Login Register Cart 0
Generic placeholder image

Anti-Cancer Agents in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1871-5206
ISSN (Online): 1875-5992

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Review Article

ADME Prediction, Structure-activity Relationship of Boswellic Acid Scaffold for the Aspect of Anticancer & Anti-inflammatory Potency

Author(s): Akhalesh Kumar, Saurabh Sharma, Sudhanshu Mishra*, Smriti Ojha and Pawan Upadhyay

Volume 23, Issue 13, 2023

Published on: 10 May, 2023

Page: [1499 - 1505] Pages: 7

DOI: 10.2174/1871520623666230417080437

Price: $65

Abstract

Nature is the chief source of various remedies which are used to cure various diseases. Boswellic acid (BA) is a secondary metabolite from the pentacyclic terpenoid compound groups that are derived from the plant genus Boswellia. The oleo gum resins of these plants are primarily composed of polysaccharides, with the remaining amounts of resin (30-60%) and essential oils (5-10%) soluble in organic solvents. BA and its analogs are also reported to exhibit various in vivo and biological responses for example anti-inflammatory, anti-tumor, free radical scavenging activity, etc. Among all analogs, 11-keto-β-boswellic acid (KBA) and 3-O-acetyl-11-keto-β-boswellic acid (AKBA) has been demonstrated to be the most effective at reducing cytokine production and inhibiting the inflammatory responsecausing enzymes. In this review, we summarized the computational ADME prediction via the SwissADME computational tool and the structure-activity relationship of the Boswellic acid scaffold for the aspect of anticancer and antiinflammatory potency. In addition to these research findings which are associated with the therapy of acute inflammation and some cancers, the potential of boswellic acids against other disorders was also discussed.

Keywords: Natural remedies, SwissADME, boswellic acid, anti-inflammatory, anti-cancer, pentacyclic.

