secologanin (BioDeep_00000000682)

 

Secondary id: BioDeep_00000017440, BioDeep_00000404134

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

化学式: C17H24O10 (388.1369)
中文名称: 裂番木鳖苷, 断马钱子苷
谱图信息: 最多检出来源 Viridiplantae(plant) 24.95%

分子结构信息

SMILES: C=CC1C(OC2OC(CO)C(O)C(O)C2O)OC=C(C(=O)OC)C1CC=O
InChI: InChI=1S/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3/t8-,9+,11-,12-,13+,14-,16+,17+/m1/s1

描述信息

Secologanin is a member of the class of compounds known as terpene glycosides. Terpene glycosides are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Thus, secologanin is considered to be an isoprenoid lipid molecule. Secologanin is soluble (in water) and a very weakly acidic compound (based on its pKa). Secologanin can be found in a number of food items such as oyster mushroom, flaxseed, nectarine, and cereals and cereal products, which makes secologanin a potential biomarker for the consumption of these food products. Secologanin is a secoiridoid monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with dopamine or tryptamine to form ipecac and terpene indole alkaloids, respectively .
Secologanin, a secoiridoid glucoside, is a pivotal terpenoid intermediate in the biosynthesis of biologically active monoterpenoid indole alkaloids such as reserpine, ajmaline, and vinblastine. Secologanin synthase (cytochrome P450 isoform CYP72A1) catalyzes the oxidative cleavage of loganin into Secologanin[1][2].
Secologanin, a secoiridoid glucoside, is a pivotal terpenoid intermediate in the biosynthesis of biologically active monoterpenoid indole alkaloids such as reserpine, ajmaline, and vinblastine. Secologanin synthase (cytochrome P450 isoform CYP72A1) catalyzes the oxidative cleavage of loganin into Secologanin[1][2].

同义名列表

23 个代谢物同义名

methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate; Methyl (2S,3R,4S)-4-(formylmethyl)-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylic acid; METHYL (2S,3R,4S)-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylic acid; Methyl (2S,3R,4S)-4-(formylmethyl)-2-(b-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylic acid; Methyl (2S,3R,4S)-4-(formylmethyl)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylic acid; 3-Ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylic acid, methyl ester; methyl (2S,3R,4S)-4-(formylmethyl)-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate; METHYL (2S,3R,4S)-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylic acid; METHYL (2S,3R,4S)-2-(b-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylic acid; METHYL (2S,3R,4S)-2-(BETA-D-GLUCOPYRANOSYLOXY)-4-(2-OXOETHYL)-3-VINYL-3,4-DIHYDRO-2H-PYRAN-5-CARBOXYLATE; 3-Ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylic acid, methyl ester; Methyl (2S,3R,4S)-4-(formylmethyl)-2-(b-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate; 3-Ethenyl-2-(b-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylic acid, methyl ester; Methyl (2S,3R,4S)-4-(formylmethyl)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate; 3-Ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylate, methyl ester; METHYL (2S,3R,4S)-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate; METHYL (2S,3R,4S)-2-(b-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate; 3-Ethenyl-2-(b-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylate, methyl ester; 3-Ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylate, methyl ester; (-)-Secologanin; Secologanin; NSC640525; Secologanin



数据库引用编号

24 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(3)

PlantCyc(2)

代谢反应

240 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(3)

WikiPathways(0)

Plant Reactome(231)

INOH(0)

PlantCyc(5)

COVID-19 Disease Map(0)

PathBank(1)

PharmGKB(0)

