Mezerein (BioDeep_00000001012)

 

Secondary id: BioDeep_00000180926, BioDeep_00000910976

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


2,4-Pentadienoic acid, 5-phenyl-, (2S,3aR,3bS,3cS,4aR,5S,5aS,8aR,8bR,9R,10R,10aS)-3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-(hydroxymethyl)-7,9-dimethyl-10a-(1-methylethenyl)-6-oxo-2-phenyl-6H-2,8b-epoxyoxireno(6,7)azulene(5,4-e)-1,3-benzodioxol-10-yl ester, (2E,4E)-

化学式: C38H38O10 (654.2464848)
中文名称: 欧瑞香脂, 密执毒素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 12.5%

分子结构信息

SMILES: C=C(C)C12OC3(c4ccccc4)OC1C1C4OC4(CO)C(O)C4(O)C(=O)C(C)=CC4C1(O3)C(C)C2OC(=O)C=CC=Cc1ccccc1
InChI: InChI=1S/C38H38O10/c1-21(2)36-30(44-27(40)18-12-11-15-24-13-7-5-8-14-24)23(4)37-26-19-22(3)29(41)35(26,43)33(42)34(20-39)31(45-34)28(37)32(36)46-38(47-36,48-37)25-16-9-6-10-17-25/h5-19,23,26,28,30-33,39,42-43H,1,20H2,2-4H3/b15-11+,18-12+/t23-,26-,28+,30-,31+,32-,33-,34+,35-,36+,37+,38?/m1/s1

描述信息

Crystals or white powder. (NTP, 1992)
Mezerein is a diterpenoid.
D009676 - Noxae > D002273 - Carcinogens
D000970 - Antineoplastic Agents

同义名列表

10 个代谢物同义名

2,4-Pentadienoic acid, 5-phenyl-, (2S,3aR,3bS,3cS,4aR,5S,5aS,8aR,8bR,9R,10R,10aS)-3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-(hydroxymethyl)-7,9-dimethyl-10a-(1-methylethenyl)-6-oxo-2-phenyl-6H-2,8b-epoxyoxireno(6,7)azulene(5,4-e)-1,3-benzodioxol-10-yl ester, (2E,4E)-; [(1R,2R,6S,7S,8R,10S,11S,12R,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-prop-1-en-2-yl-9,13,15,19-tetraoxahexacyclo[12.4.1.01,11.02,6.08,10.012,16]nonadec-3-en-17-yl] (2E,4E)-5-phenylpenta-2,4-dienoate; 2,4-Pentadienoic acid,5-phenyl-,(2S,3aR,3bS,3cS,4aR,5S,5aS,8aR,8bR,9R,10R,10aS)-3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-(hydroxymethyl)-7,9-dimethyl-10a-(1-methylethenyl)-6-oxo-2-phen; 5-phenyl-2,4-pentadionate daphnetoxin; 1alpha-alkyldaphnane; tigliane-daphnane; SMP2_000004; Mezerein; daphnane; Mezerein



数据库引用编号

18 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)

