1-Methoxy-4-(2-propenyl)benzene (BioDeep_00000396723)

 

Secondary id: BioDeep_00000003765, BioDeep_00000861362

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


InChI=1/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H

化学式: C10H12O (148.08881019999998)
中文名称: 草蒿脑, 4-烯丙基苯甲醚
谱图信息: 最多检出来源 Viridiplantae(plant) 0.25%

分子结构信息

SMILES: c1c(ccc(c1)CC=C)OC
InChI: InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3

描述信息

1-Methoxy-4-(2-propenyl)benzene, also known as methylchavicol or estragol, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. 1-Methoxy-4-(2-propenyl)benzene is a sweet, alcohol, and anise tasting compound. 1-Methoxy-4-(2-propenyl)benzene is found, on average, in the highest concentration within a few different foods, such as anises, fennels, and sweet basils and in a lower concentration in cumins, tarragons, and parsley. 1-Methoxy-4-(2-propenyl)benzene has also been detected, but not quantified, in several different foods, such as citrus, chinese cinnamons, caraway, fats and oils, and cloves. This could make 1-methoxy-4-(2-propenyl)benzene a potential biomarker for the consumption of these foods. 1-Methoxy-4-(2-propenyl)benzene, with regard to humans, has been linked to the inborn metabolic disorder celiac disease.
Estragole is a colorless liquid with odor of anise. Insoluble in water. Isolated from rind of persea gratissima grath. and from oil of estragon. Found in oils of Russian anise, basil, fennel turpentine, tarragon oil, anise bark oil. (NTP, 1992)
Estragole is a phenylpropanoid that is chavicol in which the hydroxy group is replaced by a methoxy group. It has a role as a flavouring agent, an insect attractant, a plant metabolite, a genotoxin and a carcinogenic agent. It is an alkenylbenzene, a monomethoxybenzene and a phenylpropanoid. It is functionally related to a chavicol.
Estragole is a natural product found in Vitis rotundifolia, Chaerophyllum macrospermum, and other organisms with data available.
See also: Anise Oil (part of).
Constituent of many essential oils. Found in apple, bilberry and orange fruits and juices. Flavouring agent.
A phenylpropanoid that is chavicol in which the hydroxy group is replaced by a methoxy group.
Estragole (4-Allylanisole), a relatively nontoxic volatile terpenoid ether, is a major component of the essential oil of many plants. Estragole dose-dependently blocks nerve excitability[1]. Estragole displays anti-toxoplasma activity[2].
Estragole (4-Allylanisole), a relatively nontoxic volatile terpenoid ether, is a major component of the essential oil of many plants. Estragole dose-dependently blocks nerve excitability[1]. Estragole displays anti-toxoplasma activity[2].

同义名列表

77 个代谢物同义名

InChI=1/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H; 4-06-00-03817 (Beilstein Handbook Reference); BENZENE,1-ALLYL,4-METHOXY METHYLCHAVICOL; 1-METHOXY-4-(2-PROPENYL)BENZENE [HSDB]; Benzene, 1-methoxy-4-(2-propen-1-yl)-; 1-Methoxy-4-(2-propenyl)benzene, 9CI; 4-Allylanisole, purum, >=97.0\\% (GC); 4-Allylanisole, analytical standard; 1-methoxy-4-(prop-2-en-1-yl)benzene; 1-Methoxy-4-(2-propen-1-yl)-Benzene; Benzene, 1-methoxy-4-(2-propenyl)-; 1-Methoxy-4-(2-propen-1-yl)benzene; Benzene, 1-methoxy, 4-prop-2-enyl; 1 -Methoxy-4-(2-propenyl) benzene; 1-methoxy-4-(2-propenyl)-benzene; 1-METHOXY-4-(2-PROPENYL)BENZENE; Estragole, analytical standard; 1-methoxy-4-prop-2-enylbenzene; 3-(4-Methoxyphenyl)-1-propene; 3-(p-Methoxyphenyl)-1-propene; Para-allylanisole (estragole); Allylphenyl methyl ether, p-; Methyl chavicole (estragole); Ether, p-allylphenyl methyl; 4-Allylanisole, >=98\\%, FCC; 3-(p-Methoxyphenyl)propene; 3-(4-Methoxyphenyl)propene; p-Allylphenyl methyl ether; Estragol (methylchavicol); 1-allyl-4-methoxy-benzene; 4-Allyl-1-methoxybenzene; 1-Allyl-4-methoxybenzene; 4-methoxy allylbenzene; p-methoxy allylbenzene; Chavicol methyl ether; p-Allylmethoxybenzene; 4-Methoxyallylbenzene; 4-Allylmethoxybenzene; Chavicyl methyl ether; p-Methoxyallylbenzene; 4-Allylanisole, 98\\%; Estragole (natural); Chavicol, O-methyl-; para-allylanisole; Chavicol, methyl-; Anisole, p-allyl-; O-Methyl-Chavicol; O-Methylchavicol; Methyl chavicole; ESTRAGOLE [FHFI]; methyl chavicol; p-Allyl-Anisole; UNII-9NIW07V3ET; ESTRAGOLE [FCC]; Methyl-Chavicol; p-allylanisole; ESTRAGOLE [MI]; Methylchavicol; 4-allylanisole; WLN: 1U2R DO1; 4-allylanisol; Isoanthethole; Tox21_302930; Tox21_202387; Estragenole; Isoanethole; 9NIW07V3ET; Estragole; Esdragole; Esteragol; FEMA 2411; AI3-16052; Esdragon; Estragol; Esdragol; Terragon; Tarragon



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(1)

PlantCyc(1)

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)