« Previous Next »
Graphical Abstract

[1]
Mishra, S.; Verma, P.; Gupta, S.; Pandey, S.; Ojha, S. Nanocarrier and herbal based transdermal patch: An advantage over other drug delivery systems. Ann. Ayurvedic Med., 2022, 11(2), 145-156.
[http://dx.doi.org/10.5455/AAM.11486]
[2]
Mishra, S.; Bishnoi, R.S.; Maurya, R.; Jain, D. Boswellia serrata ROXB. - A bioactive herbs with various pharmacological activities. Asian J. Pharm. Clin. Res., 2020, 33-39.
[http://dx.doi.org/10.22159/ajpcr.2020.v13i11.39354]
[3]
Sharma, D.; Mishra, S.; Rajput, A.; Raj, K.; Malviya, R. Pathophysiology and biomarkers for breast cancer: Management using herbal medicines. Curr. Nutr. Food Sci., 2021, 17(9), 974-984.
[http://dx.doi.org/10.2174/1573401317666210713114216]
[4]
Daina, A.; Michielin, O.; Zoete, V. SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci. Rep., 2017, 7(1), 42717.
[http://dx.doi.org/10.1038/srep42717] [PMID: 28256516]
[5]
Safayhi, H.; Rall, B.; Sailer, E.R.; Ammon, H.P. Inhibition by boswellic acids of human leukocyte elastase. J. Pharmacol. Exp. Ther., 1997, 281(1), 460-463.
[PMID: 9103531]
[6]
Henkel, A.; Kather, N.; Mönch, B.; Northoff, H.; Jauch, J.; Werz, O. Boswellic acids from frankincense inhibit lipopolysaccharide functionality through direct molecular interference. Biochem. Pharmacol., 2012, 83(1), 115-121.
[http://dx.doi.org/10.1016/j.bcp.2011.09.026] [PMID: 22001311]
[7]
Siddiqui, M.Z. Boswellia serrata, a potential antiinflammatory agent: An overview. Indian J. Pharm. Sci., 2011, 73(3), 255-261.
[PMID: 22457547]
[8]
Vo, N.N.Q.; Nomura, Y.; Muranaka, T.; Fukushima, E.O. Structure-activity relationships of pentacyclic triterpenoids as inhibitors of cyclooxygenase and lipoxygenase enzymes. J. Nat. Prod., 2019, 82(12), 3311-3320.
[http://dx.doi.org/10.1021/acs.jnatprod.9b00538] [PMID: 31774676]
[9]
Li, C.; He, Q.; Xu, Y.; Lou, H.; Fan, P. Synthesis of 3-O-acetyl-11-keto-β-boswellic acid (AKBA)-derived amides and their mitochondria-targeted antitumor activities. ACS Omega, 2022, 7(11), 9853-9866.
[http://dx.doi.org/10.1021/acsomega.2c00203] [PMID: 35350335]
[10]
Khan, M.A.; Ali, R.; Parveen, R.; Najmi, A.K.; Ahmad, S. Pharmacological evidences for cytotoxic and antitumor properties of Boswellic acids from Boswellia serrata. J. Ethnopharmacol., 2016, 191, 315-323.
[http://dx.doi.org/10.1016/j.jep.2016.06.053] [PMID: 27346540]
[11]
Iram, F.; Khan, S.A.; Husain, A. Phytochemistry and potential therapeutic actions of Boswellic acids: A mini-review. Asian Pac. J. Trop. Biomed., 2017, 7(6), 513-523.
[http://dx.doi.org/10.1016/j.apjtb.2017.05.001]
[12]
Hussain, H.; Al-Harrasi, A.; Csuk, R.; Shamraiz, U.; Green, I.R.; Ahmed, I.; Khan, I.A.; Ali, Z. Therapeutic potential of boswellic acids: A patent review (1990-2015). Expert Opin. Ther. Pat., 2017, 27(1), 81-90.
[http://dx.doi.org/10.1080/13543776.2017.1235156] [PMID: 27646163]
[13]
Anthoni, C.; Laukoetter, M.G.; Rijcken, E.; Vowinkel, T.; Mennigen, R.; Müller, S.; Senninger, N.; Russell, J.; Jauch, J.; Bergmann, J.; Granger, D.N.; Krieglstein, C.F. Mechanisms underlying the anti-inflammatory actions of boswellic acid derivatives in experimental colitis. Am. J. Physiol. Gastrointest. Liver Physiol., 2006, 290(6), G1131-G1137.
[http://dx.doi.org/10.1152/ajpgi.00562.2005] [PMID: 16423918]
[14]
Harish, D.; Solanki, N. Chromatographic methods used for characterization of boswellic acids. MOJ Drug Des Develop Ther., 2018, 2(4), 195-201.
[15]
Kvasnica, M.; Urban, M.; Dickinson, N.J.; Sarek, J. Pentacyclic triterpenoids with nitrogen- and sulfur-containing heterocycles: Synthesis and medicinal significance. Nat. Prod. Rep., 2015, 32(9), 1303-1330.
[http://dx.doi.org/10.1039/C5NP00015G] [PMID: 26030604]
[16]
Lv, M.; Zhuang, X.; Zhang, Q.; Cheng, Y.; Wu, D.; Wang, X.; Qiao, T. Acetyl-11-keto-β-boswellic acid enhances the cisplatin sensitivity of non-small cell lung cancer cells through cell cycle arrest, apoptosis induction, and autophagy suppression via p21-dependent signaling pathway. Cell Biol. Toxicol., 2021, 37(2), 209-228.
[http://dx.doi.org/10.1007/s10565-020-09541-5] [PMID: 32562082]
[17]
Ismail, S.; Rao, K.; Bhaskar, M. Evaluation of anti-inflammatory activity of Boswellia serrata on carrageenan induced paw edema in albino Wistar rats. Int. J. Res. Med. Sci., 2016, 4(7), 2980-2986.
[http://dx.doi.org/10.18203/2320-6012.ijrms20161989]
[18]
Alluri, V.K.; Kundimi, S.; Sengupta, K.; Golakoti, T.; Kilari, E.K. An anti-inflammatory composition of Boswellia serrata resin extracts alleviates pain and protects cartilage in monoiodoacetate-induced osteoarthritis in rats. Evid. Based Complement. Alternat. Med., 2020, 2020, 1-12.
