dammarenediol (BioDeep_00000000930)

 

Secondary id: BioDeep_00000179420

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


(3S,5R,8R,9R,10R,13R,14R,17S)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

化学式: C30H52O2 (444.3967092)
中文名称: 达玛烯二醇II, 达玛烯二醇 II
谱图信息: 最多检出来源 Viridiplantae(plant) 0.13%

分子结构信息

SMILES: CC(=CCCC(C)(C1CCC2(C1CCC3C2(CCC4C3(CCC(C4(C)C)O)C)C)C)O)C
InChI: InChI=1S/C30H52O2/c1-20(2)10-9-16-30(8,32)22-13-18-28(6)21(22)11-12-24-27(5)17-15-25(31)26(3,4)23(27)14-19-29(24,28)7/h10,21-25,31-32H,9,11-19H2,1-8H3/t21-,22+,23+,24-,25+,27+,28-,29-,30+/m1/s1

描述信息

Dammarenediol-II is a tetracyclic triterpenoid that is dammarane which has a double bond between positions 24 and 25, and is substituted by hydroxy groups at the 3beta- and 20- positions. It has a role as a metabolite. It is a tetracyclic triterpenoid, a secondary alcohol and a tertiary alcohol. It derives from a hydride of a dammarane.
Dammarenediol II is a natural product found in Olea capensis, Aglaia abbreviata, and other organisms with data available.
A tetracyclic triterpenoid that is dammarane which has a double bond between positions 24 and 25, and is substituted by hydroxy groups at the 3beta- and 20- positions.

同义名列表

18 个代谢物同义名

(3S,5R,8R,9R,10R,13R,14R,17S)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; 8-methyl-18-nor-lanost-24-ene-3beta,20-diol; 8-methyl-18-nor-lanost-24-en-3beta,20-diol; 3beta-glucodammar-24-ene-3,20-diol; (20S)-dammar-24-ene-3beta,20-diol; Dammar-24-ene-3,20-diol, (20S)-; (3beta)-dammar-24-ene-3,20-diol; dammar-24-ene-20(SS),3beta-diol; 3beta-dammar-24-ene-3,20-diol; Dammar-24-ene-3beta,20-diol; Dammar-24-ene-3β,20-diol; (20S)-dammarenediol; Dammarenediol II; dammarenediol-II; DammarenediolII; dammarenediol; (+)-24-Dammarene-3beta-20S-diol; Dammarenediol II



数据库引用编号

12 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

  • ginsenosides biosynthesis: β-amyrin + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ H+ + H2O + an oxidized [NADPH-hemoprotein reductase] + oleanolate

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(2)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

