Acetylharpagide (BioDeep_00000230144)

Main id: BioDeep_00000232739

 

PANOMIX_OTCML-2023


代谢物信息卡片


(1S,4aS,5R,7S,7aS)-4a,5-Dihydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl acetate

化学式: C17H26O11 (406.1475046)
中文名称: 8-O-乙酰哈巴苷, 乙酰哈巴苷
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=O)OC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)C
InChI: InChI=1S/C17H26O11/c1-7(19)28-16(2)5-9(20)17(24)3-4-25-15(13(16)17)27-14-12(23)11(22)10(21)8(6-18)26-14/h3-4,8-15,18,20-24H,5-6H2,1-2H3/t8-,9-,10-,11+,12-,13-,14+,15+,16+,17-/m1/s1

描述信息

8-O-Acetylharpagide is a natural product found in Scrophularia deserti, Scrophularia scorodonia, and other organisms with data available.
8-O-Acetylharpagide is an iridoid isolated from Ajuga reptans with antitumoral, antiviral, antibacterial, and anti-inflammatory activities. 8-O-Acetylharpagide also has a biological activity on isolated smooth muscle preparations from guinea pig[1][2].
8-O-Acetylharpagide is an iridoid isolated from Ajuga reptans with antitumoral, antiviral, antibacterial, and anti-inflammatory activities. 8-O-Acetylharpagide also has a biological activity on isolated smooth muscle preparations from guinea pig[1][2].

同义名列表

12 个代谢物同义名

(1S,4aS,5R,7S,7aS)-4a,5-Dihydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl acetate; 8-Acetylharpagide, >=85\\% (LC/MS-ELSD); 8-?O-?Acetylharpagide; 8-O-Acetylharpagide; 8-O-acetylharpagid; 8--cetylharpagide; 3-Acetylharpagide; 8-Acetylharpagide; 8-OAc-harpagide; Acetylharpagide; MEGxp0_000602; ACon1_000486



数据库引用编号

6 个数据库交叉引用编号

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)

3 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

  • Xiuwei Shen, Chen Chen, Congcong Wen, Shuaishuai Yu, Huamin Liu, Xiaomin Gao, Lianguo Chen. A newly developed UPLC-MS/MS method for simultaneous quantitative analysis of ajuforrestin A, ajuforrestin B, ajugamacrin and 8-O-acetylharpagide derived from Ajuga plants in mice blood and the in vivo pharmacokinetics. Drug development and industrial pharmacy. 2024 Apr; 50(4):354-362. doi: 10.1080/03639045.2024.2328731. [PMID: 38456836]
  • Wei-Hsiang Hsu, Bing-Ze Lin, Jyh-Der Leu, Pin-Ho Lo, Hsueh-Yen Yu, Chao-Tsung Chen, Yuan-Heng Tu, Yun-Lian Lin, Yi-Jang Lee. Involvement of 8-O-acetylharpagide for Ajuga taiwanensis mediated suppression of senescent phenotypes in human dermal fibroblasts. Scientific reports. 2020 11; 10(1):19731. doi: 10.1038/s41598-020-76797-6. [PMID: 33184359]
  • Camille Remeur, Erell Le Borgne, Léa Gauthier, Raphaël Grougnet, Brigitte Deguin, Cyril Poullain, Marc Litaudon. HPLC-ELSD Quantification and Centrifugal Partition Chromatography Isolation of 8-O-Acetylharpagide from Oxera coronata (Lamiaceae). Phytochemical analysis : PCA. 2017 May; 28(3):242-246. doi: 10.1002/pca.2667. [PMID: 28028854]
  • Hilal A Ganaie, Md Niamat Ali, Bashir A Ganai, Maryum Meraj, Mudasar Ahmad. Antibacterial activity of 14, 15-dihydroajugapitin and 8-o-acetylharpagide isolated from Ajuga bracteosa Wall ex. Benth against human pathogenic bacteria. Microbial pathogenesis. 2017 Feb; 103(?):114-118. doi: 10.1016/j.micpath.2016.12.017. [PMID: 28012983]
  • Claudio Frezza, Alessandro Venditti, Mirella Di Cecco, Giampiero Ciaschetti, Mauro Serafini, Armandodoriano Bianco. Iridoids and phenylethanoid glycosides from the aerial parts of Ajuga tenorei, an endemic Italian species. Natural product research. 2017 Jan; 31(2):218-223. doi: 10.1080/14786419.2016.1218490. [PMID: 27492580]
  • Anna Pitschmann, Martin Zehl, Elke Heiss, Sodnomtseren Purevsuren, Ernst Urban, Verena M Dirsch, Sabine Glasl. Quantitation of phenylpropanoids and iridoids in insulin-sensitising extracts of Leonurus sibiricus L. (Lamiaceae). Phytochemical analysis : PCA. 2016 Jan; 27(1):23-31. doi: 10.1002/pca.2583. [PMID: 26333151]
  • Bin-Yu Wen, Jian-Rong Li. [Pharmacokinetics of 8-O-acetylharpagide and harpagide after oral administration of Ajuga decumbens extract in beagle dog]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2013 Jun; 38(12):2015-8. doi: NULL. [PMID: 24066603]
  • Binyu Wen, Rong He, Pengyue Li, Qihua Xu, Yanli Lu, Bo Peng, Jianrong Li. Pharmacokinetics of 8-O-acetylharpagide and harpagide after oral administration of Ajuga decumbens Thunb extract in rats. Journal of ethnopharmacology. 2013 May; 147(2):503-8. doi: 10.1016/j.jep.2013.03.048. [PMID: 23545457]
  • T Konoshima, M Takasaki, H Tokuda, H Nishino. Cancer chemopreventive activity of an iridoid glycoside, 8-acetylharpagide, from Ajuga decumbens. Cancer letters. 2000 Aug; 157(1):87-92. doi: 10.1016/s0304-3835(00)00479-1. [PMID: 10893446]
  • M Takasaki, H Tokuda, H Nishino, T Konoshima. Cancer chemopreventive agents (antitumor-promoters) from Ajuga decumbens. Journal of natural products. 1999 Jul; 62(7):972-5. doi: 10.1021/np990033w. [PMID: 10425119]
  • E Abdel-Sattar. Iridoids from Teucrium yemense. Archives of pharmacal research. 1998 Dec; 21(6):785-6. doi: 10.1007/bf02976778. [PMID: 9868558]
  • A Elbrecht, Y Chen, T Jurgens, O D Hensens, D L Zink, H T Beck, M J Balick, R Borris. 8-O-acetylharpagide is a nonsteroidal ecdysteroid agonist. Insect biochemistry and molecular biology. 1996 Jun; 26(6):519-23. doi: 10.1016/0965-1748(95)00103-4. [PMID: 8969463]
  • M C Breschi, E Martinotti, S Catalano, G Flamini, I Morelli, A M Pagni. Vasoconstrictor activity of 8-O-acetylharpagide from Ajuga reptans. Journal of natural products. 1992 Aug; 55(8):1145-8. doi: 10.1021/np50086a019. [PMID: 1431938]