(-)-Germacrene A (BioDeep_00001029299)
natural product
代谢物信息卡片
(-)-Germacrene A
化学式: C15H24 (204.18779039999998)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C=C(C)[C@@H]1C/C=C(\C)CC/C=C(\C)CC1
InChI: InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h6,9,15H,1,5,7-8,10-11H2,2-4H3/b13-6+,14-9+/t15-/m0/s1
数据库引用编号
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)
100 个相关的物种来源信息
- 182998 - Acanthospermum: LTS0022487
- 185140 - Acanthospermum australe: 10.1021/NP50050A054
- 185140 - Acanthospermum australe: LTS0022487
- 13328 - Achillea: LTS0022487
- 133233 - Achillea ptarmica: LTS0022487
- 42228 - Acoraceae: LTS0022487
- 4464 - Acorus: LTS0022487
- 4465 - Acorus calamus: 10.1016/J.PHYTOCHEM.2005.01.007
- 4465 - Acorus calamus: LTS0022487
- 105887 - Aloysia: LTS0022487
- 6101 - Anthozoa: LTS0022487
- 12947 - Aristolochia: 10.17660/ACTAHORTIC.1999.500.11
- 12947 - Aristolochia: LTS0022487
- 158540 - Aristolochia cymbifera: 10.17660/ACTAHORTIC.1999.500.11
- 158540 - Aristolochia cymbifera: LTS0022487
- 12948 - Aristolochia gigantea: 10.17660/ACTAHORTIC.1999.500.11
- 12948 - Aristolochia gigantea: LTS0022487
- 158554 - Aristolochia macroura: 10.17660/ACTAHORTIC.1999.500.11
- 158554 - Aristolochia macroura: LTS0022487
- 158574 - Aristolochia triangularis: 10.17660/ACTAHORTIC.1999.500.11
- 158574 - Aristolochia triangularis: LTS0022487
- 16727 - Aristolochiaceae: LTS0022487
- 6656 - Arthropoda: LTS0022487
- 4210 - Asteraceae: LTS0022487
- 4014 - Burseraceae: LTS0022487
- 6073 - Cnidaria: LTS0022487
- 100370 - Croton: LTS0022487
- 2815084 - Croton nepetifolius: LTS0022487
- 6970 - Dictyoptera: LTS0022487
- 112054 - Dictyopteris: LTS0022487
- 156996 - Dictyopteris divaricata: 10.1016/0031-9422(90)80058-O
- 156996 - Dictyopteris divaricata: LTS0022487
- 2874 - Dictyotaceae: LTS0022487
- 2759 - Eukaryota: LTS0022487
- 86557 - Eunicea: LTS0022487
- 437161 - Eunicea mammosa: 10.1016/0040-4039(70)89009-8
- 437161 - Eunicea mammosa: LTS0022487
- 287898 - Eunicea succinea: 10.1021/NP50034A007
- 287898 - Eunicea succinea: LTS0022487
- 3977 - Euphorbiaceae: LTS0022487
- 95763 - Frullania: LTS0022487
- 95764 - Frullania tamarisci: 10.1016/S0031-9422(01)00018-8
- 95764 - Frullania tamarisci: LTS0022487
- 400721 - Frullaniaceae: LTS0022487
- 204122 - Hyptis: LTS0022487
- 50557 - Insecta: LTS0022487
- 186771 - Jungermanniopsida: LTS0022487
- 4136 - Lamiaceae: LTS0022487
- 4447 - Liliopsida: LTS0022487
- 434676 - Linzia: LTS0022487
- 82756 - Linzia glabra: 10.1016/0031-9422(83)80212-X
- 82756 - Linzia glabra: LTS0022487
- 3402 - Magnolia: LTS0022487
- 85868 - Magnolia sieboldii: 10.1021/NP960452I
- 85868 - Magnolia sieboldii: LTS0022487
- 3401 - Magnoliaceae: LTS0022487
- 3398 - Magnoliopsida: LTS0022487
- 3195 - Marchantiophyta: LTS0022487
- 21819 - Mentha: LTS0022487
- 34256 - Mentha × piperita: 10.1080/10412905.1993.9698164
- 33208 - Metazoa: LTS0022487
- 46570 - Nasutitermes: LTS0022487
- 2949555 - Nasutitermes gracilirostris: LTS0022487
- 114639 - Nasutitermes novarumhebridarum: 10.1007/BF00980588
