Dehydroandrographolide (BioDeep_00000229979)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(3E)-3-[2-[(1S,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]furan-2-one

化学式: C20H28O4 (332.19874880000003)
中文名称: 脱水穿心莲内酯, 穿心莲丁素, 脱水穿心莲内酯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 5.26%

分子结构信息

SMILES: C=C1CCC2C(C)(CO)C(O)CCC2(C)C1CC=C1C=COC1=O
InChI: InChI=1S/C20H28O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h5,9,11,15-17,21-22H,1,4,6-8,10,12H2,2-3H3/b14-5+/t15-,16-,17+,19-,20-/m0/s1

描述信息

2(3H)-Furanone, 3-(2-((1S,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)-, (3E)- is a natural product found in Andrographis paniculata with data available.
Dehydroandrographolide can be extracted from herbal medicine Andrographis paniculata Nees. Dehydroandrographolide reduces oxidative stress in LPS-induced acute lung injury by inactivating iNOS. Dehydroandrographolide has anti-infective activity[1][2][3].
Dehydroandrographolide can be extracted from herbal medicine Andrographis paniculata Nees. Dehydroandrographolide reduces oxidative stress in LPS-induced acute lung injury by inactivating iNOS. Dehydroandrographolide has anti-infective activity[1][2][3].

同义名列表

5 个代谢物同义名

(3E)-3-[2-[(1S,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]furan-2-one; 2(3H)-Furanone, 3-(2-((1S,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)-, (3E)-; (E)-3-(2-((1S,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethylidene)furan-2(3H)-one; 14,15-Anhydroandrographolide, (1S)-; Dehydroandrographolide



数据库引用编号

9 个数据库交叉引用编号

分类词条

相关代谢途径

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PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

