ACon1_000667 (BioDeep_00000230326)

   

PANOMIX_OTCML-2023


代谢物信息卡片


4-[2-[(1R,4aS,5R,8aS)-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one

化学式: C26H40O8 (480.272304)
中文名称: 新穿心莲内酯, 穿心莲丙素, 穿心莲新甙, 穿心莲新苷, 新穿心莲素, 新穿心莲内酯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 50.88%

分子结构信息

SMILES: CC1(CCCC2(C1CCC(=C)C2CCC3=CCOC3=O)C)COC4C(C(C(C(O4)CO)O)O)O
InChI: InChI=1S/C26H40O8/c1-15-5-8-19-25(2,14-33-24-22(30)21(29)20(28)18(13-27)34-24)10-4-11-26(19,3)17(15)7-6-16-9-12-32-23(16)31/h9,17-22,24,27-30H,1,4-8,10-14H2,2-3H3/t17-,18-,19-,20-,21+,22-,24-,25+,26+/m1/s1

描述信息

Neoandrographolide is a natural product found in Tabernaemontana corymbosa, Andrographis paniculata, and Potamogeton natans with data available.
Neoandrographolide is a diterpenoid compound isolated from Andrographis paniculata.
Neoandrographolide is a diterpenoid compound isolated from Andrographis paniculata.

同义名列表

17 个代谢物同义名

4-[2-[(1R,4aS,5R,8aS)-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one; 3-(2-((1R,4aS,5R,8aS)-5,8a-dimethyl-2-methylene-5-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)decahydronaphthalen-1-yl)ethyl)furan-2(5H)-one; 3-[2-[(4aS,5R,8aS)-5,8a-Dimethyl-2-methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-5H-furan-2-one; 2(5H)-FURANONE, 3-(2-(5-((.BETA.-D-GLUCOPYRANOSYLOXY)METHYL)DECAHYDRO-5,8A-DIMETHYL-2-METHYLENE-1-NAPHTHALENYL)ETHYL)-, (1R-(1.ALPHA.,4A.BETA.,5.ALPHA.,8A.ALPHA.))-; 2(5H)-Furanone, 3-(2-(5-((beta-D-glucopyranosyloxy)methyl)decahydro-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethyl)-, (1R-(1alpha,4abeta,5alpha,8aalpha))-; 2(5H)-FURANONE, 3-(2-((1R,4AS,5R,8AS)-5-((.BETA.-D-GLUCOPYRANOSYLOXY)METHYL)DECAHYDRO-5,8A-DIMETHYL-2-METHYLENE-1-NAPHTHALENYL)ETHYL)-; 5.BETA.,9.BETA.H,10.ALPHA.-LABDA-8(20),13-DIEN-16-OIC ACID, 18-(GLUCOSYLOXY)-15-HYDROXY-, .GAMMA.-LACTONE; NEOANDROGRAPHOLIDE (CONSTITUENT OF ANDROGRAPHIS) [DSC]; Neoandrographolide, analytical standard; (-)-neoandrographolide; Neoandrographolide; Neoandrographiside; UNII-XBY0Z806J2; MEGxp0_000981; ACon1_000667; XBY0Z806J2; 1ST157228



数据库引用编号

8 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)