211 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

  • Arlene Sobrinho Ventura, Ruy Alberto Caetano Corrêa Filho, Claudia Andrea Lima Cardoso, Giovanna Rodrigues Stringhetta, Lucas de Oliveira Brasileiro, Juliana Silva Ribeiro, Scheila Anelise Pereira, Gabriela Tomas Jerônimo, Jayme Aparecido Povh. Ocimum basilicum essential oil in pacu Piaractus mesopotamicus: anesthetic efficacy, distribution, and depletion in different tissues. Veterinary research communications. 2023 Oct; ?(?):. doi: 10.1007/s11259-023-10225-8. [PMID: 37851315]
  • Zhengyu Bao, Mingcong Fan, Kanza Hannachi, Tingting Li, Jiajia Zhao, Yan Li, Haifeng Qian, Li Wang. Antifungal activity of star anise extract against Penicillium roqueforti and Aspergillus niger for bread shelf life. Food research international (Ottawa, Ont.). 2023 10; 172(?):113225. doi: 10.1016/j.foodres.2023.113225. [PMID: 37689961]
  • Tae-Kyun Hong, Seung-Hwan Lee, Jeong-Seop Shin, Kyoung-Hwa Jang, Eun-Shik Na, Chol-Soo Park, Chung-Hwan Kim, Jun-Ran Kim, Sri Renukadevi Balusamy, Haribalan Perumalsamy. Toxicological and molecular adverse effect of Illicium verum fruit constituents toward Bradysia procera. Pest management science. 2023 Mar; 79(3):1131-1139. doi: 10.1002/ps.7283. [PMID: 36358028]
  • Gholamreza Gohari, Sima Panahirad, Asghar Mohammadi, Muhittin Kulak, Mohamad Reza Dadpour, Zohreh Mehri Lighvan, Sina Sharifi, Bagher Eftekhari-Sis, Sławomir Szafert, Vasileios Fotopoulos, Ali Akbari. Characterization of Octa-aminopropyl polyhedral oligomeric silsesquioxanes (OA-POSS) nanoparticles and their effect on sweet basil (Ocimum basilicum L.) response to salinity stress. Plant physiology and biochemistry : PPB. 2023 Mar; 196(?):89-102. doi: 10.1016/j.plaphy.2023.01.019. [PMID: 36706695]
  • Subhash Shivaramu, Saravan Kumar Parepally, Varun Yennurukadirenahalli Byregowda, Kamala Jayanthi Pagadala Damodaram, Anuj Bhatnagar, Kailash Chandra Naga, Sanjeev Sharma, Manoj Kumar, Vivek Kempraj. Estragole, a potential attractant of the winged melon aphid, Aphis gossypii. Pest management science. 2023 Feb; ?(?):. doi: 10.1002/ps.7413. [PMID: 36797594]
  • Ugur Avcibasi, Mouhaman Toukour Dewa, Kadriye Busra Karatay, Ayfer Yurt Kilcar, Fazilet Zumrut Biber Muftuler. Investigation Of Bioactivity Of Estragole Isolated From Basil Plant On Brain Cancer Cell Lines Using Nuclear Method. Current radiopharmaceuticals. 2023 Jan; ?(?):. doi: 10.2174/1874471016666230110144021. [PMID: 36627786]
  • Elaheh Sadat Hosseini, Mohammad Mahdi Majidi, Mohammad Hossein Ehtemam, N Hughes. Characterization of fennel germplasm for physiological persistence and drought recovery: Association with biochemical properties. Plant physiology and biochemistry : PPB. 2023 Jan; 194(?):499-512. doi: 10.1016/j.plaphy.2022.11.037. [PMID: 36516537]
  • Daniela-Simina Stefan, Mariana Popescu, Cristina-Mihaela Luntraru, Alexandru Suciu, Mihai Belcu, Lucia-Elena Ionescu, Mihaela Popescu, Petrica Iancu, Mircea Stefan. Comparative Study of Useful Compounds Extracted from Lophanthus anisatus by Green Extraction. Molecules (Basel, Switzerland). 2022 Nov; 27(22):. doi: 10.3390/molecules27227737. [PMID: 36431837]
  • Dhouha Alimi, Azhar Hajri, Selim Jallouli, Hichem Sebai. Acaricidal and anthelmintic efficacy of Ocimum basilicum essential oil and its major constituents estragole and linalool, with insights on acetylcholinesterase inhibition. Veterinary parasitology. 2022 Sep; 309(?):109743. doi: 10.1016/j.vetpar.2022.109743. [PMID: 35714433]
  • Fatemeh Najafi, Gholamreza Kavoosi, Roghayeh Siahbalaei, Amina Kariminia. Anti-oxidative and anti-hyperglycemic properties of Agastache foeniculum essential oil and oily fraction in hyperglycemia-stimulated and lipopolysaccharide-stimulated macrophage cells: In vitro and in silico studies. Journal of ethnopharmacology. 2022 Feb; 284(?):114814. doi: 10.1016/j.jep.2021.114814. [PMID: 34775034]
  • Rajendran Senthoorraja, Kesavan Subaharan, Sowmya Manjunath, Vppalayam Shanmugam Pragadheesh, Nandagopal Bakthavatsalam, Muthu Gounder Mohan, Sengottayan Senthil-Nathan, Sekarappa Basavarajappa. Electrophysiological, behavioural and biochemical effect of Ocimum basilicum oil and its constituents methyl chavicol and linalool on Musca domestica L. Environmental science and pollution research international. 2021 Sep; 28(36):50565-50578. doi: 10.1007/s11356-021-14282-x. [PMID: 33963471]
  • Eduardo Valarezo, Vladimir Morocho, Luis Cartuche, Fernanda Chamba-Granda, Magdaly Correa-Conza, Ximena Jaramillo-Fierro, Miguel Angel Meneses. Variability of the Chemical Composition and Bioactivity between the Essential Oils Isolated from Male and Female Specimens of Hedyosmum racemosum (Ruiz & Pav.) G. Don. Molecules (Basel, Switzerland). 2021 Jul; 26(15):. doi: 10.3390/molecules26154613. [PMID: 34361766]