11 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

  • Yong-Guang Liu, Shan-Shan Zhang, Su-Wei Jin, Tian-Ji Xia, Yong-Hong Liao, Rui-Le Pan, Ming-Zhu Yan, Qi Chang. Anti-inflammatory effect and pharmacokinetics of dehydroandrographolide, an active component of Andrographis paniculata, on Poly(I:C)-induced acute lung injury. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2024 May; 174(?):116456. doi: 10.1016/j.biopha.2024.116456. [PMID: 38552441]
  • Qiru Guo, Jiali Li, Zheng Wang, Xiao Wu, Zhong Jin, Song Zhu, Hongfei Li, Delai Zhang, Wangming Hu, Huan Xu, Lan Yang, Liangqin Shi, Yong Wang. Potassium dehydroandrographolide succinate regulates the MyD88/CDH13 signaling pathway to enhance vascular injury-induced pathological vascular remodeling. Chinese journal of natural medicines. 2024 Jan; 22(1):62-74. doi: 10.1016/s1875-5364(24)60562-5. [PMID: 38278560]
  • Ning Kong, Huanshuai Guan, Xudong Duan, Ruomu Cao, Heng Li, Fangze Xing, Xueshan Du, Yi Zheng, Lei Zhang, Yiyang Li, Zeyu Liu, Run Tian, Kunzheng Wang, Delu Che, Pei Yang. Dehydroandrographolide alleviates rheumatoid arthritis by inhibiting neutrophil activation via LMIR3 in collagen induced arthritis rats. Cell cycle (Georgetown, Tex.). 2024 Jan; 23(1):1-14. doi: 10.1080/15384101.2024.2304508. [PMID: 38234233]
  • Zhichen Pu, Bangzhi Sui, Xingwen Wang, Wusuan Wang, Lingling Li, Haitang Xie. The effects and mechanisms of the anti-COVID-19 traditional Chinese medicine, Dehydroandrographolide from Andrographis paniculata (Burm.f.) Wall, on acute lung injury by the inhibition of NLRP3-mediated pyroptosis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Jun; 114(?):154753. doi: 10.1016/j.phymed.2023.154753. [PMID: 37084628]
  • Bowen Yin, Shuhua Zhang, Yuxi Huang, Yuanzhu Long, Yiguo Chen, Shiyun Zhao, Aiqun Zhou, Minghua Cao, Xiaoming Yin, Daya Luo. The antithrombosis effect of dehydroandrographolide succinate: in vitro and in vivo studies. Pharmaceutical biology. 2022 Dec; 60(1):175-184. doi: 10.1080/13880209.2021.2021948. [PMID: 35014931]
  • Pengpeng Bai, Kaixia Niu, Zhipeng Huo, Xinchi Feng, Feng Qiu. Application of 2H stable isotope labelling methodology and ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry for the metabolite identification of dehydroandrographolide in rats. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2022 Jul; 38(7):977-988. doi: 10.1007/s44211-022-00129-z. [PMID: 35616886]
  • Delu Che, Yi Zheng, Yajing Hou, Ting Li, Xueshan Du, Songmei Geng. Dehydroandrographolide targets CD300f and negatively regulated MRGPRX2-induced pseudo-allergic reaction. Phytotherapy research : PTR. 2022 May; 36(5):2173-2185. doi: 10.1002/ptr.7445. [PMID: 35312106]
  • Zhipeng Huo, Yu Wang, Xinchi Feng, Yi He, Feng Qiu. Tracking the deprotonation site of dehydroandrographolide with electrospray ionization mass spectrometry by deuteration. Rapid communications in mass spectrometry : RCM. 2021 Sep; 35(18):e9152. doi: 10.1002/rcm.9152. [PMID: 34181280]
  • Difa Liu, Zhangwei Wang, Yaoqi Liu, Yi Zhang, Eryan Guo, Mingzhen He, Junshan Liu, Shuangbing Deng, Wencai Ye, Ning Xie. Two New Isomeric Andrographolides with Anti-Inflammatory and Cytotoxic Activity. Chemistry & biodiversity. 2020 Nov; 17(11):e1900494. doi: 10.1002/cbdv.201900494. [PMID: 33022147]
  • Wenjin Guo, Juxiong Liu, Yufei Zhang, He Ma, Yuhang Li, Qian Gong, Yu Cao, Guiqiu Hu, Shengnan Xie, Shoupeng Fu. Dehydroandrographolide inhibits mastitis by activating autophagy without affecting intestinal flora. Aging. 2020 07; 12(14):14050-14065. doi: 10.18632/aging.103312. [PMID: 32702668]
  • Shujun Fu, Lemei Du, Yuan Yuan, Xin He. Quality Evaluation of Andrographis paniculata Capsules Based on Rapid and Accurate LC-ESI-MS/MS Assay of Three Diterpenoids. Journal of chromatographic science. 2019 Aug; 57(8):708-714. doi: 10.1093/chromsci/bmz044. [PMID: 31260057]
  • Delu Che, Yajing Hou, Yingnan Zeng, Chaomei Li, Yongjing Zhang, Di Wei, Shiling Hu, Rui Liu, Hongli An, Yajun Wang, Tao Zhang. Dehydroandrographolide inhibits IgE-mediated anaphylactic reactions via calcium signaling pathway. Toxicology and applied pharmacology. 2019 03; 366(?):46-53. doi: 10.1016/j.taap.2019.01.019. [PMID: 30684531]