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

  • Anchal Garg, Payal Srivastava, Praveen Chandra Verma, Sumit Ghosh. ApCPS2 contributes to medicinal diterpenoid biosynthesis and defense against insect herbivore in Andrographis paniculata. Plant science : an international journal of experimental plant biology. 2024 May; 342(?):112046. doi: 10.1016/j.plantsci.2024.112046. [PMID: 38395069]
  • Sharma Pooja Tarachand, Gopishankar Thirumoorthy, Vasantha Veerappa Lakshmaiah, Praveen Nagella. In silico molecular docking study of Andrographis paniculata phytochemicals against TNF-α as a potent anti-rheumatoid drug. Journal of biomolecular structure & dynamics. 2023 04; 41(7):2687-2697. doi: 10.1080/07391102.2022.2037463. [PMID: 35147481]
  • Dayanand Dalawai, Chetan Aware, Jyoti P Jadhav, Hosakatte Niranjana Murthy. RP-HPLC analysis of diterpene lactones in leaves and stem of different species of Andrographis. Natural product research. 2021 Jul; 35(13):2239-2242. doi: 10.1080/14786419.2019.1662004. [PMID: 31496277]
  • Nor Elliza Tajidin, Khozirah Shaari, Maulidiani Maulidiani, Nor Shariah Salleh, Bunga Raya Ketaren, Munirah Mohamad. Metabolite profiling of Andrographis paniculata (Burm. f.) Nees. young and mature leaves at different harvest ages using 1H NMR-based metabolomics approach. Scientific reports. 2019 11; 9(1):16766. doi: 10.1038/s41598-019-52905-z. [PMID: 31727911]
  • 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]
  • Wei Sun, Liang Leng, Qinggang Yin, MeiMei Xu, Mingkun Huang, Zhichao Xu, Yujun Zhang, Hui Yao, Caixia Wang, Chao Xiong, Sha Chen, Chunhong Jiang, Ning Xie, Xilong Zheng, Ying Wang, Chi Song, Reuben J Peters, Shilin Chen. The genome of the medicinal plant Andrographis paniculata provides insight into the biosynthesis of the bioactive diterpenoid neoandrographolide. The Plant journal : for cell and molecular biology. 2019 03; 97(5):841-857. doi: 10.1111/tpj.14162. [PMID: 30444296]
  • 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]
  • 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. Glucosyltransferase Capable of Catalyzing the Last Step in Neoandrographolide Biosynthesis. Organic letters. 2018 10; 20(19):5999-6002. doi: 10.1021/acs.orglett.8b02146. [PMID: 30234309]
  • Sailendra Singh, Pallavi Pandey, Sumit Ghosh, Suchitra Banerjee. Anti-cancer labdane diterpenoids from adventitious roots of Andrographis paniculata: augmentation of production prospect endowed with pathway gene expression. Protoplasma. 2018 Sep; 255(5):1387-1400. doi: 10.1007/s00709-018-1211-7. [PMID: 29560544]
  • Venu Sharma, Kamal K Kapoor, Debaraj Mukherjee, Vivek K Gupta, Manoj K Dhar, Sanjana Kaul. Camphor sulphonic acid mediated quantitative 1,3-diol protection of major Labdane diterpenes isolated from Andrographis paniculata. Natural product research. 2018 Aug; 32(15):1751-1759. doi: 10.1080/14786419.2017.1402313. [PMID: 29143537]
  • 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]
  • 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]
  • Satyanshu Kumar, Tushar Dhanani, Sonal Shah. Extraction of three bioactive diterpenoids from Andrographis paniculata: effect of the extraction techniques on extract composition and quantification of three andrographolides using high-performance liquid chromatography. Journal of chromatographic science. 2014 Oct; 52(9):1043-50. doi: 10.1093/chromsci/bmt157. [PMID: 24170124]
  • 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]
  • Alireza Valdiani, Daryush Talei, Soon Guan Tan, Mihdzar Abdul Kadir, Mahmood Maziah, Mohd Yusop Rafii, Sreenivasa Rao Sagineedu. A classical genetic solution to enhance the biosynthesis of anticancer phytochemicals in Andrographis paniculata Nees. PloS one. 2014; 9(2):e87034. doi: 10.1371/journal.pone.0087034. [PMID: 24586262]
  • 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]
  • Tao Yang, Hai-xia Shi, Zheng-tao Wang, Chang-hong Wang. Hypolipidemic effects of andrographolide and neoandrographolide in mice and rats. Phytotherapy research : PTR. 2013 Apr; 27(4):618-23. doi: 10.1002/ptr.4771. [PMID: 22744979]
  • Daryush Talei, Alireza Valdiani, Mahmood Maziah, Sreenivasa Rao Sagineedu, Mohd Said Saad. Analysis of the anticancer phytochemicals in Andrographis paniculata Nees. under salinity stress. BioMed research international. 2013; 2013(?):319047. doi: 10.1155/2013/319047. [PMID: 24371819]
  • 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]
