safrole (BioDeep_00000422693)

Main id: BioDeep_00000002554

 

natural product Volatile Flavor Compounds


代谢物信息卡片


safrole

化学式: C10H10O2 (162.06807600000002)
中文名称: 黄樟素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C=CCC1=CC2=C(C=C1)OCO2
InChI: InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2

描述信息

A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted by an allyl group at position 5. It is found in several plants, including black pepper, cinnamon and nutmeg, and is present in several essential oils, notably that of sassafras. It has insecticidal properties and has been used as a topical antiseptic. Although not thought to pose a significant carcinogenic risk to humans, findings of weak carcinogenicity in rats have resulted in the banning of its (previously widespread) use in perfumes and soaps, and as a food additive.

同义名列表

3 个代谢物同义名

safrole; Safrole; Safrole



数据库引用编号

14 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)

117 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

  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Xin Wang, Guangyun Ran, Yufen Liao, Bowen Gong, Chutian Wu, Rong Tan, Ying Liu, Shiyu Zhang, Ying Peng, Weiwei Li, Jiang Zheng. Formation of RNA adducts resulting from metabolic activation of spice ingredient safrole mediated by P450 enzymes and sulfotransferases. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2023 Feb; ?(?):113688. doi: 10.1016/j.fct.2023.113688. [PMID: 36841326]
  • Yesenia Pacheco-Hernández, Nemesio Villa-Ruano, Ramiro Cruz-Duran, Elvia Becerra-Martínez, Edmundo Lozoya-Gloria. 1 H-NMR Metabolomics Profiling and Volatile Content of 'Hoja Santa' (Piper auritum Kunth): A Millenary Edible Plant Consumed in Mexico. Chemistry & biodiversity. 2022 Dec; 19(12):e202200667. doi: 10.1002/cbdv.202200667. [PMID: 36417317]
  • Katharina Friedrich, Nicole S Wermter, Lars Andernach, Katja Witzel, Franziska S Hanschen. Formation of volatile sulfur compounds and S-methyl-l-cysteine sulfoxide in Brassica oleracea vegetables. Food chemistry. 2022 Jul; 383(?):132544. doi: 10.1016/j.foodchem.2022.132544. [PMID: 35247727]
  • Nina Reis Soares, Caio Túlio Rodrigues Correa, Jhonata Costa da Silva, Jacson Rondinelli da Silva Negreiros, Vânia Helena Techio, Giovana Augusta Torres. Comparative cytogenetics of three economically important Piper L. species from the Brazilian Amazon. Protoplasma. 2022 Jul; 259(4):1099-1108. doi: 10.1007/s00709-021-01721-2. [PMID: 34762169]
  • Ying Nie, Yuan Luo, Shajie Luo, Xiujun Cao, Guoxin Song, Chunhui Deng. Amphiphilic copolymers grafted on monodisperse magnetic microspheres as an efficient adsorbent for the extraction of safrole in the plasma. Journal of chromatography. A. 2022 Jan; 1662(?):462733. doi: 10.1016/j.chroma.2021.462733. [PMID: 34902718]
  • Mohamed Joonus Aynul Fazmiya, Arshiya Sultana, Khaleequr Rahman, Md Belal Bin Heyat, Sumbul, Faijan Akhtar, Salabat Khan, Seth Christopher Yaw Appiah. Current Insights on Bioactive Molecules, Antioxidant, Anti-Inflammatory, and Other Pharmacological Activities of Cinnamomum camphora Linn. Oxidative medicine and cellular longevity. 2022; 2022(?):9354555. doi: 10.1155/2022/9354555. [PMID: 36246399]
  • Maria Suely Siqueira Ferraz, Lêda Rita D'Antonino Faroni, Fernanda Fernandes Heleno, Adalberto Hipólito de Sousa, Lucas Henrique Figueiredo Prates, Alessandra Aparecida Zinato Rodrigues. Method Validation and Evaluation of Safrole Persistence in Cowpea Beans Using Headspace Solid-Phase Microextraction and Gas Chromatography. Molecules (Basel, Switzerland). 2021 Nov; 26(22):. doi: 10.3390/molecules26226914. [PMID: 34834007]
  • Sascha K Manier, Lea Wagmann, Armin A Weber, Markus R Meyer. Abuse of nutmeg seeds: Detectable by means of liquid chromatography-mass spectrometry techniques?. Drug testing and analysis. 2021 Jul; 13(7):1440-1444. doi: 10.1002/dta.3027. [PMID: 33720530]
