Natural product as a source of prodrug

  • Jagannathan Padmavathy Department of Pharmaceutics, Jaya College of Paramedical Sciences, College of Pharmacy, CTH Road, Thiruninravur 602024, Chennai, Tamil Nadu, India.
  • Devarajan Saravanan Department of Pharmaceutical Chemistry, Ratnam Institute of Pharmacy, Pidathapolur, Nellore 524346, Andhra Pradesh, India. http://orcid.org/0000-0002-6763-9840
Keywords: Natural product, Prodrug, Review, Source of drug
DOI: 10.3329/bjp.v12i2.31020

Abstract

The natural products are the chemical constituents that are generated from the living organism. The natural products are isolated from the plants, animals, and microorganisms which are used in drug design and drug discovery. Natural product is then modified by chemical synthesis as either total or semi-synthetic way. The natural products show various pharmaco-logical activity which can be used for the treatment of a variety of diseases. Natural products could be regarded as a source of quantifiable and chemically pure known products and also natural products can be utilized as complex mixtures subjected to chemical variability. The present review article adds up the prodrugs from natural products as well as prodrugs developed from the natural products.

References

Alam P, Alam A, Anwer MK, Alqasoumi SI. Quantitative estimation of hesperidin by HPTLC in different varieties of citrus peels. Asian Pac J Trop Biomed. 2014; 4: 262-66.

Andersen TB, López CQ, Manczak T, Martinez K, Simonsen HT. Thapsigargin: From Thapsia L. to mipsagargin. Molecules 2015; 20: 6113-127.

Atanasov AG, Waltenberger B, Pferschy-Wenzig EM, Linder T, Wawrosch C, Uhrin P, Temml V, Wang L, Schwaiger S, Heiss EH, Rollinger JM, Schuster D, Breuss JM, Bochkov V, Mihovilovic MD, Kopp B, Bauer R, Dirsch VM, Stuppner H. Discovery and resupply of pharmacologically active plant-derived natural products: A review. Biotechnol Adv. 2015; 33: 1582-614.

Babizhayev MA. Bioactivation antioxidant and transglycating properties of N-acetylcarnosine autoinduction prodrug of a dipeptide L-carnosine in mucoadhesive drug delivery eye-drop formulation: Powerful eye health application technique and therapeutic platform. Drug Test Anal. 2012; 4: 468-85.

Bang SH, Han SJ, Kim DH. Hydrolysis of arbutin to hydroquinone by skin bacteria and its effect on antioxidant activity. J Cosmet Dermatol. 2008; 7: 189-93.

Cao F, Guo JX, Ping QN, Shao Y, Liang J. Ester prodrug of scutellarin: Synthesis, physicochemical property and degradation. Yao Xue Xue Bao. 2006; 41: 595-602.

Chin YW, Balunas MJ, Chai HB, Kinghorn AD. Drug discovery from natural sources. AAPS J. 2006; 8: E239-53.

Dahan A, Khamis M, Agbaria R, Karman R. Targeted prodrugs in oral drug delivery: The modern molecular biopharmaceutical approach. Expert Opin Drug Deliv. 2012; 9: 1001-13.

Dahan A, Zimmermann EM, Shabat SB. Modern prodrug design for targeted oral drug delivery. Molecules 2014; 19: 16489-505.

Dai L, Li D, Cheng J, Liu J, Deng LH, Wang LY, Lei JD, He J. Water soluble multi-arm-polyethylene glycol–betulinic acid prodrugs: Design, synthesis, and in vivo effectiveness. Polym Chem. 2014; 5: 5775-83.

Elliott S, Burgess V. The presence of gamma-hydroxybutyric acid (GHB) and gamma-butyrolactone (GBL) in alcoholic and non-alcoholic beverages. Forensic Sci Int. 2005; 151: 289-92.

Endo A. The discovery and development of HMG-CoA reductase inhibitors. J Lipid Res. 1992; 33: 1569-82.

Farnsworth NR, Morris RW. Higher plants: The sleeping giant of drug development. Am J Pharm Sci Support Public Health. 1976; 148: 46-52.

Gurnani N, Mehta D, Gupta M, Mehta BK. Natural products: Source of potential drugs. Afr J Basic Appl Sci. 2014; 6: 171-86.

Han HK, Amidon GL. Targeted prodrug design for optimized drug delivery. AAPS Pharm Sci. 2000; 2: 48-58.

Huang SX, Yun BS, Ma M, Basu HS, Church DR, Ingenhorst G, Huang Y, Yang D, Lohman JR, Tang GL, Ju J, Liu T, Wilding G, Shen B. Leinamycin E1 acting as an anticancer prodrug activated by reactive oxygen species. Proc Natl Acad Sci. 2015; 112: 8278-83.

