3-oxo-14-deoxyandrographolide | 4176-99-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-oxo-14-deoxyandrographolide
• 英文别名: 3-Dehydro-desoxy-andrographolid；3-dehydro-14-deoxyandrographolide；4-[2-[(1R,4aS,5R,8aS)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-6-oxo-1,3,4,4a,7,8-hexahydronaphthalen-1-yl]ethyl]-2H-furan-5-one
• CAS: 4176-99-2
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: ROPZFDGMJDAXOR-LPWQTFTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 3-oxo-14-deoxyandrographolide 在 glucosyltransferase from Andrographis paniculata 作用下， 以 aq. buffer 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Glucosyltransferase Capable of Catalyzing the Last Step in Neoandrographolide Biosynthesis

  摘要：

  ApUGT, a diterpene glycosyltransferase from Andrographis paniculata, could transfer a glucose to the C-19 hydroxyl moiety of andrograpanin to form neoandrographolide. This glycosyltransferase has a broad substrate scope, and it can glycosylate 26 natural and unnatural compounds of different structural types. This study provides a basis for exploring the glycosylation mechanism of ent-labdane-type diterpenes and plays an important role in diversifying the structures used in drug discovery.

  DOI：

  10.1021/acs.orglett.8b02146
• 作为产物：
  描述：

  去氧穿心莲内酯 在 Cunninghamella blakesleana (AS 3.970) 作用下， 以 乙醇 为溶剂， 以4.17%的产率得到3-oxo-14-deoxyandrographolide
  参考文献：
  名称：

  Microbial transformation of 14-deoxy-11, 12-didehydroandrographolide and 14-deoxyandrographolide and inhibitory effects on nitric oxide production of the transformation products

  摘要：

  Microbial transformations of 14-deoxy-11, 12-didehyclroandrographolide (a) and 14-deoxyandrographolide (b) were performed by Cunninghamella blakesleana (AS 3.970), respectively. Sixteen metabolites were obtained and their structures were elucidated by spectroscopic data analyses. Among these metabolites, 3 alpha, 12S, 19-trihydroxy-8(17), 9(11)-ent-labdadien-16, 15-olide (a7), 3-oxo-8 alpha, 17 beta-epoxy-14-deoxyandrographolide (b2). 3 alpha, 17. 19-trihydroxy-8, 13-ent-labdadien-16, 15-olide (b6), and 9 beta-hydroxy-14-deoxyandrographolide (b9) are new compounds. The configuration of C-12 in metabolite a7 was determined as S by GIAO method. The proposed metabolic pathways of 14-deoxy-11, 12-didehydroandrographolide and 14-deoxyandrographolide by C blakesleana were drawn. The inhibitory effects of these compounds on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated and their preliminary structure-activity relationships (SAR) were discussed. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.06.012

文献信息

• Cytotoxic biotransformed products from andrographolide by Rhizopus stolonifer ATCC 12939
  作者：Xiangjiu He、Xiaobin Zeng、Hui Hu、Yixuan Wu

  DOI：10.1016/j.molcatb.2009.11.002

  日期：2010.3

  resolution mass spectroscopy (HR-MS), extensive NMR techniques, including 1H NMR, 13C NMR, DEPT, 1H–1H correlation spectroscopy (COSY), two dimensional nuclear Overhauser effect correlation spectroscopy (NOESY), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond coherence (HMBC). Their structures were identified to be 12(R),13(R)-12-hydroxyandrographolide (2), 12(S),13(S