9 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

  • Xinyi Wang, Yujue Wang, Zijian Liu, Hongwei Zhao, Guo-Dong Yao, Qingbo Liu, Shao-Jiang Song. New daphnane diterpenoidal 1,3,4-oxdiazole derivatives as potential anti-hepatoma agents: Synthesis, biological evaluation and molecular modeling studies. Bioorganic chemistry. 2024 Apr; 145(?):107208. doi: 10.1016/j.bioorg.2024.107208. [PMID: 38354501]
  • Lingjian Tan, Kouharu Otsuki, Mi Zhang, Takashi Kikuchi, Di Zhou, Ning Li, Li Huang, Chin-Ho Chen, Wei Li. Daphnepedunins G and H, anti-HIV macrocyclic 3,4-seco-daphnane orthoesters from Daphne pedunculata. Journal of natural medicines. 2024 Jan; 78(1):114-122. doi: 10.1007/s11418-023-01750-6. [PMID: 37713094]
  • Kouharu Otsuki, Tsubasa Kobayashi, Kazuki Nakamura, Takashi Kikuchi, Li Huang, Chin-Ho Chen, Kazuo Koike, Wei Li. LC-MS identification, isolation, and structural elucidation of anti-HIV macrocyclic daphnane orthoesters from Edgeworthia chrysantha. Fitoterapia. 2024 Jan; 172(?):105731. doi: 10.1016/j.fitote.2023.105731. [PMID: 37935270]
  • Zhuo-Yang Cheng, Jing-Xian Ren, Xiao-Bian Xue, Man Wang, Xiao-Qi Yu, Bin Lin, Guo-Dong Yao, Shao-Jiang Song, Xiao-Xiao Huang. Daphnane-type diterpenoids from Stellera chamaejasme L. and their inhibitory activity against hepatocellular carcinoma cells. Phytochemistry. 2023 Aug; 212(?):113725. doi: 10.1016/j.phytochem.2023.113725. [PMID: 37224912]
  • Kang Ding, Zi-Yao Wu, Nuan Zhang, Jun He, Fan Zhang, Jing-Jing Wu, Hong-Jin Bai, Wei-Ku Zhang, Lin Li, Jie-Kun Xu. Stelleratenoids A-F, macrocyclic daphnane orthoesters with anti-HIV activity from the roots of Stellera chamaejasme L. Phytochemistry. 2023 Jun; 210(?):113648. doi: 10.1016/j.phytochem.2023.113648. [PMID: 36963707]
  • Lingjian Tan, Kouharu Otsuki, Mi Zhang, Takashi Kikuchi, Misaki Okayasu, Isao Azumaya, Di Zhou, Ning Li, Li Huang, Chin-Ho Chen, Wei Li. Daphnepedunins A-F, Anti-HIV Macrocyclic Daphnane Orthoester Diterpenoids from Daphne pedunculata. Journal of natural products. 2022 12; 85(12):2856-2864. doi: 10.1021/acs.jnatprod.2c00894. [PMID: 36516989]
  • Xiaoyan He, Xiatiguli Abulizi, Xiaowan Li, Guoxu Ma, Zhaocui Sun, Hongyan Wei, Xudong Xu, Leiling Shi, Jing Zhang. Daphnane-Type Diterpenes from Stelleropsis tianschanica and Their Antitumor Activity. Molecules (Basel, Switzerland). 2022 Sep; 27(17):. doi: 10.3390/molecules27175701. [PMID: 36080468]
  • Babalwa Tembeni, Amanda Sciorillo, Luke Invernizzi, Thomas Klimkait, Lorena Urda, Phanankosi Moyo, Dashnie Naidoo-Maharaj, Nathan Levitties, Kwasi Gyampoh, Guorui Zu, Zhe Yuan, Karam Mounzer, Siphathimandla Nkabinde, Magugu Nkabinde, Nceba Gqaleni, Ian Tietjen, Luis J Montaner, Vinesh Maharaj. HPLC-Based Purification and Isolation of Potent Anti-HIV and Latency Reversing Daphnane Diterpenes from the Medicinal Plant Gnidia sericocephala (Thymelaeaceae). Viruses. 2022 06; 14(7):. doi: 10.3390/v14071437. [PMID: 35891417]
  • Si-Hui Mi, Peng Zhao, Qian Li, Hao Zhang, Rui Guo, Yu-Yang Liu, Bin Lin, Guo-Dong Yao, Shao-Jiang Song, Xiao-Xiao Huang. Guided isolation of daphnane-type diterpenes from Daphne genkwa by molecular network strategies. Phytochemistry. 2022 Jun; 198(?):113144. doi: 10.1016/j.phytochem.2022.113144. [PMID: 35283165]
  • Ahmed H H El-Desoky, Keisuke Eguchi, Naoki Kishimoto, Toshifumi Asano, Hikaru Kato, Yuki Hitora, Shunsuke Kotani, Teruya Nakamura, Soken Tsuchiya, Teppei Kawahara, Masato Watanabe, Mikiyo Wada, Makoto Nakajima, Takashi Watanabe, Shogo Misumi, Sachiko Tsukamoto. Isolation, Synthesis, and Structure-Activity Relationship Study on Daphnane and Tigliane Diterpenes as HIV Latency-Reversing Agents. Journal of medicinal chemistry. 2022 02; 65(4):3460-3472. doi: 10.1021/acs.jmedchem.1c01973. [PMID: 35113551]