  • Nigel J Gooderham, Samuel M Cohen, Gerhard Eisenbrand, Shoji Fukushima, F Peter Guengerich, Stephen S Hecht, Ivonne M C M Rietjens, Thomas J Rosol, Jeanne M Davidsen, Christie L Harman, Ian J Murray, Sean V Taylor. FEMA GRAS assessment of natural flavor complexes: Clove, cinnamon leaf and West Indian bay leaf-derived flavoring ingredients. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2020 Nov; 145(?):111585. doi: 10.1016/j.fct.2020.111585. [PMID: 32702506]
  • Edvaldo Balbino Alves Júnior, Rodrigo de Oliveira Formiga, Catarina Alves de Lima Serafim, Maria Elaine Cristina Araruna, Michele Liz de Souza Pessoa, Roseane Carvalho Vasconcelos, Thais Gomes de Carvalho, Tamires Gonçalves de Jesus, Aurigena Antunes Araújo, Raimundo Fernandes de Araujo Junior, Giciane Carvalho Vieira, Marianna Vieira Sobral, Leônia Maria Batista. Estragole prevents gastric ulcers via cytoprotective, antioxidant and immunoregulatory mechanisms in animal models. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2020 Oct; 130(?):110578. doi: 10.1016/j.biopha.2020.110578. [PMID: 32750650]
  • J S Rosa, L Oliveira, R M O F Sousa, C B Escobar, M Fernandes-Ferreira. Bioactivity of some Apiaceae essential oils and their constituents against Sitophilus zeamais (Coleoptera: Curculionidae). Bulletin of entomological research. 2020 Jun; 110(3):406-416. doi: 10.1017/s0007485319000774. [PMID: 31813390]
  • Bernhard H Monien, Benjamin Sachse, Bela Niederwieser, Klaus Abraham. Detection of N-Acetyl-S-[3'-(4-methoxyphenyl)allyl]-l-Cys (AMPAC) in Human Urine Samples after Controlled Exposure to Fennel Tea: A New Metabolite of Estragole and trans-Anethole. Chemical research in toxicology. 2019 11; 32(11):2260-2267. doi: 10.1021/acs.chemrestox.9b00287. [PMID: 31565931]
  • Laura Marabini, Corrado L Galli, Pierpaolo La Fauci, Marina Marinovich. Effect of plant extracts on the genotoxicity of 1'-hydroxy alkenylbenzenes. Regulatory toxicology and pharmacology : RTP. 2019 Jul; 105(?):36-41. doi: 10.1016/j.yrtph.2019.03.017. [PMID: 30935955]
  • Domenico Cautela, Filomena Monica Vella, Domenico Castaldo, Bruna Laratta. Characterization of essential oil recovered from fennel horticultural wastes. Natural product research. 2019 Jul; 33(13):1964-1968. doi: 10.1080/14786419.2018.1478827. [PMID: 29846092]
  • Nurhayat Tabanca, Marco Masi, Nancy D Epsky, Paola Nocera, Alessio Cimmino, Paul E Kendra, Jerome Niogret, Antonio Evidente. Laboratory Evaluation of Natural and Synthetic Aromatic Compounds as Potential Attractants for Male Mediterranean fruit Fly, Ceratitis capitata. Molecules (Basel, Switzerland). 2019 Jun; 24(13):. doi: 10.3390/molecules24132409. [PMID: 31261896]
  • Alexander V Samet, Oksana G Shevchenko, Vyacheslav V Rusak, Eduard M Chartov, Andrey B Myshlyavtsev, Daniil A Rusanov, Marina N Semenova, Victor V Semenov. Antioxidant Activity of Natural Allylpolyalkoxybenzene Plant Essential Oil Constituents. Journal of natural products. 2019 Jun; ?(?):. doi: 10.1021/acs.jnatprod.8b00878. [PMID: 31244145]
  • Maryam Akhbari, Reza Kord, Saeedeh Jafari Nodooshan, Sepideh Hamedi. Analysis and evaluation of the antimicrobial and anticancer activities of the essential oil isolated from Foeniculum vulgare from Hamedan, Iran. Natural product research. 2019 Jun; 33(11):1629-1632. doi: 10.1080/14786419.2017.1423310. [PMID: 29308661]
  • Mina Arbabi, Hassanali Naghdi Badi, Mohammadreza Labbafi, Ali Mehrafarin, Ebrahim Saboki. Morphophysiological and Phytochemical Variability in Some Wild Populations of Ducrosia anethifolia from Iran. Chemistry & biodiversity. 2018 Dec; 15(12):e1800301. doi: 10.1002/cbdv.201800301. [PMID: 30240144]
  • João Vito B Freitas, Elenilson G Alves Filho, Lorena Mara A Silva, Guilherme J Zocolo, Edy S de Brito, Nilce V Gramosa. Chemometric analysis of NMR and GC datasets for chemotype characterization of essential oils from different species of Ocimum. Talanta. 2018 Apr; 180(?):329-336. doi: 10.1016/j.talanta.2017.12.053. [PMID: 29332819]
  • Sara Levorato, Luca Dominici, Cristina Fatigoni, Claudia Zadra, Rita Pagiotti, Massimo Moretti, Milena Villarini. In vitro toxicity evaluation of estragole-containing preparations derived from Foeniculum vulgare Mill. (fennel) on HepG2 cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2018 Jan; 111(?):616-622. doi: 10.1016/j.fct.2017.12.014. [PMID: 29233689]
  • Iveta Bartoňková, Zdeněk Dvořák. Essential oils of culinary herbs and spices display agonist and antagonist activities at human aryl hydrocarbon receptor AhR. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2018 Jan; 111(?):374-384. doi: 10.1016/j.fct.2017.11.049. [PMID: 29191726]