- 114639 - Nasutitermes novarumhebridarum: LTS0022487
- 1962918 - Nasutitermes torresi: 10.1007/BF00980588
- 1962918 - Nasutitermes torresi: LTS0022487
- 114645 - Nasutitermes triodiae: 10.1007/BF00980588
- 114645 - Nasutitermes triodiae: LTS0022487
- 2696291 - Ochrophyta: LTS0022487
- 39173 - Ocimum: LTS0022487
- 39350 - Ocimum basilicum: 10.1080/10412905.1995.9698501
- 39350 - Ocimum basilicum: LTS0022487
- 2870 - Phaeophyceae: LTS0022487
- 58019 - Pinopsida: LTS0022487
- 13215 - Piper: LTS0022487
- 425145 - Piper cernuum: 10.1055/S-2001-18363
- 425145 - Piper cernuum: LTS0022487
- 16739 - Piperaceae: LTS0022487
- 44191 - Plexauridae: LTS0022487
- 3362 - Podocarpaceae: LTS0022487
- 173697 - Protium: LTS0022487
- 246847 - Protium heptaphyllum: 10.1080/10412905.1995.9698581
- 246847 - Protium heptaphyllum: LTS0022487
- 56902 - Prumnopitys: LTS0022487
- 120636 - Prumnopitys ferruginoides: 10.1080/10412905.1994.9699344
- 904557 - Rugelia: LTS0022487
- 904558 - Rugelia nudicaulis: 10.1016/S0031-9422(82)85037-1
- 904558 - Rugelia nudicaulis: LTS0022487
- 41629 - Saussurea: LTS0022487
- 324593 - Saussurea costus: 10.1016/S0031-9422(01)00291-6
- 324593 - Saussurea costus: LTS0022487
- 35493 - Streptophyta: LTS0022487
- 46569 - Termitidae: LTS0022487
- 183090 - Tilesia: LTS0022487
- 183091 - Tilesia baccata: 10.1080/10412905.2000.9699552
- 183091 - Tilesia baccata: LTS0022487
- 58023 - Tracheophyta: LTS0022487
- 21910 - Verbenaceae: LTS0022487
- 33090 - Viridiplantae: LTS0022487
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
- Houchao Xu, Tobias G Köllner, Feng Chen, Jeroen S Dickschat. Functional and Mechanistic Characterization of the 4,5-diepi-Isoishwarane Synthase from the Liverwort Radula lindenbergiana.
Chembiochem : a European journal of chemical biology.
2024 Apr; 25(8):e202400104. doi:
10.1002/cbic.202400104. [PMID: 38372483] - N R Kiran, Ananth Krishna Narayanan, Soumyajit Mohapatra, Priyanka Gupta, Dinesh A Nagegowda. Analysis of root volatiles and functional characterization of a root-specific germacrene A synthase in Artemisia pallens.
Planta.
2024 Feb; 259(3):58. doi:
10.1007/s00425-024-04334-0. [PMID: 38308700] - Wenjuan Li, Jie Mai, Lu Lin, Zhi-Gang Zhang, Rodrigo Ledesma-Amaro, Weiliang Dong, Xiao-Jun Ji. Combination of microbial and chemical synthesis for the sustainable production of β-elemene, a promising plant-extracted anticancer compound.
Biotechnology and bioengineering.
2023 Sep; ?(?):. doi:
10.1002/bit.28544. [PMID: 37661795] - Eric Fordjour, Chun-Li Liu, Yunpeng Hao, Isaac Sackey, Yankun Yang, Xiuxia Liu, Ye Li, Tianwei Tan, Zhonghu Bai. Engineering Escherichia coli BL21 (DE3) for high-yield production of germacrene A, a precursor of β-elemene via combinatorial metabolic engineering strategies.
Biotechnology and bioengineering.
2023 Jun; ?(?):. doi:
10.1002/bit.28467. [PMID: 37309999] - Dong-Mei Xie, Qiang Zhang, Ling-Kai Xin, Guo-Kai Wang, Cong-Bin Liu, Min-Jian Qin. Cloning and Functional Characterization of Two Germacrene A Oxidases Isolated from Xanthium sibiricum.
Molecules (Basel, Switzerland).
