11-Keto β-Boswellic Acid (BioDeep_00000620632)

Main id: BioDeep_00000017378

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid

化学式: C30H46O4 (470.3395916)
中文名称: 11-酮基-beta-乳香酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1CCC2(CCC3(C(=CC(=O)C4C3(CCC5C4(CCC(C5(C)C(=O)O)O)C)C)C2C1C)C)C
InChI: InChI=1S/C30H46O4/c1-17-8-11-26(3)14-15-28(5)19(23(26)18(17)2)16-20(31)24-27(4)12-10-22(32)30(7,25(33)34)21(27)9-13-29(24,28)6/h16-18,21-24,32H,8-15H2,1-7H3,(H,33,34)/t17-,18+,21-,22-,23+,24-,26-,27+,28-,29-,30-/m1/s1

描述信息

11-Keto-beta-boswellic acid (11-Keto-β-boswellic acid) is a pentacyclic triterpenic acid of the oleogum resin from the bark of the Boswellia serrate tree, popularly known as Indian Frankincense. 11-Keto-beta-boswellic acid has the anti-inflammatory activity is primarily due to inhibit 5-lipoxygenase (5-LOX) and subsequent leukotriene and nuclear factor-kappa B (NF-κB) activation and tumor necrosis factor alpha generation production[1].
11-Keto-beta-boswellic acid (11-Keto-β-boswellic acid) is a pentacyclic triterpenic acid of the oleogum resin from the bark of the Boswellia serrate tree, popularly known as Indian Frankincense. 11-Keto-beta-boswellic acid has the anti-inflammatory activity is primarily due to inhibit 5-lipoxygenase (5-LOX) and subsequent leukotriene and nuclear factor-kappa B (NF-κB) activation and tumor necrosis factor alpha generation production[1].
11-Keto-beta-boswellic acid (11-Keto-β-boswellic acid) is a pentacyclic triterpenic acid of the oleogum resin from the bark of the Boswellia serrate tree, popularly known as Indian Frankincense. 11-Keto-beta-boswellic acid has the anti-inflammatory activity is primarily due to inhibit 5-lipoxygenase (5-LOX) and subsequent leukotriene and nuclear factor-kappa B (NF-κB) activation and tumor necrosis factor alpha generation production[1].

同义名列表

11 个代谢物同义名

(3R,4R,6aR,6bS,8aR,11R,12S,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4a,5,6,7,8,9,10,11,12,12a,14a-tetradecahydropicene-4-carboxylic acid; 11-Keto β-Boswellic Acid; (3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid; 3-Hydroxy-11-oxo-(3alpha,4beta)-Urs-12-en-23-oic acid; Urs-12-en-24-oic acid, 3alpha-hydroxy-11-oxo- (8CI); 3a-Hydroxy-11-oxo-12-ursen-24-oic acid; 11-Keto-beta-boswellic acid; 11-Keto-b-boswellic acid; 11-Oxo-b-boswellic acid; 11-Keto-β-boswellic acid; 11-?Keto-?beta-?boswellic acid



数据库引用编号

10 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。

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BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