  • Waranya Chatuphonprasert, Tawun Remsungnen, Nobuo Nemoto, Kanokwan Jarukamjorn. Different AhR binding sites of diterpenoid ligands from Andrographis paniculata caused differential CYP1A1 induction in primary culture in mouse hepatocytes. Toxicology in vitro : an international journal published in association with BIBRA. 2011 Dec; 25(8):1757-63. doi: 10.1016/j.tiv.2011.09.004. [PMID: 21963808]
  • Petra H Pfisterer, Judith M Rollinger, Lilianna Schyschka, Anita Rudy, Angelika M Vollmar, Hermann Stuppner. Neoandrographolide from Andrographis paniculata as a potential natural chemosensitizer. Planta medica. 2010 Oct; 76(15):1698-700. doi: 10.1055/s-0030-1249876. [PMID: 20446243]
  • Arvind S Negi, J K Kumar, Suaib Luqman, Karuna Shanker, M M Gupta, S P S Khanuja. Recent advances in plant hepatoprotectives: a chemical and biological profile of some important leads. Medicinal research reviews. 2008 Sep; 28(5):746-72. doi: 10.1002/med.20115. [PMID: 17979145]
  • Jun Liu, Zheng-Tao Wang, Li-Li Ji, Bao-Xue Ge. Inhibitory effects of neoandrographolide on nitric oxide and prostaglandin E2 production in LPS-stimulated murine macrophage. Molecular and cellular biochemistry. 2007 Apr; 298(1-2):49-57. doi: 10.1007/s11010-006-9349-6. [PMID: 17109078]
  • Jun Liu, Zheng-Tao Wang, Li-Li Ji. In vivo and in vitro anti-inflammatory activities of neoandrographolide. The American journal of Chinese medicine. 2007; 35(2):317-28. doi: 10.1142/s0192415x07004849. [PMID: 17436371]
  • Piengpen Thisoda, Nuchanart Rangkadilok, Nanthanit Pholphana, Luksamee Worasuttayangkurn, Somsak Ruchirawat, Jutamaad Satayavivad. Inhibitory effect of Andrographis paniculata extract and its active diterpenoids on platelet aggregation. European journal of pharmacology. 2006 Dec; 553(1-3):39-45. doi: 10.1016/j.ejphar.2006.09.052. [PMID: 17081514]
  • Li-Xia Chen, Ge-Xia Qu, Feng Qiu. [Studies on diterpenoids from Andrographis paniculata]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Oct; 31(19):1594-7. doi: . [PMID: 17165582]
  • Yun-Heng Shen, Rong-Tao Li, Wei-Lie Xiao, Gang Xu, Zhong-Wen Lin, Qin-Shi Zhao, Han-Dong Sun. ent-Labdane diterpenoids from Andrographis paniculata. Journal of natural products. 2006 Mar; 69(3):319-22. doi: 10.1021/np050160u. [PMID: 16562826]
  • C Wiart, K Kumar, M Y Yusof, H Hamimah, Z M Fauzi, M Sulaiman. Antiviral properties of ent-labdene diterpenes of Andrographis paniculata nees, inhibitors of herpes simplex virus type 1. Phytotherapy research : PTR. 2005 Dec; 19(12):1069-70. doi: 10.1002/ptr.1765. [PMID: 16372376]
  • Nanthanit Pholphana, Nuchanart Rangkadilok, Sanit Thongnest, Somsak Ruchirawat, Mathuros Ruchirawat, Jutamaad Satayavivad. Determination and variation of three active diterpenoids in Andrographis paniculata (Burm.f.) Nees. Phytochemical analysis : PCA. 2004 Nov; 15(6):365-71. doi: 10.1002/pca.789. [PMID: 15595451]
  • Alpana Srivastava, Himanshu Misra, Ram K Verma, Madan M Gupta. Chemical fingerprinting of Andrographis paniculata using HPLC, HPTLC and densitometry. Phytochemical analysis : PCA. 2004 Sep; 15(5):280-5. doi: 10.1002/pca.779. [PMID: 15508831]
  • Du Qizhen, Gerold Jerz, Peter Winterhalter. Separation of andrographolide and neoandrographolide from the leaves of Andrographis paniculata using high-speed counter-current chromatography. Journal of chromatography. A. 2003 Jan; 984(1):147-51. doi: 10.1016/s0021-9673(02)01831-9. [PMID: 12564684]
  • Javzan Batkhuu, Koichi Hattori, Fumihide Takano, Shinji Fushiya, Ko-ichi Oshiman, Yoshiaki Fujimiya. Suppression of NO production in activated macrophages in vitro and ex vivo by neoandrographolide isolated from Andrographis paniculata. Biological & pharmaceutical bulletin. 2002 Sep; 25(9):1169-74. doi: 10.1248/bpb.25.1169. [PMID: 12230111]
  • A Basak, S Cooper, A G Roberge, U K Banik, M Chrétien, N G Seidah. Inhibition of proprotein convertases-1, -7 and furin by diterpines of Andrographis paniculata and their succinoyl esters. The Biochemical journal. 1999 Feb; 338 ( Pt 1)(?):107-13. doi: . [PMID: 9931305]
  • A Kapil, I B Koul, S K Banerjee, B D Gupta. Antihepatotoxic effects of major diterpenoid constituents of Andrographis paniculata. Biochemical pharmacology. 1993 Jul; 46(1):182-5. doi: 10.1016/0006-2952(93)90364-3. [PMID: 8347130]
  • A Puri, R Saxena, R P Saxena, K C Saxena, V Srivastava, J S Tandon. Immunostimulant agents from Andrographis paniculata. Journal of natural products. 1993 Jul; 56(7):995-9. doi: 10.1021/np50097a002. [PMID: 8377022]