secologanin (BioDeep_00000000682)

 

Secondary id: BioDeep_00000017440, BioDeep_00000404134

human metabolite PANOMIX_OTCML-2023


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 (388.13694039999996)
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) 0.08%

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

22 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



数据库引用编号

21 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)

74 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

  • 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]
  • Jin-qian Yu, Zhao-ping Wang, Heng Zhu, Gang Li, Xiao Wang. [Chemical constituents of Lonicera japonica roots and their anti-inflammatory effects]. Yao xue xue bao = Acta pharmaceutica Sinica. 2016 07; 51(7):1110-6. doi: . [PMID: 29897205]
  • Thomas Dugé de Bernonville, Emilien Foureau, Claire Parage, Arnaud Lanoue, Marc Clastre, Monica Arias Londono, Audrey Oudin, Benjamin Houillé, Nicolas Papon, Sébastien Besseau, Gaëlle Glévarec, Lucia Atehortùa, Nathalie Giglioli-Guivarc'h, Benoit St-Pierre, Vincenzo De Luca, Sarah E O'Connor, Vincent Courdavault. Characterization of a second secologanin synthase isoform producing both secologanin and secoxyloganin allows enhanced de novo assembly of a Catharanthus roseus transcriptome. BMC genomics. 2015 Aug; 16(?):619. doi: 10.1186/s12864-015-1678-y. [PMID: 26285573]
  • 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]
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