Jana S, Mandlekar S, Maratha P. Prodrug design to improve pharmacokinetics and drug delivery properties: Challenges to the discovery scientists. Curr Med Chem. 2010; 17: 3874-904.

Jia Y, Jia Z, Chen J, Zhu H, Cui M. Ursolic acid benzaldehyde chalcone leads to inhibition of cell proliferation and arrests cycle in G1/G0 phase in ovarian cancer. Bangladesh J Pharmacol. 2015; 10: 358-65.

Katz L, Baltz RH. Natural product discovery: Past, present, and future. J Int Microbiol Biotechnol. 2016; 43: 155-76.

Kim DH, Ahn T, Jung HC, Pan JG, Yun CH. Generation of the human metabolite piceatannol from the anticancer preventive agent resveratrol bay bacterial cytochrome P450 BM3. Drug Metab Dispos. 2009; 37: 932-36.

Kobashi K. Plant glycosides are natural prodrugs: Role of human intestinal flora. J Ginseng Res. 2004; 28: 1-4.

Koehn FE, Carter GT. The evolving role of natural products in drug discovery. Nat Rev Drug Discov. 2005; 4: 206-20.

Kukreja A, Wadhwa N, Tiwari A. Therapeutic role of resveratrol and piceatannol in disease prevention. J Blood Disord Transfus. 2014; 5: 1-9.

Kumar V, Saravanan D, Kumar B, Jayakumar A. Update on prodrugs from natural products. Asian Pac J Trop Med. 2014; 7: S54-59.

Lahlou M. Screening of natural products for drug discovery. Expert Opinion Drug Discov. 2007; 2: 697-705.

Lahlou M. The success of natural products in drug discovery. Pharmacol Pharm. 2013; 4: 17-31.

Lee CH, Kim JH. A review on the medicinal potentials of ginseng and ginsenosides on cardiovascular diseases. J Ginseng Res. 2014; 38: 161-66.

Lee NK, Choi SH, Park SH, Park EK, Kim DH. Antiallergic activity of hesperidin is activated by intestinal microflora. Pharmacology 2004; 71: 174-80.

Leung KW, Wong AST. Pharmacology of ginsenosides: Literature review. Chin Med. 2010; 5: 20.

Li X, Deng Y, Hu J, Wang Z, Xie R, Luo H, Hu, X. Resveratrol overcomes TRAIL resistance in human colon cancer cells. Bangladesh J Pharmacol. 2015; 10: 568-76.

Luo Y, Cobb RE, Zhao H. Recent advances in natural product discovery. Curr Opin Biotechnol. 2014; 30: 230-37.

Martín ML, San Román L, Domínguez A. In vitro activity of protoanemonin, an antifungal agent. Planta Med. 1990; 56: 66-69.

McFarland AJ, Anoopkumar-Dukie S, Arora DS, Grant GD, McDermott CM, Perkins AV, Davey AK. Molecular mechanisms underlying the effects of statins in the central nervous system. Int J Mol Sci. 2014; 15: 20607-37.

Mercer DK, Robertson J, Wright K, Miller L, Smith S, Stewart CS, O’Neil DA. A prodrug approach to the use of coumarins as a potential therapeutics for superficial mycoses. PloS ONE. 2013; 8: 1-7.

Miyake Y, Shimoi K, Kumazawa S, Yamamoto K, Kinae N, Osawa T. Identification and antioxidant activity of flavonoid metabolites in plasma and urine of eriocitrin-treated rats. J Agric Food Chem. 2000; 48: 3217-24.

Montenegro L, Carbone C, Maniscalco C, Lambusta D, Nicolosi G, Ventura CA, Puglisi G. In vitro evaluation of quercetin-3-O-acyl esters as topical prodrugs. Int J Pharm. 2007; 336: 257-62.

Ovadje P, Roma A, Steckle M, Nicoletti L, Arnason JT, Pandey S. Advances in the research and development of natural health products as main stream cancer therapeutics. Evid Based Complement Altern Med. 2015; 2015: 1-12.

Patil S, Lis LG, Schumacher RJ, Norris BJ, Morgan ML, Cuellar RA, Blazar BR, Suryanarayanan R, Gurvich VJ, Georg GI. Phosphonooxymethyl prodrug of triptolide: Synthesis, physicochemical characterization, and efficacy in human colon adenocarcinoma and ovarian cancer xenografts. J Med Chem. 2015; 58: 9334-44.

Qaralleh H. Chemical and bioactive diversities of marine sponge Neopetrosia. Bangladesh J Pharmacol. 2016; 11: 433-52.

Rafii F. The role of colonic bacteria in the metabolism of the natural isoflavone daidzin to equol. Metabilites 2015; 5: 56-73.