52 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

  • Mei-Li Zhao, Xiang-Yu Li, Cheng-Xiang Lan, Zi-Ling Yuan, Jia-Lin Zhao, Ying Huang, Zhang-Li Hu, Bin Jia. Promoting Photosynthetic Production of Dammarenediol-II in Chlamydomonas reinhardtii via Gene Loading and Culture Optimization. International journal of molecular sciences. 2023 Jul; 24(13):. doi: 10.3390/ijms241311002. [PMID: 37446180]
  • Yujie Zheng, Rongyu Shao, Pengguo Xia, Zongsuo Liang, Kaijing Yan. Activity and function studies of the promoter cis-acting elements of the key enzymes in saponins biosynthesis of DS from Panax notoginseng. Protoplasma. 2022 Jan; 259(1):163-171. doi: 10.1007/s00709-021-01653-x. [PMID: 33934214]
  • Yingbin Wu, Yue Chen, Zheng Xu, Ming Xiang. Dammarenediol suppresses the growth, migration and invasion of human osteosarcoma cells by modulating PI3K/Akt and STAT-3 signaling pathways. Journal of B.U.ON. : official journal of the Balkan Union of Oncology. 2020 Sep; 25(5):2444-2448. doi: . [PMID: 33277868]
  • Jung Yeon Han, So-Hyeon Baek, Hye Jeong Jo, Do Won Yun, Yong Eui Choi. Genetically modified rice produces ginsenoside aglycone (protopanaxadiol). Planta. 2019 Oct; 250(4):1103-1110. doi: 10.1007/s00425-019-03204-4. [PMID: 31168665]
  • Jian Li, Lan Ma, Shuting Zhang, Cailian Zuo, Na Song, Shusheng Zhu, Jinsong Wu. Transcriptome analysis of 1- and 3-year-old Panax notoginseng roots and functional characterization of saponin biosynthetic genes DS and CYP716A47-like. Planta. 2019 Apr; 249(4):1229-1237. doi: 10.1007/s00425-018-03083-1. [PMID: 30607503]
  • Jinxin Li, Juan Wang, Xiaolei Wu, Dahui Liu, Jing Li, Jianli Li, Shujie Liu, Wenyuan Gao. Jasmonic acid and methyl dihydrojasmonate enhance saponin biosynthesis as well as expression of functional genes in adventitious roots of Panax notoginseng F.H. Chen. Biotechnology and applied biochemistry. 2017 Mar; 64(2):225-238. doi: 10.1002/bab.1477. [PMID: 26777985]
  • Fanglong Zhao, Peng Bai, Ting Liu, Dashuai Li, Xiangmei Zhang, Wenyu Lu, Yingjin Yuan. Optimization of a cytochrome P450 oxidation system for enhancing protopanaxadiol production in Saccharomyces cerevisiae. Biotechnology and bioengineering. 2016 08; 113(8):1787-95. doi: 10.1002/bit.25934. [PMID: 26757342]
  • Dashuai Li, Qiang Zhang, Zhijiang Zhou, Fanglong Zhao, Wenyu Lu. Heterologous biosynthesis of triterpenoid dammarenediol-II in engineered Escherichia coli. Biotechnology letters. 2016 Apr; 38(4):603-9. doi: 10.1007/s10529-015-2032-9. [PMID: 26739962]
  • Ju-Hyeon Chun, Prakash Babu Adhikari, Seong-Bum Park, Jung-Yeon Han, Yong-Eui Choi. Production of the dammarene sapogenin (protopanaxadiol) in transgenic tobacco plants and cultured cells by heterologous expression of PgDDS and CYP716A47. Plant cell reports. 2015 Sep; 34(9):1551-60. doi: 10.1007/s00299-015-1806-9. [PMID: 25981048]
  • Le Wang, Shou-Jing Zhao, Hao-Jie Cao, Yao Sun. The isolation and characterization of dammarenediol synthase gene from Panax quinquefolius and its heterologous co-expression with cytochrome P450 gene PqD12H in yeast. Functional & integrative genomics. 2014 Sep; 14(3):545-57. doi: 10.1007/s10142-014-0384-1. [PMID: 24929308]
  • Jung-Yeon Han, Hong-Yan Wang, Yong-Eui Choi. Production of dammarenediol-II triterpene in a cell suspension culture of transgenic tobacco. Plant cell reports. 2014 Feb; 33(2):225-33. doi: 10.1007/s00299-013-1523-1. [PMID: 24141692]
  • Y-L Liang, S-J Zhao, L-X Xu, X-Y Zhang. Heterologous expression of dammarenediol synthase gene in an engineered Saccharomyces cerevisiae. Letters in applied microbiology. 2012 Nov; 55(5):323-9. doi: 10.1111/j.1472-765x.2012.03295.x. [PMID: 22897704]
  • Mi-Hyun Lee, Jung-Yeon Han, Hyun-Jung Kim, Yun-Soo Kim, Gyung Hye Huh, Yong-Eui Choi. Dammarenediol-II production confers TMV tolerance in transgenic tobacco expressing Panax ginseng dammarenediol-II synthase. Plant & cell physiology. 2012 Jan; 53(1):173-82. doi: 10.1093/pcp/pcr160. [PMID: 22102695]
  • Ok Tae Kim, Jei Wan Lee, Kyong Hwan Bang, Young Chang Kim, Dong Yun Hyun, Seon Woo Cha, Yong Eui Choi, Mei Lan Jin, Baik Hwang. Characterization of a dammarenediol synthase in Centella asiatica (L.) Urban. Plant physiology and biochemistry : PPB. 2009 Nov; 47(11-12):998-1002. doi: 10.1016/j.plaphy.2009.08.001. [PMID: 19796960]
  • B L Poehland, B K Carté, T A Francis, L J Hyland, H S Allaudeen, N Troupe. In vitro antiviral activity of dammar resin triterpenoids. Journal of natural products. 1987 Jul; 50(4):706-13. doi: 10.1021/np50052a022. [PMID: 2828553]
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