Madecassic (BioDeep_00000230834)

Main id: BioDeep_00000400537

 

PANOMIX_OTCML-2023 Chemicals and Drugs natural product


代谢物信息卡片


(1S,2R,4aS,6aS,6bR,8R,8aR,9R,10R,11R,12aR,12bR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

化学式: C30H48O6 (504.3450708)
中文名称: 羟基积雪草苷, 羟基积雪草酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1CCC2(CCC3(C(=CCC4C3(CC(C5C4(CC(C(C5(C)CO)O)O)C)O)C)C2C1C)C)C(=O)O
InChI: InChI=1S/C30H48O6/c1-16-9-10-30(25(35)36)12-11-28(5)18(22(30)17(16)2)7-8-21-26(3)13-20(33)24(34)27(4,15-31)23(26)19(32)14-29(21,28)6/h7,16-17,19-24,31-34H,8-15H2,1-6H3,(H,35,36)/t16-,17+,19-,20-,21-,22+,23-,24+,26-,27+,28-,29-,30+/m1/s1

描述信息

Madecassic acid is a pentacyclic triterpenoid that is ursane substituted by a carboxy group at position 28 and hydroxy groups at positions 2, 3, 6 and 23 (the 2alpha,3beta,6beta stereoisomer). It has a role as an antioxidant and a plant metabolite. It is a pentacyclic triterpenoid, a tetrol and a monocarboxylic acid. It derives from a hydride of an ursane.
Madecassic acid is a natural product found in Siphoneugena densiflora, Centella erecta, and Centella asiatica with data available.
See also: Centella asiatica flowering top (part of) ... View More ...
A pentacyclic triterpenoid that is ursane substituted by a carboxy group at position 28 and hydroxy groups at positions 2, 3, 6 and 23 (the 2alpha,3beta,6beta stereoisomer).
C1907 - Drug, Natural Product > C28269 - Phytochemical > C1905 - Triterpenoid Compound
C274 - Antineoplastic Agent > C1931 - Antineoplastic Plant Product
Madecassic acid is isolated from Centella asiatica (Umbelliferae). Madecassic acid has anti-inflammatory properties caused by iNOS, COX-2, TNF-alpha, IL-1beta, and IL-6 inhibition via the downregulation of NF-κB activation in RAW 264.7 macrophage cells[1].
Madecassic acid is isolated from Centella asiatica (Umbelliferae). Madecassic acid has anti-inflammatory properties caused by iNOS, COX-2, TNF-alpha, IL-1beta, and IL-6 inhibition via the downregulation of NF-κB activation in RAW 264.7 macrophage cells[1].

同义名列表

27 个代谢物同义名

(1S,2R,4aS,6aS,6bR,8R,8aR,9R,10R,11R,12aR,12bR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid; (1S,2R,4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid; (1S,2R,4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylicacid; Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2.alpha.,3.beta.,4.alpha.,6.beta.)-; Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2alpha,3beta,4alpha,6beta)-; URS-12-EN-28-OIC ACID, 2.ALPHA.,3.BETA.,6.BETA.,23-TETRAHYDROXY-; (2alpha,3beta,6beta)-2,3,6,23-tetrahydroxyurs-12-en-28-oic acid; 2.ALPHA.,3.BETA.,6.BETA.,23-TETRAHYDROXY-URS-12-EN-28-OIC ACID; Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2a,3b,4a,6b)-; URS-12-EN-28-OIC ACID, 2alpha,3beta,6beta,23-TETRAHYDROXY-; MADECASSIC ACID (CONSTITUENT OF CENTELLA ASIATICA) [DSC]; 2alpha,3beta,6beta,23-TETRAHYDROXY-URS-12-EN-28-OIC ACID; 2alpha,3beta,6beta,23-Tetrahydroxyurs-12-en-28-oic Acid; MADECASSIC ACID (CONSTITUENT OF CENTELLA ASIATICA); Callicos CellAwake Mask madecassol; 6.BETA.-HYDROXYASIATIC ACID; 6beta-hydroxyasiatic acid; MADECASSIC ACID [WHO-DD]; MADECASSIC ACID [INCI]; 6-Hydroxyasiatic acid; Madecassic Acid; madasiatic acid; UNII-M7O1N24J82; ORISTRACT MDA; Brahmic acid; M7O1N24J82; Madecassic