  • Bruna Celeida Silva Santos, Andressa Soares Pires, Célia Hitomi Yamamoto, Mara Rubia Costa Couri, Alex Gutterres Taranto, Maria Silvana Alves, Ana Lúcia Dos Santos de Matos Araújo, Orlando Vieira de Sousa. Methyl Chavicol and Its Synthetic Analogue as Possible Antioxidant and Antilipase Agents Based on the In Vitro and In Silico Assays. Oxidative medicine and cellular longevity. 2018; 2018(?):2189348. doi: 10.1155/2018/2189348. [PMID: 29849872]
  • Ran Li, Vaishnavi Amarr Reddy, Jingjing Jin, Chakaravarthy Rajan, Qian Wang, Genhua Yue, Chin Huat Lim, Nam-Hai Chua, Jian Ye, Rajani Sarojam. Comparative transcriptome analysis of oil palm flowers reveals an EAR-motif-containing R2R3-MYB that modulates phenylpropene biosynthesis. BMC plant biology. 2017 Nov; 17(1):219. doi: 10.1186/s12870-017-1174-4. [PMID: 29169327]
  • Andrea Muráriková, Anton Ťažký, Jarmila Neugebauerová, Alexandra Planková, Josef Jampílek, Pavel Mučaji, Peter Mikuš. Characterization of Essential Oil Composition in Different Basil Species and Pot Cultures by a GC-MS Method. Molecules (Basel, Switzerland). 2017 Jul; 22(7):. doi: 10.3390/molecules22071221. [PMID: 28726757]
  • Babak Abdollahi Mandoulakani, Elham Eyvazpour, Morteza Ghadimzadeh. The effect of drought stress on the expression of key genes involved in the biosynthesis of phenylpropanoids and essential oil components in basil (Ocimum basilicum L.). Phytochemistry. 2017 Jul; 139(?):1-7. doi: 10.1016/j.phytochem.2017.03.006. [PMID: 28366608]
  • Yar-Khing Yauk, Edwige J F Souleyre, Adam J Matich, Xiuyin Chen, Mindy Y Wang, Blue Plunkett, Andrew P Dare, Richard V Espley, Sumathi Tomes, David Chagné, Ross G Atkinson. Alcohol acyl transferase 1 links two distinct volatile pathways that produce esters and phenylpropenes in apple fruit. The Plant journal : for cell and molecular biology. 2017 Jul; 91(2):292-305. doi: 10.1111/tpj.13564. [PMID: 28380280]
  • Elasyed A Omer, Saber F Hendawy, Rasha F Ismail, Giacomo L Petretto, Jonathan P Rourke, Giorgio Pintore. Acclimatization study of Tagetes lucida L. in Egypt and the chemical characterization of its essential oils. Natural product research. 2017 Jul; 31(13):1509-1517. doi: 10.1080/14786419.2017.1278594. [PMID: 28152613]
  • María J Jordán, María Quílez, María C Luna, Farzaneh Bekhradi, José A Sotomayor, Pedro Sánchez-Gómez, María I Gil. Influence of water stress and storage time on preservation of the fresh volatile profile of three basil genotypes. Food chemistry. 2017 Apr; 221(?):169-177. doi: 10.1016/j.foodchem.2016.10.059. [PMID: 27979148]
  • Santosh Shiwakoti, Osama Saleh, Shital Poudyal, Abdulssamad Barka, Yanping Qian, Valtcho D Zheljazkov. Yield, Composition and Antioxidant Capacity of the Essential Oil of Sweet Basil and Holy Basil as Influenced by Distillation Methods. Chemistry & biodiversity. 2017 Apr; 14(4):. doi: 10.1002/cbdv.201600417. [PMID: 28028933]
  • Juan Carlos Romero-Benavides, Ana Lucía Ruano, Ronal Silva-Rivas, Paola Castillo-Veintimilla, Sara Vivanco-Jaramillo, Natalia Bailon-Moscoso. Medicinal plants used as anthelmintics: Ethnomedical, pharmacological, and phytochemical studies. European journal of medicinal chemistry. 2017 Mar; 129(?):209-217. doi: 10.1016/j.ejmech.2017.02.005. [PMID: 28231520]
  • Sara Keramati, Hemmatollah Pirdashti, Valliollah Babaeizad, Ali Dehestani. Essential oil composition of sweet basil (Ocimum basilicum L.) in symbiotic relationship with Piriformospora indica and paclobutrazol application under salt stress. Acta biologica Hungarica. 2016 Dec; 67(4):412-423. doi: 10.1556/018.67.2016.4.7. [PMID: 28000503]
  • Atul Anand, Ramesha H Jayaramaiah, Supriya D Beedkar, Priyanka A Singh, Rakesh S Joshi, Fayaj A Mulani, Bhushan B Dholakia, Sachin A Punekar, Wasudeo N Gade, Hirekodathakallu V Thulasiram, Ashok P Giri. Comparative functional characterization of eugenol synthase from four different Ocimum species: Implications on eugenol accumulation. Biochimica et biophysica acta. 2016 11; 1864(11):1539-47. doi: 10.1016/j.bbapap.2016.08.004. [PMID: 27519164]
  • Lindaiane Bezerra Rodrigues, Anita Oliveira Brito Pereira Bezerra Martins, Francisco Rafael Alves Santana Cesário, Fyama Ferreira E Castro, Thaís Rodrigues de Albuquerque, Maria Neyze Martins Fernandes, Bruno Anderson Fernandes da Silva, Lucindo José Quintans Júnior, José Galberto Martins da Costa, Henrique Douglas Melo Coutinho, Roseli Barbosa, Irwin Rose Alencar de Menezes. Anti-inflammatory and antiedematogenic activity of the Ocimum basilicum essential oil and its main compound estragole: In vivo mouse models. Chemico-biological interactions. 2016 Sep; 257(?):14-25. doi: 10.1016/j.cbi.2016.07.026. [PMID: 27474066]
  • Surapan Jitviriyanon, Phanida Phanthong, Pattamapan Lomarat, Nuntavan Bunyapraphatsara, Sarthorn Porntrakulpipat, Nuanchan Paraksa. In vitro study of anti-coccidial activity of essential oils from indigenous plants against Eimeria tenella. Veterinary parasitology. 2016 Sep; 228(?):96-102. doi: 10.1016/j.vetpar.2016.08.020. [PMID: 27692340]
