Ophiobolin A (BioDeep_00000007196)
代谢物信息卡片
(+)-Ophiobolin A
化学式: C25H36O4 (400.2613)
中文名称: 蛇孢菌素A
谱图信息:
最多检出来源 Homo sapiens(lipidomics) 17.8%
分子结构信息
SMILES: CC(=C[C@H]1C[C@H](C)[C@]2(CC[C@]3(C)C[C@H]4[C@@H](C(=CC[C@@H]23)C=O)C(=O)C[C@@]4(C)O)O1)C
InChI: InChI=1S/C25H36O4/c1-15(2)10-18-11-16(3)25(29-18)9-8-23(4)12-19-22(20(27)13-24(19,5)28)17(14-26)6-7-21(23)25/h6,10,14,16,18-19,21-22,28H,7-9,11-13H2,1-5H3/b17-6-/t16-,18-,19-,21+,22+,23+,24+,25-/m0/s1
数据库引用编号
16 个数据库交叉引用编号
- ChEBI: CHEBI:7777
- KEGG: C09145
- PubChem: 5281387
- PubChem: 4598
- Metlin: METLIN41265
- ChEMBL: CHEMBL522808
- LipidMAPS: LMPR0105050001
- CAS: 4611-05-6
- PMhub: MS000095388
- PMhub: MS000020489
- PubChem: 11337
- KNApSAcK: C00003460
- 3DMET: B02716
- NIKKAJI: J14.566A
- RefMet: Ophiobolin A
- KNApSAcK: 7777
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)
5 个相关的物种来源信息
- 74410 - Bipolaris cookei: 10.1021/NP50065A046
- 5016 - Bipolaris maydis:
- 5016 - Bipolaris maydis: 10.1039/C29710000164
- 101162 - Bipolaris oryzae:
- 95732 - Bipolaris sorghicola: 10.1021/NP50065A046
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
- Maurizio Vurro, Helen E Townley, Rachel Morrison, Angela Boari, Marco Masi, Antonio Evidente. Augmented phytotoxic effect of nanoencapsulated ophiobolin A.
Natural product research.
2022 Mar; 36(5):1143-1150. doi:
10.1080/14786419.2020.1860975. [PMID: 33342291] - Mahnaz Amini, Yiming Chang, Ulrich Wissenbach, Veit Flockerzi, Gabriel Schlenstedt, Andreas Beck. Activity of the yeast vacuolar TRP channel TRPY1 is inhibited by Ca2+-calmodulin binding.
The Journal of biological chemistry.
2021 10; 297(4):101126. doi:
10.1016/j.jbc.2021.101126. [PMID: 34461097] - Shoji Maehara, Chihiro Yamane, Chinami Kitamura, Minako Hinokuma, Toshiyuki Hata. High ophiobolin A production in endophytic fungus Bipolaris sp. associated with Datura metel.
Natural product research.
2020 Oct; 34(20):2990-2992. doi:
10.1080/14786419.2019.1597352. [PMID: 30990079] - Danny Q Thach, Zachary G Brill, Huck K Grover, Kenneth V Esguerra, Jordan K Thompson, Thomas J Maimone. Total Synthesis of (+)-6-epi-Ophiobolin A.
Angewandte Chemie (International ed. in English).
2020 01; 59(4):1532-1536. doi:
10.1002/anie.201913150. [PMID: 31693792] - Marco Masi, Ramesh Dasari, Antonio Evidente, Veronique Mathieu, Alexander Kornienko. Chemistry and biology of ophiobolin A and its congeners.
Bioorganic & medicinal chemistry letters.
2019 04; 29(7):859-869. doi:
10.1016/j.bmcl.2019.02.007. [PMID: 30765189] - Anikó Pósa, Renáta Szabó, Zita Szalai, Krisztina Kupai, Zoltán Deim, Zsolt Murlasits, Ottó Bencsik, András Szekeres, Csaba Vágvölgyi, László Balogh, Béla Juhász, Zoltán Szilvássy, Csaba Varga. The effect of acute ophiobolin A treatment on HO-mediated inflammatory processes.
Human & experimental toxicology.
2017 Jun; 36(6):594-602. doi:
10.1177/0960327116658107. [PMID: 27402683] - Christopher Chidley, Sunia A Trauger, Kıvanç Birsoy, Erin K O'Shea. The anticancer natural product ophiobolin A induces cytotoxicity by covalent modification of phosphatidylethanolamine.
eLife.
2016 07; 5(?):. doi:
10.7554/elife.14601. [PMID: 27403889] - Vittoria Locato, Esther Novo Uzal, Sara Cimini, Maria Chiara Zonno, Antonio Evidente, Alessandra Micera, Christine H Foyer, Laura De Gara. Low concentrations of the toxin ophiobolin A lead to an arrest of the cell cycle and alter the intracellular partitioning of glutathione between the nuclei and cytoplasm.
Journal of experimental botany.
