2,3-Oxidosqualene (BioDeep_00000910960)
代谢物信息卡片
2,3-Oxidosqualene
化学式: C30H50O (426.3861)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(=CCCC(=CCCC(=CCCC=C(C)CCC=C(C)CCC1C(O1)(C)C)C)C)C
InChI: InChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+
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)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
| 亚细胞结构定位 | 关联基因列表 |
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文献列表
- Qian Zhou, Peng Sun, Hao-Ming Xiong, Jiali Xie, Guo-Yuan Zhu, Dean J Tantillo, Ancheng C Huang. Insight into neofunctionalization of 2,3-oxidosqualene cyclases in B,C-ring-opened triterpene biosynthesis in quinoa.
The New phytologist.
2024 Jan; 241(2):764-778. doi:
10.1111/nph.19345. [PMID: 37904576] - Yanan Huang, Helu Liu, Yang Zhou, Zaiqing Lu, Yujin Pu, Haibin Zhang. Cloning and functional characterization of the oxidative squalene cyclase gene in the deep-sea holothurian Chiridota sp.
Gene.
2023 Nov; ?(?):147971. doi:
10.1016/j.gene.2023.147971. [PMID: 37949417] - Jinling Li, Shuai Wang, Yinan Miao, Ya Wan, Chun Li, Ying Wang. Mining and modification of Oryza sativa-derived squalene epoxidase for improved β-amyrin production in Saccharomyces cerevisiae.
Journal of biotechnology.
2023 Aug; 375(?):1-11. doi:
10.1016/j.jbiotec.2023.08.004. [PMID: 37597655] - Fan Zhang, Yunpeng Wang, Jingyang Yue, Rongrong Zhang, Yong-Er Hu, Ruoshi Huang, Ai-Jia Ji, B Andes Hess, Zhongqiu Liu, Lixin Duan, Ruibo Wu. Discovering a uniform functional trade-off of the CBC-type 2,3-oxidosqualene cyclases and deciphering its chemical logic.
Science advances.
2023 06; 9(23):eadh1418. doi:
10.1126/sciadv.adh1418. [PMID: 37285431] - Xiao-Chao Chen, Yun Lu, Yuan Liu, Jia-Wei Zhou, Yi-Feng Zhang, Hai-Yun Gao, Dan Li, Wei Gao. Identification of a cytochrome P450 from Tripterygium hypoglaucum (Levl.) Hutch that catalyzes polpunonic acid formation in celastrol biosynthesis.
Chinese journal of natural medicines.
2022 Sep; 20(9):691-700. doi:
10.1016/s1875-5364(22)60205-x. [PMID: 36162954] - Jing Wang, Yanhong Guo, Xue Yin, Xiaoning Wang, Xiaoquan Qi, Zheyong Xue. Diverse triterpene skeletons are derived from the expansion and divergent evolution of 2,3-oxidosqualene cyclases in plants.
Critical reviews in biochemistry and molecular biology.
2022 04; 57(2):113-132. doi:
10.1080/10409238.2021.1979458. [PMID: 34601979] - Jing Yin, Jie Yang, Hongsi Ma, Tian Liang, Ying Li, Jialei Xiao, Hongmei Tian, Zhiqiang Xu, Yaguang Zhan. Expression characteristics and function of CAS and a new beta-amyrin synthase in triterpenoid synthesis in birch (Betula platyphylla Suk.).
Plant science : an international journal of experimental plant biology.
2020 May; 294(?):110433. doi:
10.1016/j.plantsci.2020.110433. [PMID: 32234222] - Gaurav Srivastava, Sandeep, Anchal Garg, Rajesh Chandra Misra, Chandan Singh Chanotiya, Sumit Ghosh. Transcriptome analysis and functional characterization of oxidosqualene cyclases of the arjuna triterpene saponin pathway.
Plant science : an international journal of experimental plant biology.
2020 Mar; 292(?):110382. doi:
10.1016/j.plantsci.2019.110382. [PMID: 32005387] - Rong Tian, Wei Gu, Yuchen Gu, Chao Geng, Fei Xu, Qinan Wu, Jianguo Chao, Wenda Xue, Chen Zhou, Fan Wang. Methyl jasmonate promote protostane triterpenes accumulation by up-regulating the expression of squalene epoxidases in Alisma orientale.
Scientific reports.