  • Yuqi Fan, Dongyue Yang, Xuhua Huang, Guangzhe Yao, Wei Wang, Mengyuan Gao, Xiaohua Jia, Huizi Ouyang, Yanxu Chang, Jun He. Pharmacokinetic Study of Safrole and Methyl Eugenol after Oral Administration of the Essential Oil Extracts of Asarum in Rats by GC-MS. BioMed research international. 2021; 2021(?):6699033. doi: 10.1155/2021/6699033. [PMID: 33829063]
  • Xiangqian Ye, Xiaoling Zou, Fafu Tian, Honglin He. Feasibility study on recycled vegetable oil waste and recycled polyethylene for the modification of aged asphalt. PloS one. 2021; 16(1):e0244159. doi: 10.1371/journal.pone.0244159. [PMID: 33400695]
  • 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]
  • Chia-Jung Lee, Chun-Wei Huang, Lih-Geeng Chen, Ching-Chiung Wang. (+)-Erythro-Δ8'-7S,8R-Dihydroxy-3,3',5'-Trimethoxy-8-O-4'-Neolignan, an Anti-Acne Component in Degreasing Myristica fragrans Houtt. Molecules (Basel, Switzerland). 2020 Oct; 25(19):. doi: 10.3390/molecules25194563. [PMID: 33036279]
  • Merja A Neukamm, Hannes M Schwelm, Simon Vieser, Nadine Schiesel, Volker Auwärter. Detection of Nutmeg Abuse by Gas Chromatography-Mass Spectrometric Screening of Urine. Journal of analytical toxicology. 2020 Jan; 44(1):103-108. doi: 10.1093/jat/bkz054. [PMID: 31504590]
  • Linlin Hu, Fei Wu, Jie He, Lingjun Zhong, Yifan Song, Hua Shao. Cytotoxicity of safrole in HepaRG cells: studies on the role of CYP1A2-mediated ortho-quinone metabolic activation. Xenobiotica; the fate of foreign compounds in biological systems. 2019 Dec; 49(12):1504-1515. doi: 10.1080/00498254.2019.1590882. [PMID: 30865484]
  • Li-Jun Yue, Xi-Yu Zhu, Rui-Sha Li, Hui-Jing Chang, Bing Gong, Chong-Chong Tian, Chang Liu, Yun-Xing Xue, Qing Zhou, Tian-Shu Xu, Dong-Jin Wang. S‑allyl‑cysteine sulfoxide (alliin) alleviates myocardial infarction by modulating cardiomyocyte necroptosis and autophagy. International journal of molecular medicine. 2019 Nov; 44(5):1943-1951. doi: 10.3892/ijmm.2019.4351. [PMID: 31573046]
  • Han-Hsing Tsou, Hsiao-Tung Ko, Chia-Tzu Chen, Tse-Wen Wang, Chien-Hung Lee, Tsung-Yun Liu, Hsiang-Tsui Wang. Betel quid containing safrole enhances metabolic activation of tobacco specific 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Environmental pollution (Barking, Essex : 1987). 2019 Aug; 251(?):13-21. doi: 10.1016/j.envpol.2019.04.080. [PMID: 31071628]
  • 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]
  • 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]
  • Kamlesh S Yadav, Pratibha Yadav, Satyawati Sharma, Sunil K Khare. Role of Musa paradisiaca ascorbate peroxidase in the transformation of methyl phenyl sulfide to its sulfoxide. International journal of biological macromolecules. 2019 Feb; 122(?):962-968. doi: 10.1016/j.ijbiomac.2018.11.014. [PMID: 30408454]
  • Toshihide Takeshita, Fumiya Tao, Nobuhiko Kojima, Robert A Kanaly. Triple quadrupole mass spectrometry comparative DNA adductomics of Hep G2 cells following exposure to safrole. Toxicology letters. 2019 Jan; 300(?):92-104. doi: 10.1016/j.toxlet.2018.10.023. [PMID: 30394309]
  • Ai-Hong Yang, Lei Zhang, De-Xian Zhi, Wen-Li Liu, Xue Gao, Xin He. Identification and analysis of the reactive metabolites related to the hepatotoxicity of safrole. Xenobiotica; the fate of foreign compounds in biological systems. 2018 Nov; 48(11):1164-1172. doi: 10.1080/00498254.2017.1399227. [PMID: 29082813]
  • A L Wollenberg, T M O'Shea, J H Kim, A Czechanski, L G Reinholdt, M V Sofroniew, T J Deming. Injectable polypeptide hydrogels via methionine modification for neural stem cell delivery. Biomaterials. 2018 09; 178(?):527-545. doi: 10.1016/j.biomaterials.2018.03.057. [PMID: 29657091]
