(-)-Maackiain (BioDeep_00000002486)

 

Secondary id: BioDeep_00000016721, BioDeep_00000018131, BioDeep_00000600448

natural product PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


(1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-16-ol

化学式: C16H12O5 (284.0684702)
中文名称: 马卡因, (+)-高丽槐素, 高丽槐素
谱图信息: 最多检出来源 Viridiplantae(plant) 0.1%

Reviewed

Last reviewed on 2024-07-09.

Cite this Page

(-)-Maackiain. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/(-)-maackiain (retrieved 2024-11-24) (BioDeep RN: BioDeep_00000002486). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: c1(ccc2c(c1)OC[C@@H]1[C@H]2Oc2c1cc1c(c2)OCO1)O
InChI: InChI=1S/C16H12O5/c17-8-1-2-9-12(3-8)18-6-11-10-4-14-15(20-7-19-14)5-13(10)21-16(9)11/h1-5,11,16-17H,6-7H2

描述信息

(-)-maackiain is the (-)-enantiomer of maackiain. It is an enantiomer of a (+)-maackiain.
Maackiain is a natural product found in Tephrosia virginiana, Leptolobium bijugum, and other organisms with data available.

(-)-Maackiain. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=2035-15-6 (retrieved 2024-07-09) (CAS RN: 2035-15-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
(-)-Maackiain is a pterocarpan phytoalexin produced from Sophora flavescens. (-)-Maackiain is toxic to several genera of fungal pathogens of legume and non legume hosts[1].
(-)-Maackiain is a pterocarpan phytoalexin produced from Sophora flavescens. (-)-Maackiain is toxic to several genera of fungal pathogens of legume and non legume hosts[1].
(-)-Maackiain is a pterocarpan phytoalexin produced from Sophora flavescens. (-)-Maackiain is toxic to several genera of fungal pathogens of legume and non legume hosts[1].
(-)-Maackiain is a pterocarpan phytoalexin produced from Sophora flavescens. (-)-Maackiain is toxic to several genera of fungal pathogens of legume and non legume hosts[1].

同义名列表

31 个代谢物同义名

(1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-16-ol; (1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.0?,??.0?,?.0??,??]icosa-2,4(8),9,13,15,17-hexaen-16-ol; 6H-[1,3]Dioxolo[4,5:5,6]benzofuro[3,2-c][1]benzopyran-3-ol, 6a.alpha.,12a.alpha.-dihydro-, (-)-; 6H-[1,3]Dioxolo[4,5:5,6]benzofuro[3,2-c][1]benzopyran-3-ol, 6a,12a-dihydro-, (6aR,12aR)-; 6H-[1,3]Dioxolo[4,5:5,6]benzofuro[3,2-c][1]benzopyran-3-ol, 6a,12a-dihydro-, (6aR-cis)-; 6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol, 6a,12a-dihydro-, (6aR,12aR)-; 6H-(1,3)Dioxolo(5,6)benzofuro(3,2-c)(1)benzopyran-3-ol, 6a,12a-dihydro-, (6aR-cis)-; (6aR,12aR)-6a,12a-Dihydro-6H-[1,3]dioxolo[4,5:5,6]benzofuro[3,2-c]chromen-3-ol; (6ar,12ar)-6a,12a-dihydro-6h-[1,3]dioxolo[5,6][1]benzofuro[3,2-c]chromen-3-ol; 6a,12a-dihydro-6H-(1,3)dioxolo(5,6)benzofuro(3,2-c)(1)benzopyran-3-ol; (6aR,12aR)-3-hydroxy-8,9-methylenedioxypterocarpane; 3-Hydroxy-8,9-methylenedioxypterocarpan; (-)-Maackiain , HPLC Grade; inermin, (6aR-cis)-isomer; inermin, (6aS-cis)-isomer; (-)-(6aR,12aR)-maackiain; Trifolirhizin aglycone; (-?)?-Maackiain; (+/-)-Maackiain; (-) -Maackiain; (-)-Maackiain; (+)-Maackiain; L-Maackiain; Maackiaine; Maackiain; Inermine; CHEBI:99; inermin; Demethylpterocarpin; (-)-Maackiain; Maackiaine



数据库引用编号

44 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(5)

PlantCyc(1)

代谢反应

16 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(6)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(10)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

