antofine (BioDeep_00000236272)

   

PANOMIX_OTCML-2023


代谢物信息卡片


InChI=1/C23H25NO3/c1-25-15-6-7-16-18(10-15)20-12-23(27-3)22(26-2)11-19(20)17-9-14-5-4-8-24(14)13-21(16)17/h6-7,10-12,14H,4-5,8-9,13H2,1-3H3/t14-/m1/s

  化学式: C23H25NO3 (363.1834)
中文名称:
  谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 94%

分子结构信息

SMILES: COC1=CC2=C(C=C1)C3=C(CC4CCCN4C3)C5=CC(=C(C=C52)OC)OC
InChI: InChI=1S/C23H25NO3/c1-25-15-6-7-16-18(10-15)20-12-23(27-3)22(26-2)11-19(20)17-9-14-5-4-8-24(14)13-21(16)17/h6-7,10-12,14H,4-5,8-9,13H2,1-3H3/t14-/m1/s1


描述信息

(-)-antofine is an organic heteropentacyclic compound that is (13aR)-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline substituted at positions 2, 3 and 6 by methoxy groups. It is an alkaloid produced by relatives of the milkweed family and exhibits antiviral, anti-inflammatory, antiadipogenic and antitumorigenic activities. It has a role as an antineoplastic agent, a plant metabolite, a phytotoxin, an antimicrobial agent, an anti-inflammatory agent, an antiviral agent and an angiogenesis inhibitor. It is an organic heteropentacyclic compound, an aromatic ether, an alkaloid and an alkaloid antibiotic.
(13aR)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine is a natural product found in Ficus septica, Vincetoxicum paniculatum, and other organisms with data available.
An organic heteropentacyclic compound that is (13aR)-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline substituted at positions 2, 3 and 6 by methoxy groups. It is an alkaloid produced by relatives of the milkweed family and exhibits antiviral, anti-inflammatory, antiadipogenic and antitumorigenic activities.

同义名列表

13 个代谢物同义名

InChI=1/C23H25NO3/c1-25-15-6-7-16-18(10-15)20-12-23(27-3)22(26-2)11-19(20)17-9-14-5-4-8-24(14)13-21(16)17/h6-7,10-12,14H,4-5,8-9,13H2,1-3H3/t14-/m1/s; dibenzo[f,h]pyrrolo[1,2-b]isoquinoline, 9,11,12,13,13a,14-hexahydro-2,3,6-trimethoxy-, (13aR)-; (13aR)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline; (R)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline; 2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline; 9,11,12,13,13a,14-hexahydro-2,3,6-trimethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinoline; (13aR)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine; 2,3,6-trimethoxy-9,10,11,12,12a,13-hexahydro-9a-aza-cyclopenta[b]triphenylene; 7-Demethoxytylophorine; (R)-(-)-antofine; (-)-Antofine; (R)-antofine; antofine



数据库引用编号

10 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)