2022 May; 27(10):. doi:
10.3390/molecules27103322. [PMID: 35630799] - Katarina Cankar, Paul Bundock, Robert Sevenier, Suvi T Häkkinen, Johanna Christina Hakkert, Jules Beekwilder, Ingrid M van der Meer, Michiel de Both, Dirk Bosch. Inactivation of the germacrene A synthase genes by CRISPR/Cas9 eliminates the biosynthesis of sesquiterpene lactones in Cichorium intybus L.
Plant biotechnology journal.
2021 12; 19(12):2442-2453. doi:
10.1111/pbi.13670. [PMID: 34270859] - Milica Bogdanović, Katarina Cankar, Milan Dragićević, Harro Bouwmeester, Jules Beekwilder, Ana Simonović, Slađana Todorović. Silencing of germacrene A synthase genes reduces guaianolide oxalate content in Cichorium intybus L.
GM crops & food.
2020; 11(1):54-66. doi:
10.1080/21645698.2019.1681868. [PMID: 31668117] - Trinh-Don Nguyen, Moonhyuk Kwon, Soo-Un Kim, Conrad Fischer, Dae-Kyun Ro. Catalytic Plasticity of Germacrene A Oxidase Underlies Sesquiterpene Lactone Diversification.
Plant physiology.
2019 11; 181(3):945-960. doi:
10.1104/pp.19.00629. [PMID: 31534022] - Junbo Gou, Fuhua Hao, Chongyang Huang, Moonhyuk Kwon, Fangfang Chen, Changfu Li, Chaoyang Liu, Dae-Kyun Ro, Huiru Tang, Yansheng Zhang. Discovery of a non-stereoselective cytochrome P450 catalyzing either 8α- or 8β-hydroxylation of germacrene A acid from the Chinese medicinal plant, Inula hupehensis.
The Plant journal : for cell and molecular biology.
2018 Jan; 93(1):92-106. doi:
10.1111/tpj.13760. [PMID: 29086444] - Stéphane G Gooré, Zana A Ouattara, Thierry A Yapi, Yves-Alain Békro, Pierre Tomi, Mathieu Paoli, Félix Tomi. Chemical composition of Ivorian Artabotrys insignis leaf oil. Combined analysis including 13C NMR, to quantify germacrene A and β-elemene.
Natural product research.
2017 Aug; 31(15):1836-1839. doi:
10.1080/14786419.2017.1292269. [PMID: 28278653] - Yating Hu, Yongjin J Zhou, Jichen Bao, Luqi Huang, Jens Nielsen, Anastasia Krivoruchko. Metabolic engineering of Saccharomyces cerevisiae for production of germacrene A, a precursor of beta-elemene.
Journal of industrial microbiology & biotechnology.
2017 07; 44(7):1065-1072. doi:
10.1007/s10295-017-1934-z. [PMID: 28547322] - Trinh-Don Nguyen, Juan A Faraldos, Maria Vardakou, Melissa Salmon, Paul E O'Maille, Dae-Kyun Ro. Discovery of germacrene A synthases in Barnadesia spinosa: The first committed step in sesquiterpene lactone biosynthesis in the basal member of the Asteraceae.
Biochemical and biophysical research communications.
2016 Oct; 479(4):622-627. doi:
10.1016/j.bbrc.2016.09.165. [PMID: 27697527] - Marimuthu Govindarajan, Mohan Rajeswary, Giovanni Benelli. Chemical composition, toxicity and non-target effects of Pinus kesiya essential oil: An eco-friendly and novel larvicide against malaria, dengue and lymphatic filariasis mosquito vectors.
Ecotoxicology and environmental safety.
2016 Jul; 129(?):85-90. doi:
10.1016/j.ecoenv.2016.03.007. [PMID: 26995063] - A B Bombo, B Appezzato-da-Glória, A-K Aschenbrenner, O Spring. Capitate glandular trichomes in Aldama discolor (Heliantheae - Asteraceae): morphology, metabolite profile and sesquiterpene biosynthesis.
Plant biology (Stuttgart, Germany).
2016 May; 18(3):455-62. doi:
10.1111/plb.12423. [PMID: 26642998] - Veronica Gonzalez, Sabrina Touchet, Daniel J Grundy, Juan A Faraldos, Rudolf K Allemann. Evolutionary and mechanistic insights from the reconstruction of α-humulene synthases from a modern (+)-germacrene A synthase.
Journal of the American Chemical Society.