  • Chun-Shun Li, Ariel M Sarotti, Peng Huang, Uyen T Dang, Julian G Hurdle, Tamara P Kondratyuk, John M Pezzuto, James Turkson, Shugeng Cao. NF-κB inhibitors, unique γ-pyranol-γ-lactams with sulfide and sulfoxide moieties from Hawaiian plant Lycopodiella cernua derived fungus Paraphaeosphaeria neglecta FT462. Scientific reports. 2017 09; 7(1):10424. doi: 10.1038/s41598-017-10537-1. [PMID: 28874704]
  • Katsunori Anezaki, Ayaka Matsuda, Takashi Matsuishi. Concentration and congener pattern of polychlorinated biphenyls in blubber and liver of Hubbs' beaked whale (Mesoplodon carlhubbsi), using a sulfoxide and an Ag-ION solid phase extraction cartridge as a simplified cleanup technique for biological samples. Marine pollution bulletin. 2016 Dec; 113(1-2):282-286. doi: 10.1016/j.marpolbul.2016.09.051. [PMID: 27707471]
  • Morina Adfa, Rizki Rahmad, Masayuki Ninomiya, Salprima Yudha S, Kaori Tanaka, Mamoru Koketsu. Antileukemic activity of lignans and phenylpropanoids of Cinnamomum parthenoxylon. Bioorganic & medicinal chemistry letters. 2016 Feb; 26(3):761-764. doi: 10.1016/j.bmcl.2015.12.096. [PMID: 26774581]
  • Jee Hwan Yi, Haribalan Perumalsamy, Karuppasamy Sankarapandian, Byeoung-Ryeol Choi, Young-Joon Ahn. Fumigant Toxicity of Phenylpropanoids Identified in Asarum sieboldii Aerial Parts to Lycoriella ingenua (Diptera: Sciaridae) and Coboldia fuscipes (Diptera: Scatopsidae). Journal of economic entomology. 2015 Jun; 108(3):1208-14. doi: 10.1093/jee/tov064. [PMID: 26470247]
  • 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]
  • Xin Chao Liu, Zhi Long Liu. Analysis of the essential oil of Illicium henryi Diels root bark and its insecticidal activity against Liposcelis bostrychophila Badonnel. Journal of food protection. 2015 Apr; 78(4):772-7. doi: 10.4315/0362-028x.jfp-14-407. [PMID: 25836404]
  • Ann M Bode, Zigang Dong. Toxic phytochemicals and their potential risks for human cancer. Cancer prevention research (Philadelphia, Pa.). 2015 Jan; 8(1):1-8. doi: 10.1158/1940-6207.capr-14-0160. [PMID: 25348854]
  • Nicholas John Sadgrove, Graham Lloyd Jones. Cytogeography of essential oil chemotypes of Eremophila longifolia F. Muell (Scrophulariaceae). Phytochemistry. 2014 Sep; 105(?):43-51. doi: 10.1016/j.phytochem.2014.05.005. [PMID: 24874947]
  • Ewelina Krol, Gabriela Pastuch-Gawolek, Dawid Nidzworski, Michal Rychlowski, Wieslaw Szeja, Grzegorz Grynkiewicz, Boguslaw Szewczyk. Synthesis and antiviral activity of a novel glycosyl sulfoxide against classical swine fever virus. Bioorganic & medicinal chemistry. 2014 May; 22(9):2662-70. doi: 10.1016/j.bmc.2014.03.027. [PMID: 24721828]
  • Xu Song, Zhongqiong Yin, Kuichuan Ye, Qin Wei, Renrong Jia, Lijun Zhou, Yonghua Du, Jiao Xu, Xiaoxia Liang, Changliang He, Gang Shu, Lizi Yin, Cheng Lv. Anti-hepatoma effect of safrole from Cinnamomum longepaniculatum leaf essential oil in vitro. International journal of clinical and experimental pathology. 2014; 7(5):2265-72. doi: . [PMID: 24966935]
  • Megumi Iwasa, Toshiki Iwasaki, Toshirou Ono, Mitsuo Miyazawa. Chemical composition and major odor-active compounds of essential oil from PINELLIA TUBER (dried rhizome of Pinellia ternata) as crude drug. Journal of oleo science. 2014; 63(2):127-35. doi: 10.5650/jos.ess13092. [PMID: 24500103]
  • Maria Lucia Leporatti, Giorgio Pintore, Marzia Foddai, Mario Chessa, Andrea Piana, Giacomo Luigi Petretto, Maria Dolores Masia, Giuseppe Mangano, Marcello Nicoletti. Chemical, biological, morphoanatomical and antimicrobial study of Ocotea puchury-major Mart. Natural product research. 2014; 28(5):294-300. doi: 10.1080/14786419.2013.858338. [PMID: 24274027]
  • M Schäffer, T Gröger, M Pütz, R Zimmermann. Forensic profiling of sassafras oils based on comprehensive two-dimensional gas chromatography. Forensic science international. 2013 Jun; 229(1-3):108-15. doi: 10.1016/j.forsciint.2013.03.046. [PMID: 23683915]