156 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
Cytoplasm 4 ACE, ACLY, CYP2E1, ZMYND8
Peripheral membrane protein 3 CYP1B1, CYP2E1, GBA1
Endoplasmic reticulum membrane 5 CYP1A2, CYP1B1, CYP2E1, RTN3, UGT8
Nucleus 2 TOP1, ZMYND8
cytosol 3 ACACA, ACLY, GSR
trans-Golgi network 1 GBA1
nucleoplasm 3 ACLY, TOP1, ZMYND8
Cell membrane 1 ACE
Multi-pass membrane protein 1 RTN3
Golgi apparatus membrane 1 RTN3
dendritic shaft 1 ZMYND8
Golgi apparatus 2 GBA1, RTN3
Golgi membrane 1 RTN3
lysosomal membrane 2 GAA, GBA1
mitochondrial inner membrane 1 CYP2E1
Cytoplasm, cytosol 2 ACACA, ACLY
Lysosome 3 ACE, GAA, GBA1
endosome 1 ACE
plasma membrane 3 ACE, GAA, RTN3
Membrane 5 ACE, ACLY, CYP1B1, GAA, UGT8
extracellular exosome 5 ACE, ACLY, GAA, GBA1, GSR
Lysosome membrane 2 GAA, GBA1
Lumenal side 1 GBA1
endoplasmic reticulum 3 GBA1, RTN3, UGT8
extracellular space 3 ACE, ARTN, RTN3
lysosomal lumen 2 GAA, GBA1
mitochondrion 3 ACACA, CYP1B1, GSR
intracellular membrane-bounded organelle 4 CYP1A2, CYP1B1, CYP2E1, GAA
Microsome membrane 3 CYP1A2, CYP1B1, CYP2E1
postsynaptic density 1 RTN3
Single-pass type I membrane protein 1 ACE
Secreted 3 ACE, ARTN, GAA
extracellular region 4 ACE, ACLY, ARTN, GAA
Single-pass membrane protein 1 UGT8
mitochondrial matrix 1 GSR
external side of plasma membrane 2 ACE, GSR
actin cytoskeleton 1 ACACA
dendritic spine 1 ZMYND8
perikaryon 1 TOP1
nucleolus 2 TOP1, ZMYND8
P-body 1 TOP1
Mitochondrion inner membrane 1 CYP2E1
neuron projection 1 RTN3
chromatin 1 ZMYND8
Chromosome 2 TOP1, ZMYND8
brush border membrane 1 ACE
Nucleus, nucleolus 1 TOP1
sperm midpiece 1 ACE
fibrillar center 2 ACACA, TOP1
Nucleus, nucleoplasm 1 TOP1
tertiary granule membrane 1 GAA
basal plasma membrane 1 ACE
ficolin-1-rich granule lumen 1 ACLY
male germ cell nucleus 1 TOP1
azurophil granule membrane 1 GAA
azurophil granule lumen 1 ACLY
protein-DNA complex 1 TOP1
ficolin-1-rich granule membrane 1 GAA
site of DNA damage 1 ZMYND8
autolysosome lumen 1 GAA
[Angiotensin-converting enzyme, soluble form]: Secreted 1 ACE
[Isoform Testis-specific]: Cell membrane 1 ACE