  • S Zhang, J Jiang, Q Luan. Genetic and correlation analysis of oleoresin chemical components in slash pine. Genetics and molecular research : GMR. 2016 Aug; 15(3):. doi: 10.4238/gmr.15038982. [PMID: 27706657]
  • Eleni Fitsiou, Gregoria Mitropoulou, Katerina Spyridopoulou, Angeliki Tiptiri-Kourpeti, Manolis Vamvakias, Haido Bardouki, Mihalis Ι Panayiotidis, Alex Galanis, Yiannis Kourkoutas, Katerina Chlichlia, Aglaia Pappa. Phytochemical Profile and Evaluation of the Biological Activities of Essential Oils Derived from the Greek Aromatic Plant Species Ocimum basilicum, Mentha spicata, Pimpinella anisum and Fortunella margarita. Molecules (Basel, Switzerland). 2016 Aug; 21(8):. doi: 10.3390/molecules21081069. [PMID: 27537869]
  • Azadeh Barfi, Habibollah Nazem, Iman Saeidi, Moazameh Peyrovi, Maryam Afsharzadeh, Behruz Barfi, Hossein Salavati. In-syringe reversed dispersive liquid-liquid microextraction for the evaluation of three important bioactive compounds of basil, tarragon and fennel in human plasma and urine samples. Journal of pharmaceutical and biomedical analysis. 2016 Mar; 121(?):123-134. doi: 10.1016/j.jpba.2016.01.003. [PMID: 26802527]
  • Liisa Uusitalo, Maija Salmenhaara, Merja Isoniemi, Alicia Garcia-Alvarez, Lluís Serra-Majem, Lourdes Ribas-Barba, Paul Finglas, Jenny Plumb, Pirkko Tuominen, Kirsti Savela. Intake of selected bioactive compounds from plant food supplements containing fennel (Foeniculum vulgare) among Finnish consumers. Food chemistry. 2016 Mar; 194(?):619-25. doi: 10.1016/j.foodchem.2015.08.057. [PMID: 26471600]
  • Daniele Fraternale, Guido Flamini, Donata Ricci. Essential Oil Composition and Antigermination Activity of Artemisia dracunculus (Tarragon). Natural product communications. 2015 Aug; 10(8):1469-72. doi: ". [PMID: 26434144]
  • Yar-Khing Yauk, David Chagné, Sumathi Tomes, Adam J Matich, Mindy Y Wang, Xiuyin Chen, Ratnasiri Maddumage, Martin B Hunt, Daryl D Rowan, Ross G Atkinson. The O-methyltransferase gene MdoOMT1 is required for biosynthesis of methylated phenylpropenes in ripe apple fruit. The Plant journal : for cell and molecular biology. 2015 Jun; 82(6):937-950. doi: 10.1111/tpj.12861. [PMID: 25904040]
  • Wei Ding, Dan D Levy, Michelle E Bishop, Mason G Pearce, Kelly J Davis, Alan M Jeffrey, Jian-Dong Duan, Gary M Williams, Gene A White, Lascelles E Lyn-Cook, Mugimane G Manjanatha. In vivo genotoxicity of estragole in male F344 rats. Environmental and molecular mutagenesis. 2015 May; 56(4):356-65. doi: 10.1002/em.21918. [PMID: 25361439]
  • Dongmei Duan, Liping Chen, Xiuyan Yang, Ya Tu, Shuang Jiao. Antidepressant-like effect of essential oil isolated from Toona ciliata Roem. var. yunnanensis. Journal of natural medicines. 2015 Apr; 69(2):191-7. doi: 10.1007/s11418-014-0878-0. [PMID: 25465853]
  • Thallita C B Andrade, Sidney G De Lima, Rivelilson M Freitas, Márcio S Rocha, Torequl Islam, Teresinha G Da Silva, Gardenia C G Militão. Isolation, characterization and evaluation of antimicrobial and cytotoxic activity of estragole, obtained from the essential oil of Croton zehntneri (Euphorbiaceae). Anais da Academia Brasileira de Ciencias. 2015 Mar; 87(1):173-82. doi: 10.1590/0001-3765201520140111. [PMID: 25789792]
  • Hana Moon, Min Jung Kim, Hee Jin Son, Hae-Jin Kweon, Jung Tae Kim, Yiseul Kim, Jaewon Shim, Byung-Chang Suh, Mee-Ra Rhyu. Five hTRPA1 Agonists Found in Indigenous Korean Mint, Agastache rugosa. PloS one. 2015; 10(5):e0127060. doi: 10.1371/journal.pone.0127060. [PMID: 25978436]
  • Sylvia D F Souza, Carolina S L Franca, Edenilson S Niculau, Larissa C B Costa, José E B Pinto, Péricles B Alves, Rosilene M Marçal. Antispasmodic effect of Ocimum selloi essential oil on the guinea-pig ileum. Natural product research. 2015; 29(22):2125-8. doi: 10.1080/14786419.2014.989392. [PMID: 25560465]
  • Hanaa Yamani, Nitin Mantri, Paul D Morrison, Edwin Pang. Analysis of the volatile organic compounds from leaves, flower spikes, and nectar of Australian grown Agastache rugosa. BMC complementary and alternative medicine. 2014 Dec; 14(?):495. doi: 10.1186/1472-6882-14-495. [PMID: 25510964]
  • Pedro Henrique Bezerra Cabral, Rafael de Morais Campos, Manassés Claudino Fonteles, Cláudia Ferreira Santos, José Henrique Leal Cardoso, Nilberto Robson Falcão do Nascimento. Effects of the essential oil of Croton zehntneri and its major components, anethole and estragole, on the rat corpora cavernosa. Life sciences. 2014 Sep; 112(1-2):74-81. doi: 10.1016/j.lfs.2014.07.022. [PMID: 25084123]
  • Amber Khan, Aijaz Ahmad, Luqman Ahmad Khan, Nikhat Manzoor. Ocimum sanctum (L.) essential oil and its lead molecules induce apoptosis in Candida albicans. Research in microbiology. 2014 Jul; 165(6):411-9. doi: 10.1016/j.resmic.2014.05.031. [PMID: 24858938]
