Sesamolin (BioDeep_00000230070)

Main id: BioDeep_00000018229

 

PANOMIX_OTCML-2023


代谢物信息卡片


1,3-Benzodioxole, 5-(4-(1,3-benzodioxol-5-yloxy)tetrahydro-1H,3H-furo(3,4-c)furan-1-yl)-, (1S-(1alpha,3a alpha,4alpha,6a alpha))-

化学式: C20H18O7 (370.1052478)
中文名称: 芝麻林素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1C2C(COC2OC3=CC4=C(C=C3)OCO4)C(O1)C5=CC6=C(C=C5)OCO6
InChI: InChI=1S/C20H18O7/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)27-12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1

描述信息

Sesamolin is a member of benzodioxoles.
Sesamolin is a natural product found in Lantana camara, Torenia violacea, and other organisms with data available.
See also: Sesame Oil (part of).
Sesaminol, isolated from Sesamum indicum, has antioxidative activity, Sesaminol inhibits lipid peroxidation and shows neuroprotection effect. Sesaminol potently inhibits MAPK cascades by preventing phosphorylation of JNK, p38 MAPKs, and caspase-3 but not ERK-MAPK expression[1][2][3][4].
Sesaminol, isolated from Sesamum indicum, has antioxidative activity, Sesaminol inhibits lipid peroxidation and shows neuroprotection effect. Sesaminol potently inhibits MAPK cascades by preventing phosphorylation of JNK, p38 MAPKs, and caspase-3 but not ERK-MAPK expression[1][2][3][4].

同义名列表

15 个代谢物同义名

1,3-Benzodioxole, 5-(4-(1,3-benzodioxol-5-yloxy)tetrahydro-1H,3H-furo(3,4-c)furan-1-yl)-, (1S-(1alpha,3a alpha,4alpha,6a alpha))-; 5-[[(3S,3aR,6R,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]oxy]-1,3-benzodioxole; 5-[[(3S,3aR,6R,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrouro[3,4-c]uran-6-yl]oxy]-1,3-benzodioxole; 1,3-Benzodioxole,5-[4-(1,3-benzodioxol-5-yloxy)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-,(1S,3aR,4R,6aR)-; 5-(((1R,3aR,4S,6aR)-4-(Benzo[d][1,3]dioxol-5-yl)hexahydrofuro[3,4-c]furan-1-yl)oxy)benzo[d][1,3]dioxole; (1S,3AR,4R,6AR)-5-(4-(1,3-BENZODIOXOL-5-YLOXY)TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1-YL)-1,3-BENZODIOXOLE; 5-[(1S,3aR,4R,6aR)-4-(2H-1,3-benzodioxol-5-yloxy)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxole; 1,3-BENZODIOXOL-5-YL (1R,3AR,4S,6AR)-4-(1,3-BENZODIOXOL-5-YL)PERHYDROFURO(3,4-C)FURAN-1-YL ETHER; UNII-7A90TJ149G; SESAMOLIN [MI]; (+)-sesamolin; 7A90TJ149G; AI3-20978; SESAMOLIN; A1-06842



数据库引用编号

8 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(0)

代谢反应

77 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(75)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