文献列表

  • Justin C Miller, Mary A Schuler. Single mutations toggle the substrate selectivity of multifunctional Camptotheca secologanic acid synthases. The Journal of biological chemistry. 2022 09; 298(9):102237. doi: 10.1016/j.jbc.2022.102237. [PMID: 35809640]
  • Yang Yu, Mei-Fen Bao, Jing Wu, Jing Chen, Yu-Rong Yang, Johann Schinnerl, Xiang-Hai Cai. Tabernabovines A-C: Three Monoterpenoid Indole Alkaloids from the Leaves of Tabernaemontana bovina. Organic letters. 2019 08; 21(15):5938-5942. doi: 10.1021/acs.orglett.9b02060. [PMID: 31294995]
  • Trevor Kidd, Michael Lae Easson, Yang Qu, Vincenzo De Luca. Inter-organ transport of secologanin allows assembly of monoterpenoid indole alkaloids in a Catharanthus roseus mutant. Phytochemistry. 2019 Mar; 159(?):119-126. doi: 10.1016/j.phytochem.2018.12.017. [PMID: 30611871]
  • Chunyan Jiao, Cheng Song, Siyan Zheng, Yingpeng Zhu, Qing Jin, Yongping Cai, Yi Lin. Metabolic Profiling of Dendrobium officinale in Response to Precursors and Methyl Jasmonate. International journal of molecular sciences. 2018 Mar; 19(3):. doi: 10.3390/ijms19030728. [PMID: 29510516]
  • Jonathan J Powell, Jason Carere, Gaurav Sablok, Timothy L Fitzgerald, Jiri Stiller, Michelle L Colgrave, Donald M Gardiner, John M Manners, John P Vogel, Robert J Henry, Kemal Kazan. Transcriptome analysis of Brachypodium during fungal pathogen infection reveals both shared and distinct defense responses with wheat. Scientific reports. 2017 12; 7(1):17212. doi: 10.1038/s41598-017-17454-3. [PMID: 29222453]
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  • Vonny Salim, Brent Wiens, Sayaka Masada-Atsumi, Fang Yu, Vincenzo De Luca. 7-deoxyloganetic acid synthase catalyzes a key 3 step oxidation to form 7-deoxyloganetic acid in Catharanthus roseus iridoid biosynthesis. Phytochemistry. 2014 May; 101(?):23-31. doi: 10.1016/j.phytochem.2014.02.009. [PMID: 24594312]
  • Keisuke Asada, Vonny Salim, Sayaka Masada-Atsumi, Elizabeth Edmunds, Mai Nagatoshi, Kazuyoshi Terasaka, Hajime Mizukami, Vincenzo De Luca. A 7-deoxyloganetic acid glucosyltransferase contributes a key step in secologanin biosynthesis in Madagascar periwinkle. The Plant cell. 2013 Oct; 25(10):4123-34. doi: 10.1105/tpc.113.115154. [PMID: 24104568]
  • Liqun Xia, Martin Ruppert, Meitian Wang, Santosh Panjikar, Haili Lin, Chitra Rajendran, Leif Barleben, Joachim Stöckigt. Structures of alkaloid biosynthetic glucosidases decode substrate specificity. ACS chemical biology. 2012 Jan; 7(1):226-34. doi: 10.1021/cb200267w. [PMID: 22004291]
  • Md Sarfaraj Hussain, Sheeba Fareed, Saba Ansari, Md Akhlaquer Rahman, Iffat Zareen Ahmad, Mohd Saeed. Current approaches toward production of secondary plant metabolites. Journal of pharmacy & bioallied sciences. 2012 Jan; 4(1):10-20. doi: 10.4103/0975-7406.92725. [PMID: 22368394]
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  • Yongzhen Sun, Hongmei Luo, Ying Li, Chao Sun, Jingyuan Song, Yunyun Niu, Yingjie Zhu, Liang Dong, Aiping Lv, Enzo Tramontano, Shilin Chen. Pyrosequencing of the Camptotheca acuminata transcriptome reveals putative genes involved in camptothecin biosynthesis and transport. BMC genomics. 2011 Oct; 12(?):533. doi: 10.1186/1471-2164-12-533. [PMID: 22035094]
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  • Grégory Guirimand, Anthony Guihur, Olivia Ginis, Pierre Poutrain, François Héricourt, Audrey Oudin, Arnaud Lanoue, Benoit St-Pierre, Vincent Burlat, Vincent Courdavault. The subcellular organization of strictosidine biosynthesis in Catharanthus roseus epidermis highlights several trans-tonoplast translocations of intermediate metabolites. The FEBS journal. 2011 Mar; 278(5):749-63. doi: 10.1111/j.1742-4658.2010.07994.x. [PMID: 21205206]
  • Lifang Hu, Wanqi Liang, Changsong Yin, Xiao Cui, Jie Zong, Xing Wang, Jianping Hu, Dabing Zhang. Rice MADS3 regulates ROS homeostasis during late anther development. The Plant cell. 2011 Feb; 23(2):515-33. doi: 10.1105/tpc.110.074369. [PMID: 21297036]
  • Hongmei Luo, Ying Li, Chao Sun, Qiong Wu, Jingyuan Song, Yongzhen Sun, André Steinmetz, Shilin Chen. Comparison of 454-ESTs from Huperzia serrata and Phlegmariurus carinatus reveals putative genes involved in lycopodium alkaloid biosynthesis and developmental regulation. BMC plant biology. 2010 Sep; 10(?):209. doi: 10.1186/1471-2229-10-209. [PMID: 20854695]
  • Grégory Guirimand, Vincent Courdavault, Arnaud Lanoue, Samira Mahroug, Anthony Guihur, Nathalie Blanc, Nathalie Giglioli-Guivarc'h, Benoit St-Pierre, Vincent Burlat. Strictosidine activation in Apocynaceae: towards a "nuclear time bomb"?. BMC plant biology. 2010 Aug; 10(?):182. doi: 10.1186/1471-2229-10-182. [PMID: 20723215]
  • Taiji Nomura, Toni M Kutchan. Is a metabolic enzyme complex involved in the efficient and accurate control of Ipecac alkaloid biosynthesis in Psychotria ipecacuanha?. Plant signaling & behavior. 2010 Jul; 5(7):875-7. doi: 10.4161/psb.5.7.11901. [PMID: 20495341]
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