Hydroxychavicol (BioDeep_00000229766)

   

PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


4-Allylcatechol; 2-Hydroxychavicol pound>>Hydroxychavicol

化学式: C9H10O2 (150.06807600000002)
中文名称: 4-烯丙基邻苯二酚, 4-烯丙基儿茶酚, 4-烯丙基-1,2-苯二醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C=CCC1=CC(=C(C=C1)O)O
InChI: InChI=1S/C9H10O2/c1-2-3-7-4-5-8(10)9(11)6-7/h2,4-6,10-11H,1,3H2

描述信息

4-Allylpyrocatechol is a natural product found in Dracaena draco, Piper retrofractum, and other organisms with data available.
4-Allylcatechol (4-Allylpyrocatechol, Hydroxychavicol) is an intermediate to synthetic safrole.
4-Allylcatechol (4-Allylpyrocatechol, Hydroxychavicol) is an intermediate to synthetic safrole.

同义名列表

25 个代谢物同义名

4-Allylcatechol; 2-Hydroxychavicol pound>>Hydroxychavicol; 4-Allylpyrocatechol, analytical standard; Hydroxychavicol; 4-Allylpyrocatechol; 4-(prop-2-en-1-yl)benzene-1,2-diol; 1,2-Benzenediol, 4-(2-propenyl)-; HydroxychavicolHydroxychavicol; 4-(2-propenyl)-1,2-benzenediol; 4-prop-2-enylbenzene-1,2-diol; 1,2-Dihydroxy-4-allylbenzene; 4-Allyl-1,2-dihydroxybenzene; 3,4-dihydroxy-allylbenzene; 4-Allylbenzene-1,2-diol; 4-Allyl-1,2-benzenediol; 4-allylbenzene-1,2-d; HYDROXYCHAVICOL, 2-; Desmethylisoeugenol; 4-Allylpyrocatechol; 2-hydroxychavicol; Hydroxy chavicol; hydroxychavicol; 4-allylcatechol; UNII-FG58C4J9BR; P-ALLYLCATECHOL; FG58C4J9BR; Hydroxychavicol



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

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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)