  • Le Su, Haiyan Zhang, Jing Zhao, Shangli Zhang, Yun Zhang, Baoxiang Zhao, Junying Miao. Safrole-2',3'-oxide induces atherosclerotic plaque vulnerability in apolipoprotein E-knockout mice. Toxicology letters. 2013 Feb; 217(2):129-36. doi: 10.1016/j.toxlet.2012.12.011. [PMID: 23270965]
  • Ramon Lavado, Rosaura Aparicio-Fabre, Daniel Schlenk. Effects of salinity acclimation on the pesticide-metabolizing enzyme flavin-containing monooxygenase (FMO) in rainbow trout (Oncorhynchus mykiss). Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2013 Jan; 157(1):9-15. doi: 10.1016/j.cbpc.2012.08.004. [PMID: 22981832]
  • Mario Thevis, Ines Möller, Simon Beuck, Wilhelm Schänzer. Synthesis, mass spectrometric characterization, and analysis of the PPARδ agonist GW1516 and its major human metabolites: targets in sports drug testing. Methods in molecular biology (Clifton, N.J.). 2013; 952(?):301-12. doi: 10.1007/978-1-62703-155-4_22. [PMID: 23100242]
  • Li-Ching Shen, Su-Yin Chiang, Ming-Huan Lin, Wen-Sheng Chung, Kuen-Yuh Wu. In vivo formation of N7-guanine DNA adduct by safrole 2',3'-oxide in mice. Toxicology letters. 2012 Sep; 213(3):309-15. doi: 10.1016/j.toxlet.2012.07.006. [PMID: 22820429]
  • Erryana Martati, Marelle G Boersma, Albertus Spenkelink, Dambar B Khadka, Peter J van Bladeren, Ivonne M C M Rietjens, Ans Punt. Physiologically based biokinetic (PBBK) modeling of safrole bioactivation and detoxification in humans as compared with rats. Toxicological sciences : an official journal of the Society of Toxicology. 2012 Aug; 128(2):301-16. doi: 10.1093/toxsci/kfs174. [PMID: 22588462]
  • Danielle S Fisher, Simon A Handley, Robert J Flanagan, David M Taylor. Plasma concentrations of quetiapine, N-desalkylquetiapine, o-desalkylquetiapine, 7-hydroxyquetiapine, and quetiapine sulfoxide in relation to quetiapine dose, formulation, and other factors. Therapeutic drug monitoring. 2012 Aug; 34(4):415-21. doi: 10.1097/ftd.0b013e3182603f62. [PMID: 22777152]
  • Fan Tong, Joel R Coats. Quantitative structure-activity relationships of monoterpenoid binding activities to the housefly GABA receptor. Pest management science. 2012 Aug; 68(8):1122-9. doi: 10.1002/ps.3280. [PMID: 22461383]
  • Alessandra Piras, Antonella Rosa, Bruno Marongiu, Angela Atzeri, M Assunta Dessì, Danilo Falconieri, Silvia Porcedda. Extraction and separation of volatile and fixed oils from seeds of Myristica fragrans by supercritical CO₂: chemical composition and cytotoxic activity on Caco-2 cancer cells. Journal of food science. 2012 Apr; 77(4):C448-53. doi: 10.1111/j.1750-3841.2012.02618.x. [PMID: 22429024]
  • Ana Paula C Rodrigues, Luciana M M Costa, Bruna L R Santos, Rodolfo C Maia, Ana L P Miranda, Eliezer J Barreiro, Carlos A M Fraga. Novel furfurylidene N-acylhydrazones derived from natural safrole: discovery of LASSBio-1215, a new potent antiplatelet prototype. Journal of enzyme inhibition and medicinal chemistry. 2012 Feb; 27(1):101-9. doi: 10.3109/14756366.2011.578575. [PMID: 21612374]
  • Su-ying Hu, Gang He, Bei Chen, Lang-jun Cui, Jian-xiong Yang. [Genetic diversity and volatile components of Asarum sieboldii in Qin-ba region]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2012 Feb; 35(2):188-94. doi: ". [PMID: 22822661]
  • Michael Murray. Toxicological actions of plant-derived and anthropogenic methylenedioxyphenyl-substituted chemicals in mammals and insects. Journal of toxicology and environmental health. Part B, Critical reviews. 2012; 15(6):365-95. doi: 10.1080/10937404.2012.705105. [PMID: 22934566]
  • 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]
  • Morten Hyldgaard, Tina Mygind, Rikke Louise Meyer. Essential oils in food preservation: mode of action, synergies, and interactions with food matrix components. Frontiers in microbiology. 2012; 3(?):12. doi: 10.3389/fmicb.2012.00012. [PMID: 22291693]