15 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

  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Huiqiang Wei, Jianghong Guo, Xiao Sun, Wenfeng Gou, Hongxin Ning, Haihua Shang, Qiang Liu, Wenbin Hou, Yiliang Li. Discovery of Natural Ursane-type SENP1 Inhibitors and the Platinum Resistance Reversal Activity Against Human Ovarian Cancer Cells: A Structure-Activity Relationship Study. Journal of natural products. 2022 05; 85(5):1248-1255. doi: 10.1021/acs.jnatprod.1c01166. [PMID: 35500202]
  • Ajmal Khan, Imran Khan, Sobia Ahsan Halim, Najeeb Ur Rehman, Nasiara Karim, Waqar Ahmad, Majid Khan, Rene Csuk, Ahmed Al-Harrasi. Anti-diabetic potential of β-boswellic acid and 11-keto-β-boswellic acid: Mechanistic insights from computational and biochemical approaches. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Mar; 147(?):112669. doi: 10.1016/j.biopha.2022.112669. [PMID: 35121344]
  • Hippolyt L Greve, Marcel Kaiser, Pascal Mäser, Thomas J Schmidt. Boswellic Acids Show In Vitro Activity against Leishmania donovani. Molecules (Basel, Switzerland). 2021 Jun; 26(12):. doi: 10.3390/molecules26123651. [PMID: 34203815]
  • Asma Bini Araba, Najeeb Ur Rehman, Amna Al-Araimi, Sulaiman Al-Hashmi, Sulaiman Al-Shidhani, Rene Csuk, Hidayat Hussain, Ahmed Al-Harrasi, Fahad Zadjali. New derivatives of 11-keto-β-boswellic acid (KBA) induce apoptosis in breast and prostate cancers cells. Natural product research. 2021 Mar; 35(5):707-716. doi: 10.1080/14786419.2019.1593165. [PMID: 30931626]
  • Lubna Abidin, Prerna Singla, Hina Kausar, Mohd Mujeeb, Abdur Rahman, Mohd Aqil, Abul Kalam Najmi. Extraction of 11-Keto-β -Boswellic Acid from Indian Olibanum by Contemporary Extraction Modes: Optimization and Validation of HPTLC. Combinatorial chemistry & high throughput screening. 2021; 24(8):1309-1321. doi: 10.2174/1386207323666200914091733. [PMID: 32928084]
  • Umair Shamraiz, Hidayat Hussain, Najeeb Ur Rehman, Sulaiman Al-Shidhani, Aasim Saeed, Husain Yar Khan, Ajmal Khan, Lucie Fischer, René Csuk, Amin Badshah, Ahmed Al-Rawahi, Javid Hussain, Ahmed Al-Harrasi. Synthesis of new boswellic acid derivatives as potential antiproliferative agents. Natural product research. 2020 Jul; 34(13):1845-1852. doi: 10.1080/14786419.2018.1564295. [PMID: 30691289]
  • Cheng Wei Lu, Tzu Yu Lin, Su Jane Wang. 11-Keto-β-Boswellic Acid Attenuates Glutamate Release and Kainic Acid-Induced Excitotoxicity in the Rat Hippocampus. Planta medica. 2020 Apr; 86(6):434-441. doi: 10.1055/a-1107-9337. [PMID: 32097973]
  • H P T Ammon. Boswellic extracts and 11-keto-ß-boswellic acids prevent type 1 and type 2 diabetes mellitus by suppressing the expression of proinflammatory cytokines. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Oct; 63(?):153002. doi: 10.1016/j.phymed.2019.153002. [PMID: 31301539]
  • Erin Miscioscia, Justin Shmalberg, Karen C Scott. Measurement of 3-acetyl-11-keto-beta-boswellic acid and 11-keto-beta-boswellic acid in Boswellia serrata Supplements Administered to Dogs. BMC veterinary research. 2019 Aug; 15(1):270. doi: 10.1186/s12917-019-2021-7. [PMID: 31370899]
  • Haroon Khan, Kannan R R Rengasamy, Aini Pervaiz, Seyed Mohammad Nabavi, Atanas G Atanasov, Mohammad A Kamal. Plant-derived mPGES-1 inhibitors or suppressors: A new emerging trend in the search for small molecules to combat inflammation. European journal of medicinal chemistry. 2018 Jun; 153(?):2-28. doi: 10.1016/j.ejmech.2017.12.059. [PMID: 29329790]
  • Ahmed M Shehata, Leticia Quintanilla-Fend, Sabrina Bettio, Zahra Kamyabi-Moghaddam, Ursula A Kohlhofer, Werner A Scherbaum, Hermann P T Ammon. 11-Keto-β-Boswellic Acid Inhibits Lymphocyte (CD3) Infiltration Into Pancreatic Islets of Young None Obese Diabetic (NOD) Mice. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 2017 Sep; 49(9):693-700. doi: 10.1055/s-0043-112761. [PMID: 28759942]
  • Ulf Siemoneit, Lars Tausch, Daniel Poeckel, Michael Paul, Hinnak Northoff, Andreas Koeberle, Johann Jauch, Oliver Werz. Defined Structure-Activity Relationships of Boswellic Acids Determine Modulation of Ca2+ Mobilization and Aggregation of Human Platelets by Boswellia serrata Extracts. Planta medica. 2017 Aug; 83(12-13):1020-1027. doi: 10.1055/s-0043-107884. [PMID: 28403501]
