Arjunolicacid (BioDeep_00000396503)

Main id: BioDeep_00000018883

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(4aS,6aS,6bR,8aR,9R,10R,11R,12aR,12bR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,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: C30H48O5 (488.3501558)
中文名称: 阿江榄仁酸, 阿酚酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@]43C)[C@@H]2C1
InChI: InChI=1S/C30H48O5/c1-25(2)11-13-30(24(34)35)14-12-28(5)18(19(30)15-25)7-8-22-26(3)16-20(32)23(33)27(4,17-31)21(26)9-10-29(22,28)6/h7,19-23,31-33H,8-17H2,1-6H3,(H,34,35)/t19-,20+,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1

描述信息

Arjunolic acid is a pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 23 (the 2alpha,3beta stereoisomer). Isolated from Symplocos lancifolia and Juglans sinensis, it exhibits antioxidant and antimicrobial activities. It has a role as a metabolite, an antibacterial agent, an antifungal agent and an antioxidant. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of an oleanane.
Arjunolic acid is a natural product found in Musanga cecropioides, Akebia quinata, and other organisms with data available.
A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 23 (the 2alpha,3beta stereoisomer). Isolated from Symplocos lancifolia and Juglans sinensis, it exhibits antioxidant and antimicrobial activities.

同义名列表

12 个代谢物同义名

(4aS,6aS,6bR,8aR,9R,10R,11R,12aR,12bR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,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; (4aS,6aR,6aS,6bR,8aR,9R,10R,11R,12aR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid; (2,3,4)-2,3,23-Trihydroxyolean-12-en-28-oic acid; 2,3,23-Trihydroxyolean-12-en-28-oic acid; Urjinolic acid; Olean-12-en-28-oic acid, 2,3,23-trihydroxy-, (2.alpha.,3.beta.,4.alpha.)-; Olean-12-en-28-oic acid, 2,3,23-trihydroxy-, (2alpha,3beta,4alpha)-; (2alpha,3beta,4alpha)-2,3,23-trihydroxyolean-12-en-28-oic acid; (2alpha,3beta)-2,3,23-trihydroxyolean-12-en-28-oic acid; 2alpha,3beta-24-trihydroxyolean-12-en-28-oic acid; 2,3,23-trihydroxyolean-12-en-28-oic acid; Arjunolic acid, >=95\\% (LC/MS-ELSD); Arjunolic acid; Arjunolicacid



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

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)