  • Carolina Santiago, Chris Fitchett, Murray H G Munro, Juriyati Jalil, Jacinta Santhanam. Cytotoxic and Antifungal Activities of 5-Hydroxyramulosin, a Compound Produced by an Endophytic Fungus Isolated from Cinnamomum mollisimum. Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):689310. doi: 10.1155/2012/689310. [PMID: 22454674]
  • M Jin, A Kijima, Y Suzuki, D Hibi, T Inoue, Y Ishii, T Nohmi, A Nishikawa, K Ogawa, T Umemura. Comprehensive toxicity study of safrole using a medium-term animal model with gpt delta rats. Toxicology. 2011 Dec; 290(2-3):312-21. doi: 10.1016/j.tox.2011.09.088. [PMID: 22024337]
  • Roberto Parise-Filho, Michelli Pastrello, Carla Emygdio Pereira Camerlingo, Gisele Juni Silva, Leonardo Aguiar Agostinho, Thaís de Souza, Fátima Maria Motter Magri, Roberto Rodrigues Ribeiro, Carlos Alberto Brandt, Michelle Carneiro Polli. The anti-inflammatory activity of dillapiole and some semisynthetic analogues. Pharmaceutical biology. 2011 Nov; 49(11):1173-9. doi: 10.3109/13880209.2011.575793. [PMID: 22014265]
  • Abhijeet Y Deshpande, Sandip Gurav, Ravindra Punde, Vishal Zambre, Rahul Kulkarni, Sarvesh Pandey, Ashish Mungantiwar, Ramesh Mullangi. Development and validation of a highly sensitive LC-MS/MS method for simultaneous quantitation of ethionamide and ethionamide sulfoxide in human plasma: application to a human pharmacokinetic study. Biomedical chromatography : BMC. 2011 Sep; 25(9):985-94. doi: 10.1002/bmc.1554. [PMID: 21268048]
  • Stephan G Walch, Thomas Kuballa, Wolf Stühlinger, Dirk W Lachenmeier. Determination of the biologically active flavour substances thujone and camphor in foods and medicines containing sage (Salvia officinalis L.). Chemistry Central journal. 2011 Jul; 5(?):44. doi: 10.1186/1752-153x-5-44. [PMID: 21777420]
  • L S R Arambewela, L D A M Arawwawala, K G Kumaratunga, D S Dissanayake, W D Ratnasooriya, S P Kumarasingha. Investigations on Piper betle grown in Sri Lanka. Pharmacognosy reviews. 2011 Jul; 5(10):159-63. doi: 10.4103/0973-7847.91111. [PMID: 22279373]
  • 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]
  • Seyed Mehdi Razavi, Hossein Nazemiyeh, Abbas Delazar, Solmaz Asnaashari, Rogaieh Hajiboland, Satyajit D Sarker, Yadollah Omidi. Chemical variation of the essential oil of Prangos uloptera DC. at different stages of growth. Natural product research. 2011 Apr; 25(7):663-8. doi: 10.1080/14786410802270811. [PMID: 19606386]
  • Birgit Waltenberger, Daniela Schuster, Sompol Paramapojn, Wandee Gritsanapan, Gerhard Wolber, Judith M Rollinger, Hermann Stuppner. Predicting cyclooxygenase inhibition by three-dimensional pharmacophoric profiling. Part II: Identification of enzyme inhibitors from Prasaplai, a Thai traditional medicine. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2011 Jan; 18(2-3):119-33. doi: 10.1016/j.phymed.2010.08.002. [PMID: 20851587]
  • Sha Sha Chu, Cheng Fang Wang, Shu Shan Du, Shao Liang Liu, Zhi Long Liu. Toxicity of the essential oil of Illicium difengpi stem bark and its constituent compounds towards two grain storage insects. Journal of insect science (Online). 2011; 11(?):152. doi: 10.1673/031.011.15201. [PMID: 22236213]
  • Wan Mohd Nuzul Hakimi Wan Salleh, Farediah Ahmad, Khong Heng Yen, Hasnah Mohd Sirat. Chemical compositions, antioxidant and antimicrobial activities of essential oils of Piper caninum Blume. International journal of molecular sciences. 2011; 12(11):7720-31. doi: 10.3390/ijms12117720. [PMID: 22174627]
  • Nelson Zapata, Georges Lognay, Guy Smagghe. Bioactivity of essential oils from leaves and bark of Laurelia sempervirens and Drimys winteri against Acyrthosiphon pisum. Pest management science. 2010 Dec; 66(12):1324-31. doi: 10.1002/ps.2018. [PMID: 20715015]