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

  • Hirotaka Matsuo, Hitomi Kawakami, Naoko Anjiki, Noriaki Kawano, Hiroyuki Fuchino, Nobuo Kawahara, Kayo Yoshimatsu. Screening of growth inhibitors for epithelial-mesenchymal transition-induced cells by TGF-β from plant-based sources identified the active compound hydroxychavicol from Piper bitle. Journal of natural medicines. 2024 Jun; 78(3):774-783. doi: 10.1007/s11418-024-01785-3. [PMID: 38418720]
  • Akhtar Atiya, Taghreed A Majrashi, M Yasmin Begum, Uma R Lal, Barij N Sinha, Shaik Fayazuddin Abdul Qadira. A phenylpropanoid dimer from the leaves of Piper betle. Natural product research. 2023 May; 37(9):1550-1556. doi: 10.1080/14786419.2022.2025594. [PMID: 35232302]
  • Vinusri Sekar, Gnanam Ramasamy, Caroline Ravikumar. In silico Molecular Docking for assessing Anti-fungal Competency of Hydroxychavicol, a Phenolic Compound of Betel Leaf (Piper betle L.) against COVID-19 Associated Maiming Mycotic Infections. Drug development and industrial pharmacy. 2022 Mar; ?(?):1-43. doi: 10.1080/03639045.2022.2048665. [PMID: 35311433]
  • S Vinusri, R Gnanam, R Caroline, V P Santhanakrishnan, A Kandavelmani. Anticancer Potential of Hydroxychavicol Derived from Piper betle L: An in Silico and Cytotoxicity Study. Nutrition and cancer. 2022; 74(10):3701-3713. doi: 10.1080/01635581.2022.2085310. [PMID: 35703834]
  • Rutusmita Mishra, Neeladrisingha Das, Ritu Varshney, Kriti Juneja, Debabrata Sircar, Partha Roy. Betel leaf extract and its major component hydroxychavicol promote osteogenesis and alleviate glucocorticoid-induced osteoporosis in rats. Food & function. 2021 Jul; 12(14):6603-6625. doi: 10.1039/d0fo02619k. [PMID: 34105538]
  • Aiysvariyah Rajedadram, Kar Yong Pin, Sui Kiong Ling, See Wan Yan, Mee Lee Looi. Hydroxychavicol, a polyphenol from Piper betle leaf extract, induces cell cycle arrest and apoptosis in TP53-resistant HT-29 colon cancer cells. Journal of Zhejiang University. Science. B. 2021 Feb; 22(2):112-122. doi: 10.1631/jzus.b2000446. [PMID: 33615752]
  • Thae Thae San, Yue-Hu Wang, Dong-Bao Hu, Jun Yang, Dong-Dong Zhang, Meng-Yuan Xia, Xue-Fei Yang, Yong-Ping Yang. A new sesquineolignan and four new neolignans isolated from the leaves of Piper betle, a traditional medicinal plant in Myanmar. Bioorganic & medicinal chemistry letters. 2021 01; 31(?):127682. doi: 10.1016/j.bmcl.2020.127682. [PMID: 33207281]
  • Vedagiri Hemamalini, Dass Prakash M Velayutham, Loganathan Lakshmanan, Karthikeyan Muthusamy, Sivaperumal Sivaramakrishnan, Kumpati Premkumar. Inhibitory potential of Hydroxychavicol on Ehrlich ascites carcinoma model and in silico interaction on cancer targets. Natural product research. 2020 Jun; 34(11):1591-1596. doi: 10.1080/14786419.2018.1519819. [PMID: 30470141]
  • Akhtar Atiya, Barij Nayan Sinha, Uma Ranjan Lal. The new ether derivative of phenylpropanoid and bioactivity was investigated from the leaves of Piper betle L. Natural product research. 2020 Mar; 34(5):638-645. doi: 10.1080/14786419.2018.1495634. [PMID: 30169967]
  • Mei-Chi Chang, Yu-Hwa Pan, Hsyueh-Liang Wu, Yi-Jie Lu, Wan-Chuen Liao, Chien-Yang Yeh, Jang-Jaer Lee, Jiiang-Huei Jeng. Stimulation of MMP-9 of oral epithelial cells by areca nut extract is related to TGF-β/Smad2-dependent and -independent pathways and prevented by betel leaf extract, hydroxychavicol and melatonin. Aging. 2019 12; 11(23):11624-11639. doi: 10.18632/aging.102565. [PMID: 31831717]
  • Ananda Guha Majumdar, Mahesh Subramanian. Hydroxychavicol from Piper betle induces apoptosis, cell cycle arrest, and inhibits epithelial-mesenchymal transition in pancreatic cancer cells. Biochemical pharmacology. 2019 08; 166(?):274-291. doi: 10.1016/j.bcp.2019.05.025. [PMID: 31154000]