  • Liang-Mian Chen, Hui-Min Gao, Xue-Hua Hu, Jing-Jing Zhu, Wei-Hong Feng, Li-Hua Yan, Xiao-Qian Liu, Yong-Xin Zhang, Zhi-Min Wang. [Establishment of QAMS method with dehydroandrographolide as internal reference substance for quality control of Andrographis Herba]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2019 Feb; 44(4):730-739. doi: 10.19540/j.cnki.cjcmm.20181129.006. [PMID: 30989886]
  • Xiao Zhang, Hongwei Wu, Xiankuo Yu, Hanyan Luo, Yaqi Lu, Hongjun Yang, Xin Li, Zhiyong Li, Liying Tang, Zhuju Wang. Determination of Bitterness of Andrographis Herba Based on Electronic Tongue Technology and Discovery of the Key Compounds of Bitter Substances. Molecules (Basel, Switzerland). 2018 Dec; 23(12):. doi: 10.3390/molecules23123362. [PMID: 30572573]
  • Zibin Lu, Pei Xie, Dongmei Zhang, Pinghua Sun, Huayi Yang, Jiaxi Ye, Huihui Cao, Chuying Huo, Hongling Zhou, Yuyao Chen, Wencai Ye, Linzhong Yu, Junshan Liu. 3-Dehydroandrographolide protects against lipopolysaccharide-induced inflammation through the cholinergic anti-inflammatory pathway. Biochemical pharmacology. 2018 12; 158(?):305-317. doi: 10.1016/j.bcp.2018.10.034. [PMID: 30391477]
  • François Chassagne, Mohamed Haddad, Aurélien Amiel, Chiobouaphong Phakeovilay, Chanthanom Manithip, Geneviève Bourdy, Eric Deharo, Guillaume Marti. A metabolomic approach to identify anti-hepatocarcinogenic compounds from plants used traditionally in the treatment of liver diseases. Fitoterapia. 2018 Jun; 127(?):226-236. doi: 10.1016/j.fitote.2018.02.021. [PMID: 29477305]
  • Zhiyong Weng, Yue Chi, Jing Xie, Xuefeng Liu, Jiehua Hu, Fan Yang, Lihua Li. Anti-Inflammatory Activity of Dehydroandrographolide by TLR4/NF-κB Signaling Pathway Inhibition in Bile Duct-Ligated Mice. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2018; 49(3):1083-1096. doi: 10.1159/000493292. [PMID: 30196285]
  • Ming-Ju Hsieh, Chiao-Wen Lin, Hui-Ling Chiou, Shun-Fa Yang, Mu-Kuan Chen. Dehydroandrographolide, an iNOS inhibitor, extracted from Andrographis paniculata (Burm.f.) Nees, induces autophagy in human oral cancer cells. Oncotarget. 2015 Oct; 6(31):30831-49. doi: 10.18632/oncotarget.5036. [PMID: 26356821]
  • Fei-fei Liu, Chun-lin Fan, Xiao-jun Huang, Gui-yang Wang, Ying Wang, Wen-cai Ye. [HPLC Specific Fingerprint of Alcohol Extract of Andrographis paniculata]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Jul; 38(7):1505-8. doi: . [PMID: 26946847]
  • Wentao Cai, Yongtao Li, Sunrui Chen, Mengli Wang, Anding Zhang, Hongbo Zhou, Huanchun Chen, Meilin Jin. 14-Deoxy-11,12-dehydroandrographolide exerts anti-influenza A virus activity and inhibits replication of H5N1 virus by restraining nuclear export of viral ribonucleoprotein complexes. Antiviral research. 2015 Jun; 118(?):82-92. doi: 10.1016/j.antiviral.2015.03.008. [PMID: 25800824]
  • Fang-fang Xu, Shu-jun Fu, Sheng-pan Gu, Zhi-min Wang, Zhen-zhong Wang, Xin He, Wei Xiao. Simultaneous determination of andrographolide, dehydroandrographolide and neoandrographolide in dog plasma by LC-MS/MS and its application to a dog pharmacokinetic study of Andrographis paniculata tablet. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 May; 990(?):125-31. doi: 10.1016/j.jchromb.2015.03.014. [PMID: 25864014]
  • Zhang Xiaomeng, Wu Jiarui, Zhang Bing, Dong Ling. Potassium dehydroandrographolide succinate injection for treat- ment of infantile pneumonia: a systematic review and Meta-analysis. Journal of traditional Chinese medicine = Chung i tsa chih ying wen pan. 2015 Apr; 35(2):125-33. doi: 10.1016/s0254-6272(15)30019-4. [PMID: 25975044]
  • Hao Chen, Yun-Bao Ma, Xiao-Yan Huang, Chang-An Geng, Yong Zhao, Li-Jun Wang, Rui-Hua Guo, Wen-Juan Liang, Xue-Mei Zhang, Ji-Jun Chen. Synthesis, structure-activity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents. Bioorganic & medicinal chemistry letters. 2014 May; 24(10):2353-9. doi: 10.1016/j.bmcl.2014.03.060. [PMID: 24731274]
  • Xue Li, Jinping Hu, Baolian Wang, Li Sheng, Zhihao Liu, Shuang Yang, Yan Li. Inhibitory effects of herbal constituents on P-glycoprotein in vitro and in vivo: herb-drug interactions mediated via P-gp. Toxicology and applied pharmacology. 2014 Mar; 275(2):163-75. doi: 10.1016/j.taap.2013.12.015. [PMID: 24380838]
  • Yan-Hua Shao, Jian-Gang Wang, Xiao-Ping Lai, Xiang-Wei Wu, Ping Ding. [HPTLC fingerprint analysis of andrographolides from Andrographis paniculata]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Feb; 37(2):219-23. doi: . [PMID: 25095339]