182 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

  • Xuan-Xuan Zhang, Ya-Li Ji, Li-Ping Zhu, Zi-Han Wang, Chang-Qian Fang, Cui-Hua Jiang, Ke Pan, Jian Zhang, Zhi-Qi Yin. Arjunolic acid from Cyclocarya paliurus ameliorates diabetic retinopathy through AMPK/mTOR/HO-1 regulated autophagy pathway. Journal of ethnopharmacology. 2022 Feb; 284(?):114772. doi: 10.1016/j.jep.2021.114772. [PMID: 34688801]
  • Khurram Aamir, Hidayat Ullah Khan, Chowdhury Faiz Hossain, Mst Rejina Afrin, Patricia Regina Jusuf, Imran Waheed, Gautam Sethi, Aditya Arya. Arjunolic acid downregulates elevated blood sugar and pro-inflammatory cytokines in streptozotocin (STZ)-nicotinamide induced type 2 diabetic rats. Life sciences. 2022 Jan; 289(?):120232. doi: 10.1016/j.lfs.2021.120232. [PMID: 34919901]
  • Hany Elsawy, Mohammed Almalki, Omar Elmenshawy, Ashraf Abdel-Moneim. In vivo evaluation of the protective effects of arjunolic acid against lipopolysaccharide-induced septic myocardial injury. PeerJ. 2022; 10(?):e12986. doi: 10.7717/peerj.12986. [PMID: 35190789]
  • Ashutosh Gupta, Ramesh Kumar, Piyali Bhattacharyya, Anupam Bishayee, Abhay K Pandey. Terminalia bellirica (Gaertn.) roxb. (Bahera) in health and disease: A systematic and comprehensive review. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Oct; 77(?):153278. doi: 10.1016/j.phymed.2020.153278. [PMID: 32781393]
  • Sarita Khatkar, Arun Nanda, Shahid H Ansari. Comparative Evaluation of Conventional and Novel Extracts of Stem Bark of Terminalia arjuna for Antihypertensive Activity in BSO Induced Oxidative Stress based Rat Model. Current pharmaceutical biotechnology. 2019; 20(2):157-167. doi: 10.2174/1389201020666190222185209. [PMID: 30806310]
  • Trisha Bansal, Emeli Chatterjee, Jasdeep Singh, Arjun Ray, Bishwajit Kundu, V Thankamani, Shantanu Sengupta, Sagartirtha Sarkar. Arjunolic acid, a peroxisome proliferator-activated receptor α agonist, regresses cardiac fibrosis by inhibiting non-canonical TGF-β signaling. The Journal of biological chemistry. 2017 10; 292(40):16440-16462. doi: 10.1074/jbc.m117.788299. [PMID: 28821620]
  • Tshepiso Jan Makhafola, Esameldin Elzein Elgorashi, Lyndy Joy McGaw, Maurice Ducret Awouafack, Luc Verschaeve, Jacobus Nicolaas Eloff. Isolation and characterization of the compounds responsible for the antimutagenic activity of Combretum microphyllum (Combretaceae) leaf extracts. BMC complementary and alternative medicine. 2017 Sep; 17(1):446. doi: 10.1186/s12906-017-1935-5. [PMID: 28874162]
  • Braja Gopal Bag, Rakhi Majumdar. Self-assembly of Renewable  Nano-sized Triterpenoids. Chemical record (New York, N.Y.). 2017 09; 17(9):841-873. doi: 10.1002/tcr.201600123. [PMID: 28195390]
  • Ilhem Zebiri, Mohamed Haddad, Laurent Duca, Michel Sauvain, Lucie Paloque, Billy Cabanillas, Elsa Rengifo, Jean-Bernard Behr, Laurence Voutquenne-Nazabadioko. Biological activities of triterpenoids from Poraqueiba sericea stems. Natural product research. 2017 Jun; 31(11):1333-1338. doi: 10.1080/14786419.2016.1241998. [PMID: 27736194]
  • Subrata Pandit, Satyajyoti Kanjilal, Anshumali Awasthi, Anika Chaudhary, Dipankar Banerjee, B N Bhatt, Avinash Narwaria, Rahul Singh, Kakoli Dutta, Manu Jaggi, Anu T Singh, Neena Sharma, Chandra Kant Katiyar. Evaluation of herb-drug interaction of a polyherbal Ayurvedic formulation through high throughput cytochrome P450 enzyme inhibition assay. Journal of ethnopharmacology. 2017 Feb; 197(?):165-172. doi: 10.1016/j.jep.2016.07.061. [PMID: 27457692]