  • Muchtaridi, Anas Subarnas, Anton Apriyantono, Resmi Mustarichie. Identification of compounds in the essential oil of nutmeg seeds (Myristica fragrans Houtt.) that inhibit locomotor activity in mice. International journal of molecular sciences. 2010 Nov; 11(11):4771-81. doi: 10.3390/ijms11114771. [PMID: 21151471]
  • A Arpanaei, B Winther-Jensen, E Theodosiou, P Kingshott, T J Hobley, O R T Thomas. Surface modification of chromatography adsorbents by low temperature low pressure plasma. Journal of chromatography. A. 2010 Oct; 1217(44):6905-16. doi: 10.1016/j.chroma.2010.08.069. [PMID: 20869062]
  • E Nibret, M Wink. Trypanocidal and antileukaemic effects of the essential oils of Hagenia abyssinica, Leonotis ocymifolia, Moringa stenopetala, and their main individual constituents. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2010 Oct; 17(12):911-20. doi: 10.1016/j.phymed.2010.02.009. [PMID: 20359874]
  • . 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]
  • Joshua Smith, David Tucker, Daniel Alter, Kenneth Watson, Graham Jones. Intraspecific variation in essential oil composition of Eremophila longifolia F. Muell. (Myoporaceae): evidence for three chemotypes. Phytochemistry. 2010 Sep; 71(13):1521-7. doi: 10.1016/j.phytochem.2010.06.006. [PMID: 20605032]
  • Masayuki Inoue, Naoki Shinohara, Shintaro Tanabe, Tomoaki Takahashi, Ken Okura, Hiroaki Itoh, Yuki Mizoguchi, Maiko Iida, Nayoung Lee, Shigeru Matsuoka. Total synthesis of the large non-ribosomal peptide polytheonamide B. Nature chemistry. 2010 Apr; 2(4):280-5. doi: 10.1038/nchem.554. [PMID: 21124508]
  • Lianet Monzote, Marley García, Ana Margarita Montalvo, Ramón Scull, Migdalia Miranda. Chemistry, cytotoxicity and antileishmanial activity of the essential oil from Piper auritum. Memorias do Instituto Oswaldo Cruz. 2010 Mar; 105(2):168-73. doi: 10.1590/s0074-02762010000200010. [PMID: 20428676]
  • Haribalan Perumalsamy, Nam-Jin Kim, Young-Joon Ahn. Larvicidal activity of compounds isolated from Asarum heterotropoides against Culex pipiens pallens, Aedes aegypti, and Ochlerotatus togoi (Diptera: Culicidae). Journal of medical entomology. 2009 Nov; 46(6):1420-3. doi: 10.1603/033.046.0624. [PMID: 19960690]
  • 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]
  • Jofre Carnicer, Pedro Jordano, Carlos J Melián. The temporal dynamics of resource use by frugivorous birds: a network approach. Ecology. 2009 Jul; 90(7):1958-70. doi: 10.1890/07-1939.1. [PMID: 19694143]
  • Yoshio Nakagawa, Toshinari Suzuki, Kazuo Nakajima, Hidemi Ishii, Akio Ogata. Biotransformation and cytotoxic effects of hydroxychavicol, an intermediate of safrole metabolism, in isolated rat hepatocytes. Chemico-biological interactions. 2009 Jun; 180(1):89-97. doi: 10.1016/j.cbi.2009.02.003. [PMID: 19428348]
  • Chu Chen, Daniela Spriano, Thomas Lehmann, Beat Meier. Reduction of safrole and methyleugenol in Asari radix et rhizoma by decoction. Forschende Komplementarmedizin (2006). 2009 Jun; 16(3):162-6. doi: 10.1159/000213895. [PMID: 19657200]
  • Su-Ui Lee, Ki Shuk Shim, Shi Yong Ryu, Yong Ki Min, Seong Hwan Kim. Machilin A isolated from Myristica fragrans stimulates osteoblast differentiation. Planta medica. 2009 Feb; 75(2):152-7. doi: 10.1055/s-0028-1112197. [PMID: 19096999]
  • Marcelo Maraschin, Paulo Fernando Dias, Enio Luiz Pedrotti, Hiliana Nunes, Hiliana Nunes Ferreira Morais, Ana Maria Viana, Karl Vernon Wood. Metabolomic analysis of Ocotea odorifera cell cultures: a model protocol for acquiring metabolite data. Methods in molecular biology (Clifton, N.J.). 2009; 547(?):347-58. doi: 10.1007/978-1-60327-287-2_28. [PMID: 19521858]
  • T Galeano Díaz, A Guiberteau Cabanillas, M D López Soto, J M Ortiz. Determination of fenthion and fenthion-sulfoxide, in olive oil and in river water, by square-wave adsorptive-stripping voltammetry. Talanta. 2008 Aug; 76(4):809-14. doi: 10.1016/j.talanta.2008.04.037. [PMID: 18656663]