  • Maryam Rajabi, Sudabeh Haji-Esfandiari, Behruz Barfi, Hanieh Ghanbari. Ultrasound-assisted temperature-controlled ionic-liquid dispersive liquid-phase microextraction method for simultaneous determination of anethole, estragole, and para-anisaldehyde in different plant extracts and human urine: a comparative study. Analytical and bioanalytical chemistry. 2014 Jul; 406(18):4501-12. doi: 10.1007/s00216-014-7848-y. [PMID: 24817361]
  • N A Vyry Wouatsa, Laxminarain Misra, R Venkatesh Kumar. Antibacterial activity of essential oils of edible spices, Ocimum canum and Xylopia aethiopica. Journal of food science. 2014 May; 79(5):M972-7. doi: 10.1111/1750-3841.12457. [PMID: 24758511]
  • Suzanne J P L van den Berg, Verena Klaus, Wasma Alhusainy, Ivonne M C M Rietjens. Matrix-derived combination effect and risk assessment for estragole from basil-containing plant food supplements (PFS). Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Dec; 62(?):32-40. doi: 10.1016/j.fct.2013.08.019. [PMID: 23959103]
  • Giselle Tamayo-Castillo, Víctor Vásquez, María Isabel Ríos, María Victoria Rodríguez, Godofredo Solano, Susana Zacchino, Mahabir P Gupta. Isolation of major components from the roots of Godmania aesculifolia and determination of their antifungal activities. Planta medica. 2013 Dec; 79(18):1749-55. doi: 10.1055/s-0033-1351025. [PMID: 24356871]
  • Mohammad Reza Pirmoradi, Mohammad Moghaddam, Nasrin Farhadi. Chemotaxonomic analysis of the aroma compounds in essential oils of two different Ocimum basilicum L. varieties from Iran. Chemistry & biodiversity. 2013 Jul; 10(7):1361-71. doi: 10.1002/cbdv.201200413. [PMID: 23847081]
  • He Qin Li, Qi Zhi Liu, Zhi Long Liu, Shu Shan Du, Zhi Wei Deng. Chemical composition and nematicidal activity of essential oil of Agastache rugosa against Meloidogyne incognita. Molecules (Basel, Switzerland). 2013 Apr; 18(4):4170-80. doi: 10.3390/molecules18044170. [PMID: 23571530]
  • Heibatullah Kalantari, Hamid Galehdari, Zahra Zaree, Rudolf Gesztelyi, Balazs Varga, David Haines, Mariann Bombicz, Arpad Tosaki, Bela Juhasz. Toxicological and mutagenic analysis of Artemisia dracunculus (tarragon) extract. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Jan; 51(?):26-32. doi: 10.1016/j.fct.2012.07.052. [PMID: 23010670]
  • Alicia Paini, Ans Punt, Gabriele Scholz, Eric Gremaud, Bert Spenkelink, Gerrit Alink, Benoît Schilter, Peter J van Bladeren, Ivonne M C M Rietjens. In vivo validation of DNA adduct formation by estragole in rats predicted by physiologically based biodynamic modelling. Mutagenesis. 2012 Nov; 27(6):653-63. doi: 10.1093/mutage/ges031. [PMID: 22844077]
  • Magaly L Mota, Lis Tavares Coelho Lobo, José M Galberto da Costa, Leandro S Costa, Hugo A O Rocha, Luiz F Rocha e Silva, Adrian M Pohlit, Valter F de Andrade Neto. In vitro and in vivo antimalarial activity of essential oils and chemical components from three medicinal plants found in northeastern Brazil. Planta medica. 2012 May; 78(7):658-64. doi: 10.1055/s-0031-1298333. [PMID: 22441836]
  • Stefanie Weinoehrl, Bjoern Feistel, Ivo Pischel, Brigitte Kopp, Veronika Butterweck. Comparative evaluation of two different Artemisia dracunculus L. cultivars for blood sugar lowering effects in rats. Phytotherapy research : PTR. 2012 Apr; 26(4):625-9. doi: 10.1002/ptr.3605. [PMID: 21953838]
  • Gianluca Amadei, Brian M Ross. Quantification of character-impacting compounds in Ocimum basilicum and 'Pesto alla Genovese' with selected ion flow tube mass spectrometry. Rapid communications in mass spectrometry : RCM. 2012 Feb; 26(3):219-25. doi: 10.1002/rcm.5293. [PMID: 22223305]
  • Ram Swaroop Verma, Rajendra Chandra Padalia, Amit Chauhan. Variation in the volatile terpenoids of two industrially important basil (Ocimum basilicum L.) cultivars during plant ontogeny in two different cropping seasons from India. Journal of the science of food and agriculture. 2012 Feb; 92(3):626-31. doi: 10.1002/jsfa.4620. [PMID: 21987291]
  • Asie Shojaii, Mehri Abdollahi Fard. Review of Pharmacological Properties and Chemical Constituents of Pimpinella anisum. ISRN pharmaceutics. 2012; 2012(?):510795. doi: 10.5402/2012/510795. [PMID: 22848853]
  • Vineeta Singh, Atul Kumar Gupta, S P Singh, Anil Kumar. Direct analysis in real time by mass spectrometric technique for determining the variation in metabolite profiles of Cinnamomum tamala Nees and Eberm genotypes. TheScientificWorldJournal. 2012; 2012(?):549265. doi: 10.1100/2012/549265. [PMID: 22701361]
  • Ain Raal, Anne Orav, Elmar Arak. Essential oil composition of Foeniculum vulgare Mill. fruits from pharmacies in different countries. Natural product research. 2012; 26(13):1173-8. doi: 10.1080/14786419.2010.535154. [PMID: 21827282]
