Guaiol (BioDeep_00000000940)

 

Secondary id: BioDeep_00000179618

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-.alpha.,.alpha.,3,8-tetramethyl-, [3S-(3.alpha.,5.alpha.,8.alpha.)]-

化学式: C15H26O (222.1983546)
中文名称: 愈创醇, (-)-愈创醇
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 10%

分子结构信息

SMILES: C12CC[C@H](C)C=1C[C@H](C(O)(C)C)CC[C@@H]2C
InChI: InChI=1S/C15H26O/c1-10-5-7-12(15(3,4)16)9-14-11(2)6-8-13(10)14/h10-12,16H,5-9H2,1-4H3/t10-,11-,12+/m0/s1

描述信息

Guaiol is a guaiane sesquiterpenoid.
Guaiol is a natural product found in Philotheca fitzgeraldii, Aristolochia asclepiadifolia, and other organisms with data available.
See also: Cannabis sativa subsp. indica top (part of).
Guaiol is a sesquiterpene alcohol that has been found in several traditional Chinese medicinal plants and has antiproliferative, pro-autophagic, insect repellent, and insecticidal biological activities[1][2][3].
Guaiol is a sesquiterpene alcohol that has been found in several traditional Chinese medicinal plants and has antiproliferative, pro-autophagic, insect repellent, and insecticidal biological activities[1][2][3].

同义名列表

41 个代谢物同义名

5-Azulenemethanol,2,3,4,5,6,7,8-octahydro-.alpha.,.alpha.,3,8-tetramethyl-, [3S-(3.alpha.,5.alpha.,8.alpha.)]-; Guaiol;[3S-(3alpha,5alpha,8alpha)]-1,2,3,4,5,6,7,8-octahydro-alpha,alpha,3,8-tetramethyl-5-azulenemethanol; [3S-(3alpha,5alpha,8alpha)]-1,2,3,4,5,6,7,8-octahydro-alpha,alpha,3,8-tetramethyl-5-azulenemethanol; (3S-(3alpha,5alpha,8alpha))-1,2,3,4,5,6,7,8-octahydro-alpha,alpha,3,8-tetramethyl-5-azulenemethanol; 5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-.alpha.,.alpha.,3,8-tetramethyl-, (3S,5R,8S)-; 5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-alpha,alpha,3,8-tetramethyl-, (3S,5R,8S)-; (3S,5R,8S)-1,2,3,4,5,6,7,8-OCTAHYDRO-.ALPHA.,.ALPHA.3,8-TETRAMETHYL-5-AZULENEMETHANOL; (3S,5R,8S)-1,2,3,4,5,6,7,8-OCTAHYDRO-alpha,alpha3,8-TETRAMETHYL-5-AZULENEMETHANOL; (3R,6S,10S)-6,10,alpha,alpha-Tetramethylbicyclo[5.3.0]dec-1(7)-ene-3-methanol; 2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol; 2-((3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl)propan-2-ol; 2-((3S,8S)-1,2,3,4,5,6,7,8-Octahydro-3,8-dimethylazulen-5-yl)propan-2-ol; 2-(3,8-dimethyl-1,2,3,4,5,6,7,8-octahydro-azulen-5-yl)-propan-2-ol; (-)-Guaiol, analytical standard; Champacol; Guaiac alcohol; Guai-1(5)-en-11-ol; Champaca camphor; (-)-Guaiol, 97\\%; Spectrum3_001870; UNII-I7WP008A91; Guaiac alcohol; KBio3_002822; GUAIOL [MI]; (-)-guaiol; I7WP008A91; Champacol; GUAIOL(-); Guaiol; 5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-.alpha.,.alpha.,3,8-tetramethyl-, [3S-(3.alpha.,5.alpha.,8.alpha.)]-; SPECTRUM1800009; 448575_ALDRICH; BSPBio_003320; 50900_FLUKA; 29242_FLUKA; (−)-Guaiol; CHEBI:5552; 489-86-1; NSC19941; C09676; Guaiol; Guaiol



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)