数据库引用编号

11 个数据库交叉引用编号

分类词条

相关代谢途径

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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)

32 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

  • Zaynab Mando, Huda Mando, Adlin Afzan, Khozirah Shaari, Zurina Hassan, Mohamad Nurul Azmi Mohamad Taib, Fauziahanim Zakaria. Biomarker triterpenoids of Centella asiatica as potential antidepressant agents: Combining in vivo and in silico studies. Behavioural brain research. 2024 May; 466(?):114976. doi: 10.1016/j.bbr.2024.114976. [PMID: 38599249]
  • Zeba Firdaus, Gopichand Gutti, Ankit Ganeshpurkar, Ashok Kumar, Sairam Krishnamurthy, Sushil Kumar Singh, Tryambak Deo Singh. Centella asiatica improves memory and executive function in middle-aged rats by controlling oxidative stress and cholinergic transmission. Journal of ethnopharmacology. 2024 May; 325(?):117888. doi: 10.1016/j.jep.2024.117888. [PMID: 38336185]
  • Narumon Changsan, Teerapol Srichana, Apichart Atipairin, Somchai Sawatdee. Wound healing efficacy of a polymeric spray film solution containing Centella asiatica leaf extract on acute wounds. Journal of wound care. 2023 Dec; 32(Sup12):S22-S32. doi: 10.12968/jowc.2023.32.sup12.s22. [PMID: 38063299]
  • Chunling Wei, Peiwu Cui, Xiangqian Liu. Antibacterial Activity and Mechanism of Madecassic Acid against Staphylococcus aureus. Molecules (Basel, Switzerland). 2023 Feb; 28(4):. doi: 10.3390/molecules28041895. [PMID: 36838882]
  • Li Lin, Qingyong Chen, Yue Dai, Yufeng Xia. Self-Nanoemulsifying Drug Delivery System for Enhanced Bioavailability of Madecassic Acid: In vitro and in vivo Evaluation. International journal of nanomedicine. 2023; 18(?):2345-2358. doi: 10.2147/ijn.s408115. [PMID: 37187996]
  • Liu Liu, Haobin Li, Kaiwen Hu, Qinglong Xu, Xiaoan Wen, Keguang Cheng, Caiping Chen, Haoliang Yuan, Liang Dai, Hongbin Sun. Synthesis and anti-inflammatory activity of saponin derivatives of δ-oleanolic acid. European journal of medicinal chemistry. 2021 Jan; 209(?):112932. doi: 10.1016/j.ejmech.2020.112932. [PMID: 33131725]
  • Nor Atiqah Jusril, Ain Nur Najihah Muhamad Juhari, Syahrul Imran Abu Bakar, Wan Mazlina Md Saad, Mohd Ilham Adenan. Combining In Silico and In Vitro Studies to Evaluate the Acetylcholinesterase Inhibitory Profile of Different Accessions and the Biomarker Triterpenes of Centella asiatica. Molecules (Basel, Switzerland). 2020 Jul; 25(15):. doi: 10.3390/molecules25153353. [PMID: 32721993]
  • Julie A Lawrence, Zhongping Huang, Sivaprakash Rathinavelu, Jin-Feng Hu, Eliane Garo, Michael Ellis, Vanessa L Norman, Ronald Buckle, Russell B Williams, Courtney M Starks, Gary R Eldridge. Optimized plant compound with potent anti-biofilm activity across gram-negative species. Bioorganic & medicinal chemistry. 2020 03; 28(5):115229. doi: 10.1016/j.bmc.2019.115229. [PMID: 32033878]