  • Keiji Nishiwaki, Kanae Ohigashi, Takahiro Deguchi, Kazuya Murata, Shinya Nakamura, Hideaki Matsuda, Isao Nakanishi. Structure-Activity Relationships and Docking Studies of Hydroxychavicol and Its Analogs as Xanthine Oxidase Inhibitors. Chemical & pharmaceutical bulletin. 2018 Jul; 66(7):741-747. doi: 10.1248/cpb.c18-00197. [PMID: 29695658]
  • Deepti Singh, Shwetha Narayanamoorthy, Sunita Gamre, Ananda Guha Majumdar, Manish Goswami, Umesh Gami, Susan Cherian, Mahesh Subramanian. Hydroxychavicol, a key ingredient of Piper betle induces bacterial cell death by DNA damage and inhibition of cell division. Free radical biology & medicine. 2018 05; 120(?):62-71. doi: 10.1016/j.freeradbiomed.2018.03.021. [PMID: 29550331]
  • A Syahidah, C R Saad, M D Hassan, Y Rukayadi, M H Norazian, M S Kamarudin. Phytochemical Analysis, Identification and Quantification of Antibacterial Active Compounds in Betel Leaves, Piper betle Methanolic Extract. Pakistan journal of biological sciences : PJBS. 2017; 20(2):70-81. doi: 10.3923/pjbs.2017.70.81. [PMID: 29022997]
  • Sushma Reddy Gundala, Chunhua Yang, Rao Mukkavilli, Rutugandha Paranjpe, Meera Brahmbhatt, Vaishali Pannu, Alice Cheng, Michelle D Reid, Ritu Aneja. Hydroxychavicol, a betel leaf component, inhibits prostate cancer through ROS-driven DNA damage and apoptosis. Toxicology and applied pharmacology. 2014 Oct; 280(1):86-96. doi: 10.1016/j.taap.2014.07.012. [PMID: 25064160]
  • Bui Thi Thuy Luyen, Bui Huu Tai, Nguyen Phuong Thao, Seo Young Yang, Nguyen Manh Cuong, Young In Kwon, Hae Dong Jang, Young Ho Kim. A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity. Bioorganic & medicinal chemistry letters. 2014 Sep; 24(17):4120-4. doi: 10.1016/j.bmcl.2014.07.057. [PMID: 25127165]
  • Mohd-Al-Faisal Nordin, Wan Himratul-Aznita Wan Harun, Fathilah Abdul Razak, Md Yusoff Musa. Growth inhibitory response and ultrastructural modification of oral-associated candidal reference strains (ATCC) by Piper betle L. extract. International journal of oral science. 2014 Mar; 6(1):15-21. doi: 10.1038/ijos.2013.97. [PMID: 24406634]
  • Rutugandha Paranjpe, Sushma R Gundala, N Lakshminarayana, Arpana Sagwal, Ghazia Asif, Anjali Pandey, Ritu Aneja. Piper betel leaf extract: anticancer benefits and bio-guided fractionation to identify active principles for prostate cancer management. Carcinogenesis. 2013 Jul; 34(7):1558-66. doi: 10.1093/carcin/bgt066. [PMID: 23430955]
  • Chwan-Fwu Lin, Tsong-Long Hwang, Chun-Chien Chien, Huei-Yu Tu, Horng-Liang Lay. A new hydroxychavicol dimer from the roots of Piper betle. Molecules (Basel, Switzerland). 2013 Feb; 18(3):2563-70. doi: 10.3390/molecules18032563. [PMID: 23442932]
  • Eisuke Kato, Ryo Nakagomi, Maria D P T Gunawan-Puteri, Jun Kawabata. Identification of hydroxychavicol and its dimers, the lipase inhibitors contained in the Indonesian spice, Eugenia polyantha. Food chemistry. 2013 Feb; 136(3-4):1239-42. doi: 10.1016/j.foodchem.2012.09.013. [PMID: 23194519]
  • Jayashree B Chakraborty, Sanjit K Mahato, Kalpana Joshi, Vaibhav Shinde, Srabanti Rakshit, Nabendu Biswas, Indrani Choudhury Mukherjee, Labanya Mandal, Dipyaman Ganguly, Avik A Chowdhury, Jaydeep Chaudhuri, Kausik Paul, Bikas C Pal, Jayaraman Vinayagam, Churala Pal, Anirban Manna, Parasuraman Jaisankar, Utpal Chaudhuri, Aditya Konar, Siddhartha Roy, Santu Bandyopadhyay. Hydroxychavicol, a Piper betle leaf component, induces apoptosis of CML cells through mitochondrial reactive oxygen species-dependent JNK and endothelial nitric oxide synthase activation and overrides imatinib resistance. Cancer science. 2012 Jan; 103(1):88-99. doi: 10.1111/j.1349-7006.2011.02107.x. [PMID: 21943109]