  • Chen Wang, Ping Wu, Shuai Tian, Jinghua Xue, Liangxiong Xu, Hanxiang Li, Xiaoyi Wei. Bioactive Pentacyclic Triterpenoids from the Leaves of Cleistocalyx operculatus. Journal of natural products. 2016 11; 79(11):2912-2923. doi: 10.1021/acs.jnatprod.6b00715. [PMID: 27797185]
  • Nehal M Elsherbiny, Mohamed A Eladl, Mohammed M H Al-Gayyar. Renal protective effects of arjunolic acid in a cisplatin-induced nephrotoxicity model. Cytokine. 2016 Jan; 77(?):26-34. doi: 10.1016/j.cyto.2015.10.010. [PMID: 26517155]
  • Lavanya Yaidikar, Santhrani Thakur. Arjunolic acid, a pentacyclic triterpenoidal saponin of Terminalia arjuna bark protects neurons from oxidative stress associated damage in focal cerebral ischemia and reperfusion. Pharmacological reports : PR. 2015 Oct; 67(5):890-5. doi: 10.1016/j.pharep.2015.02.003. [PMID: 26398381]
  • Jing Sun, Hui-Xia Huo, Zheng Huang, Jing Zhang, Jun Li, Peng-Fei Tu. A new γ-alkylated-γ-butyrolactone from the roots of Solanum melongena. Chinese journal of natural medicines. 2015 Sep; 13(9):699-703. doi: 10.1016/s1875-5364(15)30068-6. [PMID: 26412430]
  • Iman O Sherif. Amelioration of cisplatin-induced nephrotoxicity in rats by triterpenoid saponin of Terminalia arjuna. Clinical and experimental nephrology. 2015 Aug; 19(4):591-7. doi: 10.1007/s10157-014-1056-0. [PMID: 25389052]
  • Sankhadeep Pal, Abhijit Sarkar, Pabitra Bikash Pal, Parames C Sil. Protective effect of arjunolic acid against atorvastatin induced hepatic and renal pathophysiology via MAPK, mitochondria and ER dependent pathways. Biochimie. 2015 May; 112(?):20-34. doi: 10.1016/j.biochi.2015.02.016. [PMID: 25736991]
  • Abdullah Alyoussef. Arjunolic acid protects against DNCB-induced atopic dermatitis-like symptoms in mice by restoring a normal cytokine balance. European cytokine network. 2015 Apr; 26(2):38-45. doi: 10.1684/ecn.2015.0364. [PMID: 26553587]
  • Su Yeong Kim, Jung Eun Kim, Hee Jung Bu, Chang-Gu Hyun, Nam Ho Lee. Chemical constituents of Tilia taquetii leaves and their inhibition of MMP-1 expression and elastase activities. Natural product communications. 2014 Dec; 9(12):1683-5. doi: . [PMID: 25632458]
  • Iman O Sherif, Azza Abdel-Aziz, Osama M Sarhan. Cisplatin-induced testicular toxicity in rats: the protective effect of arjunolic acid. Journal of biochemical and molecular toxicology. 2014 Nov; 28(11):515-21. doi: 10.1002/jbt.21593. [PMID: 25130312]
  • Mohammed M H Al-Gayyar, Abdullah Al Youssef, Iman O Sherif, Mohamed E E Shams, Ahmed Abbas. Protective effects of arjunolic acid against cardiac toxicity induced by oral sodium nitrite: effects on cytokine balance and apoptosis. Life sciences. 2014 Aug; 111(1-2):18-26. doi: 10.1016/j.lfs.2014.07.002. [PMID: 25064822]
  • Fabrício F A Fernandes, Marcelo A Tomaz, Camila Z El-Kik, Marcos Monteiro-Machado, Marcelo A Strauch, Bruno L Cons, Matheus S Tavares-Henriques, Adélia C O Cintra, Valdir A Facundo, Paulo A Melo. Counteraction of Bothrops snake venoms by Combretum leprosum root extract and arjunolic acid. Journal of ethnopharmacology. 2014 Aug; 155(1):552-62. doi: 10.1016/j.jep.2014.05.056. [PMID: 24952279]
  • Bo Zhai, Julie Clark, Taotao Ling, Michele Connelly, Fabricio Medina-Bolivar, Fatima Rivas. Antimalarial evaluation of the chemical constituents of hairy root culture of Bixa orellana L. Molecules (Basel, Switzerland). 2014 Jan; 19(1):756-66. doi: 10.3390/molecules19010756. [PMID: 24406786]
  • Lourdes C Souza-Neta, Diego Menezes, Milena S Lima, Martins D Cerqueira, Frederico G Cruz, Dirceu Martins, Marcos A Vannier-Santos. Modes of action of arjunolic acid and derivatives on Trypanosoma cruzi cells. Current topics in medicinal chemistry. 2014; 14(8):1022-32. doi: 10.2174/1568026614666140324122800. [PMID: 24660682]