2019 12; 9(1):18139. doi:
10.1038/s41598-019-54629-6. [PMID: 31792343] - Asuka Suzuki, Yuko Aikawa, Ryousuke Ito, Tsutomu Hoshino. Oryza sativa Parkeol Cyclase: Changes in the Substrate-Folding Conformation and the Deprotonation Sites on Mutation at Tyr257: Importance of the Hydroxy Group and Steric Bulk.
Chembiochem : a European journal of chemical biology.
2019 11; 20(22):2862-2875. doi:
10.1002/cbic.201900314. [PMID: 31180162] - Wei Song, Shan Yan, Yi Li, Shan Feng, Jia-Jiao Zhang, Jia-Ru Li. Functional characterization of squalene epoxidase and NADPH-cytochrome P450 reductase in Dioscorea zingiberensis.
Biochemical and biophysical research communications.
2019 02; 509(3):822-827. doi:
10.1016/j.bbrc.2019.01.010. [PMID: 30638657] - Jacob Pollier, Emmelien Vancaester, Unnikrishnan Kuzhiumparambil, Claudia E Vickers, Klaas Vandepoele, Alain Goossens, Michele Fabris. A widespread alternative squalene epoxidase participates in eukaryote steroid biosynthesis.
Nature microbiology.
2019 02; 4(2):226-233. doi:
10.1038/s41564-018-0305-5. [PMID: 30478288] - Yuan Yu, Pengcheng Chang, Huan Yu, Huiyong Ren, Danning Hong, Zeyan Li, Ying Wang, Hao Song, Yixin Huo, Chun Li. Productive Amyrin Synthases for Efficient α-Amyrin Synthesis in Engineered Saccharomyces cerevisiae.
ACS synthetic biology.
2018 10; 7(10):2391-2402. doi:
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Bioresource technology.
2018 Jun; 257(?):339-343. doi:
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Plant & cell physiology.
2016 May; 57(5):1000-7. doi:
10.1093/pcp/pcw038. [PMID: 26903528] - Roland Jourdain, Alain Moga, Philippe Vingler, Charles El Rawadi, Florence Pouradier, Luc Souverain, Philippe Bastien, Nicolas Amalric, Lionel Breton. Exploration of scalp surface lipids reveals squalene peroxide as a potential actor in dandruff condition.
Archives of dermatological research.
2016 Apr; 308(3):153-63. doi:
10.1007/s00403-016-1623-1. [PMID: 26842231] - Yue-Qiao Zhen, Yu-Min Wu, Yan-Hong Sang, Yan Wang, Qiu-Yan Song, Ling Yu, Xiao-Juan Rao, Rui-Hong Dong. 2,3-Oxidosqualene cyclase protects liver cells from the injury of intermittent hypoxia by regulating lipid metabolism.
Sleep & breathing = Schlaf & Atmung.
2015 Dec; 19(4):1475-81. doi:
10.1007/s11325-015-1167-1. [PMID: 25855471] - Hikaru Seki, Keita Tamura, Toshiya Muranaka. P450s and UGTs: Key Players in the Structural Diversity of Triterpenoid Saponins.
Plant & cell physiology.
2015 Aug; 56(8):1463-71. doi:
10.1093/pcp/pcv062. [PMID: 25951908] - Monika Christen, Maria J Marcaida, Christos Lamprakis, Walter Aeschimann, Jathana Vaithilingam, Petra Schneider, Manuel Hilbert, Gisbert Schneider, Michele Cascella, Achim Stocker. Structural insights on cholesterol endosynthesis: Binding of squalene and 2,3-oxidosqualene to supernatant protein factor.
Journal of structural biology.
2015 Jun; 190(3):261-70. doi:
10.1016/j.jsb.2015.05.001. [PMID: 25987292] - Xiasheng Zheng, Hui Xu, Xinye Ma, Ruoting Zhan, Weiwen Chen. Triterpenoid saponin biosynthetic pathway profiling and candidate gene mining of the Ilex asprella root using RNA-Seq.
International journal of molecular sciences.
2014 Apr; 15(4):5970-87. doi:
10.3390/ijms15045970. [PMID: 24722569] - Luis M Peña-Rodríguez, Alejandro Yam-Puc, Nihat Knispel, Nicholas Schramek, Claudia Huber, Christoph Graßberger, Fabiola G Ramírez-Torres, Fabiola Escalante-Erosa, Karlina García-Sosa, Mickel R Hiebert-Giesbrecht, Manuel J Chan-Bacab, Gregorio Godoy-Hernández, Adelbert Bacher, Wolfgang Eisenreich. Isotopologue profiling of triterpene formation under physiological conditions. Biosynthesis of lupeol-3-(3'-R-hydroxy)-stearate in Pentalinon andrieuxii.