  • Ruey-Hong Wong, Chiung-Wen Hu, Ching-Ying Yeh, Mu-Rong Chao, Chin-Chun Chen, Jun-Huang Huang, Shih-Hsien Chang, Shin-I Lee, Hong-Shen Lee. Sulfotransferase 1A1 and glutathione S-transferase P1 genetic polymorphisms modulate the levels of urinary 8-hydroxy-2'-deoxyguanosine in betel quid chewers. Archives of toxicology. 2008 May; 82(5):313-21. doi: 10.1007/s00204-007-0248-8. [PMID: 17912498]
  • Ah-Reum Han, Hye Jeoung Kim, Minkyu Shin, Moochang Hong, Yang Seok Kim, Hyunsu Bae. Constituents of Asarum sieboldii with inhibitory activity on lipopolysaccharide (LPS)-induced NO production in BV-2 microglial cells. Chemistry & biodiversity. 2008 Feb; 5(2):346-51. doi: 10.1002/cbdv.200890033. [PMID: 18293448]
  • Eloisa Helena A Andrade, Léa Maria M Carreira, Milton Helio L da Silva, João Domingos da Silva, Cleber N Bastos, Pergentino José C Sousa, Elsie F Guimarães, José Guilherme S Maia. Variability in essential-oil composition of Piper marginatum sensu lato. Chemistry & biodiversity. 2008 Jan; 5(1):197-208. doi: 10.1002/cbdv.200890011. [PMID: 18205123]
  • Mu-qing Liu, De-cheng Zhou, Xin-yuan Xu, Yao-jie Sun, Xiao-li Zhou, Lei Han. [Clustering analysis applied to near-infrared spectroscopy analysis of Chinese traditional medicine]. Guang pu xue yu guang pu fen xi = Guang pu. 2007 Oct; 27(10):1985-8. doi: ". [PMID: 18306778]
  • Lan Fan, Guo Wang, Lian-Sheng Wang, Yao Chen, Wei Zhang, Yuan-Fei Huang, Rui-Xue Huang, Dong-Li Hu, Dan Wang, Hong-Hao Zhou. Herbal medicine yin zhi huang induces CYP3A4-mediated sulfoxidation and CYP2C19-dependent hydroxylation of omeprazole. Acta pharmacologica Sinica. 2007 Oct; 28(10):1685-92. doi: 10.1111/j.1745-7254.2007.00617.x. [PMID: 17883958]
  • Shu-Feng Zhou, Charlie Changli Xue, Xue-Qing Yu, Guangji Wang. Metabolic activation of herbal and dietary constituents and its clinical and toxicological implications: an update. Current drug metabolism. 2007 Aug; 8(6):526-53. doi: 10.2174/138920007781368863. [PMID: 17691916]
  • Xin Hang, Xiu-wei Yang. [GC-MS analysis of essential oil from nutmeg processed by different traditional methods]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Aug; 32(16):1669-75. doi: . [PMID: 18027665]
  • Woo-Chul Jung, Young-Su Jang, Tran Trung Hieu, Chong-Kyu Lee, Young-Joon Ahn. Toxicity of Myristica fagrans seed compounds against Blattella germanica (Dictyoptera: Blattellidae). Journal of medical entomology. 2007 May; 44(3):524-9. doi: 10.1603/0022-2585(2007)44[524:tomfsc]2.0.co;2. [PMID: 17547241]
  • Zhixiu Lin, Yonghong Liao, Radhakrishnan Venkatasamy, Robert C Hider, Amala Soumyanath. Amides from Piper nigrum L. with dissimilar effects on melanocyte proliferation in-vitro. The Journal of pharmacy and pharmacology. 2007 Apr; 59(4):529-36. doi: 10.1211/jpp.59.4.0007. [PMID: 17430636]
  • Wei-Chuan Chen, He-Hsiung Cheng, Chun-Jen Huang, Yih-Chau Lu, I-Shu Chen, Shiuh-Inn Liu, Shu-Shong Hsu, Hong-Tai Chang, Jong-Khing Huang, Jin-Shyr Chen, Chung-Ren Jan. The carcinogen safrole increases intracellular free Ca2+ levels and causes death in MDCK cells. The Chinese journal of physiology. 2007 Feb; 50(1):34-40. doi: . [PMID: 17593801]
  • Jochen Beyer, Dorothea Ehlers, Hans H Maurer. Abuse of nutmeg (Myristica fragrans Houtt.): studies on the metabolism and the toxicologic detection of its ingredients elemicin, myristicin, and safrole in rat and human urine using gas chromatography/mass spectrometry. Therapeutic drug monitoring. 2006 Aug; 28(4):568-75. doi: 10.1097/00007691-200608000-00013. [PMID: 16885726]