  • Jyotirmoy Ghosh, Parames C Sil. Arjunolic acid: a new multifunctional therapeutic promise of alternative medicine. Biochimie. 2013 Jun; 95(6):1098-109. doi: 10.1016/j.biochi.2013.01.016. [PMID: 23402784]
  • Prasenjit Manna, Parames C Sil. Arjunolic acid: beneficial role in type 1 diabetes and its associated organ pathophysiology. Free radical research. 2012 Jul; 46(7):815-30. doi: 10.3109/10715762.2012.683431. [PMID: 22486656]
  • Subash Chandra Verma, Chhoten Lal Jain, Madan Mohan Padhi, Ramesh Babu Devalla. Microwave extraction and rapid isolation of arjunic acid from Terminalia arjuna (Roxb. ex DC.) stem bark and quantification of arjunic acid and arjunolic acid using HPLC-PDA technique. Journal of separation science. 2012 Jul; 35(13):1627-33. doi: 10.1002/jssc.201200083. [PMID: 22761141]
  • Prasenjit Manna, Parames C Sil. Impaired redox signaling and mitochondrial uncoupling contributes vascular inflammation and cardiac dysfunction in type 1 diabetes: Protective role of arjunolic acid. Biochimie. 2012 Mar; 94(3):786-97. doi: 10.1016/j.biochi.2011.11.010. [PMID: 22155371]
  • M Gowri Ponnapalli, S Ch V A Rao Annam, Saidulu Ravirala, Sushma Sukki, Madhu Ankireddy, V Raju Tuniki. Unusual isomeric corniculatolides from mangrove, Aegiceras corniculatum. Journal of natural products. 2012 Feb; 75(2):275-9. doi: 10.1021/np200789s. [PMID: 22316191]
  • Sankhadeep Pal, Pabitra Bikash Pal, Joydeep Das, Parames C Sil. Involvement of both intrinsic and extrinsic pathways in hepatoprotection of arjunolic acid against cadmium induced acute damage in vitro. Toxicology. 2011 May; 283(2-3):129-39. doi: 10.1016/j.tox.2011.03.006. [PMID: 21420465]
  • Ivone Lucia Acebey-Castellon, Laurence Voutquenne-Nazabadioko, Huong Doan Thi Mai, Nathalie Roseau, Naima Bouthagane, Dima Muhammad, Elisabeth Le Magrex Debar, Sophie C Gangloff, Marc Litaudon, Thierry Sevenet, Nguyen Van Hung, Catherine Lavaud. Triterpenoid saponins from Symplocos lancifolia. Journal of natural products. 2011 Feb; 74(2):163-8. doi: 10.1021/np100502y. [PMID: 21288041]
  • Prasenjit Manna, Joydeep Das, Jyotirmoy Ghosh, Parames C Sil. Contribution of type 1 diabetes to rat liver dysfunction and cellular damage via activation of NOS, PARP, IkappaBalpha/NF-kappaB, MAPKs, and mitochondria-dependent pathways: Prophylactic role of arjunolic acid. Free radical biology & medicine. 2010 Jun; 48(11):1465-84. doi: 10.1016/j.freeradbiomed.2010.02.025. [PMID: 20188823]
  • Prasenjit Manna, Jyotirmoy Ghosh, Joydeep Das, Parames C Sil. Streptozotocin induced activation of oxidative stress responsive splenic cell signaling pathways: protective role of arjunolic acid. Toxicology and applied pharmacology. 2010 Apr; 244(2):114-29. doi: 10.1016/j.taap.2009.12.024. [PMID: 20053369]
  • Thiagarajan Hemalatha, Sivasami Pulavendran, Chidambaram Balachandran, Bhakthavatsalam Murali Manohar, Rengarajulu Puvanakrishnan. Arjunolic acid: a novel phytomedicine with multifunctional therapeutic applications. Indian journal of experimental biology. 2010 Mar; 48(3):238-47. doi: ". [PMID: 21046976]
  • Jyotirmoy Ghosh, Joydeep Das, Prasenjit Manna, Parames C Sil. Acetaminophen induced renal injury via oxidative stress and TNF-alpha production: therapeutic potential of arjunolic acid. Toxicology. 2010 Jan; 268(1-2):8-18. doi: 10.1016/j.tox.2009.11.011. [PMID: 19922764]
  • Prasenjit Manna, Mahua Sinha, Parames C Sil. Prophylactic role of arjunolic acid in response to streptozotocin mediated diabetic renal injury: activation of polyol pathway and oxidative stress responsive signaling cascades. Chemico-biological interactions. 2009 Oct; 181(3):297-308. doi: 10.1016/j.cbi.2009.08.004. [PMID: 19682444]