2014 Oct; 136(41):14505-12. doi:
10.1021/ja5066366. [PMID: 25230152] - Kaouthar Eljounaidi, Katarina Cankar, Cinzia Comino, Andrea Moglia, Alain Hehn, Frédéric Bourgaud, Harro Bouwmeester, Barbara Menin, Sergio Lanteri, Jules Beekwilder. Cytochrome P450s from Cynara cardunculus L. CYP71AV9 and CYP71BL5, catalyze distinct hydroxylations in the sesquiterpene lactone biosynthetic pathway.
Plant science : an international journal of experimental plant biology.
2014 Jun; 223(?):59-68. doi:
10.1016/j.plantsci.2014.03.007. [PMID: 24767116] - Oscar Cascón, Sabrina Touchet, David J Miller, Veronica Gonzalez, Juan A Faraldos, Rudolf K Allemann. Chemoenzymatic preparation of germacrene analogues.
Chemical communications (Cambridge, England).
2012 Oct; 48(78):9702-4. doi:
10.1039/c2cc35542f. [PMID: 22914774] - Nobuhiro Ikezawa, Jens Christian Göpfert, Don Trinh Nguyen, Soo-Un Kim, Paul E O'Maille, Otmar Spring, Dae-Kyun Ro. Lettuce costunolide synthase (CYP71BL2) and its homolog (CYP71BL1) from sunflower catalyze distinct regio- and stereoselective hydroxylations in sesquiterpene lactone metabolism.
The Journal of biological chemistry.
2011 Jun; 286(24):21601-11. doi:
10.1074/jbc.m110.216804. [PMID: 21515683] - Katarina Cankar, Adèle van Houwelingen, Dirk Bosch, Theo Sonke, Harro Bouwmeester, Jules Beekwilder. A chicory cytochrome P450 mono-oxygenase CYP71AV8 for the oxidation of (+)-valencene.
FEBS letters.
2011 Jan; 585(1):178-82. doi:
10.1016/j.febslet.2010.11.040. [PMID: 21115006] - Qing Liu, Mohammad Majdi, Katarina Cankar, Miriam Goedbloed, Tatsiana Charnikhova, Francel W A Verstappen, Ric C H de Vos, Jules Beekwilder, Sander van der Krol, Harro J Bouwmeester. Reconstitution of the costunolide biosynthetic pathway in yeast and Nicotiana benthamiana.
PloS one.
2011; 6(8):e23255. doi:
10.1371/journal.pone.0023255. [PMID: 21858047] - Don Trinh Nguyen, Jens Christian Göpfert, Nobuhiro Ikezawa, Gillian Macnevin, Meena Kathiresan, Jürgen Conrad, Otmar Spring, Dae-Kyun Ro. Biochemical conservation and evolution of germacrene A oxidase in asteraceae.
The Journal of biological chemistry.
2010 May; 285(22):16588-98. doi:
10.1074/jbc.m110.111757. [PMID: 20351109] - Yung-Jin Chang, Jianming Jin, Hee-Young Nam, Soo-Un Kim. Point mutation of (+)-germacrene A synthase from Ixeris dentata.
Biotechnology letters.
2005 Mar; 27(5):285-8. doi:
10.1007/s10529-005-0681-9. [PMID: 15834787] - Yonggen Lou, Ian T Baldwin. Nitrogen supply influences herbivore-induced direct and indirect defenses and transcriptional responses in Nicotiana attenuata.
Plant physiology.
2004 May; 135(1):496-506. doi:
10.1104/pp.104.040360. [PMID: 15133153] - Asaph Aharoni, Ashok P Giri, Stephan Deuerlein, Frans Griepink, Willem-Jan de Kogel, Francel W A Verstappen, Harrie A Verhoeven, Maarten A Jongsma, Wilfried Schwab, Harro J Bouwmeester. Terpenoid metabolism in wild-type and transgenic Arabidopsis plants.
The Plant cell.
2003 Dec; 15(12):2866-84. doi:
10.1105/tpc.016253. [PMID: 14630967] - Bryan T Greenhagen, Paul Griggs, Shunji Takahashi, Lyle Ralston, Joe Chappell. Probing sesquiterpene hydroxylase activities in a coupled assay with terpene synthases.
Archives of biochemistry and biophysics.
2003 Jan; 409(2):385-94. doi:
10.1016/s0003-9861(02)00613-6. [PMID: 12504906] - D Yang, F Wang, J Peng, S Ren. [GC-MS analysis and inhibitory activity of the essential oil extracted from the leaves of Lindera communis].
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials.
1999 Mar; 22(3):128-31. doi:
". [PMID: 12575094]