  • 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]
  • Anjali Pandey, Sarang Bani. Hydroxychavicol inhibits immune responses to mitigate cognitive dysfunction in rats. Journal of neuroimmunology. 2010 Sep; 226(1-2):48-58. doi: 10.1016/j.jneuroim.2010.05.031. [PMID: 20605227]
  • Intzar Ali, Farrah G Khan, Krishan A Suri, Bishan D Gupta, Naresh K Satti, Prabhu Dutt, Farhat Afrin, Ghulam N Qazi, Inshad A Khan. In vitro antifungal activity of hydroxychavicol isolated from Piper betle L. Annals of clinical microbiology and antimicrobials. 2010 Feb; 9(?):7. doi: 10.1186/1476-0711-9-7. [PMID: 20128889]
  • Anjali Pandey, Sarang Bani, Prabhu Dutt, Krishna Avtar Suri. Modulation of Th1/Th2 cytokines and inflammatory mediators by hydroxychavicol in adjuvant induced arthritic tissues. Cytokine. 2010 Jan; 49(1):114-21. doi: 10.1016/j.cyto.2009.08.015. [PMID: 19782577]
  • Kazuya Murata, Kikuyo Nakao, Noriko Hirata, Kensuke Namba, Takao Nomi, Yoshihisa Kitamura, Kenzo Moriyama, Takahiro Shintani, Munekazu Iinuma, Hideaki Matsuda. Hydroxychavicol: a potent xanthine oxidase inhibitor obtained from the leaves of betel, Piper betle. Journal of natural medicines. 2009 Jul; 63(3):355-9. doi: 10.1007/s11418-009-0331-y. [PMID: 19387769]
  • 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]
  • Sandeep Sharma, Inshad Ali Khan, Intzar Ali, Furqan Ali, Manoj Kumar, Ashwani Kumar, Rakesh Kamal Johri, Sheikh Tasduq Abdullah, Sarang Bani, Anjali Pandey, Krishan Avtar Suri, Bishan Datt Gupta, Naresh Kumar Satti, Prabhu Dutt, Ghulam Nabi Qazi. Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent. Antimicrobial agents and chemotherapy. 2009 Jan; 53(1):216-22. doi: 10.1128/aac.00045-08. [PMID: 18573934]
  • Soumyaditya Mula, Debashish Banerjee, Birija S Patro, Sayanti Bhattacharya, Atanu Barik, Sandip K Bandyopadhyay, Subrata Chattopadhyay. Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages. Bioorganic & medicinal chemistry. 2008 Mar; 16(6):2932-8. doi: 10.1016/j.bmc.2007.12.052. [PMID: 18207412]
  • M C Chang, B J Uang, C Y Tsai, H L Wu, B R Lin, C S Lee, Y J Chen, C H Chang, Y L Tsai, C J Kao, J H Jeng. Hydroxychavicol, a novel betel leaf component, inhibits platelet aggregation by suppression of cyclooxygenase, thromboxane production and calcium mobilization. British journal of pharmacology. 2007 Sep; 152(1):73-82. doi: 10.1038/sj.bjp.0707367. [PMID: 17641677]
  • Yu-Chang Chen, Jih-Jung Chen, Ya-Ling Chang, Che-Ming Teng, Wei-Yu Lin, Chin-Chung Wu, Ih-Sheng Chen. A new aristolactam alkaloid and anti-platelet aggregation constituents from Piper taiwanense. Planta medica. 2004 Feb; 70(2):174-7. doi: 10.1055/s-2004-815497. [PMID: 14994198]
  • Hisashi Matsuda, Toshio Morikawa, Hiromi Managi, Masayuki Yoshikawa. Antiallergic principles from Alpinia galanga: structural requirements of phenylpropanoids for inhibition of degranulation and release of TNF-alpha and IL-4 in RBL-2H3 cells. Bioorganic & medicinal chemistry letters. 2003 Oct; 13(19):3197-202. doi: 10.1016/s0960-894x(03)00710-8. [PMID: 12951092]
  • Wen-Bin Pan, Fang-Rong Chang, Li-Mei Wei, Yang-Chang Wu. New flavans, spirostanol sapogenins, and a pregnane genin from Tupistra chinensis and their cytotoxicity. Journal of natural products. 2003 Feb; 66(2):161-8. doi: 10.1021/np0203382. [PMID: 12608845]
  • David J Chitwood. Phytochemical based strategies for nematode control. Annual review of phytopathology. 2002; 40(?):221-49. doi: 10.1146/annurev.phyto.40.032602.130045. [PMID: 12147760]
  • A J Amonkar, M Nagabhushan, A V D'Souza, S V Bhide. Hydroxychavicol: a new phenolic antimutagen from betel leaf. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1986 Dec; 24(12):1321-4. doi: 10.1016/0278-6915(86)90065-7. [PMID: 3100406]