Grandiflorenic acid (BioDeep_00000278122)

 

Secondary id: BioDeep_00001103623

PANOMIX_OTCML-2023


代谢物信息卡片


(4S,5R,9R)-5,9-Dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadec-10-ene-5-carboxylic acid

化学式: C20H28O2 (300.2089)
中文名称: GRANDIFLORENIC ACID
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 56.82%

分子结构信息

SMILES: C=C1CC23CCC4C(C)(C(=O)O)CCCC4(C)C2=CCC1C3
InChI: InChI=1S/C20H28O2/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/h6,14-15H,1,4-5,7-12H2,2-3H3,(H,21,22)/t14-,15+,18-,19-,20-/m1/s1

描述信息

A tetracyclic diterpenoid with formula C20H28O2 which exhibits anti-inflammatory, antibacterial, antileishmanial and wound-healing properties.

同义名列表

4 个代谢物同义名

Grandiflorenic acid; (4S,5R,9R)-5,9-Dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadec-10-ene-5-carboxylic acid; Kaura-9(11),16-dien-18-oic acid; CID 161387



数据库引用编号

12 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)

8 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


文献列表

  • Tatiane Renata Fagundes, Bruna Taciane da Silva Bortoleti, Fernanda Tomiotto-Pellissier, Vírgínia Márcia Concato, Manoela Daiele Gonçalves, Nilton Syogo Arakawa, Milena Menegazzo Miranda-Sapla, Carolina Panis, Wander Rogério Pavanelli. Grandiflorenic acid from Wedelia trilobata plant induces apoptosis and autophagy cell death in breast adenocarcinoma (MCF7), lung carcinoma (A549), and hepatocellular carcinoma (HuH7.5) cells lines. Toxicon : official journal of the International Society on Toxinology. 2022 Oct; 217(?):112-120. doi: 10.1016/j.toxicon.2022.08.006. [PMID: 35995098]
  • Manoela Daiele Gonçalves, Bruna Taciane da Silva Bortoleti, Fernanda Tomiotto-Pellissier, Virginia Marcia Concato, Ricardo Luís Nascimento de Matos, Taylon Felipe Silva, Ana Carolina Jacob Rodrigues, Amanda Cristina Machado Carloto, Idessania Nazareth Costa, Danielle Lazarin-Bidóia, Milena Menegazzo Miranda-Sapla, Wander Rogério Pavanelli, Nilton Syogo Arakawa, Ivete Conchon-Costa. Grandiflorenic acid isolated from Sphagneticola trilobata against Trypanosoma cruzi: Toxicity, mechanisms of action and immunomodulation. Toxicology in vitro : an international journal published in association with BIBRA. 2022 Feb; 78(?):105267. doi: 10.1016/j.tiv.2021.105267. [PMID: 34688839]
  • Bruna Taciane da Silva Bortoleti, Manoela Daiele Gonçalves, Fernanda Tomiotto-Pellissier, Milena Menegazzo Miranda-Sapla, João Paulo Assolini, Amanda Cristina Machado Carloto, Priscila Goes Camargo de Carvalho, Ian Lucas Alves Cardoso, Andréa Name Colado Simão, Nilton Syogo Arakawa, Idessania Nazareth Costa, Ivete Conchon-Costa, Wander Rogério Pavanelli. Grandiflorenic acid promotes death of promastigotes via apoptosis-like mechanism and affects amastigotes by increasing total iron bound capacity. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Jul; 46(?):11-20. doi: 10.1016/j.phymed.2018.06.010. [PMID: 30097110]
  • Y Ruan, B J Ma, L Z Li, X L Wang. Specific 12α-hydroxylation of grandiflorenic acid by permeabilised fungus Fusarium graminearum. Natural product research. 2014; 28(9):677-9. doi: 10.1080/14786419.2014.891113. [PMID: 24650196]
  • Nemesio Villa-Ruano, Martha Guadalupe Betancourt-Jiménez, Edmundo Lozoya-Gloria. Biosynthesis of uterotonic diterpenes from Montanoa tomentosa (zoapatle). Journal of plant physiology. 2009 Dec; 166(18):1961-7. doi: 10.1016/j.jplph.2009.06.004. [PMID: 19581023]
  • Ramón E Robles-Zepeda, Edmundo Lozoya-Gloria, Mercedes G López, María L Villarreal, Enrique Ramírez-Chávez, Jorge Molina-Torres. Montanoa tomentosa glandular trichomes containing kaurenoic acids chemical profile and distribution. Fitoterapia. 2009 Jan; 80(1):12-7. doi: 10.1016/j.fitote.2008.09.002. [PMID: 18824221]
  • Braulio M Fraga, Inmaculada Cabrera, Juan M Amaro-Luis. On the structures of the diterpenes licamichauxiioic acids A and B. Journal of natural products. 2008 Nov; 71(11):1953-5. doi: 10.1021/np800370f. [PMID: 18847245]
  • Maria Amélia Diamantino Boaventura, Rondinelle Gomes Pereira, Luiza B de Oliveira Freitas, Leandro Alves Dos Reis, Henriete da Silva Vieira. Preparation and phytotoxicity of novel kaurane diterpene amides with potential use as herbicides. Journal of agricultural and food chemistry. 2008 May; 56(9):2985-8. doi: 10.1021/jf0729309. [PMID: 18393433]
  • J E Page, F Balza, T Nishida, G H Towers. Biologically active diterpenes from Aspilia mossambicensis, a chimpanzee medicinal plant. Phytochemistry. 1992 Oct; 31(10):3437-9. doi: 10.1016/0031-9422(92)83702-z. [PMID: 1368857]
  • E Béjar, X Lozoya, R Enríquez, L Escobar. Comparative effect of zoapatle (Montanoa tomentosa) products and of verapamil on the in vitro uterine contractility of rat. Archivos de investigacion medica. 1984 Jul; 15(3):223-38. doi: ". [PMID: 6598740]
  • E Bejar, R Enriquez, X Lozoya. The in vitro effect of grandiflorenic acid and zoapatle aqueous crude extract upon spontaneous contractility of the rat uterus during oestrus cycle. Journal of ethnopharmacology. 1984 Jun; 11(1):87-97. doi: 10.1016/0378-8741(84)90098-9. [PMID: 6540830]
  • X Lozoya, R G Enríquez, E Bejar, A V Estrada, H Girón, H Ponce-Monter, A J Gallegos. The zoapatle V--the effect of kauradienoic acid upon uterine contractility. Contraception. 1983 Mar; 27(3):267-79. doi: 10.1016/0010-7824(83)90005-7. [PMID: 6851560]