  • Bruce C Campbell, Kathleen L Chan, Jong H Kim. Chemosensitization as a means to augment commercial antifungal agents. Frontiers in microbiology. 2012; 3(?):79. doi: 10.3389/fmicb.2012.00079. [PMID: 22393330]
  • Dmitry Obolskiy, Ivo Pischel, Bjoern Feistel, Nikolay Glotov, Michael Heinrich. Artemisia dracunculus L. (tarragon): a critical review of its traditional use, chemical composition, pharmacology, and safety. Journal of agricultural and food chemistry. 2011 Nov; 59(21):11367-84. doi: 10.1021/jf202277w. [PMID: 21942448]
  • Ahmed Yahya Al-Maskri, Muhammad Asif Hanif, Masoud Yahya Al-Maskari, Alfie Susan Abraham, Jamal Nasser Al-sabahi, Omar Al-Mantheri. Essential oil from Ocimum basilicum (Omani Basil): a desert crop. Natural product communications. 2011 Oct; 6(10):1487-90. doi: ". [PMID: 22164790]
  • Ragaa Hosny Mohamad, Amal Mohamad El-Bastawesy, Mohamad Gamil Abdel-Monem, Assmaa Mahmoud Noor, Hussain Abdel Rahman Al-Mehdar, Sabry Mohamad Sharawy, Mahmuod Mohamad El-Merzabani. Antioxidant and anticarcinogenic effects of methanolic extract and volatile oil of fennel seeds (Foeniculum vulgare). Journal of medicinal food. 2011 Sep; 14(9):986-1001. doi: 10.1089/jmf.2008.0255. [PMID: 21812646]
  • Remigius Chizzola. Composition of the essential oils from Anthriscus cerefolium var. trichocarpa and A. caucalis growing wild in the urban area of Vienna (Austria). Natural product communications. 2011 Aug; 6(8):1147-50. doi: ". [PMID: 21922923]
  • E Martati, M G Boersma, A Spenkelink, D B Khadka, A Punt, J Vervoort, P J van Bladeren, I M C M Rietjens. Physiologically based biokinetic (PBBK) model for safrole bioactivation and detoxification in rats. Chemical research in toxicology. 2011 Jun; 24(6):818-34. doi: 10.1021/tx200032m. [PMID: 21446753]
  • Cheng Fang Wang, Kai Yang, Hai Ming Zhang, Jie Cao, Rui Fang, Zhi Long Liu, Shu Shan Du, Yong Yan Wang, Zhi Wei Deng, Ligang Zhou. Components and insecticidal activity against the maize weevils of Zanthoxylum schinifolium fruits and leaves. Molecules (Basel, Switzerland). 2011 Apr; 16(4):3077-88. doi: 10.3390/molecules16043077. [PMID: 21490556]
  • Celia Diezel, Danny Kessler, Ian T Baldwin. Pithy protection: Nicotiana attenuata's jasmonic acid-mediated defenses are required to resist stem-boring weevil larvae. Plant physiology. 2011 Apr; 155(4):1936-46. doi: 10.1104/pp.110.170936. [PMID: 21300916]
  • M Băjan, Ana Clara Aprotosoaie, A Spac, Ursula Stănescu. [Chemical composition of essential oil obtained from Romanian fennel fruits]. Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi. 2011 Apr; 115(2):590-4. doi: ". [PMID: 21870762]
  • Amber Khan, Aijaz Ahmad, Feroz Akhtar, Snowber Yousuf, Immaculata Xess, Luqman Ahmad Khan, Nikhat Manzoor. Induction of oxidative stress as a possible mechanism of the antifungal action of three phenylpropanoids. FEMS yeast research. 2011 Feb; 11(1):114-22. doi: 10.1111/j.1567-1364.2010.00697.x. [PMID: 21114624]
  • Abdelaaty A Shahat, Abeer Y Ibrahim, Saber F Hendawy, Elsayed A Omer, Faiza M Hammouda, Fawzia H Abdel-Rahman, Mahmoud A Saleh. Chemical composition, antimicrobial and antioxidant activities of essential oils from organically cultivated fennel cultivars. Molecules (Basel, Switzerland). 2011 Feb; 16(2):1366-77. doi: 10.3390/molecules16021366. [PMID: 21285921]
  • Moises Martinez-Velazquez, Gustavo Adolfo Castillo-Herrera, Rodrigo Rosario-Cruz, Jose Miguel Flores-Fernandez, Julisa Lopez-Ramirez, Rodolfo Hernandez-Gutierrez, Eugenia del Carmen Lugo-Cervantes. Acaricidal effect and chemical composition of essential oils extracted from Cuminum cyminum, Pimenta dioica and Ocimum basilicum against the cattle tick Rhipicephalus (Boophilus) microplus (Acari: Ixodidae). Parasitology research. 2011 Feb; 108(2):481-7. doi: 10.1007/s00436-010-2069-6. [PMID: 20865426]
  • D W Bristol. NTP 3-month toxicity studies of estragole (CAS No. 140-67-0) administered by gavage to F344/N rats and B6C3F1 mice. Toxicity report series. 2011 Jan; ?(82):1-111. doi: . [PMID: 21445103]
  • Amber Khan, Aijaz Ahmad, Feroz Akhtar, Snowber Yousuf, Immaculata Xess, Luqman A Khan, Nikhat Manzoor. Ocimum sanctum essential oil and its active principles exert their antifungal activity by disrupting ergosterol biosynthesis and membrane integrity. Research in microbiology. 2010 Dec; 161(10):816-23. doi: 10.1016/j.resmic.2010.09.008. [PMID: 20868749]
  • Jemal Hussien, Ariaya Hymete, Jens Rohloff. Volatile constituents and biological activities of Pycnostachys abyssinica and Pycnostachys eminii extracts. Pharmaceutical biology. 2010 Dec; 48(12):1384-91. doi: 10.3109/13880209.2010.486406. [PMID: 20738219]
  • Varsha J Galani, B G Patel, D G Rana. Sphaeranthus indicus Linn.: A phytopharmacological review. International journal of Ayurveda research. 2010 Oct; 1(4):247-53. doi: 10.4103/0974-7788.76790. [PMID: 21455454]