  • Christian Bailly. Yuanhuacin and Related Anti-Inflammatory and Anticancer Daphnane Diterpenes from Genkwa Flos-An Overview. Biomolecules. 2022 01; 12(2):. doi: 10.3390/biom12020192. [PMID: 35204693]
  • Kouharu Otsuki, Mi Zhang, Takashi Kikuchi, Minami Tsuji, Miyuko Tejima, Zi-Song Bai, Di Zhou, Li Huang, Chin-Ho Chen, Kuo-Hsiung Lee, Ning Li, Kazuo Koike, Wei Li. Identification of anti-HIV macrocyclic daphnane orthoesters from Wikstroemia ligustrina by LC-MS analysis and phytochemical investigation. Journal of natural medicines. 2021 Sep; 75(4):1058-1066. doi: 10.1007/s11418-021-01551-9. [PMID: 34287744]
  • Shi-Fei Li, Xue Liang, Xing-Kang Wu, Xiang Gao, Li-Wei Zhang. Discovering the Mechanisms of Wikstroelide E as a Potential HIV-Latency-Reversing Agent by Transcriptome Profiling. Journal of natural products. 2021 04; 84(4):1022-1033. doi: 10.1021/acs.jnatprod.0c01039. [PMID: 33721994]
  • Rihan Xie, Guiyang Xia, Jianxun Zhu, Pengcheng Lin, Xiaona Fan, Jiachen Zi. Daphnane-type diterpenoids from Euphorbia fischeriana Steud and their cytotoxic activities. Fitoterapia. 2021 Mar; 149(?):104810. doi: 10.1016/j.fitote.2020.104810. [PMID: 33359422]
  • Yun-Yao Liu, Yan-Ping Liu, Xiao-Ping Wang, Ze-Hua Qiao, Xiao-Mei Yu, Yi-Zhu Zhu, Lan Xie, Lei Qiang, Yan-Hui Fu. Bioactive daphnane diterpenes from Wikstroemia chuii with their potential anti-inflammatory effects and anti-HIV activities. Bioorganic chemistry. 2020 12; 105(?):104388. doi: 10.1016/j.bioorg.2020.104388. [PMID: 33130343]
  • Rong-Rong Pan, Chun-Yan Zhang, Yuan Li, Bing-Bing Zhang, Liang Zhao, Ying Ye, Ya-Nan Song, Miao Zhang, Hong-Yun Tie, Hong Zhang, Jian-Yong Zhu. Daphnane Diterpenoids from Daphne genkwa Inhibit PI3K/Akt/mTOR Signaling and Induce Cell Cycle Arrest and Apoptosis in Human Colon Cancer Cells. Journal of natural products. 2020 04; 83(4):1238-1248. doi: 10.1021/acs.jnatprod.0c00003. [PMID: 32223193]
  • Hua-Ding Zhao, Yan Lu, Min Yan, Chin-Ho Chen, Susan L Morris-Natschke, Kuo-Hsiung Lee, Dao-Feng Chen. Rapid Recognition and Targeted Isolation of Anti-HIV Daphnane Diterpenes from Daphne genkwa Guided by UPLC-MSn. Journal of natural products. 2020 01; 83(1):134-141. doi: 10.1021/acs.jnatprod.9b00993. [PMID: 31860304]
  • José Manuel Calderón-Montaño, Sara María Martínez-Sánchez, Estefanía Burgos-Morón, Emilio Guillén-Mancina, Julio José Jiménez-Alonso, Felipe García, Abelardo Aparicio, Miguel López-Lázaro. Screening for selective anticancer activity of plants from Grazalema Natural Park, Spain. Natural product research. 2019 Dec; 33(23):3454-3458. doi: 10.1080/14786419.2018.1480620. [PMID: 29842791]
  • Yue-Xian Jin, Lei-Ling Shi, Da-Peng Zhang, Hong-Yan Wei, Yuan Si, Guo-Xu Ma, Jing Zhang. A Review on Daphnane-Type Diterpenoids and Their Bioactive Studies. Molecules (Basel, Switzerland). 2019 May; 24(9):. doi: 10.3390/molecules24091842. [PMID: 31086098]
  • Feng Liu, Xueyuan Yang, Yue Liang, Bangjian Dong, Guochen Su, Muhetaer Tuerhong, Da-Qing Jin, Jing Xu, Yuanqiang Guo. Daphnane diterpenoids with nitric oxide inhibitory activities and interactions with iNOS from the leaves of Trigonostemon thyrsoideus. Phytochemistry. 2018 Mar; 147(?):57-67. doi: 10.1016/j.phytochem.2017.12.010. [PMID: 29289737]
  • Baek-Soo Han, Kyoung-Shim Kim, Yu Jin Kim, Hoe-Yune Jung, Young-Mi Kang, Kyu-Suk Lee, Mi-Jin Sohn, Chun-Hyung Kim, Kwang-Soo Kim, Won-Gon Kim. Daphnane Diterpenes from Daphne genkwa Activate Nurr1 and Have a Neuroprotective Effect in an Animal Model of Parkinson's Disease. Journal of natural products. 2016 06; 79(6):1604-9. doi: 10.1021/acs.jnatprod.6b00110. [PMID: 27228307]