  • Zhirong Yao, Jun Li, Sixiang Zhou, Yun Zhang, Pengfei Tu. [Triterpenoids from leaves of Ilex cornuta]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Apr; 34(8):999-1001. doi: ". [PMID: 19639785]
  • Prasenjit Manna, Mahua Sinha, Parames C Sil. Protective role of arjunolic acid in response to streptozotocin-induced type-I diabetes via the mitochondrial dependent and independent pathways. Toxicology. 2009 Mar; 257(1-2):53-63. doi: 10.1016/j.tox.2008.12.008. [PMID: 19133311]
  • Jyotirmoy Ghosh, Joydeep Das, Prasenjit Manna, Parames C Sil. Cytoprotective effect of arjunolic acid in response to sodium fluoride mediated oxidative stress and cell death via necrotic pathway. Toxicology in vitro : an international journal published in association with BIBRA. 2008 Dec; 22(8):1918-26. doi: 10.1016/j.tiv.2008.09.010. [PMID: 18845235]
  • Mahua Sinha, Prasenjit Manna, Parames C Sil. Arjunolic acid attenuates arsenic-induced nephrotoxicity. Pathophysiology : the official journal of the International Society for Pathophysiology. 2008 Oct; 15(3):147-56. doi: 10.1016/j.pathophys.2008.03.001. [PMID: 18434106]
  • Prasenjit Manna, Mahua Sinha, Parames C Sil. Arsenic-induced oxidative myocardial injury: protective role of arjunolic acid. Archives of toxicology. 2008 Mar; 82(3):137-49. doi: 10.1007/s00204-007-0272-8. [PMID: 18197399]
  • Mahua Sinha, Prasenjit Manna, Parames C Sil. Protective effect of arjunolic acid against arsenic-induced oxidative stress in mouse brain. Journal of biochemical and molecular toxicology. 2008 Feb; 22(1):15-26. doi: 10.1002/jbt.20209. [PMID: 18273903]
  • Prasenjit Manna, Mahua Sinha, Parames C Sil. Protection of arsenic-induced testicular oxidative stress by arjunolic acid. Redox report : communications in free radical research. 2008; 13(2):67-77. doi: 10.1179/135100008x259169. [PMID: 18339249]
  • Prasenjit Manna, Mahua Sinha, Prasanta Pal, Parames C Sil. Arjunolic acid, a triterpenoid saponin, ameliorates arsenic-induced cyto-toxicity in hepatocytes. Chemico-biological interactions. 2007 Dec; 170(3):187-200. doi: 10.1016/j.cbi.2007.08.001. [PMID: 17854788]
  • Prasenjit Manna, Mahua Sinha, Parames C Sil. Protection of arsenic-induced hepatic disorder by arjunolic acid. Basic & clinical pharmacology & toxicology. 2007 Nov; 101(5):333-8. doi: 10.1111/j.1742-7843.2007.00132.x. [PMID: 17910617]
  • Rudiyansyah, Mary J Garson. Secondary metabolites from the wood bark of Durio zibethinus and Durio kutejensis. Journal of natural products. 2006 Aug; 69(8):1218-21. doi: 10.1021/np050553t. [PMID: 16933881]
  • Dong Wang, Mingyu Xia, Zheng Cui. New triterpenoids isolated from the root bark of Ulmus pumila L. Chemical & pharmaceutical bulletin. 2006 Jun; 54(6):775-8. doi: 10.1248/cpb.54.775. [PMID: 16755042]
  • M Sumitra, P Manikandan, D A Kumar, N Arutselvan, K Balakrishna, B M Manohar, R Puvanakrishnan. Experimental myocardial necrosis in rats: role of arjunolic acid on platelet aggregation, coagulation and antioxidant status. Molecular and cellular biochemistry. 2001 Aug; 224(1-2):135-42. doi: 10.1023/a:1011927812753. [PMID: 11693190]
  • Y Kashiwada, H K Wang, T Nagao, S Kitanaka, I Yasuda, T Fujioka, T Yamagishi, L M Cosentino, M Kozuka, H Okabe, Y Ikeshiro, C Q Hu, E Yeh, K H Lee. Anti-AIDS agents. 30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids. Journal of natural products. 1998 Sep; 61(9):1090-5. doi: 10.1021/np9800710. [PMID: 9748372]