The Journal of organic chemistry.
2014 Apr; 79(7):2864-73. doi:
10.1021/jo402677w. [PMID: 24606167] - Ryousuke Ito, Ippei Hashimoto, Yukari Masukawa, Tsutomu Hoshino. Effect of cation-π interactions and steric bulk on the catalytic action of oxidosqualene cyclase: a case study of Phe728 of β-amyrin synthase from Euphorbia tirucalli L.
Chemistry (Weinheim an der Bergstrasse, Germany).
2013 Dec; 19(50):17150-8. doi:
10.1002/chem.201301917. [PMID: 24203491] - Ryousuke Ito, Yukari Masukawa, Tsutomu Hoshino. Purification, kinetics, inhibitors and CD for recombinant β-amyrin synthase from Euphorbia tirucalli L and functional analysis of the DCTA motif, which is highly conserved among oxidosqualene cyclases.
The FEBS journal.
2013 Mar; 280(5):1267-80. doi:
10.1111/febs.12119. [PMID: 23294602] - Zheyong Xue, Lixin Duan, Dan Liu, Jie Guo, Song Ge, Jo Dicks, Paul ÓMáille, Anne Osbourn, Xiaoquan Qi. Divergent evolution of oxidosqualene cyclases in plants.
The New phytologist.
2012 Mar; 193(4):1022-1038. doi:
10.1111/j.1469-8137.2011.03997.x. [PMID: 22150097] - Yoshi-Shige Inagaki, Graham Etherington, Katrin Geisler, Ben Field, Melissa Dokarry, Kousuke Ikeda, Yukako Mutsukado, Jo Dicks, Anne Osbourn. Investigation of the potential for triterpene synthesis in rice through genome mining and metabolic engineering.
The New phytologist.
2011 Jul; 191(2):432-448. doi:
10.1111/j.1469-8137.2011.03712.x. [PMID: 21501172] - Marko Lens, Marie-Helen Podesta Marty. Assessment of the kinetics of the antioxidative capacity of topical antioxidants.
Journal of drugs in dermatology : JDD.
2011 Mar; 10(3):262-7. doi:
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Biological & pharmaceutical bulletin.
2009 Sep; 32(9):1504-9. doi:
10.1248/bpb.32.1504. [PMID: 19721223] - Elena Babiychuk, Pierrette Bouvier-Navé, Vincent Compagnon, Masashi Suzuki, Toshiya Muranaka, Marc Van Montagu, Sergei Kushnir, Hubert Schaller. Allelic mutant series reveal distinct functions for Arabidopsis cycloartenol synthase 1 in cell viability and plastid biogenesis.
Proceedings of the National Academy of Sciences of the United States of America.
2008 Feb; 105(8):3163-8. doi:
10.1073/pnas.0712190105. [PMID: 18287026] - Kiyotaka Nakagawa, Daigo Ibusuki, Yoshihiro Suzuki, Shinji Yamashita, Ohki Higuchi, Shinichi Oikawa, Teruo Miyazawa. Ion-trap tandem mass spectrometric analysis of squalene monohydroperoxide isomers in sunlight-exposed human skin.
Journal of lipid research.
2007 Dec; 48(12):2779-87. doi:
10.1194/jlr.d700016-jlr200. [PMID: 17848584] - Monica Ottaviani, Theodosis Alestas, Enrica Flori, Arianna Mastrofrancesco, Christos C Zouboulis, Mauro Picardo. Peroxidated squalene induces the production of inflammatory mediators in HaCaT keratinocytes: a possible role in acne vulgaris.
The Journal of investigative dermatology.
2006 Nov; 126(11):2430-7. doi:
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Plant & cell physiology.
2006 May; 47(5):565-71. doi:
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2005 Dec; 127(51):18008-9. doi:
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10.1016/s0076-6879(00)19057-3. [PMID: 10907548] - B Eisele, R Budzinski, P Müller, R Maier, M Mark. Effects of a novel 2,3-oxidosqualene cyclase inhibitor on cholesterol biosynthesis and lipid metabolism in vivo.
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1997 Mar; 38(3):564-75. doi:
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