  • Daniel Kulakowski, Christopher Kitalong, Adam Negrin, Van-Ray Tadao, Michael J Balick, Edward J Kennelly. Traditional preparation of Phaleria nisidai, a Palauan tea, reduces exposure to toxic daphnane-type diterpene esters while maintaining immunomodulatory activity. Journal of ethnopharmacology. 2015 Sep; 173(?):273-9. doi: 10.1016/j.jep.2015.06.023. [PMID: 26102551]
  • Daniel M Kulakowski, Shi-Biao Wu, Michael J Balick, Edward J Kennelly. Merging bioactivity with liquid chromatography-mass spectrometry-based chemometrics to identify minor immunomodulatory compounds from a Micronesian adaptogen, Phaleria nisidai. Journal of chromatography. A. 2014 Oct; 1364(?):74-82. doi: 10.1016/j.chroma.2014.08.049. [PMID: 25218635]
  • Sheng-Zhuo Huang, Xuan Zhang, Qing-Yun Ma, Hua Peng, Yong-Tang Zheng, Jiang-Miao Hu, Hao-Fu Dai, Jun Zhou, You-Xing Zhao. Anti-HIV-1 tigliane diterpenoids from Excoecaria acertiflia Didr. Fitoterapia. 2014 Jun; 95(?):34-41. doi: 10.1016/j.fitote.2014.02.018. [PMID: 24613801]
  • Xu-Dong Zhang, Wei Ni, Huan Yan, Gen-Tao Li, Hui-Min Zhong, Yan Li, Hai-Yang Liu. Daphnane-type diterpenoid glucosides and further constituents of Euphorbia pilosa. Chemistry & biodiversity. 2014 May; 11(5):760-6. doi: 10.1002/cbdv.201300154. [PMID: 24827685]
  • Yuan-Yuan Cheng, Huan Chen, Hong-Ping He, Yu Zhang, Shi-Fei Li, Gui-Hua Tang, Ling-Li Guo, Wei Yang, Feng Zhu, Yong-Tang Zheng, Shun-Lin Li, Xiao-Jiang Hao. Anti-HIV active daphnane diterpenoids from Trigonostemon thyrsoideum. Phytochemistry. 2013 Dec; 96(?):360-9. doi: 10.1016/j.phytochem.2013.10.005. [PMID: 24210372]
  • Sheng Zhuo Huang, Xing Jie Zhang, Xing Yao Li, Ling Mei Kong, He Zhong Jiang, Qing Yun Ma, Yu Qing Liu, Jiang Miao Hu, Yong Tang Zheng, Yan Li, Jun Zhou, You Xing Zhao. Daphnane-type diterpene esters with cytotoxic and anti-HIV-1 activities from Daphne acutiloba Rehd. Phytochemistry. 2012 Mar; 75(?):99-107. doi: 10.1016/j.phytochem.2011.11.013. [PMID: 22196934]
  • Ling Zhang, Rong-Hua Luo, Fei Wang, Ze-Jun Dong, Liu-Meng Yang, Yong-Tang Zheng, Ji-Kai Liu. Daphnane diterpenoids isolated from Trigonostemon thyrsoideum as HIV-1 antivirals. Phytochemistry. 2010 Nov; 71(16):1879-83. doi: 10.1016/j.phytochem.2010.08.008. [PMID: 20810137]
  • Bing-Dong Lin, Mei-Ling Han, Yin-Chun Ji, Hua-Dong Chen, Sheng-Ping Yang, Sheng Zhang, Mei-Yu Geng, Jian-Min Yue. Trigoxyphins A-G: diterpenes from Trigonostemon xyphophylloides. Journal of natural products. 2010 Jul; 73(7):1301-5. doi: 10.1021/np100320h. [PMID: 20593838]
  • Sharon Chow, Mary T Fletcher, Ross A McKenzie. Analysis of daphnane orthoesters in poisonous Australian pimelea species by liquid chromatography-tandem mass spectrometry. Journal of agricultural and food chemistry. 2010 Jun; 58(12):7482-7. doi: 10.1021/jf101752r. [PMID: 20507137]
  • Noppamas Soonthornchareonnon, Monnun Sakayarojkul, Masahiko Isaka, Vanna Mahakittikun, Wongsatit Chuakul, Prapai Wongsinkongman. Acaricidal daphnane diterpenoids from Trigonostemon reidioides (KURZ) CRAIB roots. Chemical & pharmaceutical bulletin. 2005 Feb; 53(2):241-3. doi: 10.1248/cpb.53.241. [PMID: 15684528]
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  • L Saraiva, P Fresco, E Pinto, H Portugal, J Gonçalves. Differential activation by daphnetoxin and mezerein of PKC-isotypes alpha, beta I, delta and zeta. Planta medica. 2001 Dec; 67(9):787-90. doi: 10.1055/s-2001-18843. [PMID: 11745011]
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