[http://dx.doi.org/10.1155/2020/7381625] [PMID: 32565872]
[19]
Ahmad, S.; Khan, S.A.; Kindelin, A.; Mohseni, T.; Bhatia, K.; Hoda, M.N.; Ducruet, A.F. Acetyl-11-keto-β-boswellic acid (AKBA) attenuates oxidative stress, inflammation, complement activation and cell death in brain endothelial cells following OGD/reperfusion. Neuromol. Med., 2019, 21(4), 505-516.
[http://dx.doi.org/10.1007/s12017-019-08569-z] [PMID: 31515728]
[20]
Soni, K.K.; Meshram, D.; Lawal, T.O.; Patel, U.; Mahady, G.B. Fractions of Boswellia serrata suppress LTA4, LTC4, cyclooxygenase-2 activities and mRNA in HL-60 cells and reduce lung inflammation in BALB/c mice. Curr. Drug Discov. Technol., 2021, 18(1), 95-104.
[http://dx.doi.org/10.2174/1570163817666200127112928] [PMID: 31985381]
[21]
Sharma, A.; Bhatia, S.; Kharya, M.D.; Gajbhiye, V.; Ganesh, N.; Namdeo, A.G.; Mahadik, K.R. Anti-inflammatory and analgesic activity of different fractions of Boswellia serrata. Int. J. Phytomed., 2010, 2(1)
[22]
Hartmann, R.M.; Fillmann, H.S.; Morgan Martins, M.I.; Meurer, L.; Marroni, N.P. Boswellia serrata has beneficial anti-inflammatory and antioxidant properties in a model of experimental colitis. Phytother. Res., 2014, 28(9), 1392-1398.
[http://dx.doi.org/10.1002/ptr.5142] [PMID: 24619538]
[23]
El Gaafary, M.; Büchele, B.; Syrovets, T.; Agnolet, S.; Schneider, B.; Schmidt, C.Q.; Simmet, T. An α-acetoxy-tirucallic acid isomer inhibits Akt/mTOR signaling and induces oxidative stress in prostate cancer cells. J. Pharmacol. Exp. Ther., 2015, 352(1), 33-42.
[http://dx.doi.org/10.1124/jpet.114.217323] [PMID: 25316122]
[24]
Efferth, T.; Oesch, F. Anti-inflammatory and anti-cancer activities of frankincense: Targets, treatments and toxicities. Semin. Cancer Biol., 2020, 80, 39-57.
[25]
Sharma, T.; Jana, S. Boswellic acids as natural anticancer medicine: Precious gift to humankind. J. Herb. Med., 2020, 20, 100313.
[http://dx.doi.org/10.1016/j.hermed.2019.100313]
[26]
Park, B.; Prasad, S.; Yadav, V.; Sung, B.; Aggarwal, B.B. Boswellic acid suppresses growth and metastasis of human pancreatic tumors in an orthotopic nude mouse model through modulation of multiple targets. PLoS One, 2011, 6(10), e26943.
[http://dx.doi.org/10.1371/journal.pone.0026943] [PMID: 22066019]
[27]
Ranjbarnejad, T.; Saidijam, M.; Moradkhani, S.; Najafi, R. Methanolic extract of Boswellia serrata exhibits anti-cancer activities by targeting microsomal prostaglandin E synthase-1 in human colon cancer cells. Prostaglandins Other Lipid Mediat., 2017, 131, 1-8.
[http://dx.doi.org/10.1016/j.prostaglandins.2017.05.003] [PMID: 28549801]
[28]
Mashhadi, F.F.; Salimi, S.; Forouzandeh, F.; Naghsh, N. Comparison of anticancer activity of hydroalcoholic extracts of Curcuma longa L., Peganum harmala L., and Boswellia serrata on HeLa cells. Jundishapur J. Nat. Pharm. Prod., 2017, 12(2)
[29]
Ravanan, P.; Singh, S.K.; Rao, G.S.R.S.; Kondaiah, P. Growth inhibitory, apoptotic and anti-inflammatory activities displayed by a novel modified triterpenoid, cyano enone of methyl boswellates. J. Biosci., 2011, 36(2), 297-307.
[http://dx.doi.org/10.1007/s12038-011-9056-7] [PMID: 21654084]
[30]
Takahashi, M.; Sung, B.; Shen, Y.; Hur, K.; Link, A.; Boland, C.R.; Aggarwal, B.B.; Goel, A. Boswellic acid exerts antitumor effects in colorectal cancer cells by modulating expression of the let-7 and miR-200 microRNA family. Carcinogenesis, 2012, 33(12), 2441-2449.
[http://dx.doi.org/10.1093/carcin/bgs286] [PMID: 22983985]
[31]
Shen, Y.; Takahashi, M.; Byun, H.M.; Link, A.; Sharma, N.; Balaguer, F.; Leung, H.C.; Boland, C.R.; Goel, A. Boswellic acid induces epigenetic alterations by modulating DNA methylation in colorectal cancer cells. Cancer Biol. Ther., 2012, 13(7), 542-552.
[http://dx.doi.org/10.4161/cbt.19604] [PMID: 22415137]
[32]
Qurishi, Y. Hamid, A; Sharma, PR; Wani, ZA; Mondhe, DM; Singh, SK; Zargar, MA; Andotra, SS; Shah, BA; Taneja, SC; Saxena, AK. NF-κB down-regulation and PARP cleavage by novel 3-α-butyryloxy-β-boswellic acid results in cancer cell specific apoptosis and in vivo tumor regression. Anticancer. Agents Med. Chem., 2013, 13(5), 777-790.
[33]
Lu, M.; Xia, L.; Hua, H.; Jing, Y. Acetyl-keto-β-boswellic acid induces apoptosis through a death receptor 5-mediated pathway in prostate cancer cells. Cancer Res., 2008, 68(4), 1180-1186.
[http://dx.doi.org/10.1158/0008-5472.CAN-07-2978] [PMID: 18281494]

Rights & Permissions Print Cite
Article Metrics
35
2
© 2024 Bentham Science Publishers | Privacy Policy