of Hydrogenated Kaurenoic Acid for Controlling Anthracnose in Common Bean Plants. Journal of agricultural and food chemistry. 2017 Mar; 65(8):1489-1495. doi: 10.1021/acs.jafc.6b05159. [PMID: 28161946]
  • Giovana Fucina, Lilian Wünsch Rocha, Gislaine Francieli da Silva, Silmara Mendes Hoepers, Fernanda Peres Ferreira, Thais Guaratini, Valdir Cechinel Filho, Ruth Meri Lucinda-Silva, Nara Lins Meira Quintão, Tania Mari Bellé Bresolin. Topical anti-inflammatory phytomedicine based on Sphagneticola trilobata dried extracts. Pharmaceutical biology. 2016 Nov; 54(11):2465-2474. doi: 10.3109/13880209.2016.1160249. [PMID: 27046333]
  • Tânia da Silveira Agostini-Costa, Ismael Silva Gomes, Maira Christina Marques Fonseca, Araci Molnar Alonso, Rita de Cassia Alves Pereira, Ilio Montanari Junior, Joseane Padilha da Silva, Ana Maria Soares Pereira, Dijalma Barbosa da Silva, Roberto Fontes Vieira, Ana Paula Artimonte Vaz. Effect of Accessions and Environment Conditions on Coumarin, O-Coumaric and Kaurenoic Acids Levels of Mikania laevigata. Planta medica. 2016 Nov; 82(16):1431-1437. doi: 10.1055/s-0042-108339. [PMID: 27336315]
  • Monique Rodrigues Moreira, Ariana Borges Souza, Sandra Soares, Thamires Chiquini Bianchi, Daniele de Souza Eugênio, Danieli Cristina Lemes, Carlos Henrique Gomes Martins, Thaís da Silva Moraes, Denise Crispim Tavares, Natália Helen Ferreira, Sergio Ricardo Ambrósio, Rodrigo Cassio Sola Veneziani. ent-Kaurenoic acid-rich extract from Mikania glomerata: In vitro activity against bacteria responsible for dental caries. Fitoterapia. 2016 Jul; 112(?):211-6. doi: 10.1016/j.fitote.2016.06.007. [PMID: 27316976]
  • Katrin Geisler, Niels Berg Jensen, Macaire M S Yuen, Lina Madilao, Jörg Bohlmann. Modularity of Conifer Diterpene Resin Acid Biosynthesis: P450 Enzymes of Different CYP720B Clades Use Alternative Substrates and Converge on the Same Products. Plant physiology. 2016 05; 171(1):152-64. doi: 10.1104/pp.16.00180. [PMID: 26936895]
  • Celia Bustos-Brito, Mariano Sánchez-Castellanos, Baldomero Esquivel, José S Calderón, Fernando Calzada, Lilian Yépez-Mulia, Pedro Joseph-Nathan, Gabriel Cuevas, Leovigildo Quijano. ent-Kaurene Glycosides from Ageratina cylindrica. Journal of natural products. 2015 Nov; 78(11):2580-7. doi: 10.1021/acs.jnatprod.5b00488. [PMID: 26517282]
  • Kyoung Jin Lee, Kwang Ho Song, Wonmin Choi, Yeong Shik Kim. A strategy for the separation of diterpenoid isomers from the root of Aralia continentalis by countercurrent chromatography: The distribution ratio as a substitute for the partition coefficient and a three-phase solvent system. Journal of chromatography. A. 2015 Aug; 1406(?):224-30. doi: 10.1016/j.chroma.2015.06.038. [PMID: 26138601]
  • Leonora Mendoza, Alejandra Ribera, Alejandra Saavedra, Evelyn Silva, Ramiro Araya-Maturana, Milena Cotoras. Action mechanism for 3β-hydroxykaurenoic acid and 4,4-dimethylanthracene-1,9,10(4H)-trione on Botrytis cinerea. Mycologia. 2015 Jul; 107(4):661-6. doi: 10.3852/14-162. [PMID: 25977212]
  • Sho Miyazaki, Masatoshi Nakajima, Hiroshi Kawaide. Hormonal diterpenoids derived from ent-kaurenoic acid are involved in the blue-light avoidance response of Physcomitrella patens. Plant signaling & behavior. 2015; 10(2):e989046. doi: 10.4161/15592324.2014.989046. [PMID: 25751581]
  • Sho Miyazaki, Hikaru Toyoshima, Masahiro Natsume, Masatoshi Nakajima, Hiroshi Kawaide. Blue-light irradiation up-regulates the ent-kaurene synthase gene and affects the avoidance response of protonemal growth in Physcomitrella patens. Planta. 2014 Jul; 240(1):117-24. doi: 10.1007/s00425-014-2068-4. [PMID: 24715198]
  • Theophine C Okoye, Peter A Akah, Edwin O Omeje, Festus B C Okoye, Chukwuemeka S Nworu. Anticonvulsant effect of kaurenoic acid isolated from the root bark of Annona senegalensis. Pharmacology, biochemistry, and behavior. 2013 Aug; 109(?):38-43. doi: 10.1016/j.pbb.2013.05.001. [PMID: 23664900]
  • V C Fernandes, S I V Pereira, J Coppede, J S Martins, W F Rizo, R O Beleboni, M Marins, P S Pereira, A M S Pereira, A L Fachin. The epimer of kaurenoic acid from Croton antisyphiliticus is cytotoxic toward B-16 and HeLa tumor cells through apoptosis induction. Genetics and molecular research : GMR. 2013 Apr; 12(2):1005-11. doi: 10.4238/2013.april.2.16. [PMID: 23613246]
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  • Federico Martinelli, Sandra L Uratsu, Ute Albrecht, Russell L Reagan, My L Phu, Monica Britton, Vincent Buffalo, Joseph Fass, Elizabeth Leicht, Weixiang Zhao, Dawei Lin, Raissa D'Souza, Cristina E Davis, Kim D Bowman, Abhaya M Dandekar. Transcriptome profiling of citrus fruit response to huanglongbing disease. PloS one. 2012; 7(5):e38039. doi: 10.1371/journal.pone.0038039. [PMID: 22675433]
  • Björn Hamberger, Toshiyuki Ohnishi, Britta Hamberger, Armand Séguin, Jörg Bohlmann. Evolution of diterpene metabolism: Sitka spruce CYP720B4 catalyzes multiple oxidations in resin acid biosynthesis of conifer defense against insects. Plant physiology. 2011 Dec; 157(4):1677-95. doi: 10.1104/pp.111.185843. [PMID: 21994349]
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  • Sho Miyazaki, Takumi Katsumata, Masahiro Natsume, Hiroshi Kawaide. The CYP701B1 of Physcomitrella patens is an ent-kaurene oxidase that resists inhibition by uniconazole-P. FEBS letters. 2011 Jun; 585(12):1879-83. doi: 10.1016/j.febslet.2011.04.057. [PMID: 21545802]
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