  穿心莲内酯（的生物转化1）由匍枝根霉ATCC 12939进行了研究。分离并鉴定出十种生物转化产物。通过高分辨率质谱（HR-MS），广泛的NMR技术阐明了它们的结构，包括1 H NMR，13 C NMR，DEPT，1 H– 1 H相关光谱（COSY），二维核Overhauser效应相关光谱（NOESY） ），异核多重量子相干性（HMQC）和异核多重键相干性（HMBC）。它们的结构被鉴定为12（R），13（R）-12-羟基穿心莲内酯（2），12（S），13（S）-12-羟基穿心莲内酯（3），异穿心莲内酯（4），3-脱氢异穿心莲内酯（5），14-脱氧-11,12-二氢氢化穿心莲内酯（6），3-氧代-14-脱氧-11 ，12-去氢穿心莲内酯（7），3-脱水（8），14-去氧（9），3-脱氢-14-去氧（10）和3-脱氢-14-去氧-19-酸（11）。其中，化合物5和11是新化合物。stolonif
• Microbial transformation of deoxyandrographolide by Cunninghamella echinulata
  作者：Feng Yun Li、Peter R. Cang、Shan Shan Huang、Bao Jing Zhang、Xiu Lan Xin、Ji Hong Yao、Qi Zhou、Yan Tian、Sha Deng、Xiao Chi Ma

  DOI：10.1016/j.molcatb.2010.11.001

  日期：2011.2

  The capabilities of twenty strains of filamentous fungi (from 9 genera) to transform deoxyandrographolide (1) were screened. And eleven derivatives of 1 transformed by Cunninghamella echinulata AS 3.3400 were isolated. Their chemical structures were identified by spectral methods including 2D NM R. Among them, 3-oxo-7 alpha-hydroxy-14-deoxyandrographolide (2), 3-oxo-8 beta,17 alpha-epoxy-14-deoxyandrographolide (3), 8 alpha-formyl-14-deoxyandrographolide (4), 8 beta-methoxyl-17 alpha-hydroxyl-14-deoxyandro-grapholide (5) and 3 alpha,17,19-trihydroxyl-7,13-ent-labdadien-15,16-olide (6), are new compounds. And their structure-activity relationships (SAR) were also discussed. (c) 2010 Elsevier B.V. All rights reserved.
• Glucosyltransferase Capable of Catalyzing the Last Step in Neoandrographolide Biosynthesis
  作者：Yuan Li、Hui-Xin Lin、Jian Wang、Jian Yang、Chang-Jiang-Sheng Lai、Xing Wang、Bao-Wei Ma、Jin-Fu Tang、Yong Li、Xin-Lin Li、Juan Guo、Wei Gao、Lu-Qi Huang

  DOI：10.1021/acs.orglett.8b02146

  日期：2018.10.5

  ApUGT, a diterpene glycosyltransferase from Andrographis paniculata, could transfer a glucose to the C-19 hydroxyl moiety of andrograpanin to form neoandrographolide. This glycosyltransferase has a broad substrate scope, and it can glycosylate 26 natural and unnatural compounds of different structural types. This study provides a basis for exploring the glycosylation mechanism of ent-labdane-type diterpenes and plays an important role in diversifying the structures used in drug discovery.
• Microbial transformation of 14-deoxy-11, 12-didehydroandrographolide and 14-deoxyandrographolide and inhibitory effects on nitric oxide production of the transformation products
  作者：Li-Xia Chen、Yu-Lei Zhuang、Lan Shen、En-Long Ma、Hua-Jie Zhu、Feng Zhao、Feng Qiu

  DOI：10.1016/j.molcatb.2011.06.012

  日期：2011.11

  Microbial transformations of 14-deoxy-11, 12-didehyclroandrographolide (a) and 14-deoxyandrographolide (b) were performed by Cunninghamella blakesleana (AS 3.970), respectively. Sixteen metabolites were obtained and their structures were elucidated by spectroscopic data analyses. Among these metabolites, 3 alpha, 12S, 19-trihydroxy-8(17), 9(11)-ent-labdadien-16, 15-olide (a7), 3-oxo-8 alpha, 17 beta-epoxy-14-deoxyandrographolide (b2). 3 alpha, 17. 19-trihydroxy-8, 13-ent-labdadien-16, 15-olide (b6), and 9 beta-hydroxy-14-deoxyandrographolide (b9) are new compounds. The configuration of C-12 in metabolite a7 was determined as S by GIAO method. The proposed metabolic pathways of 14-deoxy-11, 12-didehydroandrographolide and 14-deoxyandrographolide by C blakesleana were drawn. The inhibitory effects of these compounds on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated and their preliminary structure-activity relationships (SAR) were discussed. (C) 2011 Elsevier B.V. All rights reserved.