  • Nur Nadia Mohd Razali, Chin Theng Ng, Lai Yen Fong. Cardiovascular Protective Effects of Centella asiatica and Its Triterpenes: A Review. Planta medica. 2019 Nov; 85(16):1203-1215. doi: 10.1055/a-1008-6138. [PMID: 31539918]
  • Jorge Arancibia-Radich, Raquel González-Blázquez, Martín Alcalá, Miriam Martín-Ramos, Marta Viana, Silvia Arribas, Carla Delporte, María S Fernández-Alfonso, Beatriz Somoza, Marta Gil-Ortega. Beneficial effects of murtilla extract and madecassic acid on insulin sensitivity and endothelial function in a model of diet-induced obesity. Scientific reports. 2019 01; 9(1):599. doi: 10.1038/s41598-018-36555-1. [PMID: 30679477]
  • Renu Arora, Ritesh Kumar, Amit Agarwal, K H Reeta, Y K Gupta. Comparison of three different extracts of Centella asiatica for anti-amnesic, antioxidant and anticholinergic activities: in vitro and in vivo study. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Sep; 105(?):1344-1352. doi: 10.1016/j.biopha.2018.05.156. [PMID: 30021372]
  • Yuan-Man Hsu, Yi-chih Hung, Lihong Hu, Yi-ju Lee, Mei-chin Yin. Anti-Diabetic Effects of Madecassic Acid and Rotundic Acid. Nutrients. 2015 Dec; 7(12):10065-75. doi: 10.3390/nu7125512. [PMID: 26633490]
  • Ting Wang, Zhifeng Wei, Yannong Dou, Yan Yang, Dandan Leng, Lingyi Kong, Yue Dai, Yufeng Xia. Intestinal interleukin-10 mobilization as a contributor to the anti-arthritis effect of orally administered madecassoside: a unique action mode of saponin compounds with poor bioavailability. Biochemical pharmacology. 2015 Mar; 94(1):30-8. doi: 10.1016/j.bcp.2015.01.004. [PMID: 25600909]
  • Ting Wang, Dan-Dan Leng, Fei-Fei Gao, Chun-Jie Jiang, Yu-Feng Xia, Yue Dai. A LC-ESI-MS method for the simultaneous determination of madecassoside and its metabolite madecassic acid in rat plasma: comparison pharmacokinetics in normal and collagen-induced arthritic rats. Chinese journal of natural medicines. 2014 Dec; 12(12):943-51. doi: 10.1016/s1875-5364(14)60138-2. [PMID: 25556066]
  • Wiesława Bylka, Paulina Znajdek-Awiżeń, Elżbieta Studzińska-Sroka, Aleksandra Dańczak-Pazdrowska, Małgorzata Brzezińska. Centella asiatica in dermatology: an overview. Phytotherapy research : PTR. 2014 Aug; 28(8):1117-24. doi: 10.1002/ptr.5110. [PMID: 24399761]
  • Chao Wang, Jing Yang, Ping Zhao, Qi Zhou, Zhinan Mei, Guangzhong Yang, Xinzhou Yang, Yunjiang Feng. Chemical constituents from Eucalyptus citriodora Hook leaves and their glucose transporter 4 translocation activities. Bioorganic & medicinal chemistry letters. 2014 Jul; 24(14):3096-9. doi: 10.1016/j.bmcl.2014.05.014. [PMID: 24894556]
  • Qian Shen, Lu-shan Yu, Hui Zhou, Su Zeng. [Simultaneous determination of madecassoside, asiaticoside and their aglycones in Centella asiatica (L.) urban extracts by RP-HPLC]. Zhejiang da xue xue bao. Yi xue ban = Journal of Zhejiang University. Medical sciences. 2014 03; 43(2):135-40. doi: 10.3785/j.issn.1008-9292.2014.03.002. [PMID: 24782366]