  • Yong-Xi Song, Shi-Ping Liu, Zhao Jin, Jian-Fei Qin, Zhi-Yuan Jiang. Qualitative and quantitative analysis of Andrographis paniculata by rapid resolution liquid chromatography/time-of-flight mass spectrometry. Molecules (Basel, Switzerland). 2013 Sep; 18(10):12192-207. doi: 10.3390/molecules181012192. [PMID: 24084022]
  • Qi Zhao, Jie Ding, Haiyan Jin, Lan Ding, Nanqi Ren. A green method using a micellar system for determination of andrographolide and dehydroandrographolide in human plasma. Journal of chromatographic science. 2013 Apr; 51(4):341-8. doi: 10.1093/chromsci/bms146. [PMID: 22977119]
  • Minghua Yang, Junsong Wang, Lingyi Kong. Quantitative analysis of four major diterpenoids in Andrographis paniculata by 1H NMR and its application for quality control of commercial preparations. Journal of pharmaceutical and biomedical analysis. 2012 Nov; 70(?):87-93. doi: 10.1016/j.jpba.2012.05.037. [PMID: 22738787]
  • Xiaoying Yin, Qingshan Liu, Yifan Jiang, Yongming Luo. Development of andrographolide molecularly imprinted polymer for solid-phase extraction. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2011 Jun; 79(1):191-6. doi: 10.1016/j.saa.2011.02.034. [PMID: 21420352]
  • Shuijun Li, Ding Yang, Mengqi Zhang, Juzhen Zhou, Rui Li, Chuan Lu, Yun Liu, Yanmei Liu, Yiping Wang, Chen Yu. Determination of dehydroandrographolide succinate in human plasma by liquid chromatography tandem mass spectrometry (LC-MS/MS): Method development, validation and clinical pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Aug; 878(24):2274-9. doi: 10.1016/j.jchromb.2010.06.030. [PMID: 20638916]
  • Ning-Bo Gong, Li-Juan Lü, Chao Liu, Lin Ma, Ruo-Yun Chen, Yang Lü. [A quantitation method for andrographolide and dehydroandrographolide by X-ray powder diffraction Fourier fingerprint pattern technique]. Yao xue xue bao = Acta pharmaceutica Sinica. 2010 May; 45(5):673-6. doi: ". [PMID: 20931774]
  • Li Xu, Da-wei Xiao, Sheng Lou, Jian-jun Zou, Yu-bing Zhu, Hong-wei Fan, Guang-ji Wang. A simple and sensitive HPLC-ESI-MS/MS method for the determination of andrographolide in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Feb; 877(5-6):502-6. doi: 10.1016/j.jchromb.2008.12.065. [PMID: 19158000]
  • Ligang Chen, Aimin Yu, Xiaodong Zhuang, Kui Zhang, Xiupin Wang, Lan Ding, Hanqi Zhang. Determination of andrographolide and dehydroandrographolide in rabbit plasma by on-line solid phase extraction of high-performance liquid chromatography. Talanta. 2007 Nov; 74(1):146-52. doi: 10.1016/j.talanta.2007.05.043. [PMID: 18371624]
  • Xin Hong, Tian-lai Huang, Shui-qing Mi, Shao-Mei Ye, Wei-ping Ou, Ning-sheng Wang. [Pharmacokinetics of Chuanxinlian tablet in healthy Chinese volunteers]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2007 Apr; 30(4):439-41. doi: NULL. [PMID: 17674799]
  • Yanfang Zhao, Xingping Luo, Yongfei Ming, Hongli Zhang, Xiujuan Li, Liren Chen, Yongmin Li. [Fast determination of andrographolide and dehydroandrographolide in Xiaoyanlidan Tablets by microemulsion electrokinetic chromatography]. Se pu = Chinese journal of chromatography. 2006 May; 24(3):294-7. doi: ". [PMID: 16929852]
  • Zhao Yanfang, Luo Xingping, Zhai Zongde, Chen Liren, Li Yongmin. Simultaneous determination of andrographolide and dehydroandrographolide in Andrographis paniculata and Chinese medicinal preparations by microemulsion electrokinetic chromatography. Journal of pharmaceutical and biomedical analysis. 2006 Jan; 40(1):157-61. doi: 10.1016/j.jpba.2005.04.003. [PMID: 15894448]
  • Rong-Li Qiu, Lin Li, Xiang Li, Hai-Xia Zhang, Jian-Wei Chen. [Effect of ultra-fine powder technique on dissolution rates of andrographolide and dehydroandrographolide in Andrographis paniculata]. Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine. 2004 Nov; 2(6):456-8. doi: 10.3736/jcim20040618. [PMID: 15539030]
  • Xiao-dan Huang, Zi-ren Su, Xiao-ping Lai, Shu-hai Lin, Xiao-bing Dong, Zhong-qiu Liu, Pei-shan Xie. [Changes of dehydroandrographolide's contents of andrographis tablet in the process of production]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2002 Dec; 27(12):911-3. doi: ". [PMID: 12776529]
  • Xiao-Qin Xu, Guang-Lin Hu, Jin-Can Shen, Qi Li, Xiao-Ru Wang. [Determination of andrographolide and dehydroandrographolide in Andrographis paniculata nees materials and related patent medicines by reversed-phase high performance liquid chromatography]. Se pu = Chinese journal of chromatography. 2002 Sep; 20(5):446-8. doi: ". [PMID: 16358699]