378 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

  • Saveta G Mladenova, Monika N Todorova, Martina S Savova, Milen I Georgiev, Liliya V Mihaylova. Maackiain Mimics Caloric Restriction through aak-2-Mediated Lipid Reduction in Caenorhabditis elegans. International journal of molecular sciences. 2023 Dec; 24(24):. doi: 10.3390/ijms242417442. [PMID: 38139270]
  • Xing Jiang, Xiaonan Yang, Yanxia Shi, Yan Long, Wenqing Su, Wendong He, Kunhua Wei, Jianhua Miao. Maackiain inhibits proliferation and promotes apoptosis of nasopharyngeal carcinoma cells by inhibiting the MAPK/Ras signaling pathway. Chinese journal of natural medicines. 2023 Mar; 21(3):185-196. doi: 10.1016/s1875-5364(23)60420-0. [PMID: 37003641]
  • Janakiraman V, Sudhan M, Abubakar Wani, Sheikh F Ahmad, Ahmed Nadeem, Ashutosh Sharma, Shiek S S J Ahmed. Pharmacoscreening, molecular dynamics, and quantum mechanics of inermin from Panax ginseng: a crucial molecule inhibiting exosomal protein target associated with coronary artery disease progression. PeerJ. 2023; 11(?):e16481. doi: 10.7717/peerj.16481. [PMID: 38077444]
  • Saveta G Mladenova, Martina S Savova, Andrey S Marchev, Claudio Ferrante, Giustino Orlando, Martin Wabitsch, Milen I Georgiev. Anti-adipogenic activity of maackiain and ononin is mediated via inhibition of PPARγ in human adipocytes. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 May; 149(?):112908. doi: 10.1016/j.biopha.2022.112908. [PMID: 35367764]
  • Na Lu, Guojun Tan, Hongling Tan, Xing Zhang, Yunling Lv, Xiujuan Song, Daofeng You, Ziyuan Gao. Maackiain Prevents Amyloid-Beta-Induced Cellular Injury via Priming PKC-Nrf2 Pathway. BioMed research international. 2022; 2022(?):4243210. doi: 10.1155/2022/4243210. [PMID: 35782063]
  • Wen-Lin Yuan, Zheng-Rui Huang, Si-Jia Xiao, Ji Ye, Wei-Dong Zhang, Yun-Heng Shen. [Metabolites and metabolic pathways of maackiain in rats based on UPLC-Q-TOF-MS]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2021 Dec; 46(23):6278-6288. doi: 10.19540/j.cnki.cjcmm.20210902.201. [PMID: 34951255]
  • Guangfei Wei, Yongzhong Chen, Xiaotong Guo, Jianhe Wei, Linlin Dong, Shilin Chen. Biosyntheses characterization of alkaloids and flavonoids in Sophora flavescens by combining metabolome and transcriptome. Scientific reports. 2021 04; 11(1):7388. doi: 10.1038/s41598-021-86970-0. [PMID: 33795823]
  • Jiahong Guo, Junying Li, Hua Wei, Zhaozhi Liang. Maackiain Protects the Kidneys of Type 2 Diabetic Rats via Modulating the Nrf2/HO-1 and TLR4/NF-κB/Caspase-3 Pathways. Drug design, development and therapy. 2021; 15(?):4339-4358. doi: 10.2147/dddt.s326975. [PMID: 34703210]
  • Jin-Won Huh, Jung-Hoon Lee, Eekhyoung Jeon, Hyung Won Ryu, Sei-Ryang Oh, Kyung-Seop Ahn, Hyun Sik Jun, Un-Hwan Ha. Maackiain, a compound derived from Sophora flavescens, increases IL-1β production by amplifying nigericin-mediated inflammasome activation. FEBS open bio. 2020 08; 10(8):1482-1491. doi: 10.1002/2211-5463.12899. [PMID: 32428336]
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  • Yannan Li, Jing Ning, Yan Wang, Chao Wang, Chengpeng Sun, Xiaokui Huo, Zhenlong Yu, Lei Feng, Baojing Zhang, Xiangge Tian, Xiaochi Ma. Drug interaction study of flavonoids toward CYP3A4 and their quantitative structure activity relationship (QSAR) analysis for predicting potential effects. Toxicology letters. 2018 Sep; 294(?):27-36. doi: 10.1016/j.toxlet.2018.05.008. [PMID: 29753067]
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  • Hyun Woo Lee, Hyung Won Ryu, Myung-Gyun Kang, Daeui Park, Sei-Ryang Oh, Hoon Kim. Potent selective monoamine oxidase B inhibition by maackiain, a pterocarpan from the roots of Sophora flavescens. Bioorganic & medicinal chemistry letters. 2016 10; 26(19):4714-4719. doi: 10.1016/j.bmcl.2016.08.044. [PMID: 27575476]
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  • Soo Min Jang, Soo Hyeon Bae, Woong-Kee Choi, Jung Bae Park, Doyun Kim, Jee Sun Min, Hunseung Yoo, Minseok Kang, Keun Ho Ryu, Soo Kyung Bae. Pharmacokinetic properties of trifolirhizin, (-)-maackiain, (-)-sophoranone and 2-(2,4-dihydroxyphenyl)-5,6-methylenedioxybenzofuran after intravenous and oral administration of Sophora tonkinensis extract in rats. Xenobiotica; the fate of foreign compounds in biological systems. 2015; 45(12):1092-104. doi: 10.3109/00498254.2015.1041181. [PMID: 26068519]
  • Hunseung Yoo, Hee-Sung Chae, Young-Mi Kim, Minseok Kang, Keun Ho Ryu, Hee Chul Ahn, Kee Dong Yoon, Young-Won Chin, Jinwoong Kim. Flavonoids and arylbenzofurans from the rhizomes and roots of Sophora tonkinensis with IL-6 production inhibitory activity. Bioorganic & medicinal chemistry letters. 2014 Dec; 24(24):5644-5647. doi: 10.1016/j.bmcl.2014.10.077. [PMID: 25467151]
  • Hunseung Yoo, Keun Ho Ryu, Soo Kyung Bae, Jinwoong Kim. Simultaneous determination of trifolirhizin, (-)-maackiain, (-)-sophoranone, and 2-(2,4-dihydroxyphenyl)-5,6-methylenedioxybenzofuran from Sophora tonkinensis in rat plasma by liquid chromatography with tandem mass spectrometry and its application to a pharmacokinetic study. Journal of separation science. 2014 Nov; 37(22):3235-44. doi: 10.1002/jssc.201400691. [PMID: 25156071]
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