  • Hamid Reza Sadeghnia, Fatemeh Arjmand, Ahmad Ghorbani. NEUROPROTECTIVE EFFECT OF BOSWELLIA SERRATA AND ITS ACTIVE CONSTITUENT ACETYL 11-KETO-β-BOSWELLIC ACID AGAINST OXYGEN-GLUCOSE-SERUM DEPRIVATION-INDUCED CELL INJURY. Acta poloniae pharmaceutica. 2017 May; 74(3):911-920. doi: NULL. [PMID: 29513961]
  • Khemraj Bairwa, Sanjay Madhukar Jachak. Nanoparticle formulation of 11-keto-β-boswellic acid (KBA): anti-inflammatory activity and in vivo pharmacokinetics. Pharmaceutical biology. 2016 Dec; 54(12):2909-2916. doi: 10.1080/13880209.2016.1194437. [PMID: 27305832]
  • Ying-Ni Pan, Xiao-Xu Liang, Li-Ying Niu, Yan-Nian Wang, Xin Tong, Hui-Ming Hua, Jiang Zheng, Dong-Ya Meng, Xiao-Qiu Liu. Comparative studies of pharmacokinetics and anticoagulatory effect in rats after oral administration of Frankincense and its processed products. Journal of ethnopharmacology. 2015 Aug; 172(?):118-23. doi: 10.1016/j.jep.2015.06.029. [PMID: 26117531]
  • A M Shehata, L Quintanilla-Fend, S Bettio, J Jauch, T Scior, W A Scherbaum, H P T Ammon. 11-Keto-β-Boswellic Acids Prevent Development of Autoimmune Reactions, Insulitis and Reduce Hyperglycemia During Induction of Multiple Low-Dose Streptozotocin (MLD-STZ) Diabetes in Mice. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 2015 Jun; 47(6):463-9. doi: 10.1055/s-0035-1547293. [PMID: 25951322]
  • Hui Wang, Chenning Zhang, Yun Wu, Yu Ai, David Y-W Lee, Ronghua Dai. Comparative pharmacokinetic study of two boswellic acids in normal and arthritic rat plasma after oral administration of Boswellia serrata extract or Huo Luo Xiao Ling Dan by LC-MS. Biomedical chromatography : BMC. 2014 Oct; 28(10):1402-8. doi: 10.1002/bmc.3182. [PMID: 24806456]
  • Moritz Verhoff, Stefanie Seitz, Michael Paul, Stefan M Noha, Johann Jauch, Daniela Schuster, Oliver Werz. Tetra- and pentacyclic triterpene acids from the ancient anti-inflammatory remedy frankincense as inhibitors of microsomal prostaglandin E(2) synthase-1. Journal of natural products. 2014 Jun; 77(6):1445-51. doi: 10.1021/np500198g. [PMID: 24844534]
  • Yue Wang, Yan Sun, Chao Wang, Xiaokui Huo, Pinduan Liu, Changyuan Wang, Baojing Zhang, Libin Zhan, Houli Zhang, Sa Deng, Yanyan Zhao, Xiaochi Ma. Biotransformation of 11-keto-β-boswellic acid by Cunninghamella blakesleana. Phytochemistry. 2013 Dec; 96(?):330-6. doi: 10.1016/j.phytochem.2013.07.018. [PMID: 23962801]
  • Shimaa M Elshazly, Dalia M Abd El Motteleb, Noha N Nassar. The selective 5-LOX inhibitor 11-keto-β-boswellic acid protects against myocardial ischemia reperfusion injury in rats: involvement of redox and inflammatory cascades. Naunyn-Schmiedeberg's archives of pharmacology. 2013 Sep; 386(9):823-33. doi: 10.1007/s00210-013-0885-9. [PMID: 23771412]
  • Jan Hüsch, Kathleen Gerbeth, Gert Fricker, Constanze Setzer, Jürgen Zirkel, Herbert Rebmann, Manfred Schubert-Zsilavecz, Mona Abdel-Tawab. Effect of phospholipid-based formulations of Boswellia serrata extract on the solubility, permeability, and absorption of the individual boswellic acid constituents present. Journal of natural products. 2012 Oct; 75(10):1675-82. doi: 10.1021/np300009w. [PMID: 23013292]
  • Carsten Skarke, Karina Kuczka, Lars Tausch, Oliver Werz, Tanja Rossmanith, Jeffrey S Barrett, Sebastian Harder, Wolfgang Holtmeier, Joachim A Schwarz. Increased bioavailability of 11-keto-β-boswellic acid following single oral dose frankincense extract administration after a standardized meal in healthy male volunteers: modeling and simulation considerations for evaluating drug exposures. Journal of clinical pharmacology. 2012 Oct; 52(10):1592-600. doi: 10.1177/0091270011422811. [PMID: 22167571]
  • Feng Wang, Zhan-Lin Li, Hong-Hua Cui, Hui-Ming Hua, Yong-Kui Jing, Sheng-Wang Liang. Two new triterpenoids from the resin of Boswellia carterii. Journal of Asian natural products research. 2011 Mar; 13(3):193-7. doi: 10.1080/10286020.2010.548808. [PMID: 21409679]