148 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

  • Xiaohui Yang, Junling Yang, Xiaoxia Gu, Yuhua Tao, Hongjuan Ji, Xian Miao, Shuijie Shen, Haiyang Zang. (-)-Guaiol triggers immunogenic cell death and inhibits tumor growth in non-small cell lung cancer. Molecular and cellular biochemistry. 2022 Nov; ?(?):. doi: 10.1007/s11010-022-04613-y. [PMID: 36441354]
  • Yaoying Zeng, Yanbin Pan, Bo Zhang, Yingbin Luo, Jianhui Tian, Yuli Wang, Xudong Ju, Jianchun Wu, Yan Li. Integrating Network Pharmacology, Molecular Docking, and Experimental Validation to Investigate the Mechanism of (-)-Guaiol Against Lung Adenocarcinoma. Medical science monitor : international medical journal of experimental and clinical research. 2022 Jul; 28(?):e937131. doi: 10.12659/msm.937131. [PMID: 35871777]
  • María Fernanda Panamito, Nicole Bec, Valeria Valdivieso, Melissa Salinas, James Calva, Jorge Ramírez, Christian Larroque, Chabaco Armijos. Chemical Composition and Anticholinesterase Activity of the Essential Oil of Leaves and Flowers from the Ecuadorian Plant Lepechinia paniculata (Kunth) Epling. Molecules (Basel, Switzerland). 2021 May; 26(11):. doi: 10.3390/molecules26113198. [PMID: 34071744]
  • Natasa Mohd Shakri, Wan Mohd Nuzul Hakimi Wan Salleh, Shamsul Khamis, Nor Azah Mohamad Ali, Muhammad Helmi Nadri. Composition of the essential oils of three Malaysian Xylopia species (Annonaceae). Zeitschrift fur Naturforschung. C, Journal of biosciences. 2020 Nov; 75(11-12):479-484. doi: 10.1515/znc-2020-0096. [PMID: 32960782]
  • Xiaohui Yang, Jiabei Zhu, Jianchun Wu, Nan Huang, Zhongqi Cui, Yingbin Luo, Fenyong Sun, Qiuhui Pan, Yan Li, Qingyuan Yang. (-)-Guaiol regulates autophagic cell death depending on mTOR signaling in NSCLC. Cancer biology & therapy. 2018 08; 19(8):706-714. doi: 10.1080/15384047.2018.1451277. [PMID: 29611762]
  • Maria Carolina Freitas Garcia, Deivid Costa Soares, Raissa Couto Santana, Elvira Maria Saraiva, Antonio Carlos Siani, Mônica Freiman S Ramos, Maria das Graças Miranda Danelli, Thaïs Cristina Souto-Padron, Lucia H Pinto-da-Silva. The in vitro antileishmanial activity of essential oil from Aloysia gratissima and guaiol, its major sesquiterpene against Leishmania amazonensis. Parasitology. 2018 08; 145(9):1219-1227. doi: 10.1017/s0031182017002335. [PMID: 29352826]
  • Minghan Yang, Jiaoyang Luo, Kunlun Li, Shurong Hu, Tong Ding, Hao Liu, Ping Sheng, Meihua Yang. Determination and pharmacokinetic study of guaiol in rat plasma by gas chromatography-mass spectrometry with selected ion monitoring. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 May; 1085(?):30-35. doi: 10.1016/j.jchromb.2018.03.041. [PMID: 29627637]
  • Renata de F Mendes, Nícolas de C C Pinto, Josiane M da Silva, Jucélia B da Silva, Raquel C Dos S Hermisdorf, Rodrigo L Fabri, Luciana M Chedier, Elita Scio. The essential oil from the fruits of the Brazilian spice Xylopia sericea A. St.-Hil. presents expressive in-vitro antibacterial and antioxidant activity. The Journal of pharmacy and pharmacology. 2017 Mar; 69(3):341-348. doi: 10.1111/jphp.12698. [PMID: 28134988]
  • Qingyuan Yang, Jianchun Wu, Yingbin Luo, Nan Huang, Ni Zhen, Yun Zhou, Fenyong Sun, Zhi Li, Qiuhui Pan, Yan Li. (-)-Guaiol regulates RAD51 stability via autophagy to induce cell apoptosis in non-small cell lung cancer. Oncotarget. 2016 09; 7(38):62585-62597. doi: 10.18632/oncotarget.11540. [PMID: 27566579]
  • Danielle Cardoso de Alencar, Maria Lúcia Belém Pinheiro, José Lamak da Silva Pereira, João Ernesto de Carvalho, Francinete Ramos Campos, Alessandra Freitas Serain, Ricardo Brunelli Tirico, Alvaro José Hernández-Tasco, Emmanoel Vilaça Costa, Marcos José Salvador. Chemical composition of the essential oil from the leaves of Anaxagorea brevipes (Annonaceae) and evaluation of its bioactivity. Natural product research. 2016; 30(9):1088-92. doi: 10.1080/14786419.2015.1101103. [PMID: 26586465]