  • Claudio F Sturino, Nicolas Lachance, Michael Boyd, Carl Berthelette, Marc Labelle, Lianhai Li, Bruno Roy, John Scheigetz, Nancy Tsou, Christine Brideau, Elizabeth Cauchon, Marie-Claude Carriere, Danielle Denis, Gillian Greig, Stacia Kargman, Sonia Lamontagne, Marie-Claude Mathieu, Nicole Sawyer, Deborah Slipetz, Gary O'Neill, Zhaoyin Wang, Robert Zamboni, Kathleen M Metters, Robert N Young. Identification of an indole series of prostaglandin D2 receptor antagonists. Bioorganic & medicinal chemistry letters. 2006 Jun; 16(11):3043-8. doi: 10.1016/j.bmcl.2006.02.062. [PMID: 16529930]
  • Zi-min Yuan, Jing Wang, Jial Lv, Tian-zhu Jia. [Comparing analysis of components in volatile oils of nutmeg and prepared nutmeg by GC-MS]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 May; 31(9):737-9. doi: ". [PMID: 17048680]
  • Jing Zhao, Junying Miao, Baoxiang Zhao, Shangli Zhang, Deling Yin. Suppressing Akt phosphorylation and activating Fas by safrole oxide inhibited angiogenesis and induced vascular endothelial cell apoptosis in the presence of fibroblast growth factor-2 and serum. The international journal of biochemistry & cell biology. 2006; 38(9):1603-13. doi: 10.1016/j.biocel.2006.03.018. [PMID: 16702019]
  • Hugh A Barton, V James Cogliano, Lynn Flowers, Larry Valcovic, R Woodrow Setzer, Tracey J Woodruff. Assessing susceptibility from early-life exposure to carcinogens. Environmental health perspectives. 2005 Sep; 113(9):1125-33. doi: 10.1289/ehp.7667. [PMID: 16140616]
  • Tajuddin, Shamshad Ahmad, Abdul Latif, Iqbal Ahmad Qasmi, Kunwar Mohammad Yusuf Amin. An experimental study of sexual function improving effect of Myristica fragrans Houtt. (nutmeg). BMC complementary and alternative medicine. 2005 Jul; 5(?):16. doi: 10.1186/1472-6882-5-16. [PMID: 16033651]
  • Sebastien Dugravot, Nathalie Mondy, Nicole Mandon, Eric Thibout. Increased sulfur precursors and volatiles production by the leek Allium porrum in response to specialist insect attack. Journal of chemical ecology. 2005 Jun; 31(6):1299-314. doi: 10.1007/s10886-005-5287-0. [PMID: 16222772]
  • Rachel Mata, Iliana Morales, Olga Pérez, Isabel Rivero-Cruz, Laura Acevedo, Isolda Enriquez-Mendoza, Robert Bye, Scott Franzblau, Barbara Timmermann. Antimycobacterial compounds from Piper sanctum. Journal of natural products. 2004 Dec; 67(12):1961-8. doi: 10.1021/np0401260. [PMID: 15620234]
  • A Simić, M D Soković, M Ristić, S Grujić-Jovanović, J Vukojević, P D Marin. The chemical composition of some Lauraceae essential oils and their antifungal activities. Phytotherapy research : PTR. 2004 Sep; 18(9):713-7. doi: 10.1002/ptr.1516. [PMID: 15478207]
  • Yune-Fang Ueng, Chih-Hang Hsieh, Ming-Jaw Don, Chin-Wen Chi, Li-Kang Ho. Identification of the main human cytochrome P450 enzymes involved in safrole 1'-hydroxylation. Chemical research in toxicology. 2004 Aug; 17(8):1151-6. doi: 10.1021/tx030055p. [PMID: 15310247]
  • Arnold Schecter, George W Lucier, Michael L Cunningham, Kamal M Abdo, Greg Blumenthal, Andrew G Silver, Ron Melnick, Christopher Portier, Dana B Barr, John R Barr, Stephen B Stanfill, Donald G Patterson, Larry L Needham, Woodhall Stopford, Scott Masten, Jill Mignogna, Kuang Chi Tung. Human consumption of methyleugenol and its elimination from serum. Environmental health perspectives. 2004 May; 112(6):678-80. doi: 10.1289/ehp.6766. [PMID: 15121510]
  • Bao-Xiang Zhao, Ai-Ying Du, Jun-Ying Miao, Ke-Wen Zhao, Chun-Qing Du. Effects of novel safrole oxide derivatives, 1-methoxy-3-(3,4-methylenedioxyphenyl)-2-propanol and 1-ethoxy-3-(3,4-methylenedioxyphenyl)-2-propanol, on apoptosis induced by deprivation of survival factors in vascular endothelial cells. Vascular pharmacology. 2003 Oct; 40(3):183-7. doi: 10.1016/s1537-1891(03)00050-8. [PMID: 13678651]
  • Shan-Ling Hung, Yu-Ling Chen, Yen-Ting Chen. Effects of safrole on the defensive functions of human neutrophils. Journal of periodontal research. 2003 Apr; 38(2):130-4. doi: 10.1034/j.1600-0765.2003.01652.x. [PMID: 12608906]