2015 May; 66(10):2991-3000. doi:
10.1093/jxb/erv110. [PMID: 25890975] - Ottó Bencsik, Tamás Papp, Máté Berta, Annamária Zana, Péter Forgó, György Dombi, Maria A Andersson, Mirja Salkinoja-Salonen, Csaba Vágvölgyi, András Szekeres. Ophiobolin A from Bipolaris oryzae perturbs motility and membrane integrities of porcine sperm and induces cell death on mammalian somatic cell lines.
Toxins.
2014 Sep; 6(9):2857-71. doi:
10.3390/toxins6092857. [PMID: 25251540] - Marina Bury, Esther Novo-Uzal, Anna Andolfi, Sara Cimini, Nathalie Wauthoz, Petra Heffeter, Benjamin Lallemand, Fabiana Avolio, Cédric Delporte, Alessio Cimmino, Jacques Dubois, Pierre Van Antwerpen, Maria Chiara Zonno, Maurizio Vurro, Yves Poumay, Walter Berger, Antonio Evidente, Laura De Gara, Robert Kiss, Vittoria Locato. Ophiobolin A, a sesterterpenoid fungal phytotoxin, displays higher in vitro growth-inhibitory effects in mammalian than in plant cells and displays in vivo antitumor activity.
International journal of oncology.
2013 Aug; 43(2):575-85. doi:
10.3892/ijo.2013.1979. [PMID: 23754298] - Sabine Kuhn, Johanna Bussemer, Fatima Chigri, Ute C Vothknecht. Calcium depletion and calmodulin inhibition affect the import of nuclear-encoded proteins into plant mitochondria.
The Plant journal : for cell and molecular biology.
2009 May; 58(4):694-705. doi:
10.1111/j.1365-313x.2009.03810.x. [PMID: 19175770] - Mónica Fernández-Aparicio, Anna Andolfi, Alessio Cimmino, Diego Rubiales, Antonio Evidente. Stimulation of seed germination of Orobanche species by ophiobolin A and fusicoccin derivatives.
Journal of agricultural and food chemistry.
2008 Sep; 56(18):8343-7. doi:
10.1021/jf801727y. [PMID: 18763781] - Naoko Yoshida, Mariya Koizumi, Isao Adachi, Junichi Kawakami. Inhibition of P-glycoprotein-mediated transport by terpenoids contained in herbal medicines and natural products.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2006 Dec; 44(12):2033-9. doi:
10.1016/j.fct.2006.07.003. [PMID: 16904803] - Luc De Vries, Christiane Palmier, Frederic Finana, Bruno Le Grand, Michel Perez, Didier Cussac. Pharmacological characterization of protease activated receptor-1 by a serum responsive element-dependent reporter gene assay: major role of calmodulin.
Biochemical pharmacology.
2006 May; 71(10):1449-58. doi:
10.1016/j.bcp.2006.02.001. [PMID: 16524561] - Antonio Evidente, Anna Andolfi, Alessio Cimmino, Maurizio Vurro, Mariano Fracchiolla, Raghavan Charudattan. Herbicidal potential of ophiobolins produced by Drechslera gigantea.
Journal of agricultural and food chemistry.
2006 Mar; 54(5):1779-83. doi:
10.1021/jf052843l. [PMID: 16506833] - Fatima Chigri, Jürgen Soll, Ute C Vothknecht. Calcium regulation of chloroplast protein import.
The Plant journal : for cell and molecular biology.
2005 Jun; 42(6):821-31. doi:
10.1111/j.1365-313x.2005.02414.x. [PMID: 15941396] - Stephanie Quetglas, Cecile Iborra, Nobuyuki Sasakawa, Luc De Haro, Konosuke Kumakura, Kazuki Sato, Christian Leveque, Michael Seagar. Calmodulin and lipid binding to synaptobrevin regulates calcium-dependent exocytosis.
The EMBO journal.
2002 Aug; 21(15):3970-9. doi:
10.1093/emboj/cdf404. [PMID: 12145198] - S C Lee, Y H Lee. Calcium/calmodulin-dependent signaling for appressorium formation in the plant pathogenic fungus Magnaporthe grisea.
Molecules and cells.
1998 Dec; 8(6):698-704. doi:
". [PMID: 9895122] - R Pu, K R Robinson. Cytoplasmic calcium gradients and calmodulin in the early development of the fucoid alga Pelvetia compressa.
Journal of cell science.
1998 Nov; 111 ( Pt 21)(?):3197-207. doi:
10.1242/jcs.111.21.3197. [PMID: 9763514] - T Kong Au, P Chow Leung. Identification of the binding and inhibition sites in the calmodulin molecule for ophiobolin A by site-directed mutagenesis.
Plant physiology.
1998 Nov; 118(3):965-73. doi:
10.1104/pp.118.3.965. [PMID: 9808741] - P C Leung, W A Taylor, J H Wang, C L Tipton. Ophiobolin A. A natural product inhibitor of calmodulin.
The Journal of biological chemistry.
1984 Mar; 259(5):2742-7. doi:
. [PMID: 6321479]