  • Tao Liu, Chun-Juan Wang, Hui-Qin Xie, Qing Mu. Guaiol--a naturally occurring insecticidal sesquiterpene. Natural product communications. 2013 Oct; 8(10):1353-4. doi: . [PMID: 24354171]
  • Ram S Verma, Rajesh K Verma, Rajendra C Padalia, Amit Chauhan, Anand Singh, Hemendra P Singh. Chemical diversity in the essential oil of Indian valerian (Valeriana jatamansi Jones). Chemistry & biodiversity. 2011 Oct; 8(10):1921-9. doi: 10.1002/cbdv.201100059. [PMID: 22006721]
  • Ilzenayde Araújo Neves, Claudio Augusto Gomes da Camara. Acaricidal activity against Tetranychus urticae and essential oil composition of four Croton species from Caatinga biome in northeastern Brazil. Natural product communications. 2011 Jun; 6(6):893-9. doi: ". [PMID: 21815434]
  • Jorge A Pino, Erik L Regalado, José L Rodríguez, Miguel D Fernández. Phytochemical analysis and in vitro free-radical-scavenging activities of the essential oils from leaf and fruit of Melaleuca leucadendra L. Chemistry & biodiversity. 2010 Sep; 7(9):2281-8. doi: 10.1002/cbdv.200900162. [PMID: 20860029]
  • Miriam A Apel, Marcos E L Lima, Marcos Sobral, Maria Cláudia M Young, Inês Cordeiro, Elfrides E S Schapoval, Amélia T Henriques, Paulo Roberto H Moreno. Anti-inflammatory activity of essential oil from leaves of Myrciaria tenella and Calycorectes sellowianus. Pharmaceutical biology. 2010 Apr; 48(4):433-8. doi: 10.3109/13880200903164386. [PMID: 20645723]
  • Zuoshan Feng, Yujia Bai, Fanglin Lu, Wenshu Huang, Xinmin Li, Xiaosong Hu. Effect of asafoetida extract on growth and quality of Pleurotus ferulic. International journal of molecular sciences. 2009 Dec; 11(1):41-51. doi: 10.3390/ijms11010041. [PMID: 20162000]
  • T K Praveen, S Dharmaraj, Jitendra Bajaj, S P Dhanabal, S Manimaran, M J Nanjan, Rema Razdan. Hepatoprotective activity of petroleum ether, diethyl ether, and methanol extract of Scoparia dulcis L. against CCl4-induced acute liver injury in mice. Indian journal of pharmacology. 2009 Jun; 41(3):110-4. doi: 10.4103/0253-7613.55206. [PMID: 20442817]
  • Gary A Strobel, Katreena Kluck, Wilford M Hess, Joe Sears, David Ezra, Percy N Vargas. Muscodor albus E-6, an endophyte of Guazuma ulmifolia making volatile antibiotics: isolation, characterization and experimental establishment in the host plant. Microbiology (Reading, England). 2007 Aug; 153(Pt 8):2613-2620. doi: 10.1099/mic.0.2007/008912-0. [PMID: 17660425]
  • S S Essam Abdel, Canyon Deon Vahid, Bowden Bruce, F Y Mohamed Wagdy, W Abdel Hoda Abdel, M Abdel Hamid. Efficacy of botanical extracts from Callitris glaucophylla, against Aedes aegypti and Culex annulirostris mosquitoes. Tropical biomedicine. 2006 Dec; 23(2):180-5. doi: ". [PMID: 17322820]
  • Mitsuo Miyazawa, Atsushi Sugawara. Biotransformation of (-)-guaiol by Eurotium rubrum as a biocatalyst. Natural product research. 2006 Jul; 20(8):731-4. doi: 10.1080/14786410500185774. [PMID: 16753905]
  • Leopold Jirovetz, Gerhard Buchbauer, Mohamed Pottachola Shafi, Neettiyath Kalathil Leela. Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India. Acta pharmaceutica (Zagreb, Croatia). 2003 Jun; 53(2):73-81. doi: . [PMID: 14764241]
  • John J Makangara, Stephan A Jonker, Mayunga H H Nkunya. A novel phenanthrenolide and C-benzyl dihydrochalcones from Uvaria puguensis. Natural product letters. 2002 Aug; 16(4):267-72. doi: 10.1080/10575630290020604. [PMID: 12168763]
  • X Yan, F Zhang, X Wei, Y Li. [Analysis of chemical constituents in the essential oil from roots of Litsea rotundifolia var. oblongifolia by GC/MS]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2000 Jun; 23(6):331-2. doi: ". [PMID: 12575085]
  • J Zhang, G Feng, Y Luo. [Analysis of chemical constituents in the essential oil from Evodia fargesii by GC/MS]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 1999 Jan; 22(1):30-1. doi: ". [PMID: 12575060]
  • A Pascual, M J Obregon, G M de Escobar. Tyrosine hydroxylase and the conversion of L-thyroxine into 3',3,5-triiodo-L-thyronone in the rat. Endocrinology. 1979 Jun; 104(6):1574-9. doi: 10.1210/endo-104-6-1574. [PMID: 36273]