0 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


文献列表

  • Lu Li, Zhitong Xin, Reymick Oketch Okwong, Qiuli OuYang, Jinxin Che, Jia Zhou, Nengguo Tao. Antofine inhibits postharvest green mold due to imazalil-resistant Penicillium digitatum strain Pdw03 by triggering oxidative burst. Journal of food biochemistry. 2021 06; 45(6):e13751. doi: 10.1111/jfbc.13751. [PMID: 33949723]
  • Christopher Mogg, Christopher Bonner, Li Wang, Johann Schernthaner, Myron Smith, Darrell Desveaux, Rajagopal Subramaniam. Genomic Identification of the TOR Signaling Pathway as a Target of the Plant Alkaloid Antofine in the Phytopathogen Fusarium graminearum. mBio. 2019 06; 10(3):. doi: 10.1128/mbio.00792-19. [PMID: 31186319]
  • Xiuling Yu, Peng Wei, Ziwen Wang, Yuxiu Liu, Lizhong Wang, Qingmin Wang. Design, synthesis, antiviral activity and mode of action of phenanthrene-containing N-heterocyclic compounds inspired by the phenanthroindolizidine alkaloid antofine. Pest management science. 2016 Feb; 72(2):371-8. doi: 10.1002/ps.4008. [PMID: 25809229]
  • Jayoung Song, Yongseok Kwon, Sanghee Kim, Sang Kook Lee. Antitumor activity of phenanthroindolizidine alkaloids is associated with negative regulation of Met endosomal signaling in renal cancer cells. Chemistry & biology. 2015 Apr; 22(4):504-515. doi: 10.1016/j.chembiol.2015.03.011. [PMID: 25865310]
  • Donna M Gibson, Richard H Vaughan, Lindsey R Milbrath. Invasive swallow-worts: an allelopathic role for -(-) antofine remains unclear. Journal of chemical ecology. 2015 Feb; 41(2):202-11. doi: 10.1007/s10886-015-0552-3. [PMID: 25653045]
  • Eun Jung Jang, Hyo Kyeong Kim, Hana Jeong, Ye Seul Lee, Mi Gyeong Jeong, Su Jung Bae, Sanghee Kim, Sang Kook Lee, Eun Sook Hwang. Anti-adipogenic activity of the naturally occurring phenanthroindolizidine alkaloid antofine via direct suppression of PPARγ expression. Chemistry & biodiversity. 2014 Jun; 11(6):962-9. doi: 10.1002/cbdv.201300365. [PMID: 24934681]
  • Ziwen Wang, Peng Wei, Lizhong Wang, Qingmin Wang. Design, synthesis, and anti-tobacco mosaic virus (TMV) activity of phenanthroindolizidines and their analogues. Journal of agricultural and food chemistry. 2012 Oct; 60(41):10212-9. doi: 10.1021/jf303550a. [PMID: 23035814]
  • Ziwen Wang, Peng Wei, Xu Xizhi, Yuxiu Liu, Lizhong Wang, Qingmin Wang. Design, synthesis, and antiviral activity evaluation of phenanthrene-based antofine derivatives. Journal of agricultural and food chemistry. 2012 Sep; 60(35):8544-51. doi: 10.1021/jf302746m. [PMID: 22880628]
  • Ziwen Wang, Lei Wang, Shuang Ma, Yuxiu Liu, Lizhong Wang, Qingmin Wang. Design, synthesis, antiviral activity, and SARs of 14-aminophenanthroindolizidines. Journal of agricultural and food chemistry. 2012 Jun; 60(23):5825-31. doi: 10.1021/jf3013376. [PMID: 22662864]
  • Donna M Gibson, Stuart B Krasnoff, Jeromy Biazzo, Lindsey Milbrath. Phytotoxicity of antofine from invasive swallow-worts. Journal of chemical ecology. 2011 Aug; 37(8):871-9. doi: 10.1007/s10886-011-9994-4. [PMID: 21739223]
  • Kailiang Wang, Bo Su, Ziwen Wang, Meng Wu, Zheng Li, Yanna Hu, Zhijin Fan, Na Mi, Qingmin Wang. Synthesis and antiviral activities of phenanthroindolizidine alkaloids and their derivatives. Journal of agricultural and food chemistry. 2010 Mar; 58(5):2703-9. doi: 10.1021/jf902543r. [PMID: 20000413]
  • Yue-Hu Wang, Zhong-Kai Zhang, Fu-Mei Yang, Qian-Yun Sun, Hong-Ping He, Ying-Tong Di, Shu-Zhen Mu, Yang Lu, Ying Chang, Qi-Tai Zheng, Ming Ding, Jia-Hong Dong, Xiao-Jiang Hao. Benzylphenethylamine alkaloids from Hosta plantaginea with inhibitory activity against tobacco mosaic virus and acetylcholinesterase. Journal of natural products. 2007 Sep; 70(9):1458-61. doi: 10.1021/np0702077. [PMID: 17822295]
  • Dan Staerk, Anne K Lykkeberg, Jette Christensen, Bogdan A Budnik, Fumiko Abe, Jerzy W Jaroszewski. In vitro cytotoxic activity of phenanthroindolizidine alkaloids from Cynanchum vincetoxicum and Tylophora tanakae against drug-sensitive and multidrug-resistant cancer cells. Journal of natural products. 2002 Sep; 65(9):1299-302. doi: 10.1021/np0106384. [PMID: 12350151]
  • Q Wang, L Xie, J Zhai. Tylophorine B benzene solvate. Acta crystallographica. Section C, Crystal structure communications. 2000 Feb; 56 ( Pt 2)(?):197-8. doi: 10.1107/s0108270199013499. [PMID: 10777885]
  • J M Relton, N S Gee, R Matsas, A J Turner, A J Kenny. Purification of endopeptidase-24.11 ('enkephalinase') from pig brain by immunoadsorbent chromatography. The Biochemical journal. 1983 Dec; 215(3):519-23. doi: 10.1042/bj2150519. [PMID: 6419725]