Rai M, Carpinella MC. Naturally occurring bioactive compounds. Vol 3. India, Elsevier Publisher, 2006, pp 11-12.

Raskin I, Ripoll C. Can an apple a day keep the doctor away? Curr Pharm Des. 2004; 10: 3419-29.

Rates SMK. Plants as source of drugs. Toxicon 2001; 39: 603-13.

Sawynok J. The therapeutic use of heroin: A review of the pharmacological literature. Can J Physiol Pharmacol. 1986; 64: 1-6.

Searcey M. Duocarmycins: Natures prodrugs? Curr Pharm Des. 2002; 8: 1375-89.

Shapiro TA, Fahey JW, Wade KL, Stephenson KK, Talalay P. Chemoprotective glucosinolates and isothiocyanates of broccoli sprouts: Metabolism and excretion in humans. Cancer Epidemiol Biomarkers Prev. 2001; 10: 501-08.

Sharma M. Actinomycetes: Source, identification and their applications. Int J Curr Microbiol App Sci. 2014; 3: 801-32.

Sheetal Verma, Singh SP. Current and future status of herbal medicines. Vet World. 2008; 1: 347-50.

Siddiqui AA, Iram F, Siddiqui S, Sahu K. Role of natural products in drug discovery process. Int J Drug Dev Res. 2014; 6: 172-204.

Smit BJ, Albrecht CF, Liebenberq RW, Kruger PB, Freestone M, Gouws L, Theron E, Bouic PJ, Etsebeth S, Van Jaarsveld PP. A phase 1 triol of hypoxoside as an oral prodrug for cancer therapy-absence of toxicity. S Afr Med L. 1995; 85: 865-70.

Smith DWE, McDaniel EG, Laqueur GL. Role of intestinal microorganisms in determining cycasin toxicity. Exp Biol Med. 1967; 124: 691-97.

Stella VJ, Barchardt RT, Hageman MJ, Oliyai R, Maag H, Tilley JW. Prodrugs: Challenges and rewards. Springer, New York, 2007.

Stella VJ, Charman WN, Naringrekar VH. Prodrugs: Do they have advantages in clinical practice? Drugs 1985; 29: 455-73.

Tubaro A, Del Negro P, Ragazzi E, Zampiron S, Della Loggia R. Anti-inflammatory and peripheral analgesic activity of esculetin. Pharmacol Res Commun. 1988; 20: 83-85.

van Herwerden EF, Sussmuth RD. Sources for Leads: Natural products and libraries. Handb Exp Pharmacol. 2016; 232: 91-123.

Wachowska M, Muchowicz A, Firezuk M, Gabrysiak M, Winiarska M, Wanczyk M, Bojarczuk K, Golab J. Aminolevulinic acid (ALA) as a prodrug in photodynamic therapy of cancer. Molecules 2011; 16: 4140-64.

Wang J, Lu ML, Dai HL, Zhang SP, Wang HX, Wei N. Esculetin, a coumarin derivative, exerts in vitro and in vivo antiproliferative activity against hepatocellular carcinoma by initiating a mitochondrial-dependent apoptosis pathway. Braz J Med Biol Res. 2015; 48: 245-53.

Wang X, Zhang F, Yang L, Mei Y, Long H, Zhang X, Qimuge-Suyila, SU X. Ursolic acid inhibits proliferation and induces apoptosis of cancer cells in vitro and in vivo. J Biomed Biotechnol. 2011; 2011: 1-8.

Wink M. Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Phytochemistry 2003; 64: 3-19.

Woods JR, Mo H, Bieberich AA, Alavanja T, Colby DA. Amino-derivatives of the sesquiterpene lactone class of natural products as prodrugs. Med Chem Commun. 2013; 4: 27-33.

Wu KM. A new classification of prodrugs: Regulatory perspectives. Pharmaceuticals 2009; 2: 77-81.

Xu YM, Marron MT, Seddon E, McLaughlin SP, Ray DT, Whitesell L, Gunatilaka AA. 2,3-dihydrowithaferin A-3beta-O-sulfate, a new potential prodrug of withaferin A from aeroponically grown Withania somnifera. Bioorg Med Chem. 2009; 17: 2210-14.

Yu KU, Janq IS, Kang KH, Sung CK, Kim DH. Metabolism of saikosaponin c and naringin by human intestinal bacteria. Arch Pharm Res. 1997; 20: 420-24.

Zhang Y, Gao Y, Wen X, Ma H. Current prodrugs strategies for improving oral absorption of nucleoside analogues. Asian J Pharm Sci. 2014; 9: 65-74.

Published
2017-05-05

Apply citation style format of Bangladesh Journal of Pharmacology

Section
Mini Review
Financial Support
Self-funded
Conflict of Interest
Authors declare no conflict of interest