  • . Toxicology and carcinogenesis studies of isoeugenol (CAS No. 97-54-1) in F344/N rats and B6C3F1 mice (gavage studies). National Toxicology Program technical report series. 2010 Sep; ?(551):1-178. doi: . [PMID: 21372857]
  • Christine Tschiggerl, Franz Bucar. Volatile fraction of lavender and bitter fennel infusion extracts. Natural product communications. 2010 Sep; 5(9):1431-6. doi: . [PMID: 20923003]
  • Diolimar Buitrago, Luis B Rojas, Janne Rojas, Antonio Morales. Volatile compounds from Tagetes pusilla (Asteraceae) collected from the Venezuela Andes. Natural product communications. 2010 Aug; 5(8):1283-4. doi: ". [PMID: 20839636]
  • W Alhusainy, A Paini, A Punt, J Louisse, A Spenkelink, J Vervoort, T Delatour, G Scholz, B Schilter, T Adams, P J van Bladeren, I M C M Rietjens. Identification of nevadensin as an important herb-based constituent inhibiting estragole bioactivation and physiology-based biokinetic modeling of its possible in vivo effect. Toxicology and applied pharmacology. 2010 Jun; 245(2):179-90. doi: 10.1016/j.taap.2010.02.017. [PMID: 20226806]
  • Maria Graça Miguel, Cláudia Cruz, Leonor Faleiro, Mariana T F Simões, Ana Cristina Figueiredo, José G Barroso, Luis G Pedro. Foeniculum vulgare essential oils: chemical composition, antioxidant and antimicrobial activities. Natural product communications. 2010 Feb; 5(2):319-28. doi: . [PMID: 20334152]
  • Fabrice Nesslany, Dominique Parent-Massin, Daniel Marzin. Risk assessment of consumption of methylchavicol and tarragon: the genotoxic potential in vivo and in vitro. Mutation research. 2010 Feb; 696(1):1-9. doi: 10.1016/j.mrgentox.2009.11.003. [PMID: 19913108]
  • Priyabrata Pattanayak, Pritishova Behera, Debajyoti Das, Sangram K Panda. Ocimum sanctum Linn. A reservoir plant for therapeutic applications: An overview. Pharmacognosy reviews. 2010 Jan; 4(7):95-105. doi: 10.4103/0973-7847.65323. [PMID: 22228948]
  • Annette Zeller, Kathie Horst, Michael Rychlik. Study of the metabolism of estragole in humans consuming fennel tea. Chemical research in toxicology. 2009 Dec; 22(12):1929-37. doi: 10.1021/tx900236g. [PMID: 19908891]
  • Ans Punt, Alicia Paini, Marelle G Boersma, Andreas P Freidig, Thierry Delatour, Gabriele Scholz, Benoît Schilter, Peter J van Bladeren, Ivonne M C M Rietjens. Use of physiologically based biokinetic (PBBK) modeling to study estragole bioactivation and detoxification in humans as compared with male rats. Toxicological sciences : an official journal of the Society of Toxicology. 2009 Aug; 110(2):255-69. doi: 10.1093/toxsci/kfp102. [PMID: 19447879]
  • Chiou Ling Chang, Il Kyu Cho, Qing X Li. Insecticidal activity of basil oil, trans-anethole, estragole, and linalool to adult fruit flies of Ceratitis capitata, Bactrocera dorsalis, and Bactrocera cucurbitae. Journal of economic entomology. 2009 Feb; 102(1):203-9. doi: 10.1603/029.102.0129. [PMID: 19253638]
  • Majekodunmi O Fatope, Ruchi G Marwah, Nabil M Al Hadhrami, Anthony K Onifade, John R Williams. Identification of the chemotypes of Ocimum forskolei and Ocimum basilicum by NMR spectroscopy. Chemistry & biodiversity. 2008 Nov; 5(11):2457-63. doi: 10.1002/cbdv.200890211. [PMID: 19035561]
  • Ans Punt, Andreas P Freidig, Thierry Delatour, Gabriele Scholz, Marelle G Boersma, Benoît Schilter, Peter J van Bladeren, Ivonne M C M Rietjens. A physiologically based biokinetic (PBBK) model for estragole bioactivation and detoxification in rat. Toxicology and applied pharmacology. 2008 Sep; 231(2):248-59. doi: 10.1016/j.taap.2008.04.011. [PMID: 18539307]
  • Annadurai Senthilkumar, Krishnan Kannathasan, Venugopalan Venkatesalu. Chemical constituents and larvicidal property of the essential oil of Blumea mollis (D. Don) Merr. against Culex quinquefasciatus. Parasitology research. 2008 Sep; 103(4):959-62. doi: 10.1007/s00436-008-1085-2. [PMID: 18566831]
  • Jay J Emerick, Aaron I Snyder, Nathan W Bower, Marc A Snyder. Mountain pine beetle attack associated with low levels of 4-allylanisole in ponderosa pine. Environmental entomology. 2008 Aug; 37(4):871-5. doi: 10.1603/0046-225x(2008)37[871:mpbaaw]2.0.co;2. [PMID: 18801251]
  • R O S Fontenelle, S M Morais, E H S Brito, R S N Brilhante, R A Cordeiro, N R F Nascimento, M R Kerntopf, J J C Sidrim, M F G Rocha. Antifungal activity of essential oils of Croton species from the Brazilian Caatinga biome. Journal of applied microbiology. 2008 May; 104(5):1383-90. doi: 10.1111/j.1365-2672.2007.03707.x. [PMID: 18298533]
  • Valtcho D Zheljazkov, Amber Callahan, Charles L Cantrell. Yield and oil composition of 38 basil (Ocimum basilicum L.) accessions grown in Mississippi. Journal of agricultural and food chemistry. 2008 Jan; 56(1):241-5. doi: 10.1021/jf072447y. [PMID: 18072735]