  • Judith M Rollinger, Denise V Kratschmar, Daniela Schuster, Petra H Pfisterer, Christel Gumy, Evelyne M Aubry, Sarah Brandstötter, Hermann Stuppner, Gerhard Wolber, Alex Odermatt. 11beta-Hydroxysteroid dehydrogenase 1 inhibiting constituents from Eriobotrya japonica revealed by bioactivity-guided isolation and computational approaches. Bioorganic & medicinal chemistry. 2010 Feb; 18(4):1507-15. doi: 10.1016/j.bmc.2010.01.010. [PMID: 20100662]
  • Lars Tausch, Arne Henkel, Ulf Siemoneit, Daniel Poeckel, Nicole Kather, Lutz Franke, Bettina Hofmann, Gisbert Schneider, Carlo Angioni, Gerd Geisslinger, Carsten Skarke, Wolfgang Holtmeier, Tobias Beckhaus, Michael Karas, Johann Jauch, Oliver Werz. Identification of human cathepsin G as a functional target of boswellic acids from the anti-inflammatory remedy frankincense. Journal of immunology (Baltimore, Md. : 1950). 2009 Sep; 183(5):3433-42. doi: 10.4049/jimmunol.0803574. [PMID: 19648270]
  • Xiufeng Pang, Zhengfang Yi, Xiaoli Zhang, Bokyung Sung, Weijing Qu, Xiaoyuan Lian, Bharat B Aggarwal, Mingyao Liu. Acetyl-11-keto-beta-boswellic acid inhibits prostate tumor growth by suppressing vascular endothelial growth factor receptor 2-mediated angiogenesis. Cancer research. 2009 Jul; 69(14):5893-900. doi: 10.1158/0008-5472.can-09-0755. [PMID: 19567671]
  • Phillip Krüger, Johanna Kanzer, Jessica Hummel, Gert Fricker, Manfred Schubert-Zsilavecz, Mona Abdel-Tawab. Permeation of Boswellia extract in the Caco-2 model and possible interactions of its constituents KBA and AKBA with OATP1B3 and MRP2. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2009 Feb; 36(2-3):275-84. doi: 10.1016/j.ejps.2008.10.005. [PMID: 19010411]
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  • Phillip Krüger, Rambod Daneshfar, Gunter P Eckert, Jochen Klein, Dietrich A Volmer, Ute Bahr, Walter E Müller, Michael Karas, Manfred Schubert-Zsilavecz, Mona Abdel-Tawab. Metabolism of boswellic acids in vitro and in vivo. Drug metabolism and disposition: the biological fate of chemicals. 2008 Jun; 36(6):1135-42. doi: 10.1124/dmd.107.018424. [PMID: 18356270]
  • Shailesh A Shah, Ishwarsinh S Rathod, Bhanubhai N Suhagia, Dharmesh A Patel, Vijay K Parmar, Bharat K Shah, Vikas M Vaishnavi. Estimation of boswellic acids from market formulations of Boswellia serrata extract and 11-keto beta-boswellic acid in human plasma by high-performance thin-layer chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 Apr; 848(2):232-8. doi: 10.1016/j.jchromb.2006.10.026. [PMID: 17101304]
  • Olga N Pozharitskaya, Svetlana A Ivanova, Alexander N Shikov, Valery G Makarov. Separation and quantification of terpenoids of Boswellia serrata Roxb. extract by planar chromatography techniques (TLC and AMD). Journal of separation science. 2006 Sep; 29(14):2245-50. doi: 10.1002/jssc.200600078. [PMID: 17069256]
  • S Sharma, V Thawani, L Hingorani, M Shrivastava, V R Bhate, R Khiyani. Pharmacokinetic study of 11-Keto beta-Boswellic acid. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2004 Feb; 11(2-3):255-60. doi: 10.1078/0944-7113-00290. [PMID: 15070181]
  • Astrid Kaunzinger, Alwin Baumeister, Klaus Cuda, Norbert Häring, Barbara Schug, Henning H Blume, Klaus Raddatz, Gerhard Fischer, Manfred Schubert-Zsilavecz. Determination of 11-keto-boswellic acid in human plasma. Journal of pharmaceutical and biomedical analysis. 2002 May; 28(3-4):729-39. doi: 10.1016/s0731-7085(01)00674-4. [PMID: 12008153]
  • K Krohn, M S Rao, N V Raman, M Khalilullah. High-performance thin layer chromatographic analysis of anti-inflammatory triterpenoids from Boswellia serrata Roxb. Phytochemical analysis : PCA. 2001 Nov; 12(6):374-6. doi: 10.1002/pca.606. [PMID: 11793815]
  • M A Tawab, A Kaunzinger, U Bahr, M Karas, M Wurglics, M Schubert-Zsilavecz. Development of a high-performance liquid chromatographic method for the determination of 11-keto-beta-boswellic acid in human plasma. Journal of chromatography. B, Biomedical sciences and applications. 2001 Sep; 761(2):221-7. doi: 10.1016/s0378-4347(01)00335-8. [PMID: 11587352]
  • S Schweizer, A F von Brocke, S E Boden, E Bayer, H P Ammon, H Safayhi. Workup-dependent formation of 5-lipoxygenase inhibitory boswellic acid analogues. Journal of natural products. 2000 Aug; 63(8):1058-61. doi: 10.1021/np000069k. [PMID: 10978197]