  • Jacinda T James, Fidele Tugizimana, Paul A Steenkamp, Ian A Dubery. Metabolomic analysis of methyl jasmonate-induced triterpenoid production in the medicinal herb Centella asiatica (L.) urban. Molecules (Basel, Switzerland). 2013 Apr; 18(4):4267-81. doi: 10.3390/molecules18044267. [PMID: 23579994]
  • P Puttarak, P Panichayupakaranant. Factors affecting the content of pentacyclic triterpenes in Centella asiatica raw materials. Pharmaceutical biology. 2012 Dec; 50(12):1508-12. doi: 10.3109/13880209.2012.685946. [PMID: 22966846]
  • Yan Pan, Badrul Amini Abd-Rashid, Zakiah Ismail, Rusli Ismail, Joon Wah Mak, Peter C K Pook, Hui Meng Er, Chin Eng Ong. In vitro modulatory effects on three major human cytochrome P450 enzymes by multiple active constituents and extracts of Centella asiatica. Journal of ethnopharmacology. 2010 Jul; 130(2):275-83. doi: 10.1016/j.jep.2010.05.002. [PMID: 20457244]
  • Jong-Heon Won, Ji-Sun Shin, Hee-Juhn Park, Hyun-Ju Jung, Duck-Jae Koh, Baek-Geon Jo, Jin-Yong Lee, Kijoo Yun, Kyung-Tae Lee. Anti-inflammatory effects of madecassic acid via the suppression of NF-kappaB pathway in LPS-induced RAW 264.7 macrophage cells. Planta medica. 2010 Feb; 76(3):251-7. doi: 10.1055/s-0029-1186142. [PMID: 19774506]
  • Yi-Nan Zhang, Wei Zhang, Di Hong, Lei Shi, Qiang Shen, Jing-Ya Li, Jia Li, Li-Hong Hu. Oleanolic acid and its derivatives: new inhibitor of protein tyrosine phosphatase 1B with cellular activities. Bioorganic & medicinal chemistry. 2008 Sep; 16(18):8697-705. doi: 10.1016/j.bmc.2008.07.080. [PMID: 18707891]
  • Jian Pan, Guiqing Kai, Chuanxun Yuan, Beibei Zhou, Risheng Jin, Yuan Yuan. [Separation and determination of madecassic acid in triterpenic genins of Centella asiatica by high performance liquid chromatography using beta-cyclodextrin as mobile phase additive]. Se pu = Chinese journal of chromatography. 2007 May; 25(3):316-8. doi: 10.1016/s1872-2059(07)60009-1. [PMID: 17679419]
  • Christopher D Coldren, Puziah Hashim, Johari Mohd Ali, Se-Kyung Oh, Anthony J Sinskey, ChoKyun Rha. Gene expression changes in the human fibroblast induced by Centella asiatica triterpenoids. Planta medica. 2003 Aug; 69(8):725-32. doi: 10.1055/s-2003-42791. [PMID: 14531023]
  • F X Maquart, F Chastang, A Simeon, P Birembaut, P Gillery, Y Wegrowski. Triterpenes from Centella asiatica stimulate extracellular matrix accumulation in rat experimental wounds. European journal of dermatology : EJD. 1999 Jun; 9(4):289-96. doi: ". [PMID: 10356407]
  • B M Hausen. Centella asiatica (Indian pennywort), an effective therapeutic but a weak sensitizer. Contact dermatitis. 1993 Oct; 29(4):175-9. doi: 10.1111/j.1600-0536.1993.tb03532.x. [PMID: 8281778]
  • F X Maquart, G Bellon, P Gillery, Y Wegrowski, J P Borel. Stimulation of collagen synthesis in fibroblast cultures by a triterpene extracted from Centella asiatica. Connective tissue research. 1990; 24(2):107-20. doi: 10.3109/03008209009152427. [PMID: 2354631]