32 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

  • Nelma Nyvonne Tiqu Gina, Jui-Ling Kuo, Mei-Li Wu, Show-Mei Chuang. Sesamin and sesamolin potentially inhibit adipogenesis through downregulating the peroxisome proliferator-activated receptor γ protein expression and activity in 3T3-L1 cells. Nutrition research (New York, N.Y.). 2023 Dec; 123(?):4-17. doi: 10.1016/j.nutres.2023.12.011. [PMID: 38228077]
  • Elham Ramazani, Faeze Ebrahimpour, Seyed Ahmad Emami, Abolfazl Shakeri, Behjat Javadi, Amirhossein Sahebkar, Zahra Tayarani-Najaran. Neuroprotective effects of Sesamum indicum, sesamin and sesamolin against 6-OHDA-induced apoptosis in PC12 cells. Recent advances in food, nutrition & agriculture. 2023 Aug; ?(?):. doi: 10.2174/2772574x14666230804151124. [PMID: 37539928]
  • Yuan Chi, Hong-Wei He, Cai-Yun Chen, Si-Ying Zhao, Huan Zhou, Dan Xu, Xili Liu, Gong Xu. Furofuran Lignans for Plant Protection: Discovery of Sesamolin and Its Derivatives as Novel Anti-Tobacco Mosaic Virus and Antibacterial Agents. Journal of agricultural and food chemistry. 2023 Jul; ?(?):. doi: 10.1021/acs.jafc.3c03257. [PMID: 37418668]
  • Longkai Shi, Emad Karrar, Ruijie Liu, Ming Chang, Xingguo Wang. Comparative effects of sesame lignans (sesamin, sesamolin, and sesamol) on oxidative stress and lipid metabolism in steatosis HepG2 cells. Journal of food biochemistry. 2022 08; 46(8):e14180. doi: 10.1111/jfbc.14180. [PMID: 35396857]
  • Lipeng Han, Jiahui Li, Shujie Wang, Weiwei Cheng, Lukai Ma, Guoqin Liu, Dongxue Han, Li Niu. The inhibitory effects of sesamol and sesamolin on the glycidyl esters formation during deodorization of vegetables oils. Journal of the science of food and agriculture. 2021 Jul; 101(9):3605-3612. doi: 10.1002/jsfa.10989. [PMID: 33275282]
  • Erisa Harada, Jun Murata, Eiichiro Ono, Hiromi Toyonaga, Akira Shiraishi, Kosuke Hideshima, Masayuki P Yamamoto, Manabu Horikawa. (+)-Sesamin-oxidising CYP92B14 shapes specialised lignan metabolism in sesame. The Plant journal : for cell and molecular biology. 2020 11; 104(4):1117-1128. doi: 10.1111/tpj.14989. [PMID: 32955771]
  • Yazhen Chen, Hetong Lin, Mengshi Lin, Yongzhan Zheng, Jicheng Chen. Effect of roasting and in vitro digestion on phenolic profiles and antioxidant activity of water-soluble extracts from sesame. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2020 May; 139(?):111239. doi: 10.1016/j.fct.2020.111239. [PMID: 32145351]
  • Eiichiro Ono, Toshiyuki Waki, Daiki Oikawa, Jun Murata, Akira Shiraishi, Hiromi Toyonaga, Masako Kato, Naoki Ogata, Seiji Takahashi, Masa-Atsu Yamaguchi, Manabu Horikawa, Toru Nakayama. Glycoside-specific glycosyltransferases catalyze regio-selective sequential glucosylations for a sesame lignan, sesaminol triglucoside. The Plant journal : for cell and molecular biology. 2020 03; 101(5):1221-1233. doi: 10.1111/tpj.14586. [PMID: 31654577]
  • Sepideh Ghotbzadeh Kermani, Ghodratollah Saeidi, Mohammad R Sabzalian, Alberto Gianinetti. Drought stress influenced sesamin and sesamolin content and polyphenolic components in sesame (Sesamum indicum L.) populations with contrasting seed coat colors. Food chemistry. 2019 Aug; 289(?):360-368. doi: 10.1016/j.foodchem.2019.03.004. [PMID: 30955624]
  • Kazuko Iwamoto, Shinichi Matsumura, Yuri Yoshioka, Ayami Yamamoto, Shohei Makino, Tatsuya Moriyama, Nobuhiro Zaima. Using Turmeric Oil as a Solvent Improves the Distribution of Sesamin-Sesamolin in the Serum and Brain of Mice. Lipids. 2019 05; 54(5):311-320. doi: 10.1002/lipd.12147. [PMID: 30993746]
  • Hirona Kugo, Chie Miyamoto, Ayaka Sawaragi, Kiyoto Hoshino, Yuka Hamatani, Shinichi Matsumura, Yuri Yoshioka, Tatsuya Moriyama, Nobuhiro Zaima. Sesame Extract Attenuates the Degradation of Collagen and Elastin Fibers in the Vascular Walls of Nicotine-administered Mice. Journal of oleo science. 2019; 68(1):79-85. doi: 10.5650/jos.ess18200. [PMID: 30606956]
  • Jun Murata, Eiichiro Ono, Seigo Yoroizuka, Hiromi Toyonaga, Akira Shiraishi, Shoko Mori, Masayuki Tera, Toshiaki Azuma, Atsushi J Nagano, Masaru Nakayasu, Masaharu Mizutani, Tatsuya Wakasugi, Masayuki P Yamamoto, Manabu Horikawa. Oxidative rearrangement of (+)-sesamin by CYP92B14 co-generates twin dietary lignans in sesame. Nature communications. 2017 12; 8(1):2155. doi: 10.1038/s41467-017-02053-7. [PMID: 29255253]
  • Je-Seung Jeon, Chae Lee Park, Ahmed Shah Syed, Young-Mi Kim, Il Je Cho, Chul Young Kim. Preparative separation of sesamin and sesamolin from defatted sesame meal via centrifugal partition chromatography with consecutive sample injection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2016 Feb; 1011(?):108-13. doi: 10.1016/j.jchromb.2015.12.062. [PMID: 26773888]
  • N Pathak, A Bhaduri, K V Bhat, A K Rai. Tracking sesamin synthase gene expression through seed maturity in wild and cultivated sesame species--a domestication footprint. Plant biology (Stuttgart, Germany). 2015 Sep; 17(5):1039-46. doi: 10.1111/plb.12327. [PMID: 25754459]
  • Takashi Ide, Ayana Azechi, Sayaka Kitade, Yoko Kunimatsu, Natsuko Suzuki, Chihiro Nakajima, Naoki Ogata. Comparative effects of sesame seeds differing in lignan contents and composition on fatty acid oxidation in rat liver. Journal of oleo science. 2015; 64(2):211-22. doi: 10.5650/jos.ess14182. [PMID: 25748381]
  • Paweł Górnaś, Aleksander Siger, Iveta Pugajeva, Dalija Segliņa. Sesamin and sesamolin as unexpected contaminants in various cold-pressed plant oils: NP-HPLC/FLD/DAD and RP-UPLC-ESI/MS(n) study. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2014 Apr; 31(4):567-73. doi: 10.1080/19440049.2014.884285. [PMID: 24428708]
  • Chifumi Kinugasa, Aki Naemura, Kanae Hyodo, Yoshiki Nakai, Masumi Katsuta, Junichiro Yamamoto. Experimental antithrombotic effects of sesame seed whole grains and extracts. Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis. 2011 Sep; 22(6):526-31. doi: 10.1097/mbc.0b013e328347b085. [PMID: 21577091]
  • Xuebo Liu, Naruomi Yamada, Toshihiko Osawa. Assessing the neuroprotective effect of antioxidant food factors by application of lipid-derived dopamine modification adducts. Methods in molecular biology (Clifton, N.J.). 2010; 594(?):263-73. doi: 10.1007/978-1-60761-411-1_18. [PMID: 20072923]
  • Divya Sukumar, Ranjith Arimboor, C Arumughan. HPTLC fingerprinting and quantification of lignans as markers in sesame oil and its polyherbal formulations. Journal of pharmaceutical and biomedical analysis. 2008 Aug; 47(4-5):795-801. doi: 10.1016/j.jpba.2008.03.018. [PMID: 18448304]
  • Jin Seon Lim, Yoshikazu Adachi, Yoko Takahashi, Takashi Ide. Comparative analysis of sesame lignans (sesamin and sesamolin) in affecting hepatic fatty acid metabolism in rats. The British journal of nutrition. 2007 Jan; 97(1):85-95. doi: 10.1017/s0007114507252699. [PMID: 17217563]
  • Rolis Chien-Wei Hou, Chia-Chuan Wu, Jing-Rong Huang, Yuh-Shuen Chen, Kee-Ching G Jeng. Oxidative toxicity in BV-2 microglia cells: sesamolin neuroprotection of H2O2 injury involving activation of p38 mitogen-activated protein kinase. Annals of the New York Academy of Sciences. 2005 May; 1042(?):279-85. doi: 10.1196/annals.1338.050. [PMID: 15965073]
  • Jan Frank, Afaf Kamal-Eldin, Maret G Traber. Consumption of sesame oil muffins decreases the urinary excretion of gamma-tocopherol metabolites in humans. Annals of the New York Academy of Sciences. 2004 Dec; 1031(?):365-7. doi: 10.1196/annals.1331.046. [PMID: 15753171]
  • S Hemalatha, M Raghunath, Ghafoorunissa. Dietary sesame oils inhibits iron-induced oxidative stress in rats [corrected]. The British journal of nutrition. 2004 Oct; 92(4):581-7. doi: 10.1079/bjn20041239. [PMID: 15526409]
  • Kizhiyedathu Polachira Suja, Anathasankaran Jayalekshmy, Chami Arumughan. Free radical scavenging behavior of antioxidant compounds of sesame (sesamum indicum L.) in DPPH(*) system. Journal of agricultural and food chemistry. 2004 Feb; 52(4):912-5. doi: 10.1021/jf0303621. [PMID: 14969550]
  • S Sirato-Yasumoto, M Katsuta, Y Okuyama, Y Takahashi, T Ide. Effect of sesame seeds rich in sesamin and sesamolin on fatty acid oxidation in rat liver. Journal of agricultural and food chemistry. 2001 May; 49(5):2647-51. doi: 10.1021/jf001362t. [PMID: 11368649]
  • M H Kang, M Naito, N Tsujihara, T Osawa. Sesamolin inhibits lipid peroxidation in rat liver and kidney. The Journal of nutrition. 1998 Jun; 128(6):1018-22. doi: 10.1093/jn/128.6.1018. [PMID: 9614163]
  • R Hayakawa, K Matsunaga, M Suzuki, K Hosokawa, Y Arima, C S Shin, M Yoshida. Is sesamol present in sesame oil?. Contact dermatitis. 1987 Sep; 17(3):133-5. doi: 10.1111/j.1600-0536.1987.